Issue 36, 2016

Constructing small molecular AIE luminophores through a 2,2-(2,2-diphenylethene-1,1-diyl)dithiophene core and peripheral triphenylamine with applications in piezofluorochromism, optical waveguides, and explosive detection

Abstract

In this work, we employ the Corey–Fuchs reaction followed by coupling reactions to develop a series of π-conjugated aggregation-induced emission (AIE) small-molecule luminophores (DT2A, DT3A and DT4A) through a 2,2-(2,2-diphenylethene-1,1-diyl)dithiophene (DPDT) core with different amounts and different strengths of TPA peripheral moieties. Interestingly, these molecules give obviously higher solid fluorescent quantum efficiency and AIE phenomena. In particular, the thin film of DT3A exhibited the highest fluorescent quantum efficiency of ca. 25% and the DT2A showed the highest αAIE of 78. Moreover, the excellent optical waveguide applications of DT2A and DT4A were achieved because of their excellent self-assembly properties. Meanwhile, piezofluorochromic behavior with a large red shift of 35 nm only appeared when DT4A was ground using a pestle, because DT4A inserted more TPA and changed the twisting conformation. The piezofluorochromic behavior can be recovered to its original color by fuming with solvent. Finally, DT2A and DT4A were utilized as fluorescent probes to detect nitroaromatic/nitroaliphatic compounds and showed evident fluorescence quenching. These results indicate a huge potential to develop bright AIEgens based on DPDT core units and also provide insights into understanding how piezofluorochromism, optical waveguides and explosive detection properties are influenced by alternating the spatial symmetry of AIE materials with different numbers of TPA terminal groups.

Graphical abstract: Constructing small molecular AIE luminophores through a 2,2-(2,2-diphenylethene-1,1-diyl)dithiophene core and peripheral triphenylamine with applications in piezofluorochromism, optical waveguides, and explosive detection

Supplementary files

Article information

Article type
Paper
Submitted
09 六月 2016
Accepted
27 七月 2016
First published
27 七月 2016

J. Mater. Chem. C, 2016,4, 8407-8415

Constructing small molecular AIE luminophores through a 2,2-(2,2-diphenylethene-1,1-diyl)dithiophene core and peripheral triphenylamine with applications in piezofluorochromism, optical waveguides, and explosive detection

Z. Chang, L. Jing, Y. Liu, J. Liu, Y. Ye, Y. S. Zhao, S. Yuan and J. Wang, J. Mater. Chem. C, 2016, 4, 8407 DOI: 10.1039/C6TC02395A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements