Solid-state reactions of crystals containing two kinds of polymerizable moieties of diene and diyne

Toru Odani, Shuji Okada, Chizuko Kabuto, Tatsumi Kimura, Satoru Shimada, Hiro Matsuda, Hidetoshi Oikawa, Akikazu Matsumoto, Hachiro Nakanishi

    Research output: Contribution to journalArticlepeer-review

    37 Citations (Scopus)

    Abstract

    We have investigated that photoreactivities of a series of diynediammonium dienecarboxylates in the crystalline state. In the case of 4,4′- butadiynedibenzylammonium disorbate, almost all diene moieties were polymerized during photoirradiation for 8 h. On the other hand, the conversion of diyne moieties was still low. Crystal structure of the monomer crystal indicates that the alignment of diene moieties is very similar to those of topochemically polymerizable crystals of diene derivatives. Even though the translation distance of diyne moieties is also suitable for the polymerization, the tilt angle is different from the ideal angle. It is the reason why the conversion of diyne moieties was low. By X-ray single-crystal structure analysis of the polymer crystal, we confirmed that the polymerization proceeded via topochemical reaction mechanism indeed. On the other hand, photodimerization of diene moieties in the crystals of 2,4-hexadiyne-1,6-diammonium (E, E)-muconate occurred because of the face-to-face alignment of dienes at a distance of 3.8 Å.

    Original languageEnglish
    Pages (from-to)3481-3487
    Number of pages7
    JournalCrystal Growth and Design
    Volume9
    Issue number8
    DOIs
    Publication statusPublished - 2009 Aug 5

    ASJC Scopus subject areas

    • Chemistry(all)
    • Materials Science(all)
    • Condensed Matter Physics

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