Tetraphenylethylene Based Amphiphilic Derivatives: The Self-Assembly, Photo-Responsiveness and Their Application for Erasable Fluorescent Ink

Abstract Since the discovery of aggregation induced emission (AIE) phenomenon, various stimuli-responsive materials have been rapidly developed. However, the development of self-assembled amphiphilic light-responsive materials in aqueous solution needs to be solved urgently. In this work, three new amphiphilic tetraphenylethylene (TPE) derivatives (TPE-1, TPE-2 and TPE-3) with AIE properties and photochromism were synthesized and investigated. Owing to the different electron-donating abilities of the three groups attached to TPE units, the TPE-1, TPE-2 and TPE-3 displayed blue-green, yellow-green, and orange fluorescence emission in the aggregation state respectively. Furthermore, ordered nanoparticles formed via self-assembly in aqueous solution showed interesting photocyclization behaviors, which lead to fluorescence quenching under ultraviolet light irradiation (λ = 365 nm). Therefore, the compounds can be used as anti-counterfeiting ink in the information encryption due to their amphiphilicity and photo-responsiveness. This work contributes new members to the amphiphilic light-responsive materials family and demonstrates the potential for applications in the fields of optical information storage, information security protection, and erase/rewrite systems.