Enhanced AIE and different stimuli-responses in red fluorescent (1,3-dimethyl)barbituric acid-functionalized anthracenes

• Published in: Journal of materials chemistry. C, Materials for optical and electronic devices Vol. 4; no. 4; pp. 751 - 757
• Main Authors: Yin, Guohui, Ma, Yawen, Xiong, Yao, Cao, Xiaohui, Li, Yang, Chen, Ligong
• Format: Journal Article
• Language: English
• Published: 01.01.2016
• ISSN: 2050-7526; 2050-7534
• DOI: 10.1039/C5TC03629A

Two structurally simple and red light-emitting AIE luminogens, (1,3-dimethyl)barbituric acid-functionalized anthracenes ( B-A and DMB-A ), were designed and synthesized. In comparison with DMB-A , B-A shows strikingly enhanced AIE as well as superior thermal stability ( T d , 328.5 °C vs. 280.2 °C). Moreover, distinguishable behaviors of the two red luminogens to stimuli such as (1) dissolution (in 1,4-dioxane), then solidification via removing the solvent in vacuo at 50 °C, (2) thermal treatment following stimuli-I and (3) mechanical grinding were observed. In particular, reversible switching of colours (orange ↔ red), accompanied by a fluorescence shift (Δ λ em ≈ 36 nm) was achieved by repeatedly applying stimuli (I) and (II) on luminogen B-A , whereas almost no change of luminogen DMB-A was found under the same conditions. A mechanism of solvent molecule assisted B-A molecular packing changes was proposed to illustrate the origin of B-A 's chromic phenomenon.