Gated photochromism and acidity photomodulation of a diacid dithienylethene dye

Julie Massaad, Jean Claude Micheau, Christophe Coudret, Rafael Sanchez, Gonzalo Guirado, Stéphanie Delbaere

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42 Citations (Scopus)

Abstract

The present study quantitatively analyses the gated photochromism and the acidity photomodulation properties of a diacid dithienylethene compound. Photoisomerisation between the open and closed isomers was investigated by UV/visible and 1H NMR spectroscopy. It was found that the photocyclisation quantum yield of the diacid form was remarkably high (around 90 %). Partial neutralisation of the open isomer revealed a gated photochromism as the photocyclisation quantum yield of the mono- and dianion were 50 and 67 %, respectively. A considerable photomodulation of the acidity was observed: the closed isomer is more acid than the open one by more than one pK a unit. This effect has been shown to be exploitable for a reversible photo-acid generation. This is the first time that a complete quantitative investigation that allows for the determination of the main photochromic, spectral and thermodynamic parameters of a base-sensitive photochromic diarylethene has been carried out. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish
Pages (from-to)6568-6575
JournalChemistry - A European Journal
Volume18
Issue number21
DOIs
Publication statusPublished - 21 May 2012

Keywords

  • acidity
  • diarylethenes
  • dyes/pigments
  • isomers
  • photochromism

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