Aromaticity-Enhanced pH-Responsive Electrochemiluminescence of Cyclopentadienols

Due to significantly tackling the problems of aggregation-caused quenching and water insolubility, aggregation-induced emission electrochemiluminescence (AIE-ECL) has emerged as a research highlight in aqueous detection and sensing. Herein, we reported a series of cyclopentadienols featuring excellent AIE-ECL properties on the basis of an enhanced aromaticity strategy. In detail, substituents profoundly determined ECL emission by affecting the characteristic absorption peak intensity ratio in UV-vis spectra and lowest unoccupied molecular orbital (LUMO)-highest occupied molecular orbital (HOMO) energies. It was found that 1,2,3,4,5-pentafluorophenyl cyclopentadienol (PFCD) containing an electron-withdrawing fluorine substituent, the maximum R/B band ratio, and a smaller LUMO-HOMO band gap demonstrated the best ECL performance. Meanwhile, such an AIE-ECL system displayed a wide response range toward pH (4-12) with a good linear relationship. Our research not only enriched polycyclic aromatic hydrocarbon-based AIE-ECL systems but also established an efficient pH sensor in the aqueous phase.

Automated summary

By employing an enhanced aromaticity strategy, a series of cyclopentadienols with excellent AIE-ECL properties were synthesized. It was found that different substituents significantly influenced the ECL emission by affecting the characteristic absorption peak intensity ratio in UV-vis spectra and LUMO-HOMO energies. The cyclopentadienol with an electron-withdrawing fluorine substituent demonstrated the best ECL performance and showed a wide response range to pH.