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

Massimiliano Tomasulo; Salvatore Sortino; Francisco 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, Francisco Raymo

Chemistry

Research output: Contribution to journal › Article

103 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
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

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ASJC Scopus subject areas

Molecular Medicine

Cite this

Tomasulo, M., Sortino, S., & Raymo, F. (2005). A fast and stable photochromic switch based on the opening and closing of an oxazine ring. Organic Letters, 7(6), 1109-1112. https://doi.org/10.1021/ol050045a

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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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10.1021/ol050045a