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Photoswitch based on remarkably simple naphthopyrans
Authors:Xavier Sallenave  Gaston Vermeersch  Jean-Luc Pozzo
Affiliation:a Photochemical Nanoscience, CNRS UMR 5802, 351 crs Libération, 33405 Talence Cedex, France
b NMR and Photochemistry, CNRS UMR 8009, Faculté de Pharmacie, Université Lille 2, 59006 Lille, France
c Chemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt
Abstract:Photochromic switches built around 5-carbonyl-3,3-diphenyl-3H-naphtho[2,1-b]pyran unit have been synthesized. Their open forms are constituted of a 1:1 ratio of TC and TT-isomers according to 19F and 1H NMR investigations. Electrocyclization of TT isomers back to the closed form is efficiently achieved upon visible irradiation whereas it has been found to be a particularly unfavoured thermal process. These simple 2H-chromenes could act as molecular photoswitch at ambient temperature.
Keywords:Photoswitch   Naphthopyrans   19F NMR   Photochromism
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