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Multi‐Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones
Author(s) -
Hirai Yuichi,
LaizeGénérat Lucie,
WronaPiotrowicz Anna,
Zakrzewski Janusz,
Makal Anna,
Brosseau Arnaud,
Michely Laurent,
Versace DavyLouis,
Allain Clémence,
Métivier Rémi
Publication year - 2021
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.202100294
Subject(s) - bathochromic shift , hypsochromic shift , pyrene , trimethylsilyl , chemistry , solid state , silylation , photochemistry , fluorescence , stereochemistry , organic chemistry , physics , quantum mechanics , catalysis
A series of acetyl pyrenes and pyrenyl ynones with and without tert ‐butyl groups showed distinct mechanofluorochromism (MFC). Four pairs of polymorphic solids were found out of six compounds and interestingly, each of them showed hypsochromic, bathochromic or off‐to‐on MFC. The MFC properties were rationalized by categorizing the packing schemes into herringbone, sandwich, beta and gamma motifs depending on the relative contributions of C⋅⋅⋅C (or π‐π) against C⋅⋅⋅H contacts. The bulky tert ‐butyl and trimethylsilyl groups served not only to reduce the number of aggregation patterns but also to prohibit the complete back reactions in solid state. Our results suggest that the simple pyrene derivatives may be promising candidates for a novel group of mechanically‐sensitive materials.