Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7763-7770
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number23
DOIs
Publication statusPublished - 2016 Jun 1

Keywords

  • acridones
  • crystal growth
  • molecular motion
  • structure-activity relationships
  • thermosalient effects

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives'. Together they form a unique fingerprint.

Cite this