Résumé
N-Salicilideneanilines are among the most studied thermo- and photochromic systems in the solid state. Although thermochromism is a general property of crystalline N-salicilideneanilines, photochromism is known in a limited number of cases. As a method for the construction of thermo- and photo-responsive molecular architectures, the co-crystallisation of 1,2,4,5-tetrafluoro-3,6-diiodobenzene (I2F4) with three selected imines of o-vanillin, named 1, 2 and 3, obtained through a condensation reaction with 3-aminopyridine, 4-bromoaniline and 4-iodoaniline, respectively, is reported herein. All crystals and co-crystals have been characterised by means of solid-state complementary techniques (X-ray diffraction, solid-state NMR spectroscopy, absorption and emission spectroscopy). The role of halogen bonding and crystal packing in the optical and chromic properties of all solid materials is discussed. All solids exhibit thermochromic behaviour, and three of them (2, 22 ⋅I2F4 and 32 ⋅I2F4) are also photochromic. Imine derivative 3 crystallises in two different polymorphic forms (3 A and 3 B) and a solvate (3Solv ). The bromo and iodo derivatives, 2 and 3 B, are isomorphous and form isomorphous co-crystals with I2F4, but behave differently when exposed to UV light because only crystalline 2 is photochromic. Interestingly, the replacement of bromine with iodine seems to turn off the photochromism because crystalline 3 A and 3Solv , and even the 20.7 30.3 solid solution, do not manifest photochromic behaviour.
langue originale | Anglais |
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Pages (de - à) | 5317-5329 |
Nombre de pages | 13 |
journal | Chemistry: A European Journal |
Volume | 23 |
Numéro de publication | 22 |
Les DOIs | |
Etat de la publication | Publié - 3 avr. 2017 |
Empreinte digitale
Examiner les sujets de recherche de « Halogen-Bond Effects on the Thermo- and Photochromic Behaviour of Anil-Based Molecular Co-crystals ». Ensemble, ils forment une empreinte digitale unique.Équipement
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Physico-chimie et caractérisation (PC2)
Wouters, J. (!!Manager), Aprile, C. (!!Manager) & Fusaro, L. (!!Manager)
Plateforme technologique Caracterisation physico-chimiquesEquipement/installations: Plateforme technolgique
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Plateforme Technologique Calcul Intensif
Champagne, B. (!!Manager)
Plateforme technologique Calcul intensifEquipement/installations: Plateforme technolgique
Ensembles de données
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CCDC 1483225: Experimental Crystal Structure Determination
Carletta, A. (Contributeur), Chierotti, M. R. (Contributeur), d'Agostino, S. (Contributeur), Gobetto, R. (Contributeur), Grepioni, F. (Contributeur), Spinelli, F. (Contributeur), Ventura, B. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017
DOI: 10.5517/ccdc.csd.cc1lsdzr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lsdzr&sid=DataCite
Ensemble de données
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CCDC 1483231: Experimental Crystal Structure Determination
Carletta, A. (Contributeur), Chierotti, M. R. (Contributeur), d'Agostino, S. (Contributeur), Gobetto, R. (Contributeur), Grepioni, F. (Contributeur), Spinelli, F. (Contributeur), Ventura, B. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017
DOI: 10.5517/ccdc.csd.cc1lsf5z, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lsf5z&sid=DataCite
Ensemble de données
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CCDC 1523380: Experimental Crystal Structure Determination
Carletta, A. (Contributeur), Chierotti, M. R. (Contributeur), d'Agostino, S. (Contributeur), Gobetto, R. (Contributeur), Grepioni, F. (Contributeur), Spinelli, F. (Contributeur), Ventura, B. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017
DOI: 10.5517/ccdc.csd.cc1n4699, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n4699&sid=DataCite
Ensemble de données
Thèses de l'étudiant
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Photochromic multicomponent crystalline materials based on N-salicylideneanilines
Carletta, A. (Auteur)Wouters, J. (Promoteur), Leherte, L. (Président), Champagne, B. (Jury), Leyssens, T. (Jury) & Roscini, C. (Jury), 13 sept. 2019Student thesis: Doc types › Docteur en Sciences
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