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Photochromism emergence in N-salicylidene P-aminobenzenesulfonate diallylammonium salts

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Jacquemin, P.-L. [UCL] Robeyns, Koen [UCL] Devillers, Michel [UCL] Garcia, Yann [UCL]

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=2.4×10-7s-1). Color scheme: Modulation of thermo/photochromism was achieved in a series of anil anionic switches (see figure). The available free space and the flexibility of the nearby environment around the anil account for the photochromic properties. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2015
Language Anglais
Journal information "Chemistry - A European Journal" - Vol. 21, no.18, p. 6832-6845 (2015)
Peer reviewed yes
Publisher Wiley-VCH Verlag
issn 0947-6539
Publication status Accepté/Sous presse
Affiliations UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
UCL - SST/IMCN/ASM - Analyse structurale moléculaire (plate-forme technologique)
Keywords Isomerization ; Positive ions ; Salts ; Alkyl chain lengths ; Crystal packings ; In-situ condensations ; Molecular device ; Photochromic properties ; Salicylaldehyde ; Tautomerism ; Thermochromism ; Molecular devices ; Photochromism ; Photochromism ; Tautomerism ; Thermochromism ; Dihedral angle ; Isomerization ; Modulation ; Optical properties
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Bibliographic reference Jacquemin, P.-L. ; Robeyns, Koen ; Devillers, Michel ; Garcia, Yann. Photochromism emergence in N-salicylidene P-aminobenzenesulfonate diallylammonium salts. In: Chemistry - A European Journal, Vol. 21, no.18, p. 6832-6845 (2015)
Permanent URL http://hdl.handle.net/2078.1/161570