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Issue 13, 2020
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Tetraphenylethylene-incorporated squaraine dyes: structural and theoretical insights into the diverse emission behaviors in solution and solid state

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Abstract

Endowing organic dyes with desired emissive behaviors in diverse states is of great importance for broad practical applications, but it remains a huge challenge. In this study, based on the incorporation of tetraphenylethylene (TPE) into squaraine dyes, we successfully synthesized 2TPE-SQ and TPE-SQ and both exhibited dual state emission with emission efficiencies (ΦPL) up to 0.33 and 0.75, respectively. The intense emission in the crystalline state can be ascribed to highly restricted π–π stacking, while the different degrees of intramolecular phenyl motions in 2TPE-SQ and TPE-SQ result in weak and moderate emissions in solution. Combining density functional theory (DFT) calculations, local excited (LE)/twisted intramolecular charge transfer (TICT) and excited-state intramolecular proton transfer (ESIPT) mechanisms were proposed and accounted well for their very different emission wavelengths in solution and crystalline state, respectively. Besides, other emission behaviors such as aggregation-caused quenching (ACQ), crystalline-induced emission enhancement (CIEE) and thermo-/mechanochromism of these two derivatives were verified in detail, and all these results would bring a new insight into the investigation of organic luminogens in solution and solid state.

Graphical abstract: Tetraphenylethylene-incorporated squaraine dyes: structural and theoretical insights into the diverse emission behaviors in solution and solid state

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Supplementary files

Article information


Submitted
22 Nov 2019
Accepted
11 Feb 2020
First published
12 Feb 2020

J. Mater. Chem. C, 2020,8, 4549-4556
Article type
Paper

Tetraphenylethylene-incorporated squaraine dyes: structural and theoretical insights into the diverse emission behaviors in solution and solid state

Q. Shao, K. Liang, H. Ling, Y. Wang, Z. Yan, G. Xia and H. Wang, J. Mater. Chem. C, 2020, 8, 4549
DOI: 10.1039/C9TC06406K

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