Unprecedented Solvent-Dependent Sensitivities in Highly Efficient

Feb 4, 2016 - Rose , A.; Zhu , Z.; Madigan , C. F.; Swager , T. M.; Bulovic , V. Nature 2005, 434, 876– 879 DOI: 10.1038/nature03438. [Crossref], [P...
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Unprecedented Solvent-Dependent Sensitivities in Highly Efficient Detection of Metal Ions and Nitroaromatic Compounds by a Fluorescent Barium Metal−Organic Framework Rongming Wang, Xiaobin Liu, Ao Huang, Wen Wang, Zhenyu Xiao, Liangliang Zhang, Fangna Dai, and Daofeng Sun* State Key Laboratory of Heavy Oil Processing and College of Science, China University of Petroleum (East China), Qingdao, Shandong 266580, China S Supporting Information *

ABSTRACT: The assembly of a fluorescent dicarboxylate ligand with a barium ion resulted in the formation of a 3D metal−organic framework, Ba5(ADDA)5(EtOH)2(H2O)3·5DMF (UPC-17), based on a 1D rod-shaped secondary building unit. The unprecedented solvent-dependent sensitivities of UPC-17 for the detection of Fe3+/Al3+ ions and 4-nitrophenol with high efficiency were observed for the first time. Significantly, UPC-17 exhibits superior “turn-off” detection for the Fe3+ ion in methanol and acetone emulsions but shows “turn-on” detection in tetrahydrofuran emulsion. Furthermore, the visible color changes in the detection process make them easy to distinguish by the naked eye, which further increases its application potential.

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The fluorescent sensing of MOFs for organic molecules and metal ions has been widely studied by Chen and other groups.24−31 Recently, Li and co-workers pioneered the study of fluorescent MOFs for the sensing of high explosives.32,33 Following that, a series of fluorescent MOFs based on lanthanide or transition-metal ions were synthesized and reported for the rapid sensing of NACs such as 1,3dinitrobenzene, 2,4-dinitrotoluene, 1,4-dinitrobenzene, 4-nitrophenol (4-NP), 2,4,6-trinitrophenol, 4-nitroaniline, 1-methyl-4nitrobenzene, and (4-nitrophenyl)hydrazine.34−45 For most of the reported fluorescent detections of small molecules or NACs by MOFs, the MOF materials were dispersed in an organic solvent, to which was added the analytes. In principle, the organic solvent should have a significant effect on the fluorescence emission of the MOF materials and further influence the detection sensitivity for the analytes. However, the solvent-dependent fluorescence detection of analytes with different sensitivities by fluorescent MOF materials remains unexplored to date. Herein, we report a new barium−organic framework, Ba5(ADDA)5(EtOH)2(H2O)3·5DMF (UPC-17; DMF = N,N-dimethylformamide), based on a fluorescent organic ligand, 3,3′-(anthracene-9,10-diyl)diacrylic acid (H2ADDA), and its fluorescent detection for Fe3+ ions, Al3+ ions, and 4-NP bears unprecedented solvent-dependent sensitivities in methanol (MeOH), acetone, or tetrahydrofuran (THF) emulsion.46

INTRODUCTION With the development of society, it is vital to detect harmful substances such as metal ions, small organic molecules, and nitroaromatic compounds (NACs) for the protection of human health. Although some analytical techniques such as voltammetry and spectrophotometry can detect these substances accurately,1−4 these techniques are not easily accessible. Because of their high efficiency, low-cost operation, and simplicity, fluorescent sensors have been considered as one of the most compelling devices for sensing small molecules, metal ions, and NACs.5,6 The most important step for fluorescent sensors is the design and synthesis of fluorescent materials that exhibit a change in the fluorescence emission (enhancement, quenching, or shift) upon stimulation by analytes. Metal−organic frameworks (MOFs) are a new class of crystalline materials that are built from organic ligands and metal ions/clusters.7−10 The development of porous MOFs has provided an excellent platform, where people can rationally design and synthesize functional MOF materials for practical applications such as gas storage/separation, catalysis, and fluorescent sensors. In the past, a large number of porous MOFs were synthesized and their properties in gas storage/ separation were studied and reported comprehensively.11−17 In contrast, fluorescent sensors based on MOFs drew attention from chemists only recently.18 Because MOFs are built from organic ligands and metal ions/clusters, it is possible to rationally design and construct fluorescent MOF materials based on fluorescent organic ligands or metal ions such as lanthanide ions, or a combination of both.19−23 © XXXX American Chemical Society

Received: November 22, 2015

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3D framework with 1D channels of about 7.1046 Å × 7.5688 Å along the b axis, as shown in Figure 1. A large number of

EXPERIMENTAL SECTION

Materials. Unless otherwise noted, all reagents were obtained from commercial suppliers and used without further purification. 1H NMR spectroscopy was measured on a Bruker AVANCE-300 NMR spectrometer. Powder X-ray diffraction (XRD) was measured on a Panalytical X-Pert pro diffractometer with Cu Kα radiation. Elemental analysis (C, H, and N) was performed on a PerkinElmer 240 elemental analyzer. Thermogravimetric analysis (TGA) was carried out between room temperature and 600 °C in static N2 with a heating rate of 10 °C min−1. Photoluminescence (PL) was measured on a F-2700 fluorescence spectrophotometer. Fluorescent detections of metal ions or aromatic compounds was performed by the incremental addition of analytes (0−70 μL) to 3 mL portions of emulsions of UPC-17. The emulsion was obtained by adding 2 mg of UPC-17 into 3 mL of solvent and ultrasonically dispersing it for 20 min. The 10 mmol dm−3 of analyte was prepared by using the same solvent with the detecting emulsion. Synthesis of UPC-17. A mixture of Ba(NO3)2 (26 mg, 0.12 mmol), H2ADDA (3 mg, 0.01 mmol), and 2 mL of DMF/ethanol (EtOH)/H2O (5:2:1, v/v/v) was sealed in a pressure-resistant glass tube, heated to 90 °C for 8 h, kept at 90 °C for 48 h, and then slowly cooled to 30 °C for 10 h. Pale-yellow crystals were collected, washed with EtOH, and dried in air (yield: 70%). Elem anal. Calcd for UPC17 [Ba5(ADDA)5(EtOH)2(H2O)3·5DMF/Ba5C119H113O30N5]: C, 51.42; H, 4.10; N, 2.52. Found: C, 51.08; H, 3.99; N, 2.54. Crystal Structure Determination of UPC-17. Single-crystal XRD was performed using an Aglient Technologies SuperNova Atlas Dual System, with a microfocus source (Mo Kα; λ = 0.71073 Å) and focusing multilayer mirror optics. The structure was solved by direct methods using SHELXTL and refined by full-matrix least squares on F2 using SHELX-97. Non-hydrogen atoms were refined with anisotropic displacement parameters during the final cycles. Hydrogen atoms were placed in calculated positions with isotropic displacement parameters set to 1.2Ueq of the attached atom. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited in the Cambridge Crystallographic Data Center as CCDC 1404807.

Figure 1. (a) 1D rod-shaped SBU in UPC-17. (b) 3D packing of UPC-17 along the b axis showing the 1D open channels.

uncoordinated DMF molecules reside in the channels, as confirmed by elemental analysis and TGA. After the removal of guest solvents, the solvent-accessible volume is 28.3% (1502.1 Å3) of the crystal unit cell volume (5305.4 Å3) based on the PLATON/VOID routine, and the accessible surface area is 118.0 Å2, which is obtained by using the program of Poreblazer V.3.0.2.51.47 Considering the character of the H2ADDA ligand, the solidstate PL of UPC-17 was measured at room temperature and 77 K, which is shown in Figure S7. UPC-17 exhibits strong PL emission at λmax = 546 nm at room temperature but weak PL emission at 77 K, upon excitation at 330 nm. The emission of UPC-17 can be tentatively ascribed to the intraligand π* → n or π* → π electronic transition because the free ligand of H2ADDA exhibits an emission similar to that at λmax = 560 nm with only a 14 nm shift. To further study the potential application in fluorescence detection of the analytes, detailed PL measurements were carried out by dispersing UPC-17 in various solvents. Solvent-dependent PL emission was observed, as shown in Figure 2. In particular, the PL emissions of UPC17 exhibit similar intensities but show different shifts and colors in MeOH, acetone, and THF. Compared with PL at the solid state, the emissions of UPC-17 in MeOH, acetone, and THF emulsions have shifts of 48, 10, and 8 nm, respectively. To explore the ability of UPC-17 to detect a trace quantity of analytes such as metal ions and NACs, fluorescence titrations were carried out with the incremental addition of analytes to UPC-17 dispersed in MeOH, acetone, and THF. Inspiringly, UPC-17 exhibits fast and highly efficient detection of Fe3+/Al3+ ions and 4-NP with unprecedented solvent-dependent sensitivities. As shown in Figure 3, UPC-17 can efficiently detect the Fe3+ ion in MeOH, acetone, and THF emulsions with different sensing fashion and sensitivities. When UPC-17 was dispersed in MeOH solvent, it emitted visible brightyellow-green light (Figure 3). Upon the incremental addition of the Fe3+ ion, the luminescence intensity decreased gradually, indicating its quenching effect on the PL emission of UPC-17. When 70 μL (233 μM) of a Fe3+ solution was added, nearly 90% of the initial fluorescence intensity was quenched, indicating that UPC-17 possesses high sensitivity in the detection of the Fe3+ ion through fluorescence quenching (turn-off). In contrast, only 23% of the initial fluorescence intensity was quenched when the same amount of a Fe3+ solution was added to the acetone emulsion of UPC-17,

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RESULTS AND DISCUSSION Yellow crystals of UPC-17 were synthesized by a solvothermal reaction of H2ADDA and Ba(NO3)2 in a mixed solvent of DMF, EtOH, and H2O at 90 °C for 48 h with high yield. A single-crystal XRD study reveals that UPC-17 crystallizes in the triclinic space group P1̅, and the asymmetric unit consists of five barium ions, five ADDA ligands, two coordinated EtOH molecules, and three coordinated H2O molecules. Interestingly, five crystallographically independent barium ions bear different coordination environments with coordination numbers in the range of 7−10 (Figure S1), which are similar to other barium MOFs.48,49 More interestingly, five ADDA ligands also have different coordination modes (Figure S2), and both trans and cis conformations of ADDA ligands are present in UPC-17 (Scheme 1). Meanwhile, three ligands adopt trans conformation and two adopt cis conformation to connect the barium ions. Thus, the central barium ions are connected by the carboxylate groups of ADDA ligands to generate a 1D rodshaped secondary building unit (SBU) along the a axis, which is further linked by the backbones of ADDA ligands including trans and cis conformations along the bc plane to give rise to a Scheme 1. H2ADDA Ligand

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Figure 2. (Left) PL spectra of UPC-17 dispersed in different solvents. (Right) Highlights of the PL spectra of UPC-17 dispersed in MeOH, acetone, and THF showing similar intensities and different shifts. Inset: Visible colors under UV light in three types of solvents.

Figure 3. PL intensity of UPC-17 upon the addition of different metal ions into the MeOH (a), acetone (b), and THF (c) emulsions and a comparison of the changes of the PL intensity with the addition of Fe3+ (d) and Al3+ (e) ions into the MeOH, acetone, and THF emulsions of UPC17. Inset: Photographs showing color changes upon the addition of metal ions under 365 nm UV light.

the addition of the Fe3+ ion.27,28 To the best of our knowledge, UPC-17 represents the first example with highly efficient detection of the Fe3+ ion through both fluorescence quenching (turn-off) in a MeOH solution and fluorescence enhancement (turn-on) in a THF solution. It is well-known that the luminescence intensity of an MOF highly relies on the efficiency of metal-to-ligand/ligand-to-metal or intraligand/ ligand-to-ligand energy transfer. Thus, the energy-transfer process can be positively or negatively influenced by the addition of a certain metal ion50,51 as well as the solvent used. For UPC-17, the luminescence intensity reduces gradually upon the addition of the Fe3+ ion when it is dispersed in a MeOH solvent, but the opposite result is observed in a THF solvent. According to these results, the intraligand/ligand-toligand energy-transfer process is less or more effective with the addition of the Fe3+ ion in MeOH and THF solvents, respectively. Although a MOF-based fluorescent sensor has been widely studied, there are no definite mechanisms to date. In this work,

indicating that UPC-17 have much lower sensitivity to the Fe3+ ion in acetone than in MeOH. However, fluorescence enhancement was observed when the Fe3+ ion was added to the THF emulsion of UPC-17. The luminescence intensity was enhanced by almost 4.5 times when 70 μL of a Fe3+ solution was added to the emulsion. This result indicates that UPC-17 dispersed in a THF solvent can sense the Fe3+ ion with high efficiency through fluorescence enhancement (turn-on), which is higher than that in an acetone solution but lower than that in a MeOH solution. More interestingly, the visible-bright-yellow emission of the THF emulsion of UPC-17 gradually changed to a yellow-green emission upon the gradual addition of the Fe3+ ion, which further increases the application potential of UPC17 in the detection of the Fe3+ ion because it is easy to distinguish by the naked eye based on the color change. In the past decade, although many fluorescent MOFs exhibiting selective sensing of the Fe3+ ion have been synthesized and reported, all of the reported results are based on the fluorescence quenching effect (turn-off) on the MOFs upon C

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Inorganic Chemistry UPC-17 possesses 1D channels along the 010 direction, and MeOH or acetone molecules are smaller and easier to enter into the channels in comparison with THF molecules. When the Fe3+ ion diffused into the channels with the company of different solvents, there should be a new dissociation equilibrium and coordination optimization. However, the XRD patterns of the samples soaked in different solutions could match well with the original one, indicating that UPC-17 is stable and does not form other permanent structures. Moreover, a large number of double bonds exist in the organic ligand and are nearly parallel to the anthracene rings, which possibly form a cation−π model and help the transition of electrons to increase the intensity of fluorescence emission. For further exploration, UV−vis spectroscopy was recorded (Figure S62). When the Fe3+ ion was added gradually, dissociation equilibrium and coordination optimization occurred. There is a new absorbance at ca. 405 nm in both THF and MeOH. The peak gradually turns into a wide absorbance located in the range of 350−440 nm in THF, but the absorbance intensity remains almost the same after 40 μL of a Fe3+ solution was added, which is different from those in MeOH. The results probably indicate that several new types of coordination models are formed, which help to increase the fluorescence intensity when UPC-17 is dispersed in a THF solvent. Besides its sensing of the Fe3+ ion with different sensitivities in MeOH, acetone, and THF, UPC-17 also shows highly efficient sensing of the Al3+ ion in the THF emulsion through fluorescence enhancement. The luminescence intensity of UPC-17 gradually enhanced with the addition of an Al3+ solution and reached about 8 times that of the original one after the addition of 70 μL of an Al3+ solution (Figure 3c). Meanwhile, the visible bright-yellow emission of the THF emulsion of UPC-17 gradually changed to yellow-green emission upon the addition of an Al3+ solution, which is similar to that found in the sensing of the Fe3+ ion. In contrast, no significant changes of the luminescence intensity were observed when an Al3+ solution was added to the MeOH or acetone emulsion of UPC-17, indicating that there is smaller selective sensing of the Al3+ ion in a MeOH or an acetone solution. Considering the high selectivity of UPC-17 to the Al3+ ion in the THF emulsion, the sensing of the Al3+ ion was performed in the presence of other mixed-metal ions because it is very important that the fluorescent sensing is not interfered with by the coexisting metal ions during the detection. As expected, UPC-17 exhibits good selectivity to the Al3+ ion in the presence of other metal ions. The emission spectra show that the luminescence intensity remains almost unchanged when Al3+ ions are absent but significantly increases when Al3+ ions are present (Figure S43), further indicating that detection of the Al3+ ion by UPC-17 is not influenced by the coexisting metal ions. To further explore the sensing performance of UPC-17, the detection of NACs was also performed in MeOH, acetone, and THF solutions. As is known, it is very important to detect aromatic compounds, especially for NACs with great rapidity and high selectivity.52,53 As shown in Figure 4, although all of the analytes can weaken the fluorescence intensity of UPC-17, the quenching percentages are quite different. UPC-17 exhibits highly selective detection of 4-NP with different sensitivities in these three emulsions. The highest sensitivity was observed when UPC-17 was dispersed in an acetone solution, and nearly 80% of the initial fluorescence intensity was quenched upon the addition of 70 μL (233 μM) of a 4-NP solution. Quenching

Figure 4. PL intensity upon the addition of different analytes into MeOH (a), acetone (b), and THF (c) emulsions of UPC-17 and a comparison of the quenching percentages in MeOH, acetone, and THF emulsions (d). Photographs showing the fluorescence quenching upon the addition of 4-NP under UV light (e).

percentages of 75% and 60% were observed accordingly in THF and MeOH solutions, respectively. The fluorescent quenching should derive from the photoinduced electrontransfer mechanism, that is, electron transfer from the framework of UPC-17 to the analytes. In order to further display the detection sensitivity in these three solutions, the fluorescence quenching efficiency was calculated using the Stern−Volmer (SV) equation, I0/I = KSV[A] + 1, where I0 is the initial fluorescence intensity before the addition of the analyte, I is the fluorescence intensity after the addition of the analyte, [A] is the molar concentration of the analyte, and KSV is the quenching coefficient (Figure 5). The SV plots are nearly linear at low concentrations; thus, KSV can be estimated accurately. The calculated quenching constants, KSV, are 6.35 × 103, 8.92 × 103, and 1.26 × 104 M−1 (Figures S67−S69) when UPC-17 was dispersed in MeOH, acetone, and THF, respectively. According to the results of the calculations, the effect of the solvent on the quenching efficiency of 4-NP was found to be the following order: THF > acetone > MeOH. D

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ACKNOWLEDGMENTS This work was supported by the NSFC (Grants 21271117, 21371179, and 21571187), NCET-11-0309, the Shandong Natural Science Fund for Distinguished Young Scholars (JQ201003), and the Fundamental Research Funds for the Central Universities (13CX05010A and 14CX02150A).

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Figure 5. Corresponding SV plots of the analytes in MeOH, acetone, and THF emulsions.

To evaluate the recyclability of UPC-17 on the detection of metal ions and NACs, cyclic tests were carried out. Unfortunately, the recyclability of UPC-17 is poor, which may derive from the fact that the metal ions have strong interactions with the wall of the framework such as the carboxylate oxygen atoms and NACs have strong π···π interactions with the central anthracene ring of the ligand. These interactions make it difficult to release the metal ions and NACs from the channel of the framework.39−41

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CONCLUSIONS In conclusion, a new 3D barium−organic framework (UPC-17) based on a fluorescent ligand was synthesized and characterized. UPC-17 shows unprecedented solvent-dependent sensitivities in the detection of metal ions such as Fe3+ and Al3+ and NACs such as 4-NP. More interestingly, the detection of the Fe3+ ion can be achieved in MeOH/acetone emulsion through fluorescence quenching (turn-off) and in THF emulsion through fluorescence enhancement (turn-on) with different sensitivities, which have never been reported previously. Furthermore, the visible bright-yellow emission gradually changes to yellow-green upon the addition of Fe3+ or Al3+ ions to the THF emulsion of UPC-17, which is easy to distinguish by the naked eye. A detailed study of the effect of the solvent on the detection of the analytes is needed and is currently underway in our laboratory.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.inorgchem.5b02693. Details of experimental procedures, synthesis of the ligand and UPC-17, TGA curve, IR spectrum, and powder XRD of UPC-17, emission spectra, Stern− Volmer plots, and the detection limit of UPC-17 in emulsions of different solvents with the addition of various metal cations and NACs (PDF) Crystal structural data for UPC-17 (CIF)

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest. E

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DOI: 10.1021/acs.inorgchem.5b02693 Inorg. Chem. XXXX, XXX, XXX−XXX