Development of N-aryl phenoxazines as strongly reducing organic photoredox catalysts
Date
2020
Authors
McCarthy, Blaine Gould, author
Miyake, Garret, advisor
Bandar, Jeffrey, committee member
Krummel, Amber, committee member
James, Susan, committee member
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Abstract
N-aryl phenoxazines were identified as a new family of organic photoredox catalysts capable of effecting single electron transfer reductions from the photoexcited state. A number of phenoxazines bearing different N-aryl and core substituents were synthesized, characterized, and employed as catalysts. Spectroscopic and electrochemical characterization of these phenoxazines was used to establish structure-property relationships for the design of visible-light absorbing, strongly reducing organic photoredox catalysts. The application of phenoxazines as catalysts for organocatalyzed atom transfer radical polymerization (O-ATRP), a light-driven method for the synthesis of well-defined polymers, revealed the importance of several catalyst properties for achieving control over the polymerization. Investigation of the properties and catalytic performance of N-aryl phenoxazines has provided fundamental insight into the reactivity of organic excited state reductants and photophysical properties of organic molecules. The catalysts developed through this work provide sustainable alternatives to more commonly used precious-metal containing photoredox catalysts.
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Subject
photochemistry
polymer chemistry
photoredox catalysis
catalysis