Issue 23, 2015

The effect of regioisomerism on the solid-state fluorescence of bis(piperidyl)anthracenes: structurally simple but bright AIE luminogens

Abstract

A series of regioisomers of piperidylanthracenes (PA) and bis(piperidyl)anthracenes (BPA) were synthesized and their photophysical properties examined in solution, suspension, and the solid state. Aggregation-induced emission (AIE) was observed only for 1,4-BPA and 9,10-BPA, in which two piperidyl groups are substituted at the anthracene moiety in the para-position with respect to each other. Compared to previously reported AIE luminogens, these easily obtainable para-substituted BPAs, exhibited several unique and beneficial features, such as simple structures, bright solid-state fluorescence (Φfl = 0.49 and 0.86 for 1,4-BPA and 9,10-BPA, respectively), tunable fluorescence emission, and large Stokes shifts. Results from diffuse-reflectance and fluorescence lifetime measurements demonstrated that PAs and BPAs intrinsically possess an efficient non-radiative transition pathway in the solid state, and that 1,4-BPA and 9,10-BPA may overcome this pathway. The X-ray crystallographic analysis of 1,4-BPA revealed that undesirable interchromophoric interactions can be minimised, while TD-DFT calculations suggested that the enhanced Stokes shift of 1,4-BPA arises from severe electronic repulsion between neighbouring piperidyl moieties, which presumably results in the absence of self-absorption.

Graphical abstract: The effect of regioisomerism on the solid-state fluorescence of bis(piperidyl)anthracenes: structurally simple but bright AIE luminogens

Supplementary files

Article information

Article type
Paper
Submitted
04 apr 2015
Accepted
11 may 2015
First published
11 may 2015
This article is Open Access
Creative Commons BY license

J. Mater. Chem. C, 2015,3, 5940-5950

The effect of regioisomerism on the solid-state fluorescence of bis(piperidyl)anthracenes: structurally simple but bright AIE luminogens

S. Sasaki, K. Igawa and G. Konishi, J. Mater. Chem. C, 2015, 3, 5940 DOI: 10.1039/C5TC00946D

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