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Fast photochromic sterically hindered benzo[1,3]oxazines

Paper ID Volume ID Publish Year Pages File Format Full-Text
28857 44097 2010 7 PDF Available
Title
Fast photochromic sterically hindered benzo[1,3]oxazines
Abstract

A series of new substituted benzo[1,3]oxazines presenting bulky substituents on the chiral oxazine centre were prepared from isopropyl ketones or substituted cyclohexanones. Laser irradiation of these uncoloured compounds in solution promotes the cleavage of the C–O bond and the opening of the [1,3]oxazine ring generating a zwitterionic species, incorporating a 3H-indolium cation and a 4-nitrophenolate anion, that absorbs strongly at 440 nm. The photogenerated coloured open isomers are thermally unstable and revert to the initial closed form with first order kinetics and lifetimes ranging from 13 to 68 ns. These photochromic switches are extraordinarily stable displaying no significant degradation upon repetition of various irradiation/dark cycles.

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Keywords
Photochromism; Oxazines; Photoswitches; Laser flash photolysis; Zwitterion; Indoles
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Fast photochromic sterically hindered benzo[1,3]oxazines
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 216, Issue 1, 15 November 2010, Pages 59–65
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Price was $35.95
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