Résumé
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-heterocycles, 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 π-π 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 irans-keto form. The absence of thermochromism in an N-salicylidene aniline derivative, induced by the absence of cis-keto form, 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.
langue originale | Anglais |
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Pages (de - à) | 621-637 |
Nombre de pages | 17 |
journal | European Journal of Organic Chemistry |
Numéro de publication | 4 |
Les DOIs | |
Etat de la publication | Publié - 29 janv. 2010 |
Empreinte digitale
Examiner les sujets de recherche de « Engineering solid-state molecular switches: N-salicylidene N-heterocycle derivatives ». Ensemble, ils forment une empreinte digitale unique.Ensembles de données
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CCDC 748027: Experimental Crystal Structure Determination
Garcia, Y. (Contributeur), Hidara, F. (Contributeur), Naik, A. D. (Contributeur), Robert, F. (Contributeur), Robiette, R. (Contributeur), Tinant, B. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2010
DOI: 10.5517/cct3cx5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cct3cx5&sid=DataCite
Ensemble de données
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CCDC 748026: Experimental Crystal Structure Determination
Garcia, Y. (Contributeur), Hidara, F. (Contributeur), Naik, A. D. (Contributeur), Robert, F. (Contributeur), Robiette, R. (Contributeur), Tinant, B. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2010
DOI: 10.5517/cct3cw4, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cct3cw4&sid=DataCite
Ensemble de données
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CCDC 748024: Experimental Crystal Structure Determination
Garcia, Y. (Contributeur), Hidara, F. (Contributeur), Naik, A. D. (Contributeur), Robert, F. (Contributeur), Robiette, R. (Contributeur), Tinant, B. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2010
DOI: 10.5517/cct3ct2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cct3ct2&sid=DataCite
Ensemble de données