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Diamino-Terephthalonitrile-based Single Benzene Fluorophores Featuring Strong Solution State Fluorescence and Large
Tanya Raghava1, Subhadeep Banerjee1, Anjan Chattopadhyay1
1Department of Chemistry, Birla Institute of Technology and Science Pilani, KK Birla Goa Campus, NH 17B Bypass Road, Zuarinagar, Goa 403726, India.
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.
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