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Solid-state photochromism and thermochromism of N-salicylidene pyrene derivatives

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Safin, D.A. [UCL] Bolte, M. [autre] Garcia, Yann [UCL]

N-Salicylidene pyrene derivatives of the common formula 1-pyrene-NCH-(2-OH-aryl) [aryl = C6H4 (1), 5-Cl-C 6H3 (2), 5-Br-C6H3 (3), 5-NO 2-C6H3 (4), 3,5-Cl2-C 6H2 (5), 3,5-Br2-C6H2 (6), and 3-CH3O-C6H3 (7)] have been synthesized and characterized by elemental analysis, NMR, diffuse reflectance and fluorescence spectroscopy. The crystal structures of 2, 3 and 5-7 are stabilized by an intramolecular hydrogen bond and a broad network of intermolecular π⋯π stacking interactions. All molecules, except 1, show the presence of a mixture of enol and cis- and trans-keto forms in the solid state at room temperature. Compounds 1 and 7 are exclusively thermochromic, while 5 displays negative trans-keto to cis-keto photochromism upon irradiation at λ = 546 nm, which is photoreversible upon irradiation at λ = 450 nm. The photogenerated cis-keto form of 5 is highly stable under ambient conditions and shows very negligible and slow thermal relaxation. This journal is © the Partner Organisations 2014.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2014
Language Anglais
Journal information "CrystEngComm" - Vol. 16, no. 37, p. 8786-8793 (2014)
Peer reviewed yes
Publisher Royal Society of Chemistry
e-issn 1466-8033
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Links
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Bibliographic reference Safin, D.A. ; Bolte, M. ; Garcia, Yann. Solid-state photochromism and thermochromism of N-salicylidene pyrene derivatives. In: CrystEngComm, Vol. 16, no. 37, p. 8786-8793 (2014)
Permanent URL http://hdl.handle.net/2078.1/155248