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Efficient Photoredox Cycles to Control Perylenediimide Self‐Assembly **
Author(s) -
Chen Chunfeng,
Valera Jorge S.,
Adachi Takuji B. M.,
Hermans Thomas M.
Publication year - 2023
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202202849
Subject(s) - photocatalysis , photochemistry , chemistry , ketyl , radical , electron transport chain , acetone , electron transfer , photoredox catalysis , organic chemistry , catalysis , biochemistry , benzophenone
Photoreduction of perylenediimide (PDI) derivatives has been widely studied for use in photocatalysis, hydrogen evolution, photo‐responsive gels, and organic semiconductors. Upon light irradiation, the radical anion (PDI⋅ − ) can readily be obtained, whereas further reduction to the dianion (PDI 2− ) is rare. Here we show that full 2‐electron photoreduction can be achieved using UVC light: 1) in anaerobic conditions by ‘direct photoreduction’ of PDI aggregates, or 2) by ‘indirect photoreduction’ in aerobic conditions due to acetone ketyl radicals. The latter strategy is also efficient for other dyes, such as naphthalenediimide (NDI) and methylviologen (MV 2+ ). Efficient photoreduction on the minute time‐scale using simple LED light in aerobic conditions is attractive for use in dissipative light‐driven systems and materials.