Diamino-Terephthalonitrile-based Single Benzene Fluorophores Featuring Strong Solution State Fluorescence and Large Stokes Shifts.

ABSTRACT

1°- and 2°-amines react with tetrafluoroterephthalonitrile through SNAr chemistry, creating the strongly emissive para-diamino-terephthalonitrile type single benzene fluorophores. The regioselectivity of reaction is dictated by the sterics of the initial secondary amine adduct. The molecules exhibit strong green-yellow emission and large (nearly 150 nm) Stokes shifts. Excited state analysis reveals a cooperative effect between the para-positioned amino groups through the electron-poor terephthalonitrile unit resulting in the fluorescence amplification.