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

•Acceptor-substituted polycarbazoles and polytriphenylamines showing both AIE and ICT behavior have been synthesized.•Dispersions containing polymer aggregates have been used for optical detection of 1,3,5-trinitrobenzene.•Amplified PL quenching was observed with a maximum PL quenching constant of 5.5 × 105 M−1.•One polymer (PTPATPAN) was used as PL-sensitive dopant in the Tg-detection of polystyrene.

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 × 105 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%.

Graphical abstractPolycarbazoles (PCzTPAN) or polytriphenylamines (PTPATPAN) decorated with 2,3,3-triphenylacrylonitrile side groups have been synthesized and characterized for the occurrence of aggregation-induced emission (AIE) and intramolecular charge transfer (ICT) effects. PCzTPAN and PTPATPAN dispersions in 90% water/THF were further used for the high sensitivity detection of 1,3,5-trinitrobenzene (TNB) as prototypical nitroaromatic analyte, showing amplified PL quenching with a maximum quenching constant of 5.5 × 105 M−1. Moreover, PTPATPAN was used as AIE-active fluorescent probe for detection of the glass transition temperature of a polystyrene (PS) film, exhibiting a very reliable response to the glass transition of PS, up to low probe concentration of 0.1 wt%.Download high-res image (191KB)Download full-size image