Liquid-Phase Epitaxial Growth of Azapyrene-Based Chiral Metal

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Liquid-Phase Epitaxial Growth of Azapyrene-based Chiral MOF Thin Films for Circularly Polarized Luminescence Shu-Mei Chen, Li-Mei Chang, Xue-Kang Yang, Ting Luo, Hai Xu, Zhi-Gang Gu, and Jian Zhang ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.9b11872 • Publication Date (Web): 07 Aug 2019 Downloaded from pubs.acs.org on August 8, 2019

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ACS Applied Materials & Interfaces

Liquid-Phase Epitaxial Growth of Azapyrene-based Chiral MOF Thin Films for Circularly Polarized Luminescence Shu-Mei Chen †,#, Li-Mei Chang ‡,#, Xue-Kang Yang, Ting Luo,§ Hai Xu,§* Zhi-Gang Gu‡* and Jian Zhang‡ †

College of Chemistry, Fuzhou University, Fuzhou, Fujian 350108, P.R. China.

‡

State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure

of Matter, Chinese Academy of Sciences, 350002 Fuzhou, P.R. China. §

College of Chemistry and Chemical Engineering, Central South University, Changsha

410083, P. R. China. 

National Center for Nanoscience and Technology, Beijing 100190, P. R. China

#

These authors contributed equally to the work.

KEYWORDS: Metal-Organic Framework, Homochiral, Oriented Film, Layer by Layer, Liquid-Phase Epitaxial Growth, Circularly Polarized Luminescence, Eantioselective Adsorption

ABSTRACT Development of chiral MOFs for circularly polarized luminescence is a challenge but important task. In this work, we report a first example of azapyrene-based chiral MOF thin films [Zn2Cam2DAP]n grown on functionalized substrates (named SURchirMOF-4) for CPL property. By using liquid-phase epitaxial layer-by-layer method, the resulted SURchirMOF-4 constructed from chiral camphoric acid and 2,7-diazapyrene ligand, which has high orientation and homogeneity. The circular dichroism (CD), CPL and enantioselective adsorption results show SURchirMOF-4 has strong chirality and CPL property as well as good enantioselective adsorption toward enantiomers of methyl-lactate. The synthesis of azapyrene-based chiral MOF thin films not only represent an ideal model for studying the enantioselective adsorption, but also open a valuable approach for development of chiral thin film exhibiting CPL property. 1 ACS Paragon Plus Environment

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INTRODUCTION The synthesis and applications of chiral materials have been rapidly expanded because of their important field of pharmaceutics,1 agriculture,2 biology3 and chemical engineering.4 As a new class of chiral materials, chiral metal–organic frameworks (chirMOFs)5-7 combining the features of chirality and MOFs have attracted great attention due to their fascinating potential applications in enantiomers recognition,8-10 enantioselective adsorption/ separation,11-13 asymmetric catalysis14-16 and nonlinear optics.17, 18 However, the form of MOF thin films or membranes is required for some practical applications. So far, different kinds of techniques for MOF thin films or membranes preparation have been developed for separators, devices and sensors.19-23 Particularly liquid-phase epitaxy (LPE) layer-by-layer approach affords a good candidate method for MOF thin films preparation (also known as SURMOFs), which is assembled by sequentially immersing the functionalized substrate into the metal salts and organic ligands solutions. The sample is cleaned with solvent for removing the uncoordinated precursors after each immersion step.24-27 Such MOF thin films exhibit remarkable advantages, such as controllable growth orientation, tunable thickness and high homogeneity, providing a promising thin film model for the study in coordination chemistry and growth mechanism as well as diffusion behavior of guest species. However, the preparation and application of chiral SURMOFs is still a challenging task but very important for chiral chemistry in the thin film system. In previous work, homochiral SURMOFs M2Cam2L (M = Zn or Cu; Cam = camphoric acid; L= diazabicyclo[2.2.2]-octane (dabco), 4,4-bipyridyl (bipy) and 1,4-bis(4pyridyl)benzene (bipyb)) constructed from camphoric acid and different pillared ligand (dabco, bipy and bipyb) have been studied for enanotioselective adsorption/adsorption by using quartz-crystal microbalance and gas chromatography techniques.28-31 Therefore, exploring new chiral SURMOFs for various applications is extremely urgent.

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On the other hand, recently the development of chiral materials exhibiting circularly polarized luminescence (CPL) has attracted great interest owing to their potential applications in the fields of optical displays, information transmission/storage, photoelectric devices and chiral sensors.32-34 So far, chiral materials constructed from inorganic oxides,35 organic molecules,36,

37

polymers,38 supermolecular39 and the related chiral thin films40 have been

reported for CPL properties. However, developing of chiral MOF thin film for CPL has not been reported but it is a challenge and important task.

Scheme 1. (a) Synthesis process of 2,7-diazapyrene (DAP); (b) Schematic drawing of SURchirMOF [Zn2Cam2DAP]n grown on substrate surface by LEP layer-by-layer approach along [001]. 3 ACS Paragon Plus Environment


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For preparating MOF thin films with circularly polarized luminescence, in this work the camphoric acid (H2Cam) is chosen as the chiral ligand, and a pyrene-contained molecule is synthesized as the luminescence auxiliary ligand since pyrene-based materials showed fascinating fluorescent properties. Herein, 2,7-Diazapyrene (DAP) with two pyridine groups provides an idea candidate for constructing a pillar-layered MOF with H2Cam. The synthesis process of DPA with three high-yield steps is shown in scheme 1a. Firstly the concentrated ammonium hydroxide solution reacts with the commercially available 1,4,5,8-naphthalene tetracarboxylic dianhydride to form 1,4,5,8-naphthalenetetracarboxylic diimide (1). Then the obtained compound reacts with borane under refluxing tetrahydrofuran to produce 1,2,3,6,7,8hexahydro-2,7-diazapyrene (2). Afterwards, 2,7-diazapyrene (3) can be given by oxidization with manganese dioxide under refluxing benzene. The photoluminescence and UV-vis spectra show that DAP possesses intense luminescence property (Figure S1-3), which is good candidate for assembling CPL based MOF. RESULTS AND DISCUSSION Previous reports reveal that the carboxylate and pyridine based ligand can prepare the pillar-layered MOF thin films by using liquid-phase epitaxial layer-by-layer approach, such as [M2(Cam)2dabo]n, [M2(bdc)2bipy]n.30,

[M2(Cam)2bipy]n, 41-43

[M2(Cam)2bibipy]n,

[M2(bdc)2dabo]n

and

Herein, a new pair of enantiopure chiral MOF thin films

[Zn2(Cam)2DAP]n are successfully prepared on OH-terminated substrate by LPE layer by layer method (named SURchirMOF-4), displaying a [001]-orientated MOF thin film. The structure of [Zn2(Cam)2DAP]n is simulated from the reported [Zn2(Cam)2bipy]n in the literature.44 The quartz glass was used as the substrate for examining the chirality and circularly polarized luminescence property. The gas phase QCM uptakes of enantiomers Dand L-methyl-lactate for D/L-SURchirMOF-4 demonstrates a good enantioselective adsorption (selectivity of ~26% and 28% for D- and L-SURchirMOF-4 respectively). Furthermore, the circular dichroism (CD) and CPL show SURchirMOF-4 has a strong and 4 ACS Paragon Plus Environment

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opposite CD and CPL signal in D- and L-SURchirMOF-4. The presented studies indicates that such porous MOF thin film not only provides an ideal model for studying the enantioselective adsorption, but also offers a valuable guidance for development of chiral thin film exhibiting CPL property.

Figure 1. The XRD (a) and infrared reflection adsorption IR spectroscopy (b) of [Zn2D/LCam2DAP]n

(D/L-SURchirMOF-4)

grown

on

hydroxyl-functionalized

glass

substrate; (c, d) the SEM images of D-SURchirMOF-4 grown on the substrate surface. In the structure of pillar-layered homochiral MOF [Zn2Cam2DAP]n, [Zn2Cam2]n serve as the layer while DAP act as pillars. In this work, homochiral SURMOF [Zn2Cam2DAP]n (SURchirMOF-4) was grown on hydroxyl-functionalized quartz glass adopting LPE pump method (Scheme 1b). During the epitaxial growth process, the DAP coordinate to the axial positions in zinc complexes [Zn2D/LCam2], perpendicular to the chiral [Zn2D/LCam2] layers, resulting in a [001]-direction for D/L-SURchirMOF-4, which is simialr to the reported isostructural [Zn2Cam2L]n thin films.30-31 The XRD pattern (Figure 1a) showed two diffraction peaks at 6.30° and 12.6° corresponded the (001) and (002) planes in the obtained 5 ACS Paragon Plus Environment


SURchirMOF-4 on OH-functionalized substrates, which clearly demonstrated a preferentially [001]-oriented crystal thin film was formed. The IRRAS spectrum of D/L-SURchirMOF-4 has an asymmetric vibration at ~1690 cm-1 because that the Zn-Zn axis was parallel to the substrate surface. The surface morphology of SURchirMOF-4 grown on OH-functionalized gold substrate was observed from SEM images in Figure 1c,d and Figure S4 as well as the AFM image (Figure S5), showing a highly homogeneous crystallite coating.

Figure 2. (a) photoimages of quartz glass, D- and L-SURMOF-4 grown on quartz glass under light (left) and 365 nm irradiation (right); the potoluminescent emission spectra (b) and CD spectra (c) of D- and L-SURMOF-4 grown on quartz glasses. The optical activity properties of D- and L-SURchirMOF-4 grown on quartz glasses (Figure 2a) were further studied at room temperature. The photoluminescence (Figure 2b and S6) showed SURchirMOF-4 displayed a similar intense fluorescence with the maximum emissions at 390, 410 and 432 nm when it was excited at 365 nm, which were similar as the UV-vis absorption spectra (Figure S7-8). The CD data recorded for SURchirMOFs [Zn2(Dcam)2DAP]n (D-SURchirMOF-4) and [Zn2(Lcam)2DAP]n (L-SURchirMOF-4) were shown in Figure 2c. The CD spectra showed four positive bands at 243, 271,335, 395 nm and two negative bands at 249, 307 nm for D-SURchirMOF-4 fabricated exclusively with enantiopure Dcam and DAP. Moreover, the enantiomeric pairs show dichroic absorption of equal magnitude but opposite signal. 6 ACS Paragon Plus Environment

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Figure 3. CPL spectra of D- and L-SURMOF-4. CPL is used as a unique property to evaluate the chirality of chiral materials. Recently, scientists have reported a ligand-exchange approach to form a chiral zeolitic imidazolate framework (ZIF) powder for CPL.45 However, such ligand-exchange approach usually can not exchange the ligand completely and the powder form of ZIF is also no convenient in the practical CPL application. Therefore, the in-situ epitaxial growth of MOF thin films for CPL is a promising material for CPL application. Herein, we investigate the CPL of the D- and LSURMOF-4 grown on quartz glasses. Different handedness CPL signals (Figure 3) could be observed and the relative CPL signals were at ~330 nm. The results display that the CPL signals of D- and L-SURchirMOF-4 were opposite.The corresponding glum factors (Fiugre S9) were ~ 3×10-3 and -8×10-3 for D- and L-SURchirMOF-4 respectively.



Figure 4. The mass uptake of the enantiomers D- and L-methyl lactate in D- (a) and L- (b) SURchirMOF-4 using by a gas phase QCM technique. To further study the chiral recognition of D- and L-SURchirMOF-4, the adsorption performance of enantiomers can be carried out in this work. A gas phase quartz crystal microbalance (QCM) technology has developed for investigating the enantioselectivity of homochiral MOF thin films, which can monitor mass changes with nanogram by detecting the change of resonance frequency. The D- and L-SURchirMOF-4 thin films were grown on Au coated QCM sensors. The thickness of D-SURchirMOF-4 was measured by cross section SEM and was about 320 nm (Figure S10). A pairs of enantiomers D- and L-methyl-lactate were selected as the chiral probe molecules for study their enantioselectivity. The related 8 ACS Paragon Plus Environment

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adsorption amount of D and L-methyl-Lactate for D-SURchirMOF-4 and L-SURchirMOF-4 were carried out respectively, which were shown in Figure 4. The adsorption amount of Dand L-methyl-Lactate for D-SURchirMOF-4 were ~2.08 (MD) and ~3.54 (ML) µg/cm2, respectively (Figure 4a). The different adsorption showed an important enantioselective adsorption for one enantiomer methyl-Lactate in SURchirMOF-4. When we applied the equation “ee% = (ML-MD)/(MD+ML)×100” for analysing the enantioselectivity. The enantioselectivity ee% of SURchirMOF-4 for methyl-Lactate was 26%. With the same measurement, the probe enantiomers of D/L-methyl-lactate were used for studying the enantioselective adsorption of L-SURchirMOF-4. The recorded data (Figure 4b) showed that the adsorption amounts of D- and L-methyl-Lactate were ~3.62 (MD) and ~2.02 (ML) µg/cm2 for L- SURchirMOF-4, respectively. The related enantioselectivity ee% was 28% after using the same equation, which was the respective opposite enantioselective adsorption of DSURchirMOF-4. CONCLUSIONS In summary, we have successfully synthesized new homochiral MOF thin films [Zn2Cam2DAP]n (named SURchirMOF-4) with homogeneous surface and [001]orientation from camphoric acid (H2Cam) and 2,7-diazapyrene (DAP) by using liquidphase epitaxial layer-by-layer method. Combining bifunctional thin film with chirality of ligands H2Cam and luminescence ligand DAP, CD and CPL as well as enantioselective adsorption of the obtained MOF thin films have been studied. The results show that SURchirMOF-4 has strong CPL property and good enantioselective adsorption toward enantiomers D- or L-methyl-lactate. The presented chiral MOF thin films not only provides an ideal model for studying enantioselective adsorption, but also offers a valuable guidance for development of chiral thin film exhibiting CPL property. EXPERIMENTAL SECTION



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Materials and Instrumentation. All solvents and reagents used were commercially available. PXRD was used a MiniFlex2 X-ray diffractometer using Cu-Kα radiation (λ = 0.1542 nm) in the 2θ range of 4–16°. Software JADE 6.5 was used for evaluating the XRD data. JSM6700 instrument was used for SEM images measurement. The fluorescence emission was measured by FLS-980 fluorescence spectrometer. Atomic Force Microscope (AFM) was performed on a Bruker FastSacn system. The CD spectra are recorded by CD spectrometer MOS-450. Fluorescence and CPL spectra were obainted using F-4500 fluorescence and JASCO CPL-200 spectrophotometers, respectively. The quartz glass substrate was used as the reference of the CD and CPL measurements. The samples were fixed on instrument directly and perpendiculared to the light beam during the measurement. The background spectra from the quartz glass substrates were subtracted to obtain the final processed CD and CPL spectra. UVvis spectra are measured on Lambda 900 spectrophotometer. The IRRAS technique was aslo used for SURMOFs characterization by using a Bruker VERTEX 70. Bruker OPUS® software version 5.5 was used for evaluating the IR data. Synthesis

of

1,4,5,8-Naphthalenetetracarboxylic

Naphthalenetetracarboxylic dianhydride (12.5g, 46.6mmol)

Diimide

(1).

1,4,5,8-

was dissolved in a stirred

concentrated ammonium hydroxide (625 mL, 29.5%, w/w) aqueous solution. Then the mixture was stirred for 6 hours under nitrogen and a pale yellow product diimide precipitate was obtained after filtering, washing, and drying under vacuum at 60ºC overnight. Yield: 11.9g (96%). 1H NMR (400 MHz, DMSO) δ 12.10 (s, 2H), 8.62 (s, 4H). Synthesis of 1,2,3,6,7,8-Hexahydro-2,7-diazapyrene (2). Diimide (2 g,7.52 mmol) and anhydrous THF (40 mL) was added in a three-neck flask (250 mL) with stirring and refluxing under nitrogen atmosphere. Then the suspension was added slowly, via the dropping BH3THF (80 mL, 1 M) solution. The obtained mixture was then refluxed for 60 hours. During that time there was hydrogen evolution and the color changed to orange. The HCl solution (8 mL, 6 M) was added to the mixture and refluxed for quenching the reaction after cooling 0ºC. 10 ACS Paragon Plus Environment

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Caution: At that time the mixture may foam strongly so the stirring must be kept vigorous. The liquid was evaporated and the residue was cooled to 0ºC. Afterward, potassium carbonate aqueous saturated solution was added for tuning the pH (>10). The solid was added dried completely under vacuum at 40ºC. The dry solid was extracted with refluxing benzene in a soxhlet extractor for a week. After this period, the benzene was removed in vacuo to yield 1.22 g (77%) of pure diamine which can be recrystallized from benzene to give off-white power. 1H NMR (400 MHz, CDCl3) δ 7.11 (s, 4H), 4.28 (s, 8H). 13C NMR (101 MHz, CDCl3) δ 132.90, 127.90, 120.34, 48.90. Synthesis of 2,7-Diazapyrene (3). A 500 mL round-bottom flask was charged with benzene (250 mL) and then added MnO2 (10 g, 115.02 mmol, activated grade, Aldrich). After the addition, the hot solution was filtered after refluxing for 24 hours. The filtered MnO2 was dried under vacuum and subjected to a soxhlet extraction with the benzene solution of the filtrate for 3 days. After removal of the benzene in vacuo,0.2 g (21%) of pure diazapyrene was obtain as yellow crystals. 1H NMR (400 MHz, CDCl3) δ 9.51 (s, 4H), 8.22 (s, 4H). 13C NMR (101 MHz, CDCl3) δ 144.36, 125.39, 125.20, 124.8. Preparation of OH-functionalized substrates and SURchiMOF-4 [Zn2Cam2DAP]n. The self-assembled OH-functionalized (11-mercapto-1-undecanol, MUD) on Au/Si wafer and Au coated QCM-sensor are prepared for SURMOF preparation. For CD and CPL experiments, [001] orientated SURchirMOF-4 was prepared on a hydroxyl terminal quartz glass substrate, which is similar as the reported literature28 except replacing the new ligands solutions. Quartz crystal microbalance (QCM) adsorption of SURchiMOF-4. A gas phase QCM with a flow module was used for measuring the adsorption performance of the obtained samples. The setup of the gas phase QCM and measurements as well as data evolution were followed the previous literature. 31 ASSOCIATED CONTENT



Supporting Information. Additional material characterization and figures. This material is available free of charge via the Internet at http://pubs.acs.org. AUTHOR INFORMATION Corresponding Author *Address correspondence to [email protected] and [email protected] Author Contributions All authors have given approval to the final version of the manuscript. S.-M. Chen and L.-M. Chang contributed equally to this work. ACKNOWLEDGMENT This work is supported by National Natural Science Foundation of China (21601189, 21872148 and 21871050) and The Youth Innovation Promotion Association of Chinese Academy of Sciences (2018339). CONFLICT OF INTEREST The authors declare no conflict of interest. REFERENCES (1)

Sun, C. Y.; Qin, C.; Wang, C. G.; Su, Z. M.; Wang, S.; Wang, X. L.; Yang, G. S.;

Shao, K. Z.; Lan, Y. Q.; Wang, E. B. Chiral Nanoporous Metal-Organic Frameworks with High Porosity as Materials for Drug Delivery. Adv. Mater. 2011, 23, 5629-5632. (2)

Yutthalekha, T.; Wattanakit, C.; Lapeyre, V.; Nokbin, S.; Warakulwit, C.; Limtrakul,

J.; Kuhn, A. Asymmetric Synthesis using Chiral-Encoded Metal. Nat Commun 2016, 7, 12678. (3)

Agarwal, N. P.; Matthies, M.; Gur, F. N.; Osada, K.; Schmidt, T. L. Block Copolymer

Micellization as a Protection Strategy for DNA Origami. Angew. Chem. Int. Ed. 2017, 56, 5460-5464.


Page 12 of 18

Page 13 of 18 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(4)

Luo, Z. L.; Zhang, S. G. Designer Nanomaterials using Chiral Self-Assembling

Peptide Systems andTheir Emerging Benefit for Society. Chem. Soc. Rev. 2012, 41, 47364754. (5)

Zhang, J.; Chen, S. M.; Nieto, R. A.; Wu, T.; Feng, P. Y.; Bu, X. H. A Tale of Three

Carboxylates: Cooperative Asymmetric Crystallization of a Three-Dimensional Microporous Framework from Achiral Precursors. Angew. Chem. Int. Ed. 2010, 49, 1267-1270. (6)

Zhao, X.; Nguyen, E. T.; Hong, A. N.; Feng, P. Y.; Bu, X. H. Chiral Isocamphoric

Acid: Founding a Large Family of Homochiral Porous Materials. Angew. Chem. Int. Ed. 2018, 57, 7101-7105. (7)

Gu, Z. G.; Zhan, C. H.; Zhang, J.; Bu, X. H. Chiral Chemistry of Metal-Camphorate

Frameworks. Chem. Soc. Rev. 2016, 45, 3122-3144. (8)

Das, S.; Xu, S. X.; Ben, T.; Qiu, S. L. Chiral Recognition and Separation by Chirality-

Enriched Metal-Organic Frameworks. Angew. Chem. Int. Ed. 2018, 57, 8629-8633. (9)

Zhang, S. Y.; Yang, C. X.; Shi, W.; Yan, X. P.; Cheng, P.; Wojtas, L.; Zaworotko, M.

J. A Chiral Metal-Organic Material that Enables Enantiomeric Identification and Purification. Chem-Us 2017, 3, 281-289. (10)

Martell, J. D.; Porter-Zasada, L. B.; Forse, A. C.; Siegelman, R. L.; Gonzalez, M. I.;

Oktawiec, J.; Runcevski, T.; Xu, J.; Srebro-Hooper, M.; Milner, P. J.; Colwell, K. A.; Autschbach, J.; Reimer, J. A.; Long, J. R. Enantioselective Recognition of Ammonium Carbamates in a Chiral Metal-Organic Framework. J. Am. Chem. Soc. 2017, 139, 1600016012. (11)

Liu, Y.; Xi, X. B.; Ye, C. C.; Gong, T. F.; Yang, Z. W.; Cui, Y. Chiral Metal-Organic

Frameworks Bearing Free Carboxylic Acids for Organocatalyst Encapsulation. Angew. Chem. Int. Ed. 2014, 53, 13821-13825.



(12)

Bhattacharjee, S.; Khan, M. I.; Li, X. F.; Zhu, Q. L.; Wu, X. T. Recent Progress in

Asymmetric Catalysis and Chromatographic Separation by Chiral Metal-Organic Frameworks. Catalysts 2018, 8, 120. (13)

Nickerl, G.; Henschel, A.; Grunker, R.; Gedrich, K.; Kaskel, S. Chiral Metal-Organic

Frameworks and Their Application in Asymmetric Catalysis and Stereoselective Separation. Chem. Ing. Tech. 2011, 83, 90-103. (14)

Liu, Y.; Xuan, W. M.; Cui, Y. Engineering Homochiral Metal-Organic Frameworks

for Heterogeneous Asymmetric Catalysis and Enantioselective Separation. Adv. Mater. 2010, 22, 4112-4135. (15)

Cho, S. H.; Ma, B. Q.; Nguyen, S. T.; Hupp, J. T.; Albrecht-Schmitt, T. E. A Metal-

Organic Framework Material That Functions as An Enantioselective Catalyst for Olefin Epoxidation. Chem. Commun. 2006, 2563-2565. (16)

Ma, L. Q.; Falkowski, J. M.; Abney, C.; Lin, W. B. A Series of Isoreticular Chiral

Metal-Organic Frameworks as A Tunable Platform for Asymmetric Catalysis. Nat. Chem. 2010, 2, 838-846. (17)

Liu, Y.; Xu, X.; Zheng, F. K.; Cui, Y. Chiral Octupolar Metal-Oraganoboran NLO

Frameworks with (14,3) Topology. Angew. Chem. Int. Ed. 2008, 47, 4538-4541. (18)

Liang, X. Q.; Zhang, F.; Zhao, H. X.; Ye, W.; Long, L. S.; Zhu, G. S. A Proton-

Conducting Lanthanide Metal-Organic Framework Integrated with A Dielectric Anomaly and Second-Order Nonlinear Optical Effect. Chem. Commun. 2014, 50, 6513-6516. (19)

Makiura, R.; Motoyama, S.; Umemura, Y.; Yamanaka, H.; Sakata, O.; Kitagawa, H.

Surface Nano-Architecture of A Metal-Organic Framework. Nat. Mater. 2010, 9, 565-571. (20)

Wannapaiboon, S.; Schneemann, A.; Hante, I.; Tu, M.; Epp, K.; Semrau, A. L.;

Sternemann, C.; Paulus, M.; Baxter, S. J.; Kieslich, G.; Fischer, R. A. Control of Structural Flexibility of Layered-Pillared Metal-Organic Frameworks Anchored at Surfaces. Nat Commun 2019, 10, 346. 14 ACS Paragon Plus Environment

Page 14 of 18

Page 15 of 18 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(21)

Stavila, V.; Talin, A. A.; Allendorf, M. D. MOF-based Electronic and Optoelectronic

Devices. Chem. Soc. Rev. 2014, 43, 5994-6010. (22)

Zhang, Y. Y.; Yuan, S.; Feng, X.; Li, H. W.; Zhou, J. W.; Wang, B. Preparation of

Nanofibrous Metal-Organic Framework Filters for Efficient Air Pollution Control. J. Am. Chem. Soc. 2016, 138, 5785-5788. (23)

Li, P.; Li, J. Z.; Feng, X.; Li, J.; Hao, Y. C.; Zhang, J. W.; Wang, H.; Yin, A. X.; Zhou,

J. W.; Ma, X. J.; Wang, B. Metal-Organic Frameworks with Photocatalytic Bactericidal Activity for Integrated Air Cleaning. Nat. Commun. 2019, 10, 2177. (24)

Gu, Z. G.; Zhang, J. Epitaxial Growth and Applications of Oriented Metal-Organic

Framework Thin Films. Coord. Chem. Rev. 2019, 378, 513-532. (25)

Zacher, D.; Shekhah, O.; Woll, C.; Fischer, R. A. Thin Films of Metal-Organic

Frameworks. Chem. Soc. Rev. 2009, 38, 1418-1429. (26)

Shekhah, O.; Liu, J.; Fischer, R. A.; Woll, C. MOF Thin Films: Existing and Future

Applications. Chem. Soc. Rev. 2011, 40, 1081-1106. (27)

Liu, J. X.; Woll, C. Surface-Supported Metal-Organic Framework Thin Films:

Fabrication Methods, Applications, and Challenges. Chem. Soc. Rev. 2017, 46, 5730-5770. (28)

Gu, Z. G.; Burck, J.; Bihlmeier, A.; Liu, J. X.; Shekhah, O.; Weidler, P. G.; Azucena,

C.; Wang, Z. B.; Heissler, S.; Gliemann, H.; Klopper, W.; Ulrich, A. S.; Woll, C. Oriented Circular Dichroism Analysis of Chiral Surface-Anchored Metal-Organic Frameworks Grown by Liquid-Phase Epitaxy and upon Loading with Chiral Guest Compounds. Chem. -Eur. J. 2014, 20, 9879-9882. (29)

Gu, Z. G.; Fu, W. Q.; Wu, X.; Zhang, J. Liquid-phase Epitaxial Growth of A

Homochiral MOF Thin Film on poly(L-DOPA) Functionalized Substrate for Improved Enantiomer Separation. Chem. Commun. 2016, 52, 772-775.



(30)

Gu, Z. G.; Grosjean, S.; Brase, S.; Woll, C.; Heinke, L. Enantioselective Adsorption in

Homochiral Metal-Organic Frameworks: the Pore Size Influence. Chem Commun 2015, 51, 8998-9001. (31)

Chen, S. M.; Liu, M.; Gu, Z. G.; Fu, W. Q.; Zhang, J. Chiral Chemistry of Homochiral

Porous Thin Film with Different Growth Orientations. ACS Appl. Mater. Interfaces 2016, 8, 27332-27338. (32)

Huo, S. W.; Duan, P. F.; Jiao, T. F.; Peng, Q. M.; Liu, M. H. Self-Assembled

Luminescent Quantum Dots To Generate Full-Color and White Circularly Polarized Light. Angew. Chem. Int. Ed. 2017, 56, 12174-12178. (33)

Li, M.; Li, S. H.; Zhang, D. D.; Cai, M. H.; Duan, L.; Fung, M. K.; Chen, C. F. Stable

Enantiomers Displaying Thermally Activated Delayed Fluorescence: Efficient OLEDs with Circularly Polarized Electroluminescence. Angew. Chem. Int. Ed. 2018, 57, 2889-2893. (34)

Yang, X. F.; Han, J. L.; Wang, Y. F.; Duan, P. F. Photon-Upconverting Chiral Liquid

Crystal: Significantly Amplified Upconverted Circularly Polarized Luminescence. Chem. Sci. 2019, 10, 172-178. (35)

Sugimoto, M.; Liu, X. L.; Tsunega, S.; Nakajima, E.; Abe, S.; Nakashima, T.; Kawai,

T.; Jin, R. H. Circularly Polarized Luminescence from Inorganic Materials: Encapsulating Guest Lanthanide Oxides in Chiral Silica Hosts. Chem. - Eur. J. 2018, 24, 6519-6524. (36)

Shen, Z. C.; Wang, T. Y.; Shi, L.; Tang, Z. Y.; Liu, M. H. Strong Circularly Polarized

Luminescence from the Supramolecular Gels of An Achiral Gelator: Tunable Intensity and Handedness. Chem. Sci. 2015, 6, 4267-4272. (37)

Roose, J.; Leung, A. C. S.; Wang, J.; Peng, Q.; Sung, H. H. Y.; Williams, I. D.; Tang,

B. Z. A Colour-Tunable Chiral AIEgen: Reversible Coordination, Enantiomer Discrimination and Morphology Visualization. Chem. Sci. 2016, 7, 6106-6114.


Page 16 of 18

Page 17 of 18 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(38)

Zhao, B.; Pan, K.; Deng, J. P. Intense Circularly Polarized Luminescence Contributed

by Helical Chirality of Monosubstituted Polyacetylenes. Macromolecules 2018, 51, 71047111. (39)

Haraguchi, S.; Numata, M.; Li, C.; Nakano, Y.; Fujiki, M.; Shinkai, S. Circularly

Polarized Luminescence from Supramolecular Chiral Complexes of Achiral Conjugated Polymers and a Neutral Polysaccharide. Chem. Lett. 2009, 38, 254-255. (40)

Hirahara, T.; Yoshizawa-Fujita, M.; Takeoka, Y.; Rikukawa, M. Highly Efficient

Circularly Polarized Light Emission in the Green Region from Chiral Polyfluorene-Thiophene Thin Films. Chem. Lett. 2012, 41, 905-907. (41)

Liu, B.; Shekhah, O.; Arslan, H. K.; Liu, J. X.; Woll, C.; Fischer, R. A. Enantiopure

Metal-Organic Framework Thin Films: Oriented SURMOF Growth and Enantioselective Adsorption. Angew. Chem. Int. Ed. 2012, 51, 807-810. (42)

Shekhah, O.; Hirai, K.; Wang, H.; Uehara, H.; Kondo, M.; Diring, S.; Zacher, D.;

Fischer, R. A.; Sakata, O.; Kitagawa, S.; Furukawa, S.; Woll, C. MOF-on-MOF Heteroepitaxy: Perfectly Oriented [Zn2(ndc)2(dabco)]n Grown on [Cu2(ndc)2(dabco)]n Thin Films. Dalton T. 2011, 40, 4954-4958. (43)

Shekhah, O.; Wang, H.; Paradinas, M.; Ocal, C.; Schupbach, B.; Terfort, A.; Zacher,

D.; Fischer, R. A.; Woll, C. Controlling Interpenetration in Metal-Organic Frameworks by Liquid-Phase Epitaxy. Nat. Mater. 2009, 8, 481-484. (44)

Dybtsev, D. N.; Yutkin, M. P.; Peresypkina, E. V.; Virovets, A. V.; Serre, C.; Ferey,

G.; Fedin, V. P. Isoreticular Homochiral Porous Metal-Organic Structures with Tunable Pore Sizes. Inorg. Chem. 2007, 46, 6843-6845. (45)

Zhao, T. H.; Han, J. L.; Jin, X.; Liu, Y.; Liu, M. H.; Duan, P. F. Enhanced Circularly

Polarized Luminescence from Reorganized Chiral Emitters on the Skeleton of a Zeolitic Imidazolate Framework. Angew. Chem. Int. Ed. 2019, 58, 4978-4982.



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Liquid-Phase Epitaxial Growth of Azapyrene-Based Chiral Metal

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