Gated photochromism and acidity photomodulation of a diacid dithienylethene dye

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.