Polycarbazoles and polytriphenylamines showing aggregation-induced emission (AIE) and intramolecular charge transfer (ICT) behavior for the optical detection of nitroaromatic compounds

Acceptor-substituted polycarbazoles (PCzTPAN) and polytriphenylamines (PTPATPAN) bearing electron-deficient 2,3,3-triphenylacrylonitrile (TPAN) side groups have been successfully synthesized. Both of them are aggregation-induced emission (AIE)-active and show intramolecular charge transfer (ICT) behavior. PCzTPAN and PTPATPAN aggregates in 90% water/THF were used for the detection of 1,3,5-trinitrobenzene (TNB) as prototypical nitroaromatic compound. They show amplified PL quenching upon addition of TNB with a maximum quenching constant of 5.5 x 10(5) M-1. As additional application example, the detection of the glass transition temperature of polystyrene (PS) was accomplished for PTPATPAN blended into PS at doping concentrations of 0.1-1.0 wt%. (C) 2015 Elsevier Ltd. All rights reserved.