Synthesis, characterization and solid-state emission properties of arylsilyl-substituted pyrene derivatives

Qiuhong Wang; Hui Liu; Hua Lu; Zheng Xu; Guoqiao Lai; Zhifang Li; John Mack; Zhen Shen

doi:10.1016/j.dyepig.2013.07.003

Synthesis, characterization and solid-state emission properties of arylsilyl-substituted pyrene derivatives

Qiuhong Wang, Hui Liu, Hua Lu, Zheng Xu, Guoqiao Lai, Zhifang Li, John Mack, Zhen Shen

Science

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Arylsilyl substituted pyrene derivatives were synthesized via Suzuki-Miyaura and Hagihara-Sonogashira cross-coupling reactions with boronic acid-terminated and ethynyl-terminated tetraphenylsilane at the 1-, 3-, 6- and 8-positions. The spectroscopic properties of the dyes were investigated in various solvents and in films to assess the suitability of these compounds for optoelectronic applications. A triphenylsilylphenyl substituted pyrene was found to exhibit intense emission in the solid state with an absolute fluorescence quantum yield (Φ_F) of 0.65. In contrast, the emission properties of a triphenylsilylphenyl(ethynyl) substituted pyrene were found to be somewhat weaker in the solid state (Φ_F = 0.16) and solvent polarity dependent in solution. Magnetic circular dichroism (MCD) spectroscopy, cyclic voltammetry, and theoretical calculations have been used to analyze the structure-property relationships with Michl's perimeter model used as a conceptual framework for rationalizing the key trends.

Original language	English
Pages (from-to)	771-778
Number of pages	8
Journal	Dyes and Pigments
Volume	99
Issue number	3
DOIs	https://doi.org/10.1016/j.dyepig.2013.07.003
Publication status	Published - 2013 Aug 27

Keywords

Fluorescence
Pigments
Pyrene dyes MCD spectroscopy
Solid-state emission
TD-DFT calculations

ASJC Scopus subject areas

Chemical Engineering(all)
Process Chemistry and Technology

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title = "Synthesis, characterization and solid-state emission properties of arylsilyl-substituted pyrene derivatives",

abstract = "Arylsilyl substituted pyrene derivatives were synthesized via Suzuki-Miyaura and Hagihara-Sonogashira cross-coupling reactions with boronic acid-terminated and ethynyl-terminated tetraphenylsilane at the 1-, 3-, 6- and 8-positions. The spectroscopic properties of the dyes were investigated in various solvents and in films to assess the suitability of these compounds for optoelectronic applications. A triphenylsilylphenyl substituted pyrene was found to exhibit intense emission in the solid state with an absolute fluorescence quantum yield (ΦF) of 0.65. In contrast, the emission properties of a triphenylsilylphenyl(ethynyl) substituted pyrene were found to be somewhat weaker in the solid state (ΦF = 0.16) and solvent polarity dependent in solution. Magnetic circular dichroism (MCD) spectroscopy, cyclic voltammetry, and theoretical calculations have been used to analyze the structure-property relationships with Michl's perimeter model used as a conceptual framework for rationalizing the key trends.",

keywords = "Fluorescence, Pigments, Pyrene dyes MCD spectroscopy, Solid-state emission, TD-DFT calculations",

author = "Qiuhong Wang and Hui Liu and Hua Lu and Zheng Xu and Guoqiao Lai and Zhifang Li and John Mack and Zhen Shen",

year = "2013",

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T1 - Synthesis, characterization and solid-state emission properties of arylsilyl-substituted pyrene derivatives

AU - Wang, Qiuhong

AU - Liu, Hui

AU - Lu, Hua

AU - Xu, Zheng

AU - Lai, Guoqiao

AU - Li, Zhifang

AU - Mack, John

AU - Shen, Zhen

PY - 2013/8/27

Y1 - 2013/8/27

N2 - Arylsilyl substituted pyrene derivatives were synthesized via Suzuki-Miyaura and Hagihara-Sonogashira cross-coupling reactions with boronic acid-terminated and ethynyl-terminated tetraphenylsilane at the 1-, 3-, 6- and 8-positions. The spectroscopic properties of the dyes were investigated in various solvents and in films to assess the suitability of these compounds for optoelectronic applications. A triphenylsilylphenyl substituted pyrene was found to exhibit intense emission in the solid state with an absolute fluorescence quantum yield (ΦF) of 0.65. In contrast, the emission properties of a triphenylsilylphenyl(ethynyl) substituted pyrene were found to be somewhat weaker in the solid state (ΦF = 0.16) and solvent polarity dependent in solution. Magnetic circular dichroism (MCD) spectroscopy, cyclic voltammetry, and theoretical calculations have been used to analyze the structure-property relationships with Michl's perimeter model used as a conceptual framework for rationalizing the key trends.

AB - Arylsilyl substituted pyrene derivatives were synthesized via Suzuki-Miyaura and Hagihara-Sonogashira cross-coupling reactions with boronic acid-terminated and ethynyl-terminated tetraphenylsilane at the 1-, 3-, 6- and 8-positions. The spectroscopic properties of the dyes were investigated in various solvents and in films to assess the suitability of these compounds for optoelectronic applications. A triphenylsilylphenyl substituted pyrene was found to exhibit intense emission in the solid state with an absolute fluorescence quantum yield (ΦF) of 0.65. In contrast, the emission properties of a triphenylsilylphenyl(ethynyl) substituted pyrene were found to be somewhat weaker in the solid state (ΦF = 0.16) and solvent polarity dependent in solution. Magnetic circular dichroism (MCD) spectroscopy, cyclic voltammetry, and theoretical calculations have been used to analyze the structure-property relationships with Michl's perimeter model used as a conceptual framework for rationalizing the key trends.

KW - Fluorescence

KW - Pigments

KW - Pyrene dyes MCD spectroscopy

KW - Solid-state emission

KW - TD-DFT calculations

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