Photoinduced Free Radical
Promoted Copper(I)-Catalyzed
Click Chemistry for Macromolecular Syntheses
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Abstract
Photoinduced copper(I)-catalyzed Huisgen 1,3-dipolar
cycloaddition
(CuAAC) via photoinduced electron transfer using free radical photoinitiators
has been developed as a new platform to serve as orthogonal click
system. Photoinitiators acting at near UV and visible range, namely
2, 2-dimethoxy-2-phenyl acetophenone, 2-benzyl-2-dimethylamino-4′-morpholino
butyrophenone, 2,4,6-trimethylbenzoyl)diphenylphosphine oxide, dicyclopentadienyl
bis[2,6-difluoro-3-(1-pyrrolyl)phenyl] titanium) and camphorquinone/benzyl
alcohol were tested with copper(II) chloride/<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>″,<i>N</i>″-pentamethyldiethylenetriamine complex to catalyze
the CuAAC via photoinduced electron transfer reaction. This strategy
has been applied in construction of various macromolecular architectures
including telechelic polymers and block copolymers. Spectroscopic
and chromatographic investigations revealed that successful macromolecular
syntheses have been achieved by this technique