Amine-derivatized calix[4]arenes for sensitive extraction of cupric ion and formation of amine radical cation

•New calix[4]arene amine derivatives were easily synthesized via Mannich procedure.•New calix[4]arene amine derivatives were efficient and selective receptors for Cu2+ cation.•The sensitive extraction of cupric ions and formation of calix[4]arene amine radical cation took place concurrently.•It was developed new “naked eye” chemosensor and new “turn-off” probe for cupric ions.•The generation and study of amine radical cations with calixarene derivatives has been documented for the first time.

We report herein some calix[4]arene amine (C[4]A) derivatives, which are the copper(II)-induced fluorescence “turn-off” and “naked eye” chemosensors and the agents for the formation of amine radical intermediates. In this way, concurrently, the sensitive extraction of cupric ions and the formation of amine radical cations with calixarenes have been documented for the first time. These data were confirmed by using some experimental studies such as UV–visible, fluorescence, electron spin resonance, and cyclic voltammetric.

Graphical abstractWe report herein some calix[4]arene amine derivatives, which are both the copper(II)-induced fluorescence “turn-off” and “naked eye” chemosensors and the agents for the formation of amine radical intermediates.Figure optionsDownload full-size imageDownload as PowerPoint slide