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Anisotropic Dissociation of π–π Stacking and Flipping‐Motion‐Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives
Author(s) -
Takeda Takashi,
Akutagawa Tomoyuki
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600794
Subject(s) - jumping , stacking , anisotropy , dissociation (chemistry) , chemistry , chemical physics , crystallography , molecular physics , materials science , physics , optics , organic chemistry , geology , paleontology
Ethylacridone ( 1 b ) and dicyanomethylenated acridones 2 a , b , d showed crystal‐jumping activity upon heating. This is the first example of thermosalient behavior in a simple aromatic ketone and its derivatives. A systematic investigation of the jumping behavior of derivatives with different alkyl chains by variable‐temperature X‐ray crystal‐structure analyses revealed the mechanism of this phenomenon. Anisotropic dissociation of π stacking in a dimer was important for inducing crystal jumping in 1 b , whereas the collective fluctuation/flipping motion of a dicyanomethylene unit induced crystal jumping in 2 .