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Issue 42, 2014
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2,6,9,10-Tetra(p-dibutylaminostyryl)anthracene as a multifunctional fluorescent cruciform dye

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Abstract

In this work, we have synthesized a tetradonor-capped anthracene-centered cruciform 2,6,9,10-tetra(p-dibutylaminostyryl)anthracene (TDC) and its optical properties are investigated. TDC is a light- and heat-stable dye and shows aggregation-enhanced emission (AEE), large and enhanced two-photon absorption cross sections (δ), fluorescence sensing selectively to transition metal ions such as Zn2+ and Cu2+, and appreciable piezofluorochromism (PFC), which is rarely found to exist simultaneously in cruciform or other configuration dyes. The AEE and PFC behaviours result from the existence of a strongly twisted 9,10-branch, and the large and enhanced δ is ascribed to the multiple conjugation pathways and introduction of donor end-groups. TDC possesses a non-centrosymmetric structure and a semi-disjoint Frontier molecular orbital, which could rationalize its fluorescence sensing selectively to Zn2+ and Cu2+. These findings indicate further that an anthracene ring is indeed a unique π-center that is different from other π-centers and can construct novel cruciforms with interesting optical properties.

Graphical abstract: 2,6,9,10-Tetra(p-dibutylaminostyryl)anthracene as a multifunctional fluorescent cruciform dye

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Article information


Submitted
30 Jul 2014
Accepted
29 Aug 2014
First published
02 Sep 2014

J. Mater. Chem. C, 2014,2, 9028-9034
Article type
Paper
Author version available

2,6,9,10-Tetra(p-dibutylaminostyryl)anthracene as a multifunctional fluorescent cruciform dye

W. Liu, J. Wang, Y. Gao, Q. Sun, S. Xue and W. Yang, J. Mater. Chem. C, 2014, 2, 9028
DOI: 10.1039/C4TC01680G

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