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J Am Chem Soc. 2018 Apr 11;140(14):4778-4781. doi: 10.1021/jacs.8b01001. Epub 2018 Apr 2.

Exploiting Charge-Transfer States for Maximizing Intersystem Crossing Yields in Organic Photoredox Catalysts.

Author information

1
Department of Chemistry and Biochemistry , University of Colorado , Boulder , Colorado 80309 , United States.
2
Department of Chemistry , Colorado State University , Fort Collins , Colorado 80523 , United States.

Abstract

A key feature of prominent transition-metal-containing photoredox catalysts (PCs) is high quantum yield access to long-lived excited states characterized by a change in spin multiplicity. For organic PCs, challenges emerge for promoting excited-state intersystem crossing (ISC), particularly when potent excited-state reductants are desired. Herein, we report a design exploiting orthogonal π-systems and an intermediate-energy charge-transfer excited state to maximize ISC yields (ΦISC) in a highly reducing ( E0* = -1.7 V vs SCE), visible-light-absorbing phenoxazine-based PC. Simple substitution of N-phenyl for N-naphthyl is shown to dramatically increase ΦISC from 0.11 to 0.91 without altering catalytically important properties, such as E0*.

PMID:
29595966
PMCID:
PMC5920652
DOI:
10.1021/jacs.8b01001
[Indexed for MEDLINE]
Free PMC Article

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