Sterically Frustrated Aromatic Enes with Various Colors Originating from Multiple Folded and Twisted Conformations in Crystal Polymorphs.
mechanochromism
metastable structures
overcrowded ethylene
piezochromism
thermochromism
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
16 May 2022
16 May 2022
Historique:
received:
28
01
2022
pubmed:
26
3
2022
medline:
26
3
2022
entrez:
25
3
2022
Statut:
ppublish
Résumé
Overcrowded ethylenes composed of 10-methyleneanthrone and two bulky aromatic rings contain a twisted carbon-carbon double (C=C) bond as well as a folded anthrone unit. As such, they are unique frustrated aromatic enes (FAEs). Various colored crystals of these FAEs, obtained in different solvents, correspond to multiple metastable conformations of the FAEs with various twist and fold angles of the C=C bond, as well as various dihedral angles of attached aryl units with respect to the C=C bond. The relationships between color and these parameters associated with conformational features around the C=C bond were elucidated in experimental and computational studies. Owing to the fact that they are separated by small energy barriers, the variously colored conformations in the FAE crystal change in response to various external stimuli, such as mechanical grinding, hydrostatic pressure and thermal heating.
Identifiants
pubmed: 35333427
doi: 10.1002/chem.202200286
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200286Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP20K05475
Organisme : Japan Society for the Promotion of Science
ID : JP20H05865
Organisme : Japan Society for the Promotion of Science
ID : JP21H05482
Informations de copyright
© 2022 Wiley-VCH GmbH.
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