Aza-BODIPY synthesis towards vis/NIR functional chromophores based on a Schiff base forming reaction protocol using lactams and heteroaromatic amines

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    26 Citations (Scopus)

    Abstract

    Aza-BODIPY is a class of heteroatom-containing BODIPY analogues targeting near infrared (NIR) chromophores and fluorophores. As a synthetic strategy towards aza-BODIPY structures, we have, recently, developed a Schiff base forming reaction using readily available lactams and heteroaromatic amines. Absorption and fluorescence of a series of compounds cover the whole range of the ultraviolet (UV)/visible (vis)/NIR regions. In addition, some compounds exhibit solid state emission, aggregation-induced emission enhancement, tunable fluorescence in the vis/NIR regions and non-linear optical properties. Furthermore, simple dimerization of aza-BODIPY chromophores caused unusual panchromatic absorption, whereas in combination with an N-confused porphyrin skeleton, multi-state NH tautomerism was achieved. In this Feature Article, wide applicability of this Schiff base forming reaction and optical and electrochemical properties of aza-BODIPY analogues thus synthesized are summarized including recent applications, such as bioimaging, photothermal cancer therapy and organic photovoltaics.

    Original languageEnglish
    Pages (from-to)8722-8743
    Number of pages22
    JournalChemical Communications
    Volume55
    Issue number60
    DOIs
    Publication statusPublished - 2019

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • Electronic, Optical and Magnetic Materials
    • Ceramics and Composites
    • Chemistry(all)
    • Surfaces, Coatings and Films
    • Metals and Alloys
    • Materials Chemistry

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