Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor

• Published in: Nature communications Vol. 11; no. 1; p. 161
• Main Authors: Hu, Ming, Yuan, Ying-Xue, Wang, Weizhou, Li, Dong-Mi, Zhang, Hong-Chao, Wu, Bai-Xing, Liu, Minghua, Zheng, Yan-Song
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 09.01.2020; Nature Publishing Group; Nature Portfolio
• Subjects: 2,4-D; 639/301/1005/1009; 639/638/11/511; 639/638/11/874; 639/638/298/923/966; Agrochemicals; Carboxylic acids; Chemical bonds; Emission; Enantiomers; Fluorescence; Humanities and Social Sciences; multidisciplinary; Receptors; Recognition; Rotors; Science; Science (multidisciplinary); Wavelength
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-019-13955-z

Chiral recognition, such as enantioselective interactions of enzyme with chiral agents, is one of the most important issues in the natural world. But artificial chiral receptors are much less efficient than natural ones. For tackling the chiral recognition and enantiomer excess (ee) analysis, up until now all the fluorescent receptors have been developed based on fluorescence intensity changes. Here we report that the chiral recognition of a large number of chiral carboxylic acids, including chiral agrochemicals 2,4-D, is carried out based on fluorescent colour changes rather than intensity changes of AIEgen rotors. Moreover, the fluorescence wavelength of the AIEgen rotor linearly changes with ee of the carboxylic acid, enabling the ee to be accurately measured with average absolute errors (AAE) of less than 2.8%. Theoretical calculation demonstrates that the wavelength change is ascribed to the rotation of the AIEgen rotor upon interaction with different enantiomers. Artificial receptors for chiral recognition are important in enantiomer excess analysis but current artificial detectors are based on fluorescence intensity changes only. Here the authors propose a different detection mechanism based on change of the fluorescence emission wavelength of an AIEgen rotor.