A diphenylacrylonitrile conjugated porphyrin with near-infrared emission by AIE–FRET

Abstract

Porphyrins had long been used as near-infrared-emissive fluorescent materials, but the aggregation-caused quenching (ACQ) of porphyrins limited their performance in fluorescence imaging. In this work, a novel porphyrin derivative with an aggregation-induced emission characteristic was synthesized by introducing four diphenylacrylonitrile units onto the porphyrin skeleton. The strong aggregation induced emission–fluorescence resonance energy transfer (AIE–FRET) effect was first observed for diphenylacrylonitrile units and porphyrin units. The novel porphyrin derivative exhibited not only strong fluorescence in both solution and the solid state, but also exhibited an excellent fluorescence imaging ability for living cells.