The cyano positional isomerism strategy for constructing mitochondria-targeted AIEgens with type I reactive oxygen species generation capability†

Abstract

In this work, a series of cationic luminogens (designated as PSMP isomers) were developed based on the cyano positional isomerism strategy. The isomerism of the cyano substituent on the molecular skeleton can finely regulate the optical behaviour, the type of photoinduced reactive oxygen species (ROS), and mitochondria-targeted capability of isomers. Interestingly, PSMP-4, with the cyano group installed at an appropriate location, exhibits a special aggregation-induced emission effect and potent O₂˙⁻ generation efficacy through the type I photochemistry pathway. Notably, PSMP-4 can accumulate in mitochondria with high specificity. Taking advantage of its excellent photostability, PSMP-4 realizes in situ mitochondria imaging in a washing-free manner and sensitive response to the change of mitochondrial membrane potential. The integration of comprehensive photophysical properties and mitochondrial specificity enable PSMP-4 to successfully trigger the death of cancer cells through an efficient type I photodynamic therapy process both in vitro and in multicellular tumor spheroid models.