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Bodipy Derivatives as Organic Triplet Photosensitizers for Aerobic Photoorganocatalytic Oxidative Coupling of Amines and Photooxidation of Dihydroxylnaphthalenes
journal contribution
posted on 2013-06-07, 00:00 authored by Ling Huang, Jianzhang Zhao, Song Guo, Caishun Zhang, Jie MaWe used iodo-Bodipy derivatives that
show strong absorption of
visible light and long-lived triplet excited states as organic catalysts
for photoredox catalytic organic reactions. Conventionally most of
the photocatalysts are based on the off-the-shelf compounds, usually
showing weak absorption in the visible region and short triplet excited
state lifetimes. Herein, the organic catalysts are used for two photocatalyzed
reactions mediated by singlet oxygen (1O2),
that is, the aerobic oxidative coupling of amines and the photooxidation
of dihydroxylnaphthalenes, which is coupled to the subsequent addition
of amines to the naphthoquinones, via C–H functionalization
of 1,4-naphthoquinone, to produce N-aryl-2-amino-1,4-naphthoquinones
(one-pot reaction), which are anticancer and antibiotic reagents.
The photoreactions were substantially accelerated with these new iodo-Bodipy
organic photocatalysts compared to that catalyzed with the conventional
Ru(II)/Ir(III) complexes, which show weak absorption in the visible
region and short-lived triplet excited states. Our results will inspire
the design and application of new organic triplet photosensitizers
that show strong absorption of visible light and long-lived triplet
excited state and the application of these catalysts in photoredox
catalytic organic reactions.