Solid-state photochromism and thermochromism of N-salicylidene pyrene derivatives
(2014) CrystEngComm — Vol. 16, n° 37, p. 8786-8793 (2014)
Files
CrystEngComm2014168786.pdf
Restricted Access - Adobe PDF
- 5.33 MB
Details
- Authors
- Abstract
- 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.
- Affiliations
Citations
Safin, D. A., Bolte, M., & Garcia, Y. (2014). Solid-state photochromism and thermochromism of N-salicylidene pyrene derivatives. CrystEngComm, 16(37), 8786-8793. https://doi.org/10.1039/c4ce01325e (Original work published 2014)