Extended Pyrazinacenes as a New Class of Near-Infrared Emissive Materials for Potential Bioimaging Applications

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We have continued to synthesize new pyrazinacenes mainly consisting of four or five consecutively fused pyrazine rings appended with electron-donating substituents that are redox active. Oxidized species show remarkably red-shifted absorption compared to the reduced species.We have improved the synthesis of the water-soluble tetradecaazaheptacene to give better yield. This compound has been used for cellular imaging in the near infrared region. This was possible through use of a non-cytotoxic beta-cyclodextrin delivery agent which helped to prevent chromophore aggregation in aqueous solution.We have now developed the synthesis of pyrazinacenes consisting of 8 consecutively fused pyrazine rings - now the longest-known pyrazinacenes.