Photochromism emergence in N-salicylidene p-aminobenzenesulfonate diallylammonium salts

Chemistry : a European Journal
Pierre-Loïc JacqueminYann Garcia

Abstract

N-Salicylidene p-aminobenzenesulfonate salts were prepared by in situ condensation of p-aminobenzenesulfonate diallylammonium salt and salicylaldehyde. Modulation of thermo- and photochromism was achieved by varying the alkyl chain length of the diallylammonium counter-cation. A structural-optical properties investigation reveals that both crystal packing and dihedral angle between aromatic rings of the N-salicylidene aniline switch are not sufficient to predict the occurrence of photochromism in the solid state. The available free space around the N-salicylidene p-aminobenzenesulfonate, in addition to the flexibility of the nearby environment, is shown to be of major importance for the cis→trans isomerisation to occur as well as for the stabilisation of the trans-keto form. Emergence of photochromic properties was determined from the diallylhexylammonium cation within the series of investigated counter-cations. High stability is observed for the trans-keto form of one polymorph of N-salicylidene p-aminobenzenesulfonate diallylhexylammonium salt (k = 2.4×10(-7)  s(-1)).

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Citations

Feb 28, 2017·Chemistry : a European Journal·Andrea CarlettaFabrizia Grepioni
Jun 18, 2017·Journal of the American Chemical Society·Guo-Hong NingKian Ping Loh
Mar 7, 2020·Acta Crystallographica. Section C, Structural Chemistry·Kalina MambourgJohan Wouters
Apr 28, 2021·Journal of Molecular Modeling·Makoto IsogaiHirohiko Houjou

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