University Chemistry ›› 2023, Vol. 38 ›› Issue (4): 269-276.doi: 10.3866/PKU.DXHX202211042

Special Issue:

Previous Articles     Next Articles

Synthesis and Photophysical Properties of Fluorescent Molecules with Aggregation-Induced Emission and Excited-State Intramolecular Proton Transfer Properties

Siyang Liu, Yu Sun, Yunyan Li, Yan Zhang()   

  • Received:2022-11-15 Accepted:2023-01-11 Published:2023-03-14
  • Contact: Yan Zhang


Chemistry laboratory training is an integral part of chemistry teaching. However, outdated experimental protocols present limitations and can hinder students' initiative and innate inclination toward exploration. In this study, novel scientific concepts were translated into experimental chemistry teaching. Small fluorescent molecules with aggregation-induced emission and excited-state intramolecular proton transfer properties were prepared using a carbonyl nucleophile addition reaction. The basic photophysical properties of the molecules and their fluorescence response to acid-base stimulation were evaluated experimentally. The non-toxic and non-noxious reagents used for the experiments were refluxed in ethanol for 0.5 h to implement green organic synthesis principles. The experiment was compact and the fluorescence and color changes of the as-synthesized molecules were conspicuous and remarkable. This can stimulate students' enthusiasm for experimental chemistry. In addition to the basic organic synthesis reaction, this experiment included several modern analysis and characterization methods, such as nuclear magnetic resonance, Fourier-transform infrared spectroscopy, ultraviolet-visible absorption spectroscopy, and fluorescence spectroscopy. We are confident that this intuitive and effective basic experiment can effectively stimulate and cultivate the innate curiosity of students.

Key words: Aggregation-induced emission, Excited-state intramolecular proton transfer, Green chemistry, Salicylide, p-phenylenediamine