Zhiyong Yang, Wei Qin, J. Lam
Jul 29, 2013
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Quality indicators
Journal
Chemical Science
Abstract
A heteroatom-containing organic fluorophore 1-(4-pyridinyl)-1-phenyl-2-(9-carbazolyl)ethene (CP3E) was designed and synthesized. CP3E exhibits the effect of intramolecular charge transfer (ICT) caused by the donor–acceptor interaction between its carbazole and pyridine units. Whereas it emits faintly in solution, it becomes a strong emitter in the aggregated state, demonstrating the phenomenon of aggregation-induced emission (AIE). Its emission can be reversibly switched between blue and dark states by repeated protonation and deprotonation. Such behaviour enables it to work as a fluorescent pH sensor in both solution and the solid state and as a chemosensor for detecting acidic and basic organic vapors. Analyses by NMR spectroscopy, single-crystal X-ray diffraction and computational calculations suggest that the change in electron affinity of the pyridinyl unit and molecular conformation of CP3E upon protonation and deprotonation is responsible for such sensing processes.