Detection of nitroaromatics based on aggregation induced emission of barbituric acid derivatives

Han-Jun Zhang; Yan Tian; Fu-Rong Tao; William Yu; Kai-Yue You; Lin-Rui Zhou; Xi Su; Tian-Duo Li; Yue-Zhi Cui

doi:10.1016/j.saa.2019.117168

Detection of nitroaromatics based on aggregation induced emission of barbituric acid derivatives

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Nov 5:222:117168. doi: 10.1016/j.saa.2019.117168. Epub 2019 May 29.

Authors

Han-Jun Zhang¹, Yan Tian¹, Fu-Rong Tao¹, William Yu¹, Kai-Yue You¹, Lin-Rui Zhou¹, Xi Su¹, Tian-Duo Li¹, Yue-Zhi Cui²

Affiliations

¹ School of Chemical and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, PR China.
² School of Chemical and Pharmaceutical Engineering, Qilu University of Technology, Jinan 250353, PR China. Electronic address: cyz@qlu.edu.cn.

PMID: 31226612
DOI: 10.1016/j.saa.2019.117168

Abstract

Barbituric acid derivatives with typical aggregation induced emission (AIE) are reported. Their emission wavelengths varied with water fraction of their solution. UV-visible absorption spectroscopy and theoretical calculations revealed the intramolecular charge transfer (ICT) possibility from donor to acceptor and the mechanism was confirmed as a restriction of intramolecular motion (RIM). The AIE properties were affected by the different substituents on barbituric acid. When the molecular volume increased, the AIE effect decreased. Fluorescent quenching mechanism was applied to detect nitroaromatic explosives. For 2,4,6-trinitrophenol (PA), one of the derivatives 5-(4-diphenylamino styrene)-1,3-diphenyl-barbituric acid in THF/H₂O mixture (1:9, v/v), showed amplified fluorescence quenching with a maximum Stern-Volmer quenching constant of 4.1 × 10⁴ M^-1. The solid phase paper test based on 5-(4-diphenylamino styrene)-1,3-diphenyl-barbituric acid also showed a superior sensitivity toward PA both in vapor and solution.

Keywords: Aggregation induced emission (AIE); Fluorescent sensor; Intramolecular charge transfer (ICT); Restriction of intramolecular motion (RIM).