The DOI matches its Crossref record; 78 of the 78 references it cites were found in a registry or an index.
Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis
Abstract
The structural uniqueness of covalent organic frameworks (COFs) has brought these new materials great potential for advanced applications. One of the key aspects yet to be developed is how to improve the robustness of covalently linked reticular frameworks. In order to make the best use of π-conjugated structures, we develop herein a "killing two birds with one stone" strategy and construct a series of ultrastable benzoxazole-based COFs (denoted as LZU-190, LZU-191, and LZU-192) as metal-free photocatalysts. Benefiting from the formation of benzoxazole rings through reversible/irreversible cascade reactions, the synthesized COFs exhibit permanent stability in the presence of strong acid (9 M HCl), strong base (9 M NaOH), and sunlight. Meanwhile, reticulation of the benzoxazole moiety into the π-conjugated COF frameworks decreases the optical band gap and therefore increases the capability for visible-light absorption. As a result, the excellent photoactivity and unprecedented recyclability of LZU-190 (for at least 20 catalytic runs, each with a product yield of 99%) have been illustrated in the visible-light-driven oxidative hydroxylation of arylboronic acids to phenols. This contribution represents the first report on the photocatalytic application of benzoxazole-based structures, which not only sheds new light on the exploration of robust organophotocatalysts from small molecules to extended frameworks but also offers in-depth understanding of the structure-activity relationship toward practical applications of COF materials.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
A metal-free polymeric photocatalyst for hydrogen production from water under visible light
Wang, X., Maeda, K., Thomas, A., Takanabe, K., Xin, G., Carlsson, J. M., Domen, K., & Antonietti, M. (2009) · Nature Materials · doi:10.1038/nmat2317 · Cited by 12,532
Reticular synthesis and the design of new materials
Yaghi, O. M., O'Keeffe, M., Ockwig, N. W., Chae, H. K., Eddaoudi, M., & Kim, J. (2003) · Nature · doi:10.1038/nature01650 · Cited by 9,101
Porous, Crystalline, Covalent Organic Frameworks
Côté, A. P., Benin, A. I., Ockwig, N. W., O'Keeffe, M., Matzger, A. J., & Yaghi, O. M. (2005) · Science · doi:10.1126/science.1120411 · Cited by 8,357
Romero, N. A., & Nicewicz, D. A. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00057 · Cited by 6,283
Photophysics of aromatic molecules
Sharnoff, M. (1971) · Journal of Luminescence · doi:10.1016/0022-2313(71)90011-1 · Cited by 4,482
Covalent organic frameworks (COFs): from design to applications
Ding, S.-Y., & Wang, W. (2013) · Chem. Soc. Rev. · doi:10.1039/c2cs35072f · Cited by 4,020
Self-citationThe atom, the molecule, and the covalent organic framework
Diercks, C. S., & Yaghi, O. M. (2017) · Science · doi:10.1126/science.aal1585 · Cited by 3,482
Feng, X., Ding, X., & Jiang, D. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35157a · Cited by 3,098
Applications of metal–organic frameworks in heterogeneous supramolecular catalysis
Liu, J., Chen, L., Cui, H., Zhang, J., Zhang, L., & Su, C.-Y. (2014) · Chem. Soc. Rev. · doi:10.1039/c4cs00094c · Cited by 2,894
Covalent organic frameworks comprising cobalt porphyrins for catalytic CO 2 reduction in water
Lin, S., Diercks, C. S., Zhang, Y.-B., Kornienko, N., Nichols, E. M., Zhao, Y., Paris, A. R., Kim, D., Yang, P., Yaghi, O. M., et al. (2015) · Science · doi:10.1126/science.aac8343 · Cited by 2,644
Porous, Covalent Triazine‐Based Frameworks Prepared by Ionothermal Synthesis
Kuhn, P., Antonietti, M., & Thomas, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705710 · Cited by 2,634
Furukawa, H., & Yaghi, O. M. (2009) · Journal of the American Chemical Society · doi:10.1021/ja9015765 · Cited by 2,608
Rowan, S. J., Cantrill, S. J., Cousins, G. R. L., Sanders, J. K. M., & Stoddart, J. F. (2002) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20020315)41:6<898::aid-anie898>3.0.co;2-e · Cited by 2,588
Ding, S.-Y., Gao, J., Wang, Q., Zhang, Y., Song, W.-G., Su, C.-Y., & Wang, W. (2011) · Journal of the American Chemical Society · doi:10.1021/ja206846p · Cited by 2,443
Self-citationThe Reticular Chemistry Structure Resource (RCSR) Database of, and Symbols for, Crystal Nets
O’Keeffe, M., Peskov, M. A., Ramsden, S. J., & Yaghi, O. M. (2008) · Accounts of Chemical Research · doi:10.1021/ar800124u · Cited by 2,313
Kandambeth, S., Mallick, A., Lukose, B., Mane, M. V., Heine, T., & Banerjee, R. (2012) · Journal of the American Chemical Society · doi:10.1021/ja308278w · Cited by 2,156
Covalent organic frameworks: a materials platform for structural and functional designs
Huang, N., Wang, P., & Jiang, D. (2016) · Nature Reviews Materials · doi:10.1038/natrevmats.2016.68 · Cited by 2,017
Dynamic Combinatorial Chemistry
Corbett, P. T., Leclaire, J., Vial, L., West, K. R., Wietor, J.-L., Sanders, J. K. M., & Otto, S. (2006) · Chemical Reviews · doi:10.1021/cr020452p · Cited by 1,922
Multifunctional metal–organic framework catalysts: synergistic catalysis and tandem reactions
Huang, Y.-B., Liang, J., Wang, X.-S., & Cao, R. (2017) · Chemical Society Reviews · doi:10.1039/c6cs00250a · Cited by 1,908
Chemistry of Covalent Organic Frameworks
Waller, P. J., Gándara, F., & Yaghi, O. M. (2015) · Accounts of Chemical Research · doi:10.1021/acs.accounts.5b00369 · Cited by 1,897
Ruhland, K. (2020) · Catalysis from A to Z · doi:10.1002/9783527809080.cataz06077 · Cited by 1,724
Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts
Xu, H., Gao, J., & Jiang, D. (2015) · Nature Chemistry · doi:10.1038/nchem.2352 · Cited by 1,643
Wang, C., Xie, Z., deKrafft, K. E., & Lin, W. (2011) · Journal of the American Chemical Society · doi:10.1021/ja203564w · Cited by 1,547
Recent advances in dynamic covalent chemistry
Jin, Y., Yu, C., Denman, R. J., & Zhang, W. (2013) · Chemical Society Reviews · doi:10.1039/c3cs60044k · Cited by 1,487
Segura, J. L., Mancheño, M. J., & Zamora, F. (2016) · Chemical Society Reviews · doi:10.1039/c5cs00878f · Cited by 1,409
Sequential Transformations in Organic Chemistry: A Synthetic Strategy with a Future
Tietze, L. F., & Beifuss, U. (1993) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199301313 · Cited by 1,379
Two-dimensional sp 2 carbon–conjugated covalent organic frameworks
Jin, E., Asada, M., Xu, Q., Dalapati, S., Addicoat, M. A., Brady, M. A., Xu, H., Nakamura, T., Heine, T., Chen, Q., et al. (2017) · Science · doi:10.1126/science.aan0202 · Cited by 1,334
Porous Organic Materials: Strategic Design and Structure–Function Correlation
Das, S., Heasman, P., Ben, T., & Qiu, S. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00439 · Cited by 1,286
A tunable azine covalent organic framework platform for visible light-induced hydrogen generation
Vyas, V. S., Haase, F., Stegbauer, L., Savasci, G., Podjaski, F., Ochsenfeld, C., & Lotsch, B. V. (2015) · Nature Communications · doi:10.1038/ncomms9508 · Cited by 1,263
β-Ketoenamine-Linked Covalent Organic Frameworks Capable of Pseudocapacitive Energy Storage
DeBlase, C. R., Silberstein, K. E., Truong, T.-T., Abruña, H. D., & Dichtel, W. R. (2013) · Journal of the American Chemical Society · doi:10.1021/ja409421d · Cited by 1,249
Xu, H.-Q., Hu, J., Wang, D., Li, Z., Zhang, Q., Luo, Y., Yu, S.-H., & Jiang, H.-L. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b08773 · Cited by 1,166
A hydrazone-based covalent organic framework for photocatalytic hydrogen production
Stegbauer, L., Schwinghammer, K., & Lotsch, B. V. (2014) · Chem. Sci. · doi:10.1039/c4sc00016a · Cited by 1,145
Construction of Ultrastable Porphyrin Zr Metal–Organic Frameworks through Linker Elimination
Feng, D., Chung, W.-C., Wei, Z., Gu, Z.-Y., Jiang, H.-L., Chen, Y.-P., Darensbourg, D. J., & Zhou, H.-C. (2013) · Journal of the American Chemical Society · doi:10.1021/ja408084j · Cited by 1,126
Metal–organic and covalent organic frameworks as single-site catalysts
Rogge, S. M. J., Bavykina, A., Hajek, J., Garcia, H., Olivos-Suarez, A. I., Sepúlveda-Escribano, A., Vimont, A., Clet, G., Bazin, P., Kapteijn, F., et al. (2017) · Chemical Society Reviews · doi:10.1039/c7cs00033b · Cited by 1,077
3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery
Fang, Q., Wang, J., Gu, S., Kaspar, R. B., Zhuang, Z., Zheng, J., Guo, H., Qiu, S., & Yan, Y. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b04147 · Cited by 1,065
Campbell, M. G., Sheberla, D., Liu, S. F., Swager, T. M., & Dincă, M. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201411854 · Cited by 1,063
Rationally synthesized two-dimensional polymers
Colson, J. W., & Dichtel, W. R. (2013) · Nature Chemistry · doi:10.1038/nchem.1628 · Cited by 1,016
New Porous Crystals of Extended Metal-Catecholates
Hmadeh, M., Lu, Z., Liu, Z., Gándara, F., Furukawa, H., Wan, S., Augustyn, V., Chang, R., Liao, L., Zhou, F., et al. (2012) · Chemistry of Materials · doi:10.1021/cm301194a · Cited by 947
Diacetylene Functionalized Covalent Organic Framework (COF) for Photocatalytic Hydrogen Generation
Pachfule, P., Acharjya, A., Roeser, J., Langenhahn, T., Schwarze, M., Schomäcker, R., Thomas, A., & Schmidt, J. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.7b11255 · Cited by 909
A Belt‐Shaped, Blue Luminescent, and Semiconducting Covalent Organic Framework
Wan, S., Guo, J., Kim, J., Ihee, H., & Jiang, D. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200803826 · Cited by 880
Conjugated Polymers: Catalysts for Photocatalytic Hydrogen Evolution
Zhang, G., Lan, Z., & Wang, X. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201607375 · Cited by 864
Aerobic Oxidative Coupling of Amines by Carbon Nitride Photocatalysis with Visible Light
Su, F., Mathew, S. C., Möhlmann, L., Antonietti, M., Wang, X., & Blechert, S. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201004365 · Cited by 706
Guo, J., Xu, Y., Jin, S., Chen, L., Kaji, T., Honsho, Y., Addicoat, M. A., Kim, J., Saeki, A., Ihee, H., et al. (2013) · Nature Communications · doi:10.1038/ncomms3736 · Cited by 689
Modern Molecular Photochemistry of Organic Molecules
Turro, N. J., Ramamurthy, V., & Scaiano, J. C. (2012) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2012.01178.x · Cited by 686
Ionic Covalent Organic Frameworks with Spiroborate Linkage
Du, Y., Yang, H., Whiteley, J. M., Wan, S., Jin, Y., Lee, S., & Zhang, W. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201509014 · Cited by 674
Merging Visible Light Photoredox and Gold Catalysis
Hopkinson, M. N., Tlahuext-Aca, A., & Glorius, F. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00351 · Cited by 669
Covalent Triazine Frameworks via a Low‐Temperature Polycondensation Approach
Wang, K., Yang, L., Wang, X., Guo, L., Cheng, G., Zhang, C., Jin, S., Tan, B., & Cooper, A. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201708548 · Cited by 639
Weaving of organic threads into a crystalline covalent organic framework
Liu, Y., Ma, Y., Zhao, Y., Sun, X., Gándara, F., Furukawa, H., Liu, Z., Zhu, H., Zhu, C., Suenaga, K., et al. (2016) · Science · doi:10.1126/science.aad4011 · Cited by 616
Chemical Conversion of Linkages in Covalent Organic Frameworks
Waller, P. J., Lyle, S. J., Osborn Popp, T. M., Diercks, C. S., Reimer, J. A., & Yaghi, O. M. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b08377 · Cited by 604
Beuerle, F., & Gole, B. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201710190 · Cited by 528
Zou, Y., Chen, J., Liu, X., Lu, L., Davis, R. L., Jørgensen, K. A., & Xiao, W. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201107028 · Cited by 524
Homochiral 2D Porous Covalent Organic Frameworks for Heterogeneous Asymmetric Catalysis
Wang, X., Han, X., Zhang, J., Wu, X., Liu, Y., & Cui, Y. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b07714 · Cited by 524
3D Porphyrin-Based Covalent Organic Frameworks
Lin, G., Ding, H., Chen, R., Peng, Z., Wang, B., & Wang, C. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b04141 · Cited by 517
A two-dimensional conjugated polymer framework with fully sp2-bonded carbon skeleton
Zhuang, X., Zhao, W., Zhang, F., Cao, Y., Liu, F., Bi, S., & Feng, X. (2016) · Polymer Chemistry · doi:10.1039/c6py00561f · Cited by 506
Sun, Q., Aguila, B., Perman, J., Nguyen, N., & Ma, S. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b10629 · Cited by 487
Visible‐Light‐Driven Hydrogen Evolution Using Planarized Conjugated Polymer Photocatalysts
Sprick, R. S., Bonillo, B., Clowes, R., Guiglion, P., Brownbill, N. J., Slater, B. J., Blanc, F., Zwijnenburg, M. A., Adams, D. J., & Cooper, A. I. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201510542 · Cited by 468
Kambe, T., Sakamoto, R., Kusamoto, T., Pal, T., Fukui, N., Hoshiko, K., Shimojima, T., Wang, Z., Hirahara, T., Ishizaka, K., et al. (2014) · Journal of the American Chemical Society · doi:10.1021/ja507619d · Cited by 468
Self-citationCovalent Chemistry beyond Molecules
Jiang, J., Zhao, Y., & Yaghi, O. M. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.5b10666 · Cited by 448
Photoactive Chiral Metal–Organic Frameworks for Light-Driven Asymmetric α-Alkylation of Aldehydes
Wu, P., He, C., Wang, J., Peng, X., Li, X., An, Y., & Duan, C. (2012) · Journal of the American Chemical Society · doi:10.1021/ja305367j · Cited by 445
Conjugated Microporous Polymer Nanosheets for Overall Water Splitting Using Visible Light
Wang, L., Wan, Y., Ding, Y., Wu, S., Zhang, Y., Zhang, X., Zhang, G., Xiong, Y., Wu, X., Yang, J., et al. (2017) · Advanced Materials · doi:10.1002/adma.201702428 · Cited by 424
Self-citationTessellated multiporous two-dimensional covalent organic frameworks
Jin, Y., Hu, Y., & Zhang, W. (2017) · Nature Reviews Chemistry · doi:10.1038/s41570-017-0056 · Cited by 421
Banerjee, T., Haase, F., Savasci, G., Gottschling, K., Ochsenfeld, C., & Lotsch, B. V. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b07489 · Cited by 383
Conjugated Covalent Organic Frameworks via Michael Addition–Elimination
Rao, M. R., Fang, Y., De Feyter, S., & Perepichka, D. F. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.6b12005 · Cited by 374
Salen-Based Covalent Organic Framework
Li, L.-H., Feng, X.-L., Cui, X.-H., Ma, Y.-X., Ding, S.-Y., & Wang, W. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b01523 · Cited by 350
Self-citationCao, X., Zheng, B., Rui, X., Shi, W., Yan, Q., & Zhang, H. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201308013 · Cited by 335
Pang, Z.-F., Xu, S.-Q., Zhou, T.-Y., Liang, R.-R., Zhan, T.-G., & Zhao, X. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b01244 · Cited by 323
Pitre, S. P., McTiernan, C. D., Ismaili, H., & Scaiano, J. C. (2013) · Journal of the American Chemical Society · doi:10.1021/ja406311g · Cited by 290
Luo, J., Zhang, X., & Zhang, J. (2015) · ACS Catalysis · doi:10.1021/acscatal.5b00025 · Cited by 255
Covalent organic frameworks as metal-free heterogeneous photocatalysts for organic transformations
Zhi, Y., Li, Z., Feng, X., Xia, H., Zhang, Y., Shi, Z., Mu, Y., & Liu, X. (2017) · Journal of Materials Chemistry A · doi:10.1039/c7ta07691f · Cited by 232
Calik, M., Sick, T., Dogru, M., Döblinger, M., Datz, S., Budde, H., Hartschuh, A., Auras, F., & Bein, T. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.5b10708 · Cited by 208
Liu, W., Su, Q., Ju, P., Guo, B., Zhou, H., Li, G., & Wu, Q. (2017) · ChemSusChem · doi:10.1002/cssc.201601702 · Cited by 172
Pyles, D. A., Crowe, J. W., Baldwin, L. A., & McGrier, P. L. (2016) · ACS Macro Letters · doi:10.1021/acsmacrolett.6b00486 · Cited by 158
Photocatalytic metal–organic frameworks for the aerobic oxidation of arylboronic acids
Yu, X. H., & Cohen, S. M. (2015) · Chemical Communications · doi:10.1039/c5cc01697e · Cited by 146
Synthesis and Photophysical Properties of Some Benzoxazole and Benzothiazole Compounds
So, Y., Zaleski, J. M., Murlick, C. L., & Ellaboudy, A. S. (1996) · Macromolecules · doi:10.1021/ma951431i · Cited by 102
Cho, Y., Lee, C., Ha, D.-C., & Cheon, C. (2012) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201200684 · Cited by 94
Patel, H. A., Ko, D., & Yavuz, C. T. (2014) · Chemistry of Materials · doi:10.1021/cm503627p · Cited by 51
Ou, Z., Chen, J., Wang, X., Zhang, B., & Cao, Y. (2002) · New Journal of Chemistry · doi:10.1039/b202439j · Cited by 44
Bala, M., Verma, P. K., Sharma, D., Kumar, N., & Singh, B. (2015) · Molecular Diversity · doi:10.1007/s11030-015-9572-8 · Cited by 34
Cited by
Bulk COFs and COF nanosheets for electrochemical energy storage and conversion
Li, J., Jing, X., Li, Q., Li, S., Gao, X., Feng, X., & Wang, B. (2020) · Chemical Society Reviews · doi:10.1039/d0cs00017e · Cited by 1,152
Liu, R., Tan, K. T., Gong, Y., Chen, Y., Li, Z., Xie, S., He, T., Lu, Z., Yang, H., & Jiang, D. (2021) · Chemical Society Reviews · doi:10.1039/d0cs00620c · Cited by 1,083
Chen, R., Shi, J., Ma, Y., Lin, G., Lang, X., & Wang, C. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201902543 · Cited by 697
Conjugated polymers for visible-light-driven photocatalysis
Dai, C., & Liu, B. (2020) · Energy & Environmental Science · doi:10.1039/c9ee01935a · Cited by 687
New synthetic strategies toward covalent organic frameworks
Li, Y., Chen, W., Xing, G., Jiang, D., & Chen, L. (2020) · Chemical Society Reviews · doi:10.1039/d0cs00199f · Cited by 658
Metadata
- Authors
- Wei, P.-F., Qi, M.-Z., Wang, Z.-P., Ding, S.-Y., Yu, W., Liu, Q., Wang, L.-K., Wang, H.-Z., An, W.-K., & Wang, W.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2018-03-27
- Volume
- 140
- Issue
- 13
- Pages
- 4623-4631
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2795057659
- Cited by
- 771
- References
- 78
- FWCI
- 27.83
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.