Water-Soluble 3D Covalent Organic Framework that Displays an Enhanced Enrichment Effect of Photosensitizers and Catalysts for the Reduction of Protons to H2

Gao, Zhong-Zheng; Wang, Ze-Kun; Wei, Lei; Yin, Guangqiang; Tian, Jia; Liu, Chuan-Zhi; Wang, Hui; Zhang, Dan-Wei; Zhang, Yue-Biao; Li, Xiaopeng; Liu, Yi; Li, Zhan-Ting

doi:10.1021/acsami.9b19870

Title: Water-Soluble 3D Covalent Organic Framework that Displays an Enhanced Enrichment Effect of Photosensitizers and Catalysts for the Reduction of Protons to H₂

Journal Article · 01 December 2019 · ACS Applied Materials and Interfaces

DOI: https://doi.org/10.1021/acsami.9b19870 · OSTI ID:1599840

Gao, Zhong-Zheng ^[1]; Wang, Ze-Kun ^[1]; Wei, Lei ^[2]; Yin, Guangqiang ^[3]; Tian, Jia ^[1]; Liu, Chuan-Zhi ^[1]; Wang, Hui ^[1];

^[1];

^[2];

^[3];

^[4];

^[1]

Fudan Univ., Shanghai (China)
ShanghaiTech Univ. (China)
Univ. of South Florida, Tampa, FL (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry

Covalent organic frameworks (COFs) are emerging porous polymers that have 2D or 3D long-range ordering. Currently available COFs are typically insoluble or decompose upon dissolution, which remarkably restricts their practical implementations. For 3D COFs, the achievement of noninterpenetration, which maximizes their porosity-derived applications, also remains a challenge synthetically. Here, we report the synthesis of the first highly water-soluble 3D COF (sCOF-101) from irreversible polymerization of a preorganized supramolecular organic framework through cucurbit[8]uril (CB[8])-controlled [2 + 2] photodimerization. Synchrotron X-ray scattering and diffraction analyses confirm that sCOF-101 exhibits porosity periodicity, with a channel diameter of 2.3 nm, in both water and the solid state and retains the periodicity under both strongly acidic and basic conditions. As an ordered 3D polymer, sCOF-101 can enrich [Ru(bpy)₃]²⁺ photosensitizers and redox-active polyoxometalates in water, which leads to remarkable increase of their photocatalytic activity for proton reduction to produce H2.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: National Institute of General Medical Sciences; National Natural Science Foundation of China (NNSFC); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Scientific User Facilities Division (SC-22.3)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1599840

Journal Information:: ACS Applied Materials and Interfaces, Journal Name: ACS Applied Materials and Interfaces Journal Issue: 1 Vol. 12; ISSN 1944-8244

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (55)

Graphene-Like Single-Layered Covalent Organic Frameworks: Synthesis Strategies and Application Prospects Liu, Xuan-He; Guan, Cui-Zhong; Wang, Dong Advanced Materials, Vol. 26, Issue 40 https://doi.org/10.1002/adma.201305317	journal	February 2014
Opportunities of Covalent Organic Frameworks for Advanced Applications Song, Yanpei; Sun, Qi; Aguila, Briana Advanced Science, Vol. 6, Issue 2 https://doi.org/10.1002/advs.201801410	journal	November 2018
Porous, Covalent Triazine-Based Frameworks Prepared by Ionothermal Synthesis Kuhn, Pierre; Antonietti, Markus; Thomas, Arne Angewandte Chemie International Edition, Vol. 47, Issue 18 https://doi.org/10.1002/anie.200705710	journal	April 2008
An Olefin‐Linked Covalent Organic Framework as a Flexible Thin‐Film Electrode for a High‐Performance Micro‐Supercapacitor Xu, Junsong; He, Yafei; Bi, Shuai Angewandte Chemie International Edition, Vol. 58, Issue 35 https://doi.org/10.1002/anie.201905713	journal	August 2019
Vinylene‐Linked Covalent Organic Frameworks by Base‐Catalyzed Aldol Condensation Acharjya, Amitava; Pachfule, Pradip; Roeser, Jérôme Angewandte Chemie International Edition, Vol. 58, Issue 42 https://doi.org/10.1002/anie.201905886	journal	September 2019
How to Make Weak Noncovalent Interactions Stronger Xu, Jiang-Fei; Chen, Linghui; Zhang, Xi Chemistry - A European Journal, Vol. 21, Issue 34 https://doi.org/10.1002/chem.201500568	journal	June 2015
Enhancing Hydrogen Generation Through Nanoconfinement of Sensitizers and Catalysts in a Homogeneous Supramolecular Organic Framework Yu, Shang-Bo; Qi, Qi; Yang, Bo Small, Vol. 14, Issue 24 https://doi.org/10.1002/smll.201801037	journal	May 2018
Assemblies of covalent organic framework microcrystals: multiple-dimensional manipulation for enhanced applications Yuan, Fuyu; Tan, Jing; Guo, Jia Science China Chemistry, Vol. 61, Issue 2 https://doi.org/10.1007/s11426-017-9162-3	journal	January 2018
A stable metal-covalent-supramolecular organic framework hybrid: enrichment of catalysts for visible light-induced hydrogen production Li, Xiong-Fei; Yu, Shang-Bo; Yang, Bo Science China Chemistry, Vol. 61, Issue 7 https://doi.org/10.1007/s11426-018-9234-2	journal	April 2018
Controllable macrocyclic supramolecular assemblies in aqueous solution Chen, Yong; Huang, Feihe; Li, Zhan-Ting Science China Chemistry, Vol. 61, Issue 8 https://doi.org/10.1007/s11426-018-9337-4	journal	July 2018
The art of two-dimensional soft nanomaterials Zheng, Caini; Zhu, Jinhui; Yang, Chongqing Science China Chemistry, Vol. 62, Issue 9 https://doi.org/10.1007/s11426-019-9477-y	journal	June 2019
Applications of covalent organic frameworks (COFs): From gas storage and separation to drug delivery Wu, Ming-Xue; Yang, Ying-Wei Chinese Chemical Letters, Vol. 28, Issue 6 https://doi.org/10.1016/j.cclet.2017.03.026	journal	June 2017
Cucurbit[10]uril-based chemistry Yang, Xiran; Liu, Fengbo; Zhao, Zhiyong Chinese Chemical Letters, Vol. 29, Issue 11 https://doi.org/10.1016/j.cclet.2018.01.032	journal	November 2018
Ruthenium(II)-cored supramolecular organic framework-mediated recyclable visible light photoreduction of azides to amines and cascade formation of lactams Wu, Yi-Peng; Yan, Meng; Gao, Zhong-Zheng Chinese Chemical Letters, Vol. 30, Issue 7 https://doi.org/10.1016/j.cclet.2019.03.056	journal	July 2019
Interface-Assisted Synthesis of 2D Materials: Trend and Challenges Dong, Renhao; Zhang, Tao; Feng, Xinliang Chemical Reviews, Vol. 118, Issue 13 https://doi.org/10.1021/acs.chemrev.8b00056	journal	June 2018
Predesigned Metal-Anchored Building Block for In Situ Generation of Pd Nanoparticles in Porous Covalent Organic Framework: Application in Heterogeneous Tandem Catalysis Bhadra, Mohitosh; Sasmal, Himadri Sekhar; Basu, Arghya ACS Applied Materials & Interfaces, Vol. 9, Issue 15 https://doi.org/10.1021/acsami.7b02355	journal	April 2017
Functional π-Conjugated Two-Dimensional Covalent Organic Frameworks Babu, H. Vignesh; Bai, M. G. Monika; Rajeswara Rao, M. ACS Applied Materials & Interfaces, Vol. 11, Issue 12 https://doi.org/10.1021/acsami.8b19087	journal	February 2019
Trends in Solid Adsorbent Materials Development for CO ₂ Capture Pardakhti, Maryam; Jafari, Tahereh; Tobin, Zachary ACS Applied Materials & Interfaces, Vol. 11, Issue 38 https://doi.org/10.1021/acsami.9b08487	journal	June 2019
Covalent Organic Frameworks as a Platform for Multidimensional Polymerization Bisbey, Ryan P.; Dichtel, William R. ACS Central Science, Vol. 3, Issue 6 https://doi.org/10.1021/acscentsci.7b00127	journal	May 2017
Synthesis of Benzobisoxazole-Linked Two-Dimensional Covalent Organic Frameworks and Their Carbon Dioxide Capture Properties Pyles, David A.; Crowe, Jonathan W.; Baldwin, Luke A. ACS Macro Letters, Vol. 5, Issue 9 https://doi.org/10.1021/acsmacrolett.6b00486	journal	August 2016
Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry Lee, Jae Wook; Samal, S.; Selvapalam, N. Accounts of Chemical Research, Vol. 36, Issue 8 https://doi.org/10.1021/ar020254k	journal	August 2003
Multivalency and Cooperativity in Supramolecular Chemistry Badjić, Jovica D.; Nelson, Alshakim; Cantrill, Stuart J. Accounts of Chemical Research, Vol. 38, Issue 9 https://doi.org/10.1021/ar040223k	journal	September 2005
Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki–Miyaura Coupling Reaction Ding, San-Yuan; Gao, Jia; Wang, Qiong Journal of the American Chemical Society, Vol. 133, Issue 49 https://doi.org/10.1021/ja206846p	journal	December 2011
Bulk Synthesis of Exfoliated Two-Dimensional Polymers Using Hydrazone-Linked Covalent Organic Frameworks Bunck, David N.; Dichtel, William R. Journal of the American Chemical Society, Vol. 135, Issue 40 https://doi.org/10.1021/ja408243n	journal	September 2013
A Crystalline Imine-Linked 3-D Porous Covalent Organic Framework Uribe-Romo, Fernando J.; Hunt, Joseph R.; Furukawa, Hiroyasu Journal of the American Chemical Society, Vol. 131, Issue 13, p. 4570-4571 https://doi.org/10.1021/ja8096256	journal	April 2009
Homogeneous Light-Driven Water Oxidation Catalyzed by a Tetraruthenium Complex with All Inorganic Ligands Geletii, Yurii V.; Huang, Zhuangqun; Hou, Yu Journal of the American Chemical Society, Vol. 131, Issue 22, p. 7522-7523 https://doi.org/10.1021/ja901373m	journal	June 2009
3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery Fang, Qianrong; Wang, Junhua; Gu, Shuang Journal of the American Chemical Society, Vol. 137, Issue 26 https://doi.org/10.1021/jacs.5b04147	journal	June 2015
A Dynamic Three-Dimensional Covalent Organic Framework Ma, Yun-Xiang; Li, Zhi-Jun; Wei, Lei Journal of the American Chemical Society, Vol. 139, Issue 14 https://doi.org/10.1021/jacs.7b01097	journal	March 2017
Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis Wei, Pi-Feng; Qi, Ming-Zhu; Wang, Zhi-Peng Journal of the American Chemical Society, Vol. 140, Issue 13 https://doi.org/10.1021/jacs.8b00571	journal	March 2018
Conversion of Imine to Oxazole and Thiazole Linkages in Covalent Organic Frameworks Waller, Peter J.; AlFaraj, Yasmeen S.; Diercks, Christian S. Journal of the American Chemical Society, Vol. 140, Issue 29 https://doi.org/10.1021/jacs.8b05830	journal	June 2018
Crystalline Dioxin-Linked Covalent Organic Frameworks from Irreversible Reactions Zhang, Bing; Wei, Mufeng; Mao, Haiyan Journal of the American Chemical Society, Vol. 140, Issue 40 https://doi.org/10.1021/jacs.8b08374	journal	September 2018
Covalent Organic Frameworks: Chemistry beyond the Structure Kandambeth, Sharath; Dey, Kaushik; Banerjee, Rahul Journal of the American Chemical Society, Vol. 141, Issue 5 https://doi.org/10.1021/jacs.8b10334	journal	November 2018
Guest-Dependent Dynamics in a 3D Covalent Organic Framework Chen, Yichong; Shi, Zhao-Lin; Wei, Lei Journal of the American Chemical Society, Vol. 141, Issue 7 https://doi.org/10.1021/jacs.8b13691	journal	January 2019
Porous Crystalline Olefin-Linked Covalent Organic Frameworks Lyu, Hao; Diercks, Christian S.; Zhu, Chenhui Journal of the American Chemical Society, Vol. 141, Issue 17 https://doi.org/10.1021/jacs.9b02848	journal	April 2019
Semiconducting 2D Triazine-Cored Covalent Organic Frameworks with Unsubstituted Olefin Linkages Wei, Shice; Zhang, Fan; Zhang, Wenbei Journal of the American Chemical Society, Vol. 141, Issue 36 https://doi.org/10.1021/jacs.9b06219	journal	August 2019
Three-Dimensional Tetrathiafulvalene-Based Covalent Organic Frameworks for Tunable Electrical Conductivity Li, Hui; Chang, Jianhong; Li, Shanshan Journal of the American Chemical Society, Vol. 141, Issue 34 https://doi.org/10.1021/jacs.9b06908	journal	August 2019
Conjugated organic framework with three-dimensionally ordered stable structure and delocalized π clouds Guo, Jia; Xu, Yanhong; Jin, Shangbin Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3736	journal	November 2013
Three-dimensional periodic supramolecular organic framework ion sponge in water and microcrystals Tian, Jia; Zhou, Tian-You; Zhang, Shao-Chen Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6574	journal	December 2014
A tunable azine covalent organic framework platform for visible light-induced hydrogen generation Vyas, Vijay S.; Haase, Frederik; Stegbauer, Linus Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms9508	journal	September 2015
Chemically stable polyarylether-based covalent organic frameworks Guan, Xinyu; Li, Hui; Ma, Yunchao Nature Chemistry, Vol. 11, Issue 6 https://doi.org/10.1038/s41557-019-0238-5	journal	April 2019
Tessellated multiporous two-dimensional covalent organic frameworks Jin, Yinghua; Hu, Yiming; Zhang, Wei Nature Reviews Chemistry, Vol. 1, Issue 7 https://doi.org/10.1038/s41570-017-0056	journal	July 2017
A facile, stereoselective [2 + 2] photoreaction mediated by cucurbit[8]uril Jon, Sang Yong; Ko, Young Ho; Park, Sang Hyun Chemical Communications, Issue 19 https://doi.org/10.1039/b105153a	journal	January 2001
Semiconducting polymers: the Third Generation Heeger, Alan J. Chemical Society Reviews, Vol. 39, Issue 7 https://doi.org/10.1039/b914956m	journal	January 2010
Covalent organic frameworks (COFs): from design to applications Ding, San-Yuan; Wang, Wei Chem. Soc. Rev., Vol. 42, Issue 2 https://doi.org/10.1039/c2cs35072f	journal	January 2013
Covalent organic frameworks Feng, Xiao; Ding, Xuesong; Jiang, Donglin Chemical Society Reviews, Vol. 41, Issue 18 https://doi.org/10.1039/c2cs35157a	journal	January 2012
A hydrazone-based covalent organic framework for photocatalytic hydrogen production Stegbauer, Linus; Schwinghammer, Katharina; Lotsch, Bettina V. Chem. Sci., Vol. 5, Issue 7 https://doi.org/10.1039/c4sc00016a	journal	January 2014
Solid-state polymerisation via [2+2] cycloaddition reaction involving coordination polymers Medishetty, Raghavender; Park, In-Hyeok; Lee, Shim Sung Chemical Communications, Vol. 52, Issue 21 https://doi.org/10.1039/c5cc08374e	journal	January 2016
Covalent organic frameworks based on Schiff-base chemistry: synthesis, properties and potential applications Segura, José L.; Mancheño, María J.; Zamora, Félix Chemical Society Reviews, Vol. 45, Issue 20 https://doi.org/10.1039/c5cs00878f	journal	January 2016
A mechanochemically synthesized covalent organic framework as a proton-conducting solid electrolyte Shinde, Digambar Balaji; Aiyappa, Harshitha Barike; Bhadra, Mohitosh Journal of Materials Chemistry A, Vol. 4, Issue 7 https://doi.org/10.1039/c5ta10521h	journal	January 2016
Heteropore covalent organic frameworks: a new class of porous organic polymers with well-ordered hierarchical porosities Liang, Rong-Ran; Zhao, Xin Organic Chemistry Frontiers, Vol. 5, Issue 22 https://doi.org/10.1039/c8qo00830b	journal	January 2018
Photoreaction-driven two-dimensional periodic polyrotaxane-type supramolecular nanoarchitecture Zhang, Cai-Cai; Zhang, Ying-Ming; Zhang, Zhi-Yuan Chemical Communications, Vol. 55, Issue 56 https://doi.org/10.1039/c9cc03705e	journal	January 2019
A pore-expanded supramolecular organic framework and its enrichment of photosensitizers and catalysts for visible-light-induced hydrogen production Yan, Meng; Liu, Xu-Bo; Gao, Zhong-Zheng Organic Chemistry Frontiers, Vol. 6, Issue 10 https://doi.org/10.1039/c9qo00382g	journal	January 2019
Supramolecular organic frameworks (SOFs): homogeneous regular 2D and 3D pores in water Tian, Jia; Wang, Hui; Zhang, Dan-Wei National Science Review, Vol. 4, Issue 3 https://doi.org/10.1093/nsr/nwx030	journal	March 2017
Porous, Crystalline, Covalent Organic Frameworks Côté, Adrien P.; Benin, Annabelle I.; Ockwig, Nathan W. Science, Vol. 310, Issue 5751, p. 1166-1170 https://doi.org/10.1126/science.1120411	journal	November 2005
Single-crystal x-ray diffraction structures of covalent organic frameworks Ma, Tianqiong; Kapustin, Eugene A.; Yin, Shawn X. Science, Vol. 361, Issue 6397 https://doi.org/10.1126/science.aat7679	journal	July 2018

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Title: Water-Soluble 3D Covalent Organic Framework that Displays an Enhanced Enrichment Effect of Photosensitizers and Catalysts for the Reduction of Protons to H2

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Title: Water-Soluble 3D Covalent Organic Framework that Displays an Enhanced Enrichment Effect of Photosensitizers and Catalysts for the Reduction of Protons to H₂