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Visible light-induced reduction system of diphenylviologen derivative with water-soluble porphyrin for biocatalytic carbon–carbon bond formation from CO2

Authors
  • Katagiri, Takayuki1
  • Fujita, Kohei1
  • Ikeyama, Shusaku2
  • Amao, Yutaka1, 2, 3
  • 1 Graduate School of Science, Osaka City University, Sugimoto 3-3-138, Sumiyoshi-ku, Japan , (Japan)
  • 2 Advanced Research Institute for Natural Science and Technology, Osaka City University, Sugimoto 3-3-138, Sumiyoshi-ku, Japan , (Japan)
  • 3 Research Centre for Artificial Photosynthesis (ReCAP), Osaka City University, Sugimoto 3-3-138, Sumiyoshi-ku, Japan , (Japan)
Type
Published Article
Journal
Pure and Applied Chemistry
Publisher
Walter de Gruyter GmbH
Publication Date
Sep 03, 2018
Volume
90
Issue
11
Pages
1723–1733
Identifiers
DOI: 10.1515/pac-2018-0402
Source
De Gruyter
Keywords
License
Yellow

Abstract

From the view point of green chemistry, CO2 utilization technologies with solar energy including the photoredox system have been received a lot of attention. As one of them, photoredox system containing a photosensitizer and a catalyst catalyzing a reaction of a carbon–carbon bond formation from CO2 as a feed stock were constructed. In a recent study, we reported the visible light-induced malate (C4 compound) production from pyruvate (C3 compound) and CO2 due to carbon–carbon bond formation with the system consisting an electron donor, a photosensitizer, diphenylviologen (PV2+) derivative as an electron mediator in the presence of malic enzyme (ME). However, the interaction between a photosensitizer and PV2+ derivative has not been clarified yet. In this study, water-soluble PV2+ derivative, 1,1′-bis(p-sulfonatophenyl)-4,4′-bipyridinium salt (PSV2+) was synthesized, and its electro-, photochemical properties were evaluated. Moreover, the photoredox properties of PSV2+ with water-soluble Zn porphyrin were studied using fluorescence spectroscopy and steady state irradiation. The fluorescence of Zn porphyrin was quenched by PSV2+ and the two-electron reduced form of PSV2+ were produced with Zn porphyrin with steady state irradiation. In addition, reaction solution containing triethanolamine, tetraphenylporphyrin tetrasulfonate, pyruvate, ME, Mg2+ and PSV2+ in CO2 saturated bis-tris buffer (pH 7.4) was irradiated with visible light, the oxaloacetate and malate were produced. This result indicates that PSV2+ is an efficient electron mediator in the visible light-induced redox system for carbon–carbon bond formation with ME from CO2 as a feedstock.

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