Engineering Solid-State Molecular Switches: N-Salicylidene N-Heterocycle Derivatives
(2010) European Journal of Organic Chemistry — n° 4, p. 621-637 (2010)
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- Abstract
- A supramolecular engineering approach has been developed for a novel family of N-salicylidene aniline derivatives to control their thermo- and photochromic behaviours. Hsaltrz, Habs, Hsalphen, Hsaltz and Ksaltz are versatile molecules built from N-heteyocycles, which drive the molecular arrangement to form a controlled crystal packing with predesigned optical properties. A complete structural, optical and computational study of powders of these new molecular nanoswitches is presented. An N-salicylidene aniline derivative possessing no thermo- or photoinduced chromic properties thanks to a specific molecular geometry was sought, and Habs and Hsalphen were designed to enhance pi-pi stacking interactions. A theoretical study of the crystal packing, combined with time-dependent diffuse reflectance studies of Habs, have confirmed the appearance of photochromism at room temperature completed with an unprecedented "spring-type effect" observed during the photochemical relaxation of the metastable trans-keto form. The absence of thermochromism in an N-salicylidene aniline derivative, induced by the absence of cis-keto for m, is a unique behaviour, firstly identified and explained for these types of compounds. Finally, Hsaltz and Ksaltz are the result of a molecular derivation of Hsaltrz which allow enhancing the amplitude of thermochromism of these functional materials.
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Robert, F., Naik, A., Hidara, F., Tinant, B., Robiette, R., Wouters, J., & Garcia, Y. (2010). Engineering Solid-State Molecular Switches: N-Salicylidene N-Heterocycle Derivatives. European Journal of Organic Chemistry, 4, 621-637. https://doi.org/10.1002/ejoc.200901175 (Original work published 2010)