Two-dimensional semiconducting covalent organic frameworks via condensation at arylmethyl carbon atoms

Shuai Bi; Can Yang; Wenbei Zhang; Junsong Xu; Lingmei Liu; Dongqing Wu; Xinchen Wang; Yu Han; Qifeng Liang; Fan Zhang

doi:10.1038/s41467-019-10504-6

Two-dimensional semiconducting covalent organic frameworks via condensation at arylmethyl carbon atoms

Shuai Bi, Can Yang, Wenbei Zhang, Junsong Xu, Lingmei Liu, Dongqing Wu, Xinchen Wang, Yu Han, Qifeng Liang, Fan Zhang

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Abstract

Construction of organic semiconducting materials with in-plane π-conjugated structures and robustness through carbon-carbon bond linkages, alternatively as organic graphene analogs, is extremely desired for powerfully optoelectrical conversion. However, the poor reversibility for sp2 carbon bond forming reactions makes them unavailable for building high crystalline well-defined organic structures through a self-healing process, such as covalent organic frameworks (COFs). Here we report a scalable solution-processing approach to synthesize a family of two-dimensional (2D) COFs with trans-disubstituted C = C linkages via condensation reaction at arylmethyl carbon atoms on the basis of 3,5-dicyano-2,4,6-trimethylpyridine and linear/trigonal aldehyde (i.e., 4,4″-diformyl-p-terphenyl, 4,4′-diformyl-1,1′-biphenyl, or 1,3,5-tris(4-formylphenyl)benzene) monomers. Such sp2 carbon-jointed-pyridinyl frameworks, featuring crystalline honeycomb-like structures with high surface areas, enable driving two half-reactions of water splitting separately under visible light irradiation, comparable to graphitic carbon nitride (g-C3N4) derivatives.

Original language	English (US)
Journal	Nature Communications
Volume	10
Issue number	1
DOIs	https://doi.org/10.1038/s41467-019-10504-6
State	Published - Jun 6 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We thank Shanghai Committee of Science and Technology for financial support within the project 16JC1400703. Furthermore, this work was financially supported by National Natural Science Foundation of China (21720102002, 21774072, 21574080, 21425309, 21761132002, 21861130353, and 21802022), the National Key Technologies R&D Program of China (2018YFA0209301) and the 111 Project (D16008). Open Project Program of the State Key Laboratory of Inorganic Synthesis and Preparative Chemistry (2019-01, Jilin University). S.B. acknowledges the Instrumental Analysis Center of SJTU for the NMR measurements. We thank Professor Feng Liu for his precious help.

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10.1038/s41467-019-10504-6

https://repository.kaust.edu.sa/bitstream/10754/656245/1/s41467-019-10504-6.pdf

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title = "Two-dimensional semiconducting covalent organic frameworks via condensation at arylmethyl carbon atoms",

abstract = "Construction of organic semiconducting materials with in-plane π-conjugated structures and robustness through carbon-carbon bond linkages, alternatively as organic graphene analogs, is extremely desired for powerfully optoelectrical conversion. However, the poor reversibility for sp2 carbon bond forming reactions makes them unavailable for building high crystalline well-defined organic structures through a self-healing process, such as covalent organic frameworks (COFs). Here we report a scalable solution-processing approach to synthesize a family of two-dimensional (2D) COFs with trans-disubstituted C = C linkages via condensation reaction at arylmethyl carbon atoms on the basis of 3,5-dicyano-2,4,6-trimethylpyridine and linear/trigonal aldehyde (i.e., 4,4″-diformyl-p-terphenyl, 4,4′-diformyl-1,1′-biphenyl, or 1,3,5-tris(4-formylphenyl)benzene) monomers. Such sp2 carbon-jointed-pyridinyl frameworks, featuring crystalline honeycomb-like structures with high surface areas, enable driving two half-reactions of water splitting separately under visible light irradiation, comparable to graphitic carbon nitride (g-C3N4) derivatives.",

author = "Shuai Bi and Can Yang and Wenbei Zhang and Junsong Xu and Lingmei Liu and Dongqing Wu and Xinchen Wang and Yu Han and Qifeng Liang and Fan Zhang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Shanghai Committee of Science and Technology for financial support within the project 16JC1400703. Furthermore, this work was financially supported by National Natural Science Foundation of China (21720102002, 21774072, 21574080, 21425309, 21761132002, 21861130353, and 21802022), the National Key Technologies R&D Program of China (2018YFA0209301) and the 111 Project (D16008). Open Project Program of the State Key Laboratory of Inorganic Synthesis and Preparative Chemistry (2019-01, Jilin University). S.B. acknowledges the Instrumental Analysis Center of SJTU for the NMR measurements. We thank Professor Feng Liu for his precious help.",

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doi = "10.1038/s41467-019-10504-6",

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T1 - Two-dimensional semiconducting covalent organic frameworks via condensation at arylmethyl carbon atoms

AU - Bi, Shuai

AU - Yang, Can

AU - Zhang, Wenbei

AU - Xu, Junsong

AU - Liu, Lingmei

AU - Wu, Dongqing

AU - Wang, Xinchen

AU - Han, Yu

AU - Liang, Qifeng

AU - Zhang, Fan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Shanghai Committee of Science and Technology for financial support within the project 16JC1400703. Furthermore, this work was financially supported by National Natural Science Foundation of China (21720102002, 21774072, 21574080, 21425309, 21761132002, 21861130353, and 21802022), the National Key Technologies R&D Program of China (2018YFA0209301) and the 111 Project (D16008). Open Project Program of the State Key Laboratory of Inorganic Synthesis and Preparative Chemistry (2019-01, Jilin University). S.B. acknowledges the Instrumental Analysis Center of SJTU for the NMR measurements. We thank Professor Feng Liu for his precious help.

PY - 2019/6/6

Y1 - 2019/6/6

N2 - Construction of organic semiconducting materials with in-plane π-conjugated structures and robustness through carbon-carbon bond linkages, alternatively as organic graphene analogs, is extremely desired for powerfully optoelectrical conversion. However, the poor reversibility for sp2 carbon bond forming reactions makes them unavailable for building high crystalline well-defined organic structures through a self-healing process, such as covalent organic frameworks (COFs). Here we report a scalable solution-processing approach to synthesize a family of two-dimensional (2D) COFs with trans-disubstituted C = C linkages via condensation reaction at arylmethyl carbon atoms on the basis of 3,5-dicyano-2,4,6-trimethylpyridine and linear/trigonal aldehyde (i.e., 4,4″-diformyl-p-terphenyl, 4,4′-diformyl-1,1′-biphenyl, or 1,3,5-tris(4-formylphenyl)benzene) monomers. Such sp2 carbon-jointed-pyridinyl frameworks, featuring crystalline honeycomb-like structures with high surface areas, enable driving two half-reactions of water splitting separately under visible light irradiation, comparable to graphitic carbon nitride (g-C3N4) derivatives.

AB - Construction of organic semiconducting materials with in-plane π-conjugated structures and robustness through carbon-carbon bond linkages, alternatively as organic graphene analogs, is extremely desired for powerfully optoelectrical conversion. However, the poor reversibility for sp2 carbon bond forming reactions makes them unavailable for building high crystalline well-defined organic structures through a self-healing process, such as covalent organic frameworks (COFs). Here we report a scalable solution-processing approach to synthesize a family of two-dimensional (2D) COFs with trans-disubstituted C = C linkages via condensation reaction at arylmethyl carbon atoms on the basis of 3,5-dicyano-2,4,6-trimethylpyridine and linear/trigonal aldehyde (i.e., 4,4″-diformyl-p-terphenyl, 4,4′-diformyl-1,1′-biphenyl, or 1,3,5-tris(4-formylphenyl)benzene) monomers. Such sp2 carbon-jointed-pyridinyl frameworks, featuring crystalline honeycomb-like structures with high surface areas, enable driving two half-reactions of water splitting separately under visible light irradiation, comparable to graphitic carbon nitride (g-C3N4) derivatives.

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UR - http://www.nature.com/articles/s41467-019-10504-6

UR - http://www.scopus.com/inward/record.url?scp=85066975301&partnerID=8YFLogxK

U2 - 10.1038/s41467-019-10504-6

DO - 10.1038/s41467-019-10504-6

M3 - Article

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SN - 2041-1723

VL - 10

JO - Nature Communications

JF - Nature Communications

IS - 1

ER -

Two-dimensional semiconducting covalent organic frameworks via condensation at arylmethyl carbon atoms

Abstract

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