Jump to main content
Jump to site search


Designing conjugated microporous polymers for visible light-promoted photocatalytic carbon–carbon double bond cleavage in aqueous medium

Author affiliations

Abstract

The production of valuable carbonyl compounds directly from alkenes via carbon–carbon double (C[double bond, length as m-dash]C) bond cleavage is a highly important reaction. As a promising alternative to traditional metal-catalyzed thermal reaction conditions, photocatalysis offers an environmentally friendly and sustainable synthetic strategy. However, most photocatalysts used so far were homogeneous, molecular and transition metal-based catalytic systems. Here, we report a structural design strategy of conjugated microporous polymers (CMPs) as a class of metal-free, heterogeneous, stable and reusable photocatalysts for visible light-promoted C[double bond, length as m-dash]C bond cleavage reaction. Via different electron donor and acceptor combinations in the CMP backbone structure, we systematically investigated the structural influence of the CMPs on their optical and electrochemical properties, thereby revealing the structure and performance relationship in the photocatalytic C[double bond, length as m-dash]C bond cleavage reaction. As a result, the CMP with a specific electron donor–acceptor combination containing benzothiazole as a strong electron withdrawing unit and phenyl as a weak electron donating unit was the most efficient photocatalyst. The C[double bond, length as m-dash]C bond in various alkenes, mostly styrene derivatives, could be successfully cleaved, forming aldehydes as a product with high conversion and moderate to high selectivity. The green aspect of the work is demonstrated by the utilization of visible-light, molecular oxygen as a cheap oxidant and water-based reaction medium.

Graphical abstract: Designing conjugated microporous polymers for visible light-promoted photocatalytic carbon–carbon double bond cleavage in aqueous medium

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Jun 2018, accepted on 08 Aug 2018 and first published on 08 Aug 2018


Article type: Paper
DOI: 10.1039/C8TA05772A
Citation: J. Mater. Chem. A, 2018, Advance Article
  • Open access: Creative Commons BY license
  •   Request permissions

    Designing conjugated microporous polymers for visible light-promoted photocatalytic carbon–carbon double bond cleavage in aqueous medium

    C. Ayed, L. Caire da Silva, D. Wang and K. A. I. Zhang, J. Mater. Chem. A, 2018, Advance Article , DOI: 10.1039/C8TA05772A

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements