Issue 38, 2015

Aggregation induced emission and mechanochromism in pyrenoimidazoles

Abstract

Pyrene-based solid state emitters 3a and 3b were designed and synthesized by the Pd-catalyzed Suzuki cross-coupling reaction of bromopyrenoimidazole 2 with 4-(1,2,2-triphenylvinyl)phenylboronic acid pinacol ester and 2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile. The single crystal X-ray structure of 3a was reported and revealed the twisted conformation. Their photophysical, aggregation induced emission (AIE) and mechanochromic properties were studied. Pyrenoimidazoles 3a and 3b exhibit strong AIE. 3b shows different colored emission with varying water fraction. 3a and 3b exhibit reversible mechanochromic behavior with color contrast between blue and green. The enhanced conjugation and increased amorphous nature observed after grinding are associated with mechanochromism in pyrenoimidazoles 3a and 3b.

Graphical abstract: Aggregation induced emission and mechanochromism in pyrenoimidazoles

Supplementary files

Article information

Article type
Paper
Submitted
18 Jul 2015
Accepted
01 Sep 2015
First published
02 Sep 2015

J. Mater. Chem. C, 2015,3, 9981-9988

Author version available

Aggregation induced emission and mechanochromism in pyrenoimidazoles

T. Jadhav, B. Dhokale, S. M. Mobin and R. Misra, J. Mater. Chem. C, 2015, 3, 9981 DOI: 10.1039/C5TC02181B

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