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

Research output: Contribution to journalArticlepeer-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 (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.

Original languageEnglish
Pages (from-to)771-778
Number of pages8
JournalDyes and Pigments
Volume99
Issue number3
DOIs
Publication statusPublished - 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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