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 language | English |
---|---|
Pages (from-to) | 7763-7770 |
Number of pages | 8 |
Journal | Chemistry - A European Journal |
Volume | 22 |
Issue number | 23 |
DOIs | |
Publication status | Published - 2016 Jun 1 |
Keywords
- acridones
- crystal growth
- molecular motion
- structure-activity relationships
- thermosalient effects
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry