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Issue 23, 2015
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The effect of regioisomerism on the solid-state fluorescence of bis(piperidyl)anthracenes: structurally simple but bright AIE luminogens

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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

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Supplementary files

Article information


Submitted
04 Apr 2015
Accepted
11 May 2015
First published
11 May 2015

This article is Open Access

J. Mater. Chem. C, 2015,3, 5940-5950
Article type
Paper

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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