Pyrene-Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl-Shaped π-Conjugated Systems for Creating Uniquely Curved π-Conjugated Systems

Shota Nakano, Yuto Kage, Hiroyuki Furuta, Nagao Kobayashi, Soji Shimizu

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    Pyrene-bridged boron subphthalocyanine dimers were synthesized from a mixed-condensation reaction of 2,7-di-tert-butyl-4,5,9,10-tetracyanopyrene and tetrafluorophthalonitrile, and their syn and anti isomers arising from the result of connecting two bowl-shaped boron subphthalocyanine molecules were successfully separated. Expansion of the conjugated system of boron subphthalocyanine through a pyrene bridge caused a redshift of the Q band absorption relative to the parent pyrene-fused monomer, whereas combining the curved π-conjugation of boron subphthalocyanine with the planar π-conjugation of pyrene enabled facile embracement of C60 molecules, owing to the enhanced concave-convex π-π stacking interactions. Pyrene-bridged boron subphthalocyanine (SubPc) dimers were synthesized from a mixed-condensation reaction of tetracyanopyrene and tetrafluorophthalonitrile, and their syn and anti isomers were successfully separated. In addition to the redshift of the Q band absorption, combining the curved π-conjugation of SubPc with the planar π-conjugation of pyrene enabled facile embracement of C60 molecules, owing to the enhanced concave-convex π-π stacking interactions.

    Original languageEnglish
    Pages (from-to)7706-7710
    Number of pages5
    JournalChemistry - A European Journal
    Volume22
    Issue number23
    DOIs
    Publication statusPublished - Jun 1 2016

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • Organic Chemistry

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