Synthesis, characterization, and enhanced aggregation-induced emission of oligomer methylacryloyl tetraphenylethylene and volatile organic compounds detection

Tetraphenylethylene (TPE) derivatives were studied intensively owing to their excellent aggregation-induced emission (AIE) behavior, facile synthesis, easy functionalization, and thermal stability. Herein, oligomer methylacryloyl tetraphenylethylene (TPE-MA) containing precise number of AIE luminogens was synthesized facilely by introducing methylacryloyl group onto the phenyl ring of TPE and polymerizing the monomer. The structures of TPE-MA and its oligomer were characterized by nuclear magnetic resonance spectroscopy, mass spectra, Fourier transform infrared spectrometer, and gel permeation chromatograph. The relationship between chemical structures and the photophysical properties were investigated from the aspect of UV–vis absorption, fluorescent emission spectra, (AIE property, electrochemical properties, and density functional theory studies. The results showed that the emission intensity of the oligomer TPE-MA was enhanced by twice bigger than that of its monomer, and the maximum emission wavelengths were observed red-shifted, when TPE was converted to TPE-MA monomer and its oligomer. The oligomer solution spots on the thin layer chromatography plates can be turned “off” and “on” continuously and reversibly by dichloromethane vapor, which endows the material with high sensitivity, capable of detecting volatile organic compounds.