Rational Synthesis of Interpenetrated 3D Covalent Organic Frameworks for Asymmetric Photocatalysis

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 4

PMID 34084378

Citations 11

Authors

Xing Kang

Xiaowei Wu

Xing Han

Chen Yuan

Yan Liu

Yong Cui

Affiliations

Soon will be listed here.

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 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.

Citing Articles

Photons, Excitons, and Electrons in Covalent Organic Frameworks.

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A Tailored COF for Visible-Light Photosynthesis of 2,3-Dihydrobenzofurans.

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References

Yan S, Guan X, Li H, Li D, Xue M, Yan Y . Three-dimensional Salphen-based Covalent-Organic Frameworks as Catalytic Antioxidants. J Am Chem Soc. 2019; 141(7):2920-2924. DOI: 10.1021/jacs.9b00485. View

Huang J, Han X, Yang S, Cao Y, Yuan C, Liu Y . Microporous 3D Covalent Organic Frameworks for Liquid Chromatographic Separation of Xylene Isomers and Ethylbenzene. J Am Chem Soc. 2019; 141(22):8996-9003. DOI: 10.1021/jacs.9b03075. View

Neumann M, Zeitler K . Application of microflow conditions to visible light photoredox catalysis. Org Lett. 2012; 14(11):2658-61. DOI: 10.1021/ol3005529. View

Wei H, Ning J, Cao X, Li X, Hao L . Benzotrithiophene-Based Covalent Organic Frameworks: Construction and Structure Transformation under Ionothermal Condition. J Am Chem Soc. 2018; 140(37):11618-11622. DOI: 10.1021/jacs.8b08282. View

Kang N, Park J, Ko K, Chun J, Kim E, Shin H . Tandem synthesis of photoactive benzodifuran moieties in the formation of microporous organic networks. Angew Chem Int Ed Engl. 2013; 52(24):6228-32. DOI: 10.1002/anie.201300655. View

Zhou T, Xu S, Wen Q, Pang Z, Zhao X . One-step construction of two different kinds of pores in a 2D covalent organic framework. J Am Chem Soc. 2014; 136(45):15885-8. DOI: 10.1021/ja5092936. View

Lyu H, Diercks C, Zhu C, Yaghi O . Porous Crystalline Olefin-Linked Covalent Organic Frameworks. J Am Chem Soc. 2019; 141(17):6848-6852. DOI: 10.1021/jacs.9b02848. View

Chen X, Addicoat M, Jin E, Zhai L, Xu H, Huang N . Locking covalent organic frameworks with hydrogen bonds: general and remarkable effects on crystalline structure, physical properties, and photochemical activity. J Am Chem Soc. 2015; 137(9):3241-7. DOI: 10.1021/ja509602c. View

Smith J, Jamhawi A, Jasinski J, Gallou F, Ge J, Advincula R . Organopolymer with dual chromophores and fast charge-transfer properties for sustainable photocatalysis. Nat Commun. 2019; 10(1):1837. PMC: 6478678. DOI: 10.1038/s41467-019-09316-5. View

10.

Yahiaoui O, Fitch A, Hoffmann F, Froba M, Thomas A, Roeser J . 3D Anionic Silicate Covalent Organic Framework with srs Topology. J Am Chem Soc. 2018; 140(16):5330-5333. DOI: 10.1021/jacs.8b01774. View

11.

Liu Y, Ma Y, Zhao Y, Sun X, Gandara F, Furukawa H . Weaving of organic threads into a crystalline covalent organic framework. Science. 2016; 351(6271):365-9. DOI: 10.1126/science.aad4011. View

12.

Condie A, Gonzalez-Gomez J, Stephenson C . Visible-light photoredox catalysis: aza-Henry reactions via C-H functionalization. J Am Chem Soc. 2010; 132(5):1464-5. DOI: 10.1021/ja909145y. View

13.

Shih H, Vander Wal M, Grange R, MacMillan D . Enantioselective α-benzylation of aldehydes via photoredox organocatalysis. J Am Chem Soc. 2010; 132(39):13600-3. PMC: 3056320. DOI: 10.1021/ja106593m. View

14.

Bessinger D, Ascherl L, Auras F, Bein T . Spectrally Switchable Photodetection with Near-Infrared-Absorbing Covalent Organic Frameworks. J Am Chem Soc. 2017; 139(34):12035-12042. PMC: 6400431. DOI: 10.1021/jacs.7b06599. View

15.

Zhang T, Guo X, Shi Y, He C, Duan C . Dye-incorporated coordination polymers for direct photocatalytic trifluoromethylation of aromatics at metabolically susceptible positions. Nat Commun. 2018; 9(1):4024. PMC: 6168478. DOI: 10.1038/s41467-018-05919-6. View

16.

Ning Z, Tian H . Triarylamine: a promising core unit for efficient photovoltaic materials. Chem Commun (Camb). 2009; (37):5483-95. DOI: 10.1039/b908802d. View

17.

Uribe-Romo F, Hunt J, Furukawa H, Klock C, OKeeffe M, Yaghi O . A crystalline imine-linked 3-D porous covalent organic framework. J Am Chem Soc. 2009; 131(13):4570-1. DOI: 10.1021/ja8096256. View

18.

Sprick R, Jiang J, Bonillo B, Ren S, Ratvijitvech T, Guiglion P . Tunable organic photocatalysts for visible-light-driven hydrogen evolution. J Am Chem Soc. 2015; 137(9):3265-70. DOI: 10.1021/ja511552k. View

19.

Feng X, Ding X, Jiang D . Covalent organic frameworks. Chem Soc Rev. 2012; 41(18):6010-22. DOI: 10.1039/c2cs35157a. View

20.

Liu Y, Diercks C, Ma Y, Lyu H, Zhu C, Alshmimri S . 3D Covalent Organic Frameworks of Interlocking 1D Square Ribbons. J Am Chem Soc. 2018; 141(1):677-683. DOI: 10.1021/jacs.8b12177. View