Tetra-porphyrin molecular tweezers: two binding sites linked via a polycyclic scaffold and rotating phenyl diimide core

Rhys Murphy, Rebecca Norman, J White, Michael Perkins, Martin Johnston

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    5 Citations (Scopus)

    Abstract

    The synthesis of a tetra-porphyrin molecular tweezer with two binding sites is described. The bis-porphyrin binding sites are aligned by a polycyclic scaffold and linked via a freely rotating phenyl diimide core. Synthesis was achieved using a divergent approach employing a novel coupling method for linking two polycyclic units to construct the core, with a copper(ii)-mediated phenyl boronic acid coupling found to extend to our polycyclic imide derivative. We expect this chemistry to be a powerful tool in accessing functional polycyclic supramolecular architectures in applications where north/south reactivity and/or directional interactions between modules are important. Porphyrin receptor functionalisation was undertaken last, by a four-fold ACE coupling reaction on the tetra-epoxide derivative of the core.

    Original languageEnglish
    Pages (from-to)8707-8720
    Number of pages14
    JournalOrganic and Biomolecular Chemistry
    Volume14
    Issue number37
    DOIs
    Publication statusPublished - 2016

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