Molecular fluorescence, phosphorescence, and ... - ACS Publications

Anal. Chem. 1002, 6 4 , 343R-352R

Molecular Fluorescence, Phosphorescence, and Chemiluminescence Spectrometry Isiah M. Warner* Department of Chemistry, Emory University, Atlanta, Georgia 30322

Linda B.McGown Department of Chemistry, Duke University, Durham, North Carolina 27706

A. INTRODUCTION This review covers the a proximately 2- ear period since our last review ( A I ) ,roughyy from Novemger 1989 through September 1991. A computer search of Chemical Abstracts provided most of the references. Coverage is limited to articles that describe new developments in the theory and practice of molecular luminescence for chemical analysis in the UVvisible and near-infrared region. Citations may be duplicated between sections due to content that spans several topics. In eneral, citations are limited to journal articles and usually i o not include patents, proceedin ,reports, and dissertations. However, we find it useful and X m t i v e to list some patents in section C of this review. We have also made a concerted effort to reduce the number of citations in this review. This reduction was attempted with more of a focus on articles of general interest and relevance to the field. Although we are not able to provide extensive coverage of developments in broad areas such as chromatography and biological sciences, we have tried to include inajor review articles and chapters relevant to these topics.

B. BOOKS, REVIEWS, AND CHAPTERS OF GENERAL INTEREST An ASTM s ial technical publication has been published

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on 'Laser Tec niques in Luminescence Spectroscopy" ( B I ) . Volume 12 of the Practical Spectroscopy Series has been published on the topic of "Luminescence Techniques in Chemical and Biochemical Analysis" (B2). Several reviews have focused on general aspects of luminescence methods of analysis. An extensive review of 233 references has been provided on the use of fluorogenic and fluorescent probes for pharmaceutical analysis (B3). Analytical applications of semiconductor laser fluorimetry has also been reviewed (B4). An extensive review (111references) has been provided on recent developments in the use of UV absorption and luminescence spectrometry for determination of olycyclic aromatic compounds (B5). 8 e Schryver et al. have provided an introduction to fluorescence spectroscopy (B6). Other articles have reviewed the use of fluorescencetschni ues for the study of natural and synthetic macromolecules (I38and the use of the fluorescence properties of aromatic amino acids to understand enzyme structure and dynamics (B8).

C. GENERAL INSTRUMENTATION Frequency-domain fluorescence spectroscopy continues to stimulate interest. Lakowicz and co-workers have recently described the instrumentation and a plications of this fast growing technique (CI). Wu and Mc8own have described a modified frequency-domain fluorometer for measurement of lifetimeresolved fluorescence-detectedcircular dichroism (C2). An image dissector tube has been used to ac uire two-dimensional frequency-domain measurements ( 3). A novel system for automated fluorescence detection of DNA fragmenta has been described (C4). This procedure combines chemistry, gel scanning, and robotics to minimize the tedium usually associated with traditional manual methods. A fiber-o tic-based portable laser excited automatic fluorometer (LEAFphas been described (C5). This instrument uses two-channel measurement to indicate plant photosyn-

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thetic activity through measurement of chlorophyll fluorescence. Instrumentation for improved acquisition and analysis of luminescence lifetime decays has been developed. Bieniak et al. have developed a microcomputer-based apparatus for acquisition of optical spectra and fluorescencelifetime analysis (C6). Bordel et al. have described an apparatus for time analysis of fluorescence signals (C7). This modular system is based on the use of fast gates for signal measurement. A variable-temperature apparatus for reccrding the luminescence spectra of small samples has been described by Eisinger (C8). Mathies and co-workers have described an apparatus for ultrasensitive detection of fluorescence (C9). The proposed apparatus is ca able of single particle and single molecule detection. Ingle ancfco-workers(CIO)have described instrumentation and methodology for steady-state and reaction-rate fluorescence measurement through automated standard additions. A number of novel luminescence detection systems have been described recently. Robertson and co-workers have described a scanning fluorescence detection system for measurement of different lumo hores after separation by electrophoresis (CII).Another &tector for electrophoresis,which measures fluoresence and absorption, has been described by Brownlee (CI2). Ingle and co-workers have described a method for correction of fluorescence data for inner-filter by simultaneous measurement of fluorescence and absorbance (CI3). Louis et al. have described an avalanche diode detector for time-correlated single-photon counting on a photoluminescence lifetime microscope spectrometer ( C I 4 ) . This system allows data acquisition for a com lete decay curve of several hundred thousand counts in as stort a time as a few seconds Fourier transform photoluminescence is continuing to receive attention. Antolini and Lamberti have estimated the main cause of error in the use of the Michaelson interferometer for acquisition of photoluminescence data (CI5). Thewalt and co-workers have discussed the applications and advantages of employing Fourier transform techniques for acquisition of photoluminescence data (CI6). A manuscript by Bacis and co-workersalso describes the advantages of Fourier transform photoluminescence data acquisition (CI7). A fluorescence-based optical sensor for detection of lipidsolub!e analytes has been described (CIS).This method employs a lipid layer, containing a fluorophore, whose phase transition temperature is close to the temperature of the analyte measurement.

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D. LASER-BASED TECHNIQUES We report here the recent developments and applications of lasers for luminescence measurements. As in our past reviews, the section focuses on the utility of lasers as viable excitation sources and probes of luminescence. Reviews. Several reviews can be cited regarding laser applications in luminescence over the past 2 years. Small and Jankowiak have reviewed the utility of fluorescence linenarrowing spectroscopy in the study of chemical carcinogenesis (DI). Demtroeder has reviewed laser spectroscopic techniques which provide enhanced spectral resolution and enhanced sensitivity with small samples ( 0 2 ) . Demtroeder has also reviewed the advantages and limitations of laser-induced 0 1992 American Chemical Society

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fluorescence (03). A recent review which focuses on laser applications for small volume samples has been provided by Dovichi (04). Vo Dinh has reviewed the principles and applications of laser-based luminescence spectroscopy (05). Diode lasers continue to increase in usage. Imasaka and Ishibashi have reviewed diode lasers and their use in trace analyses (06).Some recent developments in the use of laser-induced fluorescence for combustion diagn.+tics have been reported (07)Nemkovich . has rewewed the vlsible absorption and fluorescence characteristics of several dyes dissolved in polar media (08). Applications. Niessner and Krupp have reported the use of laser-induced and time-resolved aerosol fluorescence for detection and characterization of polycyclic aromatic hydrocarbons (PAHs) (09).Another study which focuses on the laser-excited fluorescence analysis of PAH vapors has been reported by Winefordner and co-workers (010). Ewald and co-workers have described a ulse laser source for analysis of Mediterranean waters (011~.A visible semiconductor laser has been described for fluorescence measurement (012). Metabolites of benz!a] yrene have been derivatized for detection by laser excite Shpol'skii spectrometry (013). Wehry and co-workers have described two applications of laser photolytic fragmentation-fluorescencespectroemetzy. One application involves the detection and quantification of nonfluorescent organic and organometallic molecules (014). Another application uses a second laser to probe fr created by the first laser (015). This approach len s additional selectivity to the fragmentation-fluorescence measurement scheme. Stringat et al. have reported the use of a continuous scanning Fourier transform (FT) spectrometer for recording high-resolution laser excited fluorescence spectra (016).This system allowed the acquisition of spectra in the near-infrared and visible region. Qian has presented a detailed statistical analysis of fluorescence correlation spectroscopy (017). Vo Dinh and co-workers have described active materials for o tically enhancing Raman and fluorescence spectroscopy (0187. A cellulose membrane coated with fumed silica microparticles was used to enhance the luminescence. A series of quasiaromatic heterocyclic molecules have been found to be useful as a new class of laser dyes (019).These dyes were found to lase with much greater efficiency than coumarin analogs with s i m i i wavelength characteristics. An image converter camera has been used to record the timedependent emission s ectral characteristics of a series of organic laser dyes (D20r Recently, Schmidt has analyzed the fluorescence emission characteristics of rhodamine dye vapors (021). Time resolution with laser excitation continues to be a useful probe of molecular dynamics. A novel spectroscopic techni ue which resonantly excites the vibronic transitions of a mo ecule, by use of a two- ulse sequence of femtosecond duration, has been reported b22). Lasers continue to be exploited to achieve the ultimate detection limit, i.e. detection of a single molecule. Keller and co-workers have reported a laser-based scheme for detecting and counting single molecules as they transit the laser beam (023).This scheme is proposed for use in DNA se uencing. Ramsey and co-workers report a different scheme ased on levitated microdro lets (024)They . reported a signal-bnoise ratio of 3 for singre molecule detection. Lasers continue to be useful excitation sources for measurementa in flow systems. Cremer et d. have recently discussed several approaches to enhancing the resolution of oneAn argon ion laser and two-parameter flow cytometry (OW). has been used for the detection of porphyrin methyl esters in %h-performance thin-layer chromatography (026).Roach and armony have described the use of argon ion laser excitation and high-performanceliquid chromatogra hy (HPLC) in combination with a Sepaniak-Yeung cell con!guration to selectively analyze lyaromatic hydrocarbons (027).Another study has reporteghe use of a frequency-doubled argon ion laser for laser-induced fluorescence detection in conventional-size li uid chromatography (028).Y e F g and Kuhr have describe! a laser-induced indirect detection scheme for capillary zone electrophoresis (CZE) (029).Another detection scheme for CZE uses a sheath flow cuvette in combination with laser-induced fluorescence (030).Winefordner and co-

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workers have described the use of a diode laser to achieve ultralow laser-induced fluorescence detection limits (031). A number of studies in the area of fluorescence line-narrowin spectroscopy have been re orted. For example, Jankowid et al. described the use of Ruorescence line-narrowing for the study of chemically initiated carcinogenesis (032,033). Hurst and Wright have described nonlinear line-narrowin of the vibronic transitions of perylene diasolved in poly(meth$ methacrylate) (034). A similar study from this group has examined the fluorescence line-narrowing spectroscopy of photosensitive organic chromophores (035). The two-photon spectrum and polarization ratio of biphenylene has been measured at room temperature by use of fluorescence-excitation and thermal-lensing techniques (036). Wirth and co-workers have discussed an improved optical arrangement for high detectability in two-photon spectroscopy (037). Lytle and co-workers have developed a fluorometer that can rapidly collect two-photon excitation spectra at submillimolar levels (038).

E. FIBER-OPTIC-BASED TECHNIQUES Interesting applications of luminescence using fiber-optics technology continue to be developed. We have tried to minimize the number of citations in this section. Therefore, we discuss only those applications which are of general interest. Reviews. Two reviews have been reported. Heiman et al. have written a review of 23 references which focuses on a variety of fiber-optic spectroscopic techniques, includin luminescence, for measurement in extreme environments t i l ) . Wolfbeis has provided a review of immobilized fluorescent probes as fiber-optic chemical sensors (E2). Applications. A number of developments in fiber-optics technology have focused on the use of this developing techin luminescence instrumentation. Srivastava and PLgopadhyay have reported the use of optical fiber in a novel photoluminescence measurement system (E3). Zung et al. have reported the design and characterization of a fiber-optic-based fluorometer (E4).Applications of this fluorometer have also been described (E5). Br' ht and ceworkers continue to exploit the advantages of &er optics for luminescence measurements. This oup has recently reported the utilit of multidimensional Korescence measurements using a figer-optic-based probe (E6,E7). Other papers from this group have described the use of dynamic fluorescence spectroscopy to increase the selectivity of fiber-optic-based measurements (E8)and an optical sensor based on immobilized 8-cyclodextrin (E9). Wolfbeis and co-workers have described new optical chemical sensors based on the Langmuil-Blod ett technique (E10).These new sensors provide reproducibfe fabrication, a well-defined layer thickness, and short response times for measurement of chemical parameters such as alkali ions, oxygen, halides, and pH. Lieberman et al. have reported the use of time resolution for improved selectivity in fiber-optic-based chemical sensors (E1I). Another fiber-optic-based chemical sensor for in situ fluorescence measurement of environmental samples has been described by Lieberman et al. (E12).The use of a tunable laser for laser-induced fluorescence analysis of PAHs on particles and in water samples has also been described (E13). Hieftje and co-workers have described a fiber-optic-based sample cell for measurement of low-temperatureluminescence (E14).This system was designed to eliminate several problems inherent to conventional refrigerated cell configurations. Barnard and Walt have described a fiber-optic sensor and associated field-portable instrumentation for continuous measurement of volatile organic compounds (E15).A procedure for optimal design of fluorescence-based fiber-optic sensors has been described by Thompson et el. (E16).A novel enantioseledive o tical sensor has been described by Wolfbeis and co-workers (&7). This sensor is based on the use of four different lipophilic (RJZ)-tartrates as carriers. A fiber-optic detection system, which integrates a luminescent sensor and commercial spectrometer for determination of an infrared beam spectrum, has been described (E18). Synovec and co-workers have described a fiber-opticsystem for absorbance and fluorescence measurements in high-temperature liquid chromatography (E19).The advantage of this approach is that it allows measurements which are not easily

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MOLECULAR FLUORESCENCE Islah Manwl Warner is Samuel Candler Dobbs Professor of Chemistry at Emory University. He recehred his B.S. degree from Southern University at Baton Rouge in 1968. From 1968 to 1973, he worked for Battelle Northwest in Richland, WA, as a Research Chemist. He entered graduate school at the University of Washington in 1973 and received his W.D. in 1977. He was on the chemistry facuky at Texas ABM University from 1977 to 82. He joined the chemistry department of Emory University in 1982. In 1984, he was one of 200 scientists awarded Presidential Young Investigator awards. His current research interests include (1) luminescence spectroscopy, (2) analytical chemistry in organized media, (3) chemometrics, and (4) environmental chemistry. He is coeditor with Professor Linda McGown of Volume I on MuMimnsional Luminescence M198SUfI"ts. Volume I I of this series is also in press. He is a member of the American Chemical Society, Society for Applied Spectroscopy, National Organization of Black Chemists and Chemical Engineers, and Sigma Xi. Llnda Balne McGown is a Professor of Chemistry at Duke University. She recehred her B.S. degree from the State University of New York at Buffalo in 1975 and her Ph.D. from the University of Washington in 1979. Texas A&M University during the 1978-79 academic year, followed by 3 years as an Assistant Professor at California State Univof Oklahoma State University in 1982 and was promoted to Associate Professor in 1985. Her research interests center on luminescence analysis, including lifetime techniques, immunochemical methods, analysis of multidimensionaldata arrays, on-line fluorescence lifetime determinations in HPLC, micellar systems, and the characterization and fingerprinting of complex samples.

accomplished with commercial instrumentation.

F. SAMPLE PREPARATION, QUENCHING, AND RELATED PHENOMENA Reviews. Only one pertinent reference in this category.

Testa has reviewed the standards and instrumental correction factors used in spectrofluorometric measurements (FI). Sample Deoxygenation. Barboy and Feitelson have described an all glass apparatus for deoxygenation of solutions during transient fluorescence studies (F2).This deoxygenation method is shown to have a number of advantages over traditional freeze-pump-thaw methods. Solvents Effects. A number of references in this category relate to studies in supercritical solvents. For example, Brennecke et al. have described a new technique based on fluorescence spectroscopy for probing solvent interactions in supercritical fluids (F3,F4). Betts and Bright have described instrumentation for measurement of fluorescence parameters in supercriticalfluids (F5). Brennecke et al. have also reported a study of the exciplex formation between naphthalene and triethylamine in supercritical carbon dioxide (F6). Bortolus et al. have reported the use of trifluoroethanol for discriminating the fluorescence of polynuclear aza-aromatic compounds from the parent hydrocarbon (F7). This discrimination is based on the observation that the fluorescence spectra of the aza-aromatic compounds are perturbed through hydrogen bonding with the trifluoroethanol. Quenching. Tine and Aaron have examined the effects of several lanthanide ions on the room-temperature fluorescence several indole derivatives (F8). This procedure has led to a fluorescence quenching method for analysis of mixtures. Datta and Bera have reported the use of fluorescence quenching to determine lectin in very dilute solution with unbelliferyl sugars (8'9). Matsuzawa et al. have reported the use of solid carbon dioxide (dry ice) to minimize quenching by oxygen in solution (FIO).

G. DATA REDUCTION Corrected Spectra. A method has been described that uses a digital technique in combination with time-resolved

spectroscopy to obtain absolute luminescence spectra (GI). Rutan and co-workers have described a Kalman filter method for correction of spectral shifts of PAHs in various solvents (G2). This iterative method allows correction for shifts in overlapped spectral responses of up to three components. Matsui has reported a correction method for fluorescence reduction by use of time-resolved fluorometry (G3). Gade et al. have described a reabsorption-reemission correction for luminescence spectra from light-scattering material (G4). Thompson and Ekkerle of the National Institute of Standards and Technology have produced a set of four standards for correcting fluorescence spectra (G5). Quantum Yields. Only one citation in this area. This is a paper from Chartier et al. which focuses on the use of thermal lens measurements to determine fluorescence quantum yields (G6). Chemometrics. Lavine et al. have developed a strategy for fluorescence signal enhancement (G7). This digital technique uses spectral estimation techniques and finite impulse response to detect the frequency content in noisy data. Multivariate data analysis of fluorescence spectra has been used to monitor chemical alterations of individual oil-prone macerals (G8). Another multivariate spectral analysis has been used to quantify an analyte in the presence of a background interference (G9).Kubista has described a new approach to the analysis of correlated data sets (G10).This procedure is based on the singular decomposition of the fluorescence data followed by Procutes rotation. Miscellaneous. Brissette et al. have developed a convenient method for evaluating the performance and dead time of a stopped-flow fluorometer (G11). Torres et al. have developed an empirical method for evaluating a derivative method for absorbance and fluorescence kinetic data (G12). Khochbin et al. have described a computer program for quantification of a specific protein by use of flow cytofluorometry (G13). Mathies and co-workers have provided procedures for optimizing high-sensitivity fluorescence detection (G14).

H. LUMINESCENCE IN ORGANIZED MEDIA Reviews. Only one paper reported in this category. In this

paper, Georges has reviewed micellar effects and analytical applications of molecular fluorescence in micelles and microemulsions (HI). Cyclodextrins. Marquez et al. have studied the warfarin-P-cyclodextrin complex (H2). An improved analytical method for determination of warfarin was developed based on the altered fluorescence properties of the compound. A method for the selective determination of benzo[ghi]perylene in a mixture of PAHs dissolved in P-cyclodextrin media has been reported (H3). Warner and co-workers have reported the utility of cyclodextrins for resolution of mixtures of polyaromatic compounds by use of cyclodextrin complexation (H4). Another study by this group focuses on the ternary complexes formed between cyclodextrins and pyrene with alcohols or nonionic surfactants (H5). A number of studies have reported the use of derivatized cyclodextrins for analytical measurements. For example, Osa and co-workers have used 2-naphthylsulfonyl derivatives of and cyclodextrinsto detect neutral organic compounds (H6) steroidal compounds (H7).Other papers from this group report the use of pyrene-appended y-cyclodextrinto achieve similar detection (H8,H9).Baeyens et al. have examined the fluorescence enhancement of dansyl amino acids and of thiol-ammonium 7-fluorobenzo-2-oxa-1,3-diazole-4-sulfonate derivatives in the presence of surfactants and cyclodextrins (HlO). Vo Dinh and co-workers have examined cyclodextrins as media for enhancing room-temperature phosphorescence (HI 1). Cyclodextrins also continue to be employed in chromatographic separations. Shimada et al. have examined the use of cyclodextrins in the mobile phase of reversed-phase high performance liquid chromatography (HPLC) to improve the separation of bile acids (2312). Surfactants/Micelles. Micellar liquid chromatography has been employed for rapid screening of illegal drugs in sport (H13). Detection limits in the picogram-injected range could be achieved with fluorescence detection. Tran has recently described the use of micellar and related media to enhance fluorescence and thermal lens measurements ANALYTICAL CHEMISTRY, VOL. 64, NO. 12, JUNE 15, 1992 345 R


(H14). Fluorescence enhancement is due to compartmentalization of the fluorophore within the micellar core, while thermal lens enhancement is due to changes in the thermooptical pro erties of the aqueous medium. Warner an8co-workers have reported the use of unconventional micelles to enhance energy transfer in reverse miH16).Both systems employ surfactants cellar systems (H15, whose counterions have been replaced with photosensitive counterions that are capable of undergoing energy transfer with select analytes in the waterpool of the reverse micelle. Both types of surfactants were synthesized in the laboratory of the investigators. Alvarez et al. have used synthetic surfactant vesicles to enhance the fluorescence of metal chelates (HI7). Aiken and Huie have reported the use of surfactants and laser excitation to im rove the detection limits of bilirubin (H18). Intramicellar fuorescence quenching of benoxaprofen in micellar solution has been studied by use of time-resolved Another study reports the fluorescence spectroscopy (H19). use of micelles to enhance the fluorescence of carbamate pesticides (H20). Fluorescence has also been used to study the micellization properties of a new surfactant, n-dodecyltriphenylphosphonium bromide (H21). The effect of surfactants on the chemiluminescence reaction between bis(2,4-dinitrophenyl)oxalate, hydrogen peroxide, and select aromatic hydrocarbons has been studied (H22). Miscellaneous. A new class of organized media for fluorescence and hosphorescence measurements has been is system involves solubilization of hystudied (H23). drophobic analytes in aqueous media through the use of water-soluble copolymers. Tris-o-thymotide and hexabisbtert-buty1thio)benzene have also been studied as new organized media for aromatic chromophores (H24).

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I. LOW-TEMPERATURE LUMINESCENCE The selectivity of low-tem erature luminescence continues to be exploited. Most of ttese studies employ Shpol'skii matrices. Garrigues and co-workers have discussed the problems associated with uantitative analysis of PAHs by use of the Sh l'skii effect (?I). Fachinger et al. have described software anrhardware for acquisition and processing of high resolution Shpol'skii data (12). A convenient fiber-optiobased sample cell for Shpol'skii and low-temperature phosphorescence spectrometry has been described (13). Wild and co-workers have used total luminescence spectroscopy to study electronic spectra of PAHs in Shpol'skii matrices (14). The analytical utility of Fourier transform (FT) UV-visible molecular luminescence spectrometry of PAHs has been evaluated in Shpol'skii solvents (15). Methoxy derivatives of benz[a]anthracene metabolites have been developed to roduce improved Shpol'skii spectra in n-alkane solvents (167. A number of applications of the Shpol'skii effect have been reported. For exam le, the applicability of Shpol'skii spectra for anal sis of PA& in tern and mussel samples has been studied 67).Hofstraat et al. have also reported the a plication of Shpol'skii fluorometry in marine environmend analysis (18). This study focused on the determination of PAHs in crude extracts of biotic samples. Bark and Force have incorporated time resolution and Sh ol'skii measurement to analyze mixtures of PAHs desorbecffrom particulate matter (19). Hofstraat and co-workers have discussed the general applicability of Shpol'skii for measurement of PAHs in complex environmental samples (110,111). A study by Saber et al. focuses on the ap lication of the Shpol'skii effect to analysis of PAHs in lake selments, marine intertidal sediments, and or anisms (112). %arcus has discussed the theory of charge-transfer spectra in frozen matrices (113). Fetzer and Zander have reported on the use of perhydrocoronene as a matrix for low-temperature luminescence measurements of high molecular weight PAHs (114).

J. TOTAL LUMINESCENCE AND SYNCHRONOUS EXCITATION SPECTROSCOPIES AND RELATED TECHNIQUES Ndou and Warner reviewed analytical applications of multidimensional absorption and luminescence spectroscopy 346R

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(51).Increasing utilization of total luminescence spectroscopy is evidenced by applications in environmental analysis, includin remote laser di ostics of natural water conditions (521,daracterization of%solved organic matter in sea water (J3),and the determination of a coumarin marker compound in road fuels (54). The total luminescence technique was also shown to be useful in fluorescencelinenarrowing spectroecopy (55). The intrinsic dependence of the line narrowing spectra on excitation wavelength can be fully exploited throu h the excitation-emission matrix (EEM) representation 0% total luminescence to facilitate interpretation of the spectra. Fluorescence lifetime dependence was added to the total luminescence spectrum through frequency-domain measurements of phase-resolved fluorescence intensity (561,thereby extending the EEM into a third, independent dimension. In this work, a data analysis method was described for the resulting excitation-emission-frequency array (EEFA) and the resolution of the EEFA for a two-component s stem into the spectra and lifetimes of the components was iemonstrated. Unlike the two-way EEM, components may be uniquely resolved from the three-way EEFA. Environmental applications of synchronous excitation spectroscop were reported, including environmental monitoring of i n 2 u s t d effluent ( ~ n characterization , of aromatic hydrocarbons in seawater (581,and discriminating among nonhumic organic materials in aqueous leaf litter extracts (J9). Health and safety applications included studies of proteins and human eye lenses (JIO),identification of PAHs in urine sam les (511) and in workplace air (512), and studies of DNl-benzo[a]pyrenediol epoxide adducts (513,514). Synchronous excitation was also used to monitor resonance and nonresonance fluorescence in supersonic jet spectrometry for the detection of anthracene derivatives in solvenbrefined coal (515). Derivative synchronous excitation techniques were ap lied to the analysis of three-component mixtures of alk&ids (JlS),determination of salicylic acids in urine (517) and in human serum and aspirin (J18),and determination of benzo[a]pyrene in air particulate samples (J19). Variable angle spectrofluorometr was used for simultaneous determination of PAHs (5207, pesticides (521), and fluorescein compounds (522).

K. SOLID-SURFACE LUMINESCENCE Hurtubise et al. reviewed studies of molecular interactions in solid-surface room-temperature phosphorescence (SSRTP) based on measurements of fluorescence and phosphorescence quantum yields and phos horescence lifetimes of model compounds adsorbed on soyid substrates, including sodium acetatesodium chloride mixtures and a-cyclodextrin-sodium chloride mixtures ( K l ) . Vo Dinh provided an overview of laser-induced luminescence spectroscopy on solid substrates, focussing on photophysical processes, effects of experimental parameters, and applications of the laser-based techniques in fluorescence and phosphorescence analysis (K2). Several instrumental developments were described b Winefordner and co-workers for automation of SSRT% analysis, including a nebulizer-based sampling system (K3), a subsequent, two-nebulizer system (K4),and a flow injection adaptation of the two-nebulizer system for continuous sample introduction (K5). Purdy and Hurtubise studied analytical figurea of merit for room-temperature phosphorescence (RTP) analysis of four model compounds on various solid substrates, including silica gel with a polyacrylate binder, filter paper, 1%poly(acry1ic acid)-NaBr, and 80% a-cyclodextrin, and found that filter paper gave the best overall results (K6).The effecta of cesium and iodide ions on RTP was studied for indole compounds on filter paper (K7)and for tryptophan and indican compounds on filter paper (KS).Filter paper that was pretreated with thallium lauryl sulfate was used for RTP analysis of PAHs (K9).In another study, filter paper was pretreated with sodium dodecyl sulfate and thallium(1) ions was shown to enhance the RTP of purine derivatives by factors in the range of 1.5-461 (KIO). Cyclodextrin enhancements of RTP in the presence of heavy atoms (KI1) and in a 1'70 cyclodextrin-sdium chloride mixture (K12) were described for various compounds. The anal ical characteristics of 8-cyclodextrin-salt mixtures for soli -surface room temperature luminescence analysis, in-

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cluding fluorescence and phosphorescence, were studied (KI3).

L. LUMINESCENCE IN CHROMATOGRAPHY AND FLOW SYSTEMS Liquid Chromatography (LC). General reviews include principles and applications of luminescence spectrometric detection (LI1, laser-induced fluorescence detection (L2-L4), principles and applications of photodiode array fluorescence chemilumenscence detection detection in capillary LC (L5), (L6),and the use of bifunctional fluorogenic reagenta for reand postcolumn derivatization of bioactive compounds (En. Developments in array detection techniques include laser-induced fluorescence detected with an intensified linear diode array detection for on-the-fly analyte identification at the sub-nanogram-injected level (L8) and fluorescence detection with a char e cou led device for two-dimensional detection (L9). The Liter levice provides enhanced dynamic range throu h a new technique, charge-dependent variable binning, a n t i s used to obtain total luminescence spectra as well as derivative and synchronousexcitation spectra. Other advances in detedion techniques include computer-controlled wavelength optimization (LIO)and solid-surface room-temperature phosphorescence detection in the nanogram-subnanogram range us a two-nebulizer system (LII). Shpol'skii fluorometry was J a s an independent technique to ascertain peak purit and estimate the number of components in eluted fractions rL12). Fluorescence lifetime detection in the frequency domain was used by Cobb and McGown for on-the-fly detection and analysis of chromatographic peaks, includin heterogeneity indication and subsequent resolution of highy overlap ing peaks (L13). Schreurs, Gooi'er, and Velthorst describetfthe use of long-lived, sensitized Tb(II1) luminescence to label eluting compounds for time-resolved luminescence detection; they reported detection limits in the sub-nanogram range for L-c steine and glutathione on-column (LI4). Jeveral applications were described for environmental and biological analysis. Fluorescence-detected liquid chromatography was compared with gas chromatography/mass spectrometry for the determination of PAHs in the same environmental samples (LI5). Measurements of the same samples using the two techniques showed that they enerally provide comparable results except at low levels, in wbch case the selectivity and sensitivity of fluorescence detection of the articular com ound determines which technique is better. fluorescence gtection was used for the determination of PAHs in environmental water samples and air filters, with detection limits in the picogram range (LI6)and for the determination of K vitamins in animal tissues (LI7).Shimada, Komine, and Oe reported the enhancement of chromatoaphic separation and subsequent fluorescence detection of de acids by the addition of 8-cyclodextrin to the mobile phase (L18). Derivatization was used for fluorimetric determination of urinary catecholamines(LI9)and adenine compounds (L20). A chiral derivatizing agent was used for the fluorescence detection of small eptides and amino acids (L21). Other derivatization-basef methods were described for detection of carboxylic acids (L23-L25), and phosphocycloserine (~5221, lipids (L26). Thin-LayerChromatography (TLC). Analytical aspecta of direct measurements of luminescence and other spectrometric signals on thin-layer chromatograms were discussed, including advantages and difficulties of direct measurement techniques (L27), reproducibility of quantitative measureand the influence of layer thickness on the ments (La), c h r o m a ya hic and optical properties of silica gel thin-layer plates in ig performance TLC (HPTLC) (L29). A system for two-dimensional fluorescence imaging in HPTLC using a solid-state video camera WLWdescribed and applications to uantitative and qualitative analysis of complex samples were emonstrated (L30). Applicationsinclude charactarization and identification of amino acid, peptide, and nucleic acid compounds (L31), patseparation application of a solvatochromicfluorescent dye for determination of nonfluorescent analytes (L32),the use of Nile red as a fluorescent rea ent for direct detection and uantitation of lipid bands on &e thin-layer plate (L33),and %e addition of a fluorescent, li o hilic re ent to the mobile phase for quantitation of phosp!o!pids o n x e thin-layer plate

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(L34). Laser fluorometry with an Ar on ion laser was used for detection of porphyrin compoun& in HPTLC (L35). Electrophoresis-Based Separation Techniques. Fluorescence detection in electrophoretic separation techniques was an active area in this review period. Cheng, Piccard, and Vo Dinh described a new instrument that uses a charge-coupled device (CCD) for fluorescencedetection in capillary zone electrophoresis (CZE) and com ared its performance with that of a photomultiplier tube-tased system (L36). The limit of optical detection for the CCD-based instrument was 4 am01 when a signal integration time of 0.2 s was used. Feasibilit on on-column detection was demonstrated. Swaile and gepaniak described the use of a photodiode array detection system to optimize detection of multiple components in a single injection of a mixture (L37). Laser-based fluorescence detection was used in capillary amino sugars electrophoresis for the analysis of proteins (B), (L39), carbohydrates (UO), primary amines (UI), amino acid derivatives (L42),and marine toxins (MI.Gamer and Yeung described the detection of nonfluorescent analytes by laserexcited fluoreacence,based on energy transfer from the excited analytes to a fluorescent reagent, thereby increasing the fluorescent background level (L44).They also described the application of an indirect detection scheme based on charge dis lacement on visible-region detection of sugars (L45)and Ufdetection of tryptic digests (L46). Luminescence techniques were also described for detection in paper electrophoresis, including room-temperature phoshorescence detection of pyrene and benzo[a]pyrenetetraEydrotetrol (BPT) compounds on a thallium-treated filter paper substrate (L47) and surface-enhanced fluorometric detection of benzo[a]pyreneand a BPT compound on a filter paper substrate, usin amorphous fumed silica as a fluorescence sensitizer (L&. Miscellaneous Chromatographic Applications and Flow Injection Analysis (FIA). Micellar liquid chromatography using sodium dodecyl sulfate micellar mobile phase was used with abso tion and fluorescence detection for rapid screenin of illegal %ugs in sports (1549). Synovec, Renn, and Moore tescribed a system for fiber-optic absorbance and fluorescence detection in high-temperature li uid chromatography and applied it to mixtures of PAAS (L50). A quenching-based approach to indirect fluorescence detection was used in capillary gas chromatogra hy (L51). Chung and Ingle investi ated quenciing and inner-filter interference effects in singfe-line FIA with fluorescence detection and generated an em irical function that can be used to generate correction 1otsPbased on distortion of the peak profile (L52). Spectro Lotometric and fluorometric detection were used in FIA for Betermination of 9-aminoacridine(L53) and roflavine (L54). In a related area, Campiglia, Berthod, and binefordner used flow injection for continuous sample introduction in solid-substrate room-temperature phosphorescence analysis (K5).

M. DYNAMIC MEASUREMENTS OF LUMINESCENCE Frequency-domain techniques were reviewed, including multifrequency lifetime determinations (MI) and phase-resolved fluorescence spectroscopy (M2). In the area of timeresolved fluorometry, reviews discussed applications to clinical microbiology and DNA probe techno10 (M3)and calmodulin (M4) and applications of femtosecony light pulses in spectroscopy (M5). Several new ap roaches to data analysis were presented. Wo and Harris xescribed a reiterative, regression algorithm for 8taining quantitative information about component amplitudes in multiexponential data and applications to fluorescence decay curves (M6). Millican and McGown demonstrated the resolution of component spectra in binary mixtures, using multiway analysis of the excitation-emission-frequenc array (EEFA) in phase-resolved fluorescence spectrosco y &7). Developments in femtosecond spectroscopy incluled a theory of ultrafast time-resolved fluorescence s ectroscopy based on the use of adiabatic approximations (b8) and femtosecond s ectroscopy of stimulated emission An infrom highly excited rhofamine dye molecules (M9). strument was described by Blok, Schakel, and Dekkers for time-resolved detection in circularly-polarized luminescence in the 10 ps-100 ms range (MIO), and Wu and McGown deANALYTICAL CHEMISTRY, VOL. 64, NO. 12, JUNE 15, 1992

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scribed a modified frequency-domain lifetime instrument for lifetime-resolved fluorescence-detectedcircular dichroism (C2). Litwiler and Bright demonstrated multifre uency phasemodulation lifetime measurements and p ase-resolved fluorescence measurements through a single optical fiber (M11). The same group also investigated the dynamica of thin ndion f i b s using multifrequency lifetime techni ues (M12). Applications of d amic techniques included %e analysis by time-resolved gorescence spectroscopy of polycyclic aromatic hydrocarbon mixtures in vapor and condensed phases and in a Shpol'skii matrix (M13),the fluorescence response of mineral oils (M14), and time-resolved fluorescence spectroscop of s inach leaves, which revealed the resence Wirt!, Chou, of at least t k e e ifetime components (M15). and Piasecki used frequency-domain fluorescence to study the effect of n-pro an01 on the internal viscosity of sodium dodecyl sulfate mice& using the rotational diffusion behavior of tetracene probe (M16).The results of the study, which indicate that the probe reorients faster with increasing alcohol concentration and that the solvation environment of the probe in the micelle is disordered structurally, are discussed in the context of propanol as a mobile phase modifier in micellar chromatography.

1

N. FLUORESCENCE POLARIZATION, MOLECULAR DYNAMICS, AND RELATED PHENOMENA Kawski has discussed s ectroscopic methods for determining the directions of t i e absorption, fluorescence, and hosphorescencetransition momenta in ordered systems (N1). 8zalay has reviewed recent a plications of polarized luminescence in biology and meicine (N2). Brittain has reviewed circularly polarized luminescence (CPL) of chiral lanthanide complexes (N3). This review also includes discussion of instrumentation for ac uisition of CPL. Weaver et al. have correlated %e results obtained with radioimmunoassay, fluorescence polarization immunoassay, and enzyme immunoassay of Cannabis metabolites with results obtained from gas chromatography/mass spectrometry (N4). Van Ginkel et al. have reevaluated the membrane fluidity concept by use of polarized fluorescence spectroscopy on different model membranes containing unsaturated lipids and sterols (N5).

0. CHEMILUMINESCENCE Reviews. Weber has reviewed the use of fluorescence, chemiluminescence,and spectrophotometry in medicine (01). Bioluminescence and its a plications in medicine have been reviewed by Campbell (027.Various chemiluminescence reactions which are useful for measurement in high-performance liquid chromatography have been reviewed ( 0 3 ) . Applications. Morton et al. have examined the spectroscopic properties of firefly luciferin and have discussed the relevance of this reaction in bioluminescence measurements ( 0 4 ) . Segawa et al. have developed a chemiluminescence method for the determination of hydrogen peroxide (05). The method is based on the reaction of hydro en peroxide with fluorescein catalyzed by horseradish peroxi&. Acetaldehyde has been determined by use of a chemiluminescence method (06).This method is based on the luminol-potassium hexacyanoferrate(1II)reaction in the presence of xanthine oxidase. The luminol-peroxide chemiluminescence has been used to develop a highly sensitive, nonselective detector for trace metals (07). The bioluminescenceof 17 nucleotides have been examined by use of the luciferin-luciferase system (08).Kamidate have reported the determination of catecholamines by use of lucigenin chemiluminescence (09). This scheme is proposed for determination of catecholamines in wine by a postcolumn reaction after separation by high-performance liquid chromatography (HPLC). Naderi and Melchior have described a sensitive chemiluminescence assay for measurement of sub-nanomolar concentrations of several biological materials (010). All of the determinations are based on the firefly luciferase reaction. Parameters relevant to the eroxyoxalate chemiluminescence reaction have been stu8ed. For example, the background chemiluminescence from the peroxyoxalate chemiluminescence reaction has been investigated (011).In addition, 348R


the effect of surfactants on the peroxyoxalate chemiluminescence of aromatic hydrocarbons has been studied (012). Yappert and Ingle have described a spectrometer for absorption corrected spectral studies of the lucigenin chemiluminescence reaction (013). The kinetics and mechanism of the chemiluminescence clock reaction, based on the horseradish peroxidase catalysis of luminol oxidation by hydrogen peroxide, has been studied (014). Milofsky and Birks have reported the first photoinitiation of peroxyoxalate chemiluminescence (015).This system was applied to the detection of amino-substituted PAHs in a flow injection system.

P. LUMINESCENCE TECHNIQUES IN BIOLOGICAL AND CLINICAL ANALYSIS Reviews. A number of reviews have appeared in this area, reflecting the continued interest in luminescence techniques for biological study and analysis. Fluorescence spectroscopy of protein structure and dynamics was reviewed by Rigler (PI). Stryer reviewed excited-state processes in proteins and the role of fluorescent probes to study protein polarity, energy transfer, and rotational motion in proteins, and as spectroscopic rulers (P2). Other reviews include recent trends and developments in the ap lication of polarized luminescence in biology and medicine 6 3 , P4), spectrophotofluorometr in the forensic analysis of biological specimens in drug over ose cases (P5),the sensitivity, selectivity, and simplicity of lufluorescence mino enic methods for biological analysis (B), and lfourier-transform IR spectroscopic sensors for bioprocessing (E'),clinical applications of luminescent analyses for and the use of fluorometry enzymes and enz e labels (Pa), in monitoring a n E n t r o 1 of cell cultures (PSI. Time-resolved fluorescence spectroscopy of tumor hotoaensitizingdrugs and skin photosensitizers was reviewex (PIO), and principles of time-resolved fluorometry and applications in viral diagnosis and DNA probe technolo were discussed (PII). Studies of Biological Kructures. Drug binding sites on human serum albumin were studied using 7-(alkylamino)coumarin-6acetic acids having alkylamino groups of various alkyl chain lengths (P12). Macromolecular binding equilibria in the lac repressor system, including protein subunit interactions and protein-operator association, were studied usin high-pressure fluorescence spectroscopy with a long-live! fluorescent probe (P13). Several studies of PAH-DNA adducts were deacribed, inclu their fluorescence spectral and decay characteristics (PI42uorimetric analysis of such adand synchronous fluorescence spectroscopy used duds (P15), with other techniques to resolve discre ancies in previous studies of adducts of human lacental fjNA (P16). Analytical Applications. {our new coumarin derivatives were studied as sensitizers of room-temperature phosphorescence of biacetyl in fats (PI7). An apparatus was described for automatic recording of action spectra, including corrected absorption and fluorescence spectra and first-derivative absorption spectra of photobiological processes (P18); spectra were acquired for photosynthesis in various algae. Fluorescence detection was combined with HPLC for the determination of adenosine nucleosides and nucleotides, for applications in blood and cultured cell analysis, and for enzyme determinations (P19).

B

Q. REAGENTS AND PROBES We have added this new category because of the increasing number of derivatization procedures that are used in fluorescencespectroscopy. In addition, the use of fluorescence probes is an increasinglyimportant application of fluorescence spectroscopy. Reviews. Goto has provided an extensive review (232 references) of fluorescence derivatization procedures for use in liquid chromatography (QI). Koller has reviewed the applications of fluorescent labels of biomolecules in cytology and flow cytometry (82). Patonay and Antoine have reviewed the utility of covalent and noncovalent near-infrared fluorogenic labels with emphasis on labeling biomolecules ( 8 3 ) . Ohkura has reviewed pre- and postcolumn derivatization procedures for use in high-performance liquid chromatogra hy [HPLC] (Q4). Em hasis of this review is on bifunctionJfluorogenic rea ents or use in biological samples. I%oteins/Amino Acids/ Amines. Jefferson et al. have reported the characterization of two new spectroscopic probes

P


for zinc(2+)-protein interactions (Q5). The synthesis and luminescence pro erties of coumarin-6-sulfonyl chloride as a novel label in dorometry and phosphorimetry has been discussed (86,87). This new reagent can be used to label amines, amino acids, and phenols. Nakajima et al. have developed thien lp idines as new fluorescent derivatizing reagenta for d k y k i n e s (Q8).A new fluorescent reagent (3-benzo 1-2-naphthaldehyde)has been developed as a precolumn ierivatization reagent for fluorescence detection of Another reagent (7-methoxycoumarin-3amino acids (89). carbonyl fluoride) has been synthesized and used as a fluorescence re ent for derivatizing primary amines for detection in HPL? (~10). The fluorescent reagent, 4-aminofluorescein, was used to derivatize primary amines through an Edman degradation (811). Grosvenor and Gray have shown that 2,4-dinitrophenylpyridium is a versatile reagent for the detection of amino acids, primary and secondary amines, thiols, thiolactones, and carboxylic acids (Q12). The chemiluminescence detection of amino acids, pe tides, and proteins usin tris(2,2/-bipyridine)ruthenium(fI)has been reported by %e et al. (Q13).Novotny and co-workers have reported the use of 3-(2-furoyl)quinoline-2-carbaldehyde as a fluorogenic reagent for the analysis of primary amines by liquid chromatography

of pyrene at silica interfaces to study the orientation, distribution, and association of sorbed molecules was evaluated and important experimental considerations were discussed (R12). Analytical applications included a discussion of the luminescence determination of phenyl-substituted silanes, including their phosphorescence and fluorescence spectra, phosphorescencelifetimes and limits of detection (R13),and a selective determination for theophylline in the presence of caffeine by Eu(III)-sensitized room-temperatureluminescence (R14).Fluorescence spectroscopy was used to determine viscosity changes in epoxy resins during curing (R15)and to study morphological changes in polyimides during curing (R16). Luminescence was applied to the analysis of complex samcoal-tar pitch fractions ples, including surface waters (R17), (R18), hot rolling emulsions (R19), paper (R20), and hair (R21).

ACKNOWLEDGMENT We gratefully acknowledge the assistance of Lorna Clarke (Secretary to I.M.W.) and Mark Volmer (ChemistryAssistant Librarian of Emory University) during the preparation of this paper.

(Q14).

Carboxylic Acids. Allenmark et al. have reported the use of N-(9-acridinyl)bromoacetamideas a new reagent for the hase-transfer-catalyzed esterification of carboxylic acids Q15). This reaction can be erformed on a microanalytical scale and ‘elds esters of hi fluorescence intensity in acid solution. &her re ents for ierivatization for carboxylic acids Yamaguchi et al. (Q16),Lee et al. (Q17), have been re rtec!!y Narita and !&.agewa (8181, Lee et al. (Q19),and JunkerBuchheit and Jork (Q20). Miscellaneous. A new reagent 1,2-bis(4-methoxypheny1)ethylenediaminel for reducing car h d r a w has been re orted (Q21). Three new reagents for drerivatization of aliehydes and ketones have been reported (Q22). The roducta of these reagents with aldehydes and ketones are horescent although the reagenta themselves are not fluorescent. Derivatization of thio-containing anal@s have been derivatized by use of 4-maleimidylsalicylicacid as a fluorescence labeling re ent (Q23). The derivatives are then used as sensitizers to Tb(I1I) luminescence in combination with time-resolved luminescence detection to im rove selectivity. A derivatizing reagent [2-(5-chlorocarbony~2-oxazol 1)-5,6meth lenedioxybenzofuran] has been reported for dcohols in d P L C (Q24). A new reagent (1,2-diamino-4,5methylenedioxybenzene) has been reported for derivatization of a-dicarbonyl compounds (Q25). A method has been developed for the spectrofluorometricdetermination of gallium (826). This analysis uses 1,5-bis(2,3-dihydroxyphenylmethy1ene)thiocarbohydrazone as a fluorogenic reagent.

P

!

6,

R. OTHER TECHNIQUES AND APPLICATIONS Miscellaneousreviews included analysis of PAHs in envilaser-excited fluorescence in crimironmental samples (RI), nalistics (R2),analytical a plications of 1,lO-anthraquinones (R3),luminescent expanzd clays as chemical sensors (R4), optical spectroscopy and mobility of adsorbed molecules (R5), and multimicrospot, multianalyte immunoassay using fluorescence measurementa for high sensitivity (R6). In the area of recent techniques, new developments in sin le-molecule fluorescence detection were described, incluiing theory and application to experimental data from a single-moleculecounter that was shown to be 3 times more sensitive than conventional fluorescence detection systems (R7,R8). Laser photolytic fragmentation-fluorescencespectrometry was applied to the determination of ammonia and ali hatic amines in the 10-50-pmol regime (R9). leveral articles described fundamental aspects and applications of luminescence. An expression for the intensity of light from a luminescent powder s a m le was derived from theory and used as the basis for a metiod to determine the true luminescence spectra and quantum yields of molecules adsorbed on light-scattering media (R10). Fine-structure fluorescence s ectra of organic adsorbates on silica were studied, and pgotoinduced transformation of some samples was observed (R11).The use of the photophysical behavior

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(Al) McGown,

L. 6.; Warner, I. M. Anal. Chem. 1990, 62, 255R-267R.

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(Dl) Jankowlak. R.; Small, G. J. A M I . Chem. 1888, 67, 1023A-1024A. 1026A, 1028A- 1029A, 1031A- 1032A. (D2) Demtroeder, W. Fresenius’ J . Anal. Chem. 1980, 337. 830-834. (D3) Demtroeder, W. NATOASI Ser., Ser. 8 1980, 247, 1-12. (04) Dovichl, N. J. Rev. Sci. Instrum. 1880, 67, 3653-3657. (D5) Vo Dlnh, T. Quim. Anal. (8arcebna) 1969, 8 , 349-363. (D6) Imasaka, T.; Ishlbashl, N. Anal. Chem. 1990, 62, 363A-364A, 367A, 369A-371A. (D7) Kohse-Hwlnghaus, K. Appl. Fhys. 8 1890, 850, 455-461. (D8) Nemkovich, N. A.; Rublnov, A. N.; Tomin, V. 1. phys.-Chem. TrennMessmethoden 1890, 22, 31-53.


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MOLECULAR FLUORESCENCE (09) Niessner, R.; Krupp, A. Part. Part. Syst. Charact. 1981, 8 , 23-28. (D10) Meilone, A.; Smlth, B. W.; Winefordner, J. D. Talanta 1890, 3 7 , 111-118. (D11) Donard, 0 . F. X.; Lamotte, M.; Beiin. C.; Ewald, M. Mar. Chem. 1889, 27, 117-136. (D12) Imasaka, T.; Tsukamoto, A.; Ishibashi, N. Anal. Chem. 1889, 67, 2285-2288. (D13) Weeks, S.; Gliies, S.; Dobson, R.; Senne, S.; D’Siiva, A. P. Anal. Chem. 1890,6 2 , 1472-1477. (D14) Jinkins, J. G.; Schendel, J.; Wehry, E. L. ASTM Spec. Tech. Publ. 1890, 7086, 123-132. (D15) Lee, S. C.; Stanton. B. J.; Wehry, E. L. Anal. Chem. 1991, 63, 744-746. (Dl6) Strlngat, R.; Fabre, G.; Clrio, L.; Ross, A. Opt. Commun. 1891,87, 179- 185. (D17) Qian, H. Biophys. Chem. 1890. 38, 49-57. (Dl8) VO Dinh, T.; Miller, G. H.; Bello, J.; Johnson, R.; Moody, R. L.; Aiak, A. ralenta 1989,36, 227-234. (D19) Pavlopouios, T. G.; Boyer, J. H. Roc. SPIE-Int. Soc. Opt. Eng. 1889, 7054,217-223. (D20) Furumoto, H. W.; Ceccon, H. Appl. fhys. Len. 1988, 73,335-337. (D21) Schmidt, J.; Penzkofer, A. Chem. fhys. 1989, 733,297-301. (D22) Scherer, N. F.; Carlson, R. J.; Matro. A.; Du, M.; Ruggiero, A. J.; Romero-Rochin, V.; Cina, J. A.; Fleming, 0. R.; Rice, S. A. J. Chem. fhyS. 1991,9 5 , 1487-1511. (D23) Shera, E. B.; Seitzinger, N. K.; Davls, L. M.; Keiier, R. A.; Soper, S. A. Chem. fhys. Len. 1990, 174, 553-557. (D24) WhHten, W. B.; Ramsey, J. M.; Arnold, S.; Bronk. B. V. Anal. Chem. 1991,63,1027-1031. (D25) Cremer, C.; Doelie, J.; Hausmann, M.; Bier, F. F.; Rohwer, P. Ber. Bunsen-Ges. fhys. Chem. 1889,9 3 , 327-335. (D26) Hub, C. W.; Wllllams, W. R. Anal. Chem. 1989. 67, 2288-2292. (D27) Roach, M. C.; Harmony, M. D. J. Chromatogr. 1988,455, 332-335. 0 2 8 ) Van de Nesse, R. J.; Hoomweg, G. P.; Gooiler, C.; Brinkman, U. A. T.; Velthorst, N. H. Anal. Chlm. Acta 1889,227, 173-179. (D29) Yeung. E.; Kuhr, W. G. U.S. Petent Application 89-306071, 1989. (D30) Cheng, Y. F.; Dovichi, N. J. ASTM Spec. Tech. fubl. 1990, 7066, 151-159. (D31) Lehotay, S.J.; Johnson, P. A.; Barber, T. E.; Wlnefordner, J. D. Appl. SpeChOSC. 1990. 44, 1577-1579. (032) Jankowlak, R.; Small, 0. J.; Nishimoto, M.; Varanasi, U.; Kim, S. K.; Geaclntov, N. E. J. fharm. Biomed. Anal. 1890,8 , 113-121. (D33) Jankowlak, R.; Small, G. J. Chem. Res. Toxlcol. 1991,4 , 256-269. (D34) Hurst, G. B.; Wright, J. C. J. Chem. fhys. 1991, 9 5 , 1479-1488. (D35) Price, B. B.; Wright, J. C. A M I . Chem. 1990. 6 2 , 1989-1994. (D36) Bich, V. T.; Binl, R.; Salvi, P. R.; Marconi, G. Chem. fhys. Len. 1990, 775, 413-418. (037) Wlrth, M. J.; Fatunmbi, H. 0. Anal. Chem. 1990,62, 973-978. (D38) Freeman, R. G.; Gililland, D. L.; Lytle, F. E. Anal. Chem. 1890, 6 2 , 2216-22 19. E. FIBERQPTICBASED TECHNIQUES

(El) Heiman, D.; Zheng, X. L.; Sprunt, S.; Goldberg, B. B.; Isaacs, E. D. Roc. SPIE-Inf. Soc.Opt. Eng. 1989, 7055, 96-104. (E2) Wolfbeis, 0. S. Appl. Fluaresc. Technol. 1889, 7 . 1-6. (E3) Srlvastava, A. K.; Bandyopadhyay, A. Rev. Scl. Insfrum. 1990, 67, 756-759. (E4) Zung, J. B.; Fuh, M. R. S.; Warner, I.M. Anal. Chim. Acto 1989,224, 235-242. (E5) Zung, J. B.; Woodlee, R. L.; Fuh, M. R. S.; Warner, I . M. R o c . SPIEInt. SOC. Opt. Eng. 1989, 7054, 69-76. (E8) Lltwiler, K. S.; Bright, F. V. ACS Symp. Ser. 1989, 403, 380-395. (E7) Bright, F. V.; Lltwiier, K. S. Anal. 0”.1988,67,1510-1513. (E81 Betts, T. A.; Bright, F. V.; Catena, G. C.; Huang. J.; Lltwiier, K. S.; Paterniti, D. P. ASTM Spec. Tech. Publ. 1990, 7066, 88-95. (E9) Lttwiler, K. S.; Catena, G. C.; Bright, F. V. Anal. Chlm. Acta 1990,237, 485-490. (E10) Schaffar, 8. B. P.; Wolfbeis, 0. S. R o c . SPIE-Int. Soc. Opt. Eng. 1989,990, 122-129. ( E l l ) Lieberman. S. H.; Inman, S.M.; Theriault, G. A. R o c . SHE-rnt. Soc. Opt. Eng. 1990, 7772, 94-98. (E121 Lieberman, S. H.; Inman, S. M.; TheriauR, G. A,; Cooper, S. S.; Maione, P. G.; Shimlzu, Y.; Lurk, P. W. Roc. SPIE-Int. SOC. Opt. Eng. 1990, 7269, 175-184. (E13) Niessner, R.; Robers, W.; Krupp, A. R o c . SPIE-Int. SOC.Opt. Eng. 1990, 7772, 145-156. (E14) Madison, R. T.; Carroll, M. K.; Hieftje. 0. M. Appl. Specfrosc. 1989, 43,422-425. (E19 Barnard. S. M.: Walt. D. R . Environ. Sci. Technol. 1991. 2 5 . 1301- 1304. (El@ Thompson, R. B.; Levine, M.; Kondracki. L. Appl. Spectrosc. 1990, 44 117-122 (E17) ’ He, H,-Uray, G.; Wolfbeis, 0. S. Anal. Chim. Acta 1991, 246, 251-257. (EM) Turley, W. D.; Iverson, C. E.; Lutz, S. S.; Fiurer, R. L.; Schaub, J. R.; Allison, S. W.; Ladlsh, J. S.;Caldweii, S. E. froc. SPIE-rnt. SOC. Opt. Eng. 1890,7772, 27-37. (E19) Synovec, R. E.; Renn, C. N.; Moore, L. K. R o c . SPIE-Int. SOC.Opt. Eng. 1990, 7772, 49-59. F. SAMPLE PREPARATION, QUENCHINQ, AND RELATED PHENOMENA

(Fl) Testa, A. C. Fluorescence News 1989,4 , 1-3. (F2) Barboy, N.; Feltelson, J. Anal. Biochem. 1888, 780, 384-386. (F3) Brennecke. J. F.; Tomasko, D. L.; Peshkin. J.; Eckert, C. A. Ind. Eng. Chem. Res. 1980,29, 1682-1890.

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(F4) Brennecke. J. F.; Eckert, C. A. ACS Symp. Sw. 1888, 406, 14-26. (F5) Betts, T. A.; Bright, F. V. Appl. Specbosc. 1980, 4 4 , 1196-1202. (F6) Brennecke, J. F.; Tomasko, D. L.; Eckert, C. A. J . fhys. Chem. 1990, 9 4 , 7692-7700. (F7) Bortolus, P.; Gaiiazzo, G.; Gennari, G. Anal. Chlm. Acta 1890,234, 353-358. (F8) Tine, A.; Aaron, J. J. Anal. Chlm. Acta 1989,227, 181-188. (F9) Datta, P. K.; b r a , S . C. Anal. Chlm. Acta 1989,220, 225-233. (F10) Matsuzawa, S.; Wakisaka, A.; Tamura, M. Anal. Chem. 1880, 62, 2654-2656. 0. DATA REDUCTION

(GI) Costa, L.; (;rum, F.; Paine, D. J. Appl. Opt. 1889, 8 , 1149-1155. (G2) Cecil. T. L.; Rutan, S. C. Anal. Chem. 1990,62, 1998-2004. (03) Matsui, T.; Suzuki, K.; Sakagami, M.; Kitamori, T. Appl. Spscbosc. 1991,45,32-35. (‘34) Gade, R.; Kaden, U.; Fassier, D. fhys.-Chem. Trenn-Messmethoden 1990,2 2 , 55-60. (G5) Thompson, A.; Eckerie, K. L. Roc. SPIE-Int. Soc. Opt. Eng. 1989, 7054., 20-25. -. (G6) Chattier, A.; Georges, J.; Mermet, J. M. Chem. fhys. Len. 1880, 771, 347-352. (G7) Lavine, B. K.; Patel, R.; Faruque, A.; Nedeijkovic, J. M.; Mohan, S. Anal. Chem. 1991,63, 708-712. (G8) Micheisen, J. K.; Khorasani, G. K. Org. oeochem. 1890, 75, 179-192. (G9) Liang, Y.; Xie, Y.; Yu, R. Chin. Scl. Bull. 1888,34. 1533-1538. (G10) Kubista, M. Chemom. Intell. Lab. Syst. 1990, 7 , 273-279. (G11) Brissette, P.; Bailou. D. P.; Massey, V. Anal. Biochem. 1889, 167, 234-238. (G12) Torres, A.; Gutierrez, M. C.; Rubio. S.; Gomez-Hens, A.; Perez-EendC to, D. Analyst (London) 1990, 775, 1377-1381. (G13) Khochbln, S.; Chabanas, A.; Albert, P.; Lawrence, J. J. Cytometry 1989, 10,484-489. (014) Mathles, R. A.; Peck, K.; Stryer, L. Anal. Chem. 1990, 6 2 , 1786-1791. ~

H. LUMINESCENCE I N ORGANIZED MEDIA

(Hl) Georges, J. Spechochlm. Acta Rev. 1980, 73,27-45. (H2) Marquez, J. C.; Hernandez, M.; Sanchez, F. G. Analyst (London) 1880, 175. 1003-1005. ..- ... (H3) Lopez Lopez, D.; Rubio Barroso, S.; Polo Diez, L. M. Fresenlus’ J. Anal. Chem. 1890. 337. 366-368. (H4) Nelson, G.; Neal; S. L:; Warner, I. M. Spectroscopy 1888,3 , 24-28. (H5) Warner, I.M.; Nelson, G. I n R o c . Int. Symp. CyclodexMns, 4th; Huber, O., Szejtii. J., Eds.; Kiuwer: Dordrecht, Netherlands, 1988; pp 485-49 1. (H6) Minato, S.; Osa.T.; Ueno, A. J. Chem. Soc., Chem. Commun. 1891, 2 , 107-108. (H7) Ueno, A.; Minato, S.; Suzuki, I.; Fukushima, M.; Ohkubo, M.; Osa,T.; Hamada, F.; Murai, K. Chem. Len. 1990,4 , 605-808. (HE) Ueno, A.; Suzuki, I.; Osa, T. Anal. Chem. 1990, 6 2 , 2461-2466. (H9) Ueno, A.; Suzuki, I.; Osa. T. Chem. Left. 1989,6 , 1059-1062. (H10) Baeyens, W.; Lin, 8.; Corbisier, V. Analyst (London) 1890, 775, 359-363. (H11) Alak, A. M.; Contolini, N., Vo Dinh, T. Anal. Chlm. Acta 1989. 217, 17 1-1 76. (H12) Shimada, K.; Komine, Y.; Oe, T. J. Liq. Chromatogr. 1889, 12, 49 1-500. (H13) Berthod, A.; Asensio, J. M.; Laserna, J. J. J. Llq. Chromatogr. 1989, 72, 2621-2634. (H14) Tran. C. D. ASTM Spec. Tech. fubl. 1880, 7066, 108-122. (H15) Mwaiupindi, A. G.; Blyshak, L. A.; Ndou, T. T.; Warner, I.M. A M I . Chem. 1991,63. 1328-1332. (H16) Blyshak, L. A.; RoiiiaTaylor. M.; Sylvester, D. W.; Underwood, A. L.; Patonay, G.; Warner, I.M. J. COWInrmface S d . 1990, 736,509-518. (H17) Gonzalez Alvarez, M. J.; Diaz Garcia, M. E.: Sanz-Medei, A. Anal. Chim. Acta 1990. 234. 181-186. (H18) Aiken, J. H.; Huie, C. W. Anal. Left. 1891,2 4 , 187-180. (H19) Yoon, M.; Chang, J. R.; Kim, D.; Kuriyama, Y.; Tokumaru, K. photochem. fhotobiol. 1881,5 4 , 75-82. (H20) De la Guardia, M.; Hernandez, M. L.; Sancenon, S.; Carrion. J. L. Coliohls Surf. 1990,48, 57-64. (H21) Jiang, Y.; Xu, J.; Chen. G. Chin. Sci. Bull. 1981. 36, 474-477. (H22) Kang, S. C.; Lee, B. G.; Kim, K. J. Bull. Kcman Chem. Soc.1991, 72, 111-113. (H23) Soutar, I.; Swanson, L. Analyst (London) 1891, 776, 671-873. (H24) Eaton, D. F.; Caspar, J. V.: Tam, W. I n fhotochem. Energy Convm., Proc Int . Conf . fhotochem . Convers Storage Solar Energy, 7th, Meting Data 1988; James, R., Jr., Meisei, D., Eds.; Elsevier: New York, 1989, pp 122-134.

.

.

I . LOW-TEMPERATURE LUMINESCENCE

(11) Rima, J.; Rizk, T. J.; Garrigues, P.; Lamotte, M. Polycycl. Aromat. Compd. 1980, 7 , 161-169. (12) Fachlnger, C.; Jarosz, J.; Martin-Bouyer, M.; Paturei, L.; Saber, A.; Vial, M. Anal. Chlm. Acta 1990,233, 207-211. (13) Madison, R. T.; Canoil, M. K.; HieftJe,G. M. Appl. Spechosc. 1988,43, 422-425. (14) Palewska, K.; Meister, E. C.; Wild, U. P. J. Lumln. 1991,50. 47-54. (15) Jones, B. T.; Giick, M. R.; Smith. B. W.; Wlnefordner. J. D. Spechochlm. Acta, Part A 1989,45A, 403-407. (16) Weeks, S.; Gilles, S.;Dobson, R.; Senne, S.; D’Silva, A. P. Anel. Chem. 1990,6 2 , 1472-1477. (17) Ariese, F.; Gooiler, C.; Velthorst, N. H.; Hofstraat, J. W. Anal. Chim. Acta 1990,232, 245-251.

MOLECULAR FLUORESCENCE (18) Hofstraat, J. W.; Van Zeijl, W. J. M.; Ariese, F.; Mastenbroek, J. W. G.; Gooijer, C.; Velthorst, N. H. Mar. Chem. 1881, 33, 301-320. (19) Bark, K. M.; Force, R. K. Appl. Spectrosc. 1880, 44, 1373-1378. (110) Arlese, F.; Gooijer, C.; Velthorst, N. H.; Hofstraat, J. W. Fresenlus' J. Anal. Chem. 1881, 339, 722-724. (111) Hofstraat, J. W.; Van Zeiji, W. J. M.; Smedes, F.; Arlese, F.; Gooijer, C.; Velthorst, N. H.; Locher. R.; Renn. A.; Wild, U. P. Roc. SPIE-Inf. Soc. Opt. Eng. 1888, 7054, 138-151. (112) Saber, A.; Morel, 0.;Paturei. L.; Jarosz, J.; Martin-Bouyer, M.; Vial, M. Fresenlus' J . Anal. Chem. 1881. 339, 716-721. (113) Marcus, R. A. J. Phys. Chem. 1880, 94, 4963-4966. (114) Fetzer, J. C.; Zander, M. 2.Naturforsch., A : Phys. Sci. 1880, 45, 8 14-8 16. J. TOTALLUMINESCENCE AND SYNCHRONOUS EXCITATION

SPECTROSCOPIES AND RELATED TECHNIQUES

(Jl) Ndou, T. T.; Warner, 1. M. Chem. Rev. 1801, 9 7 , 493-507. (J2) Dudei'zak, A. E.; Bablchenko, S. M.; Poryvkina, L. V.; Saar, K. Appl. .. Opt. 1981, 30, 453-458. (J3) Coble, P. 0.;Green, S. A.; Blough, N. V.; Gagosian, R. B. Nature (London) 1800.348.432-435, . ._.. (J4)-Shanahan, G. J.; Boley, N. P.; Traynor, A. D. Anal. R o c . (London) 1881. 28. 210-213. (J5) Hofstraat, J. W.; Locher, R.; Wild, U. P. Appl. Specwosc. 1880, 4 4 , 1317-1325. (J6) Burdick, D. S.; Tu, X. M.; McGown, L. 6.; Miillcan, D. W. J. Chemom. 1880, 4, 15-28. (J7) Stalnken, D. M.; Frank, W. ASTM Spec. Tech. Publ. 1880, 7062, 381-400. (J8) Dujmov. J.; Sucevlc, P. Chem. Ecol. 1880, 4 , 189-195. (J9) Shotyk, W.; Sposlto, G. Sol/ Scl. SOC.Am. J. 1880, 54, 1305-1310. (J10) Reo, C. M. Blochem. Biophys. Res. Commun. 1881, 776, 1351-1357. (J11) Zhao, 2.; Quan, W. J. Envlron. Scl. (Chlna) 1888, 7. 109-115. (J12) Baudot, P.; Vlriot, M. L.; Andre, J. C.; Jezequei, J. Y.; Lafontaine, M. Analusis 1881, 79, 85-97. (J13) Manchester, D. K.; Wllson, V. L.; Hsu, I . C.; Choi, J. S.; Parker, N. 6.; Mann, D. L.; Weston, A.; Harris, C. C. Carclnogenesls (London)1080, 7 7 , 553-559. (J14) Vahakangas, K.; Yrjanhelkki, E. IARC Sci. Publ. 1880, 704, 199-204. (J15) Lin, C. H.; Fukil, H.; Imasaka, T.; Ishibashl, N. Anal. Chem. 1881, 63, 1433- 1440. (J16) Garcia Sanchez, F.; Ramos Rublo, A. L.; Cruces Blanco, C.; Suau Suarez, R. Taienta 1880, 3 7 , 579-584. (J17) Salinas, F.; Munoz de la Pena, A.; Duran-Meras, 1.; Soledad Dwan, M. Analyst (London) 1880, 775, 1007-1011. (Jl8) Konstantlanos. D. G.; Ioannou, P. C.; Efstathou, C. E. Ana/yst (London) 1881, 776, 373-378. (J19) Du, Y.; Yu. L.; LI, J.; Suzuki, S. Kankyo Kagaku Kenkyu Hokoku (Chlba Dalgeku) Vol. Data 7988 1888, 14, 45-50. (J20) Oms, M. T.; Forteza, R.; Cerda, V.; Garcia, F.; Ramos, A. L. Int. J. Envkon. Anal. Chem. 1880, 42, 1-14. (J21) Garcla Sanchez, F.; Ramos Rubio, A. L.; Cerda, V.; Oms, M. T. Anal. Chim. Acta 1880. 228, 293-299. (J22) Oms,M. T.; Forteza, R.; Cerda, V.; Maspoch, S.; Coeilo, 9.; Blanco, M. Anal. Chlm. Acta 1880, 233, 159-163.

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K. SOLIPSURFACE LUMINESCENCE

(K1) Hurtubise, R. J.; Ramasamy, S. M.; Bello, J. M.; Burrell, G. J.; Citta, L. A. ACS Symp. Ser. 1888, 383, 155-166. (K2) Vo Dlnh, T. ASTM Spec. Tech. Publ. 1880, 7066, 133-143. (K3) Camplglla, A. D.; Perry, L. M.; Winefordner, J. D. Appl. Spectrosc. 1880, 43, 1341-1343. (K4) Camplglla, A. D.; Perry, L. M.; Winefordner, J. D. Appl. Spectrosc. 1080, 44, 729-732. (K5) Camplglla, A. D.; Berthod, A.; Winefordner, J. D. Anal. Chim. Acre 1880, 237, 289-293. (K6) Purdy, B. B.; Hurtubise, R. J. Microchem. J. 1888, 3 9 , 330-335. (K7) Haustein, C.; Savage, W. D.; Ishak, C. F.; Pflaum. R. T. Taienfa 1889, 36. 1065-1068. (K8) Haustein, C. H.; Garrels, R. L. Analyst (London) 1890, 775, 155-158. (K9) P e w , L. M.; CamDigila. A. D.; Winefordner, J. D. Anal. Chem. 1888, . 6 7 , 2328-2330. (K10) Aaron, J. J.; Camplglla, A. D.; Wlnefordner, J. D. Anal. Chlm. Acta 1880, 236,257-265. (K11) Alak. A. M.; Contolini, N.; Vo Dlnh, T. Anal. Chim. Acta 1888, 277, 17 1-1 76. (K12) Richmond, M. D.; Hurtubise, R. J. Appl. Spectrosc. 1888, 43, 810-81 2. (K13) Richmond. M. D.; Hurtubise, R. J. Anal. Chem. 1888, 87, 2643-2647. L. LUMINESCENCE I N CHROMATOGRAPHY AND FLOW SYSTEMS

( L l ) Baeyens, W. R. 0.; Ling, B. L.; Brinkman, U. A. T.; Schulman, S. G. J. Biolumln. Chemllumln. 1888, 4 , 484-499. (L2) Van den Beld, C. M. 6.; Lingeman, H.; Tjaden, U. R.; Van der Greef, J. Chlm. Oggi1888, 7 7 , 33-34, 37. (L3) Lingeman, H.; Van de Nesse, R. J.; Brinkman, U. A. T.; Gooijer, C.; Vekhorst, N. H. Mehodol. Surv. Blochem. Anal. 1880, 2 0 , 355-363. (L4) Van den Beld, C. M. 8.; Lingernan, H. Ract. Specwosc. 1881, 72, 237-3 16. (L5) Gluckman, J. C.; Novotny, M. V. Chromafogr. Scl. 1888, 45, 145-173. (L6) Iml, K.; Nlshkani, A.; Akitomo, H.; Tsukamoto, Y. J. Biolumin. Chemilumln. 1888, 4 , 500-504. (L7) Ohkura, Y. Anal. Sci. 1888, 5 , 371-388.

(LE) Van de Nesse, R. J.; Gooibr, C.; Hoornweg, G. P.; Brlnkrnan, U. A. T.; Velthorst, N. H.; Van der Bent, S. J. Anal. Lett. 1880, 2 3 , 1235-1244. (L9) Jalkan, R. D.; Denton, M. B. Roc. SPIE-Int. Soc. Opt. Eng. 1888, 7054, 91-102. (L10) Low, G. K. C.; Batley, G. E.;Moore, B. S. Anal. Instrum. 1888, 77, 339-350. (L11) Camplglla, A. D.; Berthod, A.; Winefordner, J. D. J. Chrometo@. 1880, 508. 37-49. (L12) Mastenbroek, J. W. G.; Arlese, F.; Gwijer, C.; Vekhorst, H. H.; Hofstraat, J. W.; Van Zeijl, W. J. M. Chemosphere 1880, 2 7 , 377-386. (L13) Cobb, W. T.; McGown, L. B. Appl. Spectrosc. 1988, 43, 1363-1367. (L14) Schreurs, M.; Gooijer, C.; Vekhorst, N. H. Anal. Chem. 1880, 6 2 , 205 1-2053. (L15) Wlse, S . A.; Hilpert, L. R.; Byrd, G. D.; May, W. E. Po/ycyci. Aromat. Compd. 1880, 7 , 81-98. (L16) Nunez, M. D.; Centrich, F. Anal. Chlm. Act8 1880, 234, 269-273. (L17) Hlrauchi. K.; Sakano, T.; Notsumoto, S.; Nagaoka, T.; Morimoto, A.; Fujlmoto, K.; Masuda, S.; Suzuki, Y. J. Chromafogr. 1089, 497, 131-137. (L18) Shlmada, K.; Komine, Y.; Oe, T. J. L i 9 . Chromatogr. 1888, 72, 491-500. (L19) Van der Hoorn, F. A. J.; Boomsma, F.; Man in 't Veld, A. J.; SchaieKamp, M. A. D. H. J. Chromatogr. 1881, 563, 348-355. (L20) Sonoki, S.; Tanaka, Y.; Hisamatsu, S.; Kobayashl, T. J. Chromatogr. 1888, 475, 311-319. (L21) Langguth, P.; Spahn, H.; Merkle, H. P. J. Chromafogr. 1880, 528, 55-64. (L22) Yoo, 0.S.; Chol, K.; Stewart, J. T. Anal. Left. 1880, 2 3 , 1245-1263. (L23) Narka, S.; Kkagawa, T. Anal. Sci. 1888, 5 , 31-34. (L24) Toyooka, T.; Ishibashi, M.; Takeda, Y.; Imai, K. Analyst (London) 1881, 776, 609-613. (L25) Lee, Y. M.; Nakamura, H.; Nakajima, T. Anal. Scl. 1888, 5 , 681-685. (L26) Rastegar, A.; Pelletler, A.; Duportail, G.; Freysz, L.; Leray, C. J. Chromafogr. 1880, 578, 157-185. (L27) Jork, H. Quent. Pap. Thin-Layer Chromafogr., Symp.; Shellard, E. J., Ed.; Academic Press: London, England, 1968; pp 79-89. (L28) Zuercher, H.; Pataki, G.; Borko, J.; Frei, R. W. J. Chromafogr. 1888, 43, 457-462. (L29) Poole, S. K.; Ahmed, H. D.; Belay, M. T.; Fernando, W. P. N.; Poole, C. F. J. Planar Chromatogr.-MW. TLC 1880, 3 , 133-140. (L30) Belchamber, R. M.; Brinkworth, S. J.; Read, H.; Roberts, J. D. M. ReCent A&. Thin-Layer Chromatogr., Meeting Date 7987; Dallas, F. A. A,, Ed.; Plenum: New York, 1988; pp 37-43. (L31) Pataki, 0.Chromafographie 1988, 7 7 - 72, 492-503. (L32) Huettenhaln, S. H.; Baker, W. Fresenius' 2.Anal. Chem. 1888, 334, 31-33. (L33) Fowler, S. D. Chem. Anal. 1880, 708, 7-14. (L34) Coiarow. L. J. Plenar Chr0mafogr.-Mod. TLC 1888. 2 , 19-23. (L35) Huie, C. W.; Williams, W. R. Anal. Chem. 1888, 67, 2288-2292. (L36) Cheng, Y. F.; Plccard, R. D.; Vo Dinh, T. Appl. Spectrosc. 1890, 4 4 , 755-765. (L37) Swalle, D. F.; Sepaniak, M. J. J. Microcolumn Sep. 1888, 7 , 155- 158. (L38) Swaile, D. F.; Sepaniak, M. J. J. Liq. Chromarogr. 1881, 74, 869-893. (L39) Liu, J.; Shlrota, 0.; Novotny, M. Anal. Chem. 1881, 63, 413-417. (L40) Liu, J.; Shirota, 0.; Wiesler, D.; Novotny, M. Proc. Natl. Aced. Scl. U . S . A . 1881, 8 8 , 2302-2306. (L41) Liu, J.; Hsleh, Y. 2.; Wiesier, D.; Novotny, M. Anal. Chem. 1881, 63, 408-412. (L42) Waldron, K. C.; Wu, S.; Earle, C. W.; Harke, H. R.; Dovichl, N. J. Electrophoresis (Weinhelm, Fed. Repub. Ger.) 1880, 7 7 , 777-780. (L43) Wright, B. W.; Ross, G. A.; Smith, R. D. J. Microcdumn Sep. 1888, 7 , 85-89. (L44) Garner, T. W.; Yeung, E. S. Anal. Chem. 1880, 6 2 , 2193-2198. (L45) Garner, T. W.; Yeung. E. S. J. Chromatogr. 1880, 575, 839-644. (L46) Hogan, B. L.; Yeung, E. S. J. Chromafogr. Sci. 1880, 2 8 , 15-18. (L47) Cheng, Y. F.; Vo Dinh, T. Anal. Left. 1880, 2 3 , 941-995. (L48) Cheng, Y. F.; Vo Dinh, T. Anal. Chim. Acfa 1880, 229, 295-297. (L49) Berthod, A.; Asensio, J. M.; Laserna, J. J. J. Li9. Chromafogr. 1988, 12. 2621-2634. .- , - - . - - - .. (L50) Synovec, R. E.; Renn, C. N.; Moore, L. K. Proc. SPIE-Inf. Soc. Opt. €no. 1880. 7772. 49-59. (L51)"Baghek H.; Creaser, C. S. Anal. Chim. Acta 1800, 233, 303-306. (L52) Chung, H. K.; Ingle, J. D., Jr. Anal. Chem. 1890, 6 2 , 2541-2547. (L53) Martinez Caiatayud, J.; Sanchez Sampedro, A,; Vlilar Clvera, P.; Gomer Benlto, C. Anal. Lett. 1890, 2 3 , 2315-2325. (L54) Martinez Caktayud, J.; Sanchez Sampedro, A,; Vlllar Clvera, P.; Gomez Benlto, C. Pharmazie 1888, 44, 795-796. M. DYNAMIC MEASUREMENTS OF LUMINESCENCE

(Ml) Bright, F. V.; Betts, T. A.; Ltwiler, K. S. Crif. Rev. Anal. Chem. 1880, 2 7 , 389-405. (M2) McGown. L. B.; Nithipatikom. K. Chem. Anal. 1880, 707, 201-218. (M3) Hurskalnen. P.: Dahien.. P.:. Siitari.. H.:. Lovaren. - . T. A&. Em. Med. Blol. ' 1888, 263, 123-130. (M4) Anderson, S. R. J. Biol. Chem. 1881, 266, 11405-11408. (M5) Rudolph, W.; Wllhelmi, B. Phys .-Chem. Trenn-Messmethoden 1890, 2 2 . 11-29. (M6) Wong, A. L.; Harris, J. M. Anal. Chem. 1888, 67, 2310-2315. (M7) Miillcan, D. W.; McGown, L. B. Anal. Chem. 1980, 62, 2242-2247. (ME) Lin, S. H.; Fain, B.; Yeh, C. Y. Phys. Rev. A 1880, 4 7 , 2718-2729. (M9) Laermer, F.; Israel, W.; Elsaesser, T. J. Opt. SOC. Am. 8 : Opt. PhyS. 1890, 7 , 1604-1609. (M10) Blok, P. M. L.; Schakel, P.; Dekkers, H. P. J. M. Meas. Scl. Techno/. 1880, 7 , 126-130. ANALYTICAL CHEMISTRY, VOL. 64, NO. 12, JUNE 15, 1992

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MOLECULAR FLUORESCENCE (M11) Litwiler, K. S.; Bright, F. V. ACS Symp. Ser.1989, 403, 360-395. (M12) Lltwiler, K. S.; Kluczynskl, P. M.; Bright, F. V. Anal. Chem. 1991, 63, 797-602. Bark. K. M.; Force, R. K. Talenta 1991, 38. 161-166. (M14) C " a n l . P.; Colombo, A.; Koechler, C.; Ommetto, N.; Qi, p.; ~ o s s l , G. Appl. apt. 1991, 30. 26-35. (MIS) (kuias, Y.; Moya, I.; Schmuck, G. Photosynth. Res. 19S0, 25, 299-307. -. . . ..

(M16) Wirth, M. J.; Chou, S. H.; Piaseckl, D. A. Anal. Chem. 1991, 63, 146-151. N. FLUORESCENCE POLARIZATION, MOLECULAR DYNAMICS, AND RELATED PHENOMENA

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(01) Webec, K. Am. Hlg. Rada Tokskol1988, 19, 135-141. (02) Campbell, A. K. Essays Biochem. 1989. 24, 41-61. (03) Imi,K.; Nlshkani, A,; Akitomo, H.; Tsukamoto, Y. J . Biolumin. Chemi/um/n. 1988,4,500-504. (04) Morton, R. A.; Hopkins, T. A.; Seilger, H. H. Biochemistry 1989, 8 , 1596-1607. (05) Segawa, T.; Kamldate, T.; Watanabe, H. Anal. Sci. 1990, 6 , 763-764. (06) %to, K.; Tanaka, S. Anal. Chim. Acta 1990, 236, 459-482. (07) Jones, P.; Williams, T.; EWon. L. Anal. Chim. Acta 1990, 237. 291-298. (08) Kiessling, M.; Winsel. K.; Freytag, B. Isotopenpraxis 1990, 2 6 , 330-331. (09) Kamidete, T.; Yoshlda, K.; Segawa, T.; Watanabe, H. Anal. Sci. 1989. 5, 359-360. (010) Naderi, S.; Melchlor, D. L. Anal. Biochem. 1090, 790, 304-306. (011) Mann, 8.; Grayeskl, M. L. Anal. Chem. 1990, 62, 1532-1536. Kim, K. J. Bull. Korean Chem. SOC. 1991, (012) Kang, S. C.; Lee, B. 0.; 72, 111-113. (013) Yappert, M. C.; Ingle, J. D., Jr. Appl. Spectrosc. 1989, 43, 767-771. (014) Candy, T. E. G.; Hodgson, M.; Jones, P. J . Chem. Soc., Perkin Trans. leeo, 2 , 1385-1388. (015) Milofsky, R. E.; Birks, J. W. Anal. Chem. 1990, 6 2 , 105o-io55. P. LUMINESCENCE TECHNIOUES I N BIOLOGICAL AND CLINICAL ANALYSIS

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