Multi-purpose barbituric acid derivatives with aggregation induced emission

Hanjun Zhang; Yuezhi Cui; Furong Tao; Datong Zhang; Zhen Xu; Li Guo

doi:10.1016/j.saa.2019.117320

Multi-purpose barbituric acid derivatives with aggregation induced emission

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Dec 5:223:117320. doi: 10.1016/j.saa.2019.117320. Epub 2019 Jun 27.

Authors

Hanjun Zhang¹, Yuezhi Cui², Furong Tao¹, Datong Zhang¹, Zhen Xu³, Li Guo¹

Affiliations

¹ School of Chemical and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, PR China.
² School of Chemical and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, PR China. Electronic address: cyz@qlu.edu.cn.
³ School of Chemical and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, PR China. Electronic address: zx@qlu.edu.cn.

PMID: 31288170
DOI: 10.1016/j.saa.2019.117320

Abstract

Three D-π-A barbituric acid derivatives with simple structure and intramolecular charge transfer (ICT) mechanisms were synthesized. Molecular dynamics simulations have successfully explained that CB-1 exhibits the best aggregate induced emission (AIE) activity due to the electron-deficient barbituric acid and the electron-rich carbazole exhibit a conformation which similar to π-π stacking, resulting in a strong electrostatic attraction between the molecules, meanwhile the N-atom substituent of the carbazole is n-propane plays a hydrophobic role. At the same time, barbituric acid derivatives also have mechanochromic fluorescent properties. In addition, CB-1 and CB-3 exhibited outstanding fluorescence stability than CB-2 in aggregation state which can be used to detect nitroaromatic explosives in aqueous media. The Stern-Volmer quenching constant (K_sv) of CB-1 and CB-3 is 6.6 × 10⁴ and 1 × 10⁵ M^-1, respectively.

Keywords: Aggregation induced emission (AIE); Fluorescent sensor; Intramolecular charge transfer (ICT); Mechanochromic fluorescence (MCF).