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Rational synthesis of interpenetrated 3D covalent organic frameworks for asymmetric photocatalysis

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Abstract

Covalent organic frameworks (COFs) show great promise as heterogeneous photocatalysts, but they have not yet been explored for asymmetric photocatalysis, which is important for the sustainable production of pharmaceuticals and fine chemicals. We report here a pair of twofold interpenetrated 3D COFs adopting a rare (3,4)-connected ffc topology for photocatalytic asymmetric reactions by imine condensation of rectangular and trigonal building blocks. Both COFs containing a photoredox triphenylamine moiety are efficient photocatalysts for the cross-dehydrogenative coupling reactions and asymmetric α-alkylation of aldehydes integrated with a chiral imidazolidinone catalyst. Under visible-light irradiation, the targeted chiral products are produced in satisfactory yields with up to 94% enantiomeric excess, which are comparable to those of reported reactions using molecular metal complexes or organic dyes as photosensitizers. Whereas the COFs became amorphous after catalysis, they can be recrystallized through solvent-assisted linker exchange and reused without performance loss. This is the first report utilizing COFs as photocatalysts to promote enantioselective photochemical reactions.

Graphical abstract: Rational synthesis of interpenetrated 3D covalent organic frameworks for asymmetric photocatalysis

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Supplementary files

Article information


Submitted
27 Sep 2019
Accepted
17 Dec 2019
First published
19 Dec 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Rational synthesis of interpenetrated 3D covalent organic frameworks for asymmetric photocatalysis

X. Kang, X. Wu, X. Han, C. Yuan, Y. Liu and Y. Cui, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04882K

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