A fast and stable photochromic switch based on the opening and closing of an oxazine ring

Massimiliano Tomasulo; Salvatore Sortino; Françisco M. Raymo

doi:10.1021/ol050045a

A fast and stable photochromic switch based on the opening and closing of an oxazine ring

Massimiliano Tomasulo, Salvatore Sortino, Françisco M. Raymo

Chemistry

Research output: Contribution to journal › Article › peer-review

105 Scopus citations

Abstract

(Chemical Equation Presented) We have designed a molecular switch based on the photoinduced opening and thermal closing of an oxazine ring. Ultraviolet excitation of this molecule induces the cleavage of a [C-O] bond to form a p-nitrophenolate chromophore in less than 10 ns with a quantum yield of ca. 0.1. The photogenerated isomer reverts thermally to the original oxazine within 50 ns. Our photochromic switch survives more than 3000 excitation cycles without decomposing, even in air-saturated solutions.

Original language	English (US)
Pages (from-to)	1109-1112
Number of pages	4
Journal	Organic letters
Volume	7
Issue number	6
DOIs	https://doi.org/10.1021/ol050045a
State	Published - Mar 17 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol050045a

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abstract = "(Chemical Equation Presented) We have designed a molecular switch based on the photoinduced opening and thermal closing of an oxazine ring. Ultraviolet excitation of this molecule induces the cleavage of a [C-O] bond to form a p-nitrophenolate chromophore in less than 10 ns with a quantum yield of ca. 0.1. The photogenerated isomer reverts thermally to the original oxazine within 50 ns. Our photochromic switch survives more than 3000 excitation cycles without decomposing, even in air-saturated solutions.",

author = "Massimiliano Tomasulo and Salvatore Sortino and Raymo, {Fran{\c c}isco M.}",

year = "2005",

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AU - Raymo, Françisco M.

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N2 - (Chemical Equation Presented) We have designed a molecular switch based on the photoinduced opening and thermal closing of an oxazine ring. Ultraviolet excitation of this molecule induces the cleavage of a [C-O] bond to form a p-nitrophenolate chromophore in less than 10 ns with a quantum yield of ca. 0.1. The photogenerated isomer reverts thermally to the original oxazine within 50 ns. Our photochromic switch survives more than 3000 excitation cycles without decomposing, even in air-saturated solutions.

AB - (Chemical Equation Presented) We have designed a molecular switch based on the photoinduced opening and thermal closing of an oxazine ring. Ultraviolet excitation of this molecule induces the cleavage of a [C-O] bond to form a p-nitrophenolate chromophore in less than 10 ns with a quantum yield of ca. 0.1. The photogenerated isomer reverts thermally to the original oxazine within 50 ns. Our photochromic switch survives more than 3000 excitation cycles without decomposing, even in air-saturated solutions.

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