Selected solid-state behaviour of three di-tert-butyl-substituted N-salicylideneaniline derivatives: temperature-induced phase transitions and chromic behaviour

Mason, Helen E.; Howard, Judith A.K.; Sparkes, Hazel A.

doi:10.1107/s2053229621008780

Selected solid-state behaviour of three di-tert-butyl-substituted N-salicylideneaniline derivatives: temperature-induced phase transitions and chromic behaviour

Mason, Helen E.; Howard, Judith A.K.; Sparkes, Hazel A.

Authors

Helen E. Mason

Judith A.K. Howard

Hazel A. Sparkes

Abstract

The synthesis, single-crystal structures and chromic behaviour of three related Schiff bases, namely, (E)-2,4-di-tert-butyl-6-{[(4-fluorophenyl)imino]methyl}phenol, C21H26FNO, 1, (E)-2,4-di-tert-butyl-6-{[(4-chlorophenyl)imino]methyl}phenol, C21H26ClNO, 2, and (E)-6-{[(4-bromophenyl)imino]methyl}-2,4-di-tert-butylphenol, C21H26BrNO, 3, are reported. Two polymorphs of 1 were obtained, which were found to have different photochromic properties. Schiff bases 2 and 3 were found to be isostructural and underwent a phase transition upon cooling which was attributed to the dynamic disorder in one of the tert-butyl groups resolving at low temperature. All of the structures were found to exist in the enol rather than the keto form based on the C—O(H) and imine C=N bond lengths, and contained an intramolecular O—H⋯N hydrogen bond alongside weaker intermolecular C—H⋯O contacts.

Citation

Mason, H. E., Howard, J. A., & Sparkes, H. A. (2021). Selected solid-state behaviour of three di-tert-butyl-substituted N-salicylideneaniline derivatives: temperature-induced phase transitions and chromic behaviour. Acta Crystallographica Section C: Structural Chemistry, 77(10), 659-667. https://doi.org/10.1107/s2053229621008780

Journal Article Type	Article
Acceptance Date	Aug 23, 2021
Online Publication Date	Sep 29, 2021
Publication Date	2021-10
Deposit Date	Jan 19, 2022
Publicly Available Date	Jan 20, 2022
Journal	Acta Crystallographica Section C Structural Chemistry
Publisher	International Union of Crystallography
Peer Reviewed	Peer Reviewed
Volume	77
Issue	10
Pages	659-667
DOI	https://doi.org/10.1107/s2053229621008780

Files

Published Journal Article (1.3 Mb)
PDF

Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/

Copyright Statement
The article Selected solid-state behaviour of three di-tert-butyl-substituted N-salicylideneaniline derivatives: temperature-induced phase transitions and chromic behaviour [Mason et al. (2021). Acta Cryst. C77, 659-667, https://doi.org/10.1107/S2053229621008780] is published under an open-access licence, so you are free to reuse it without restriction provided there is attribution for the article.