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

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    31 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

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