Tuning the solid-state luminescence of bodipy derivatives with bulky arylsilyl groups: Synthesis and spectroscopic properties

Hua Lu, Qiuhong Wang, Lizhi Gai, Zhifang Li, Yuan Deng, Xuqiong Xiao, Guoqiao Lai, Zhen Shen

Research output: Contribution to journalArticlepeer-review

114 Citations (Scopus)

Abstract

Boron dipyrromethenes (BODIPYs) with bulky triphenylsilylphenyl(ethynyl) and triphenylsilylphenyl substituents on pyrrole sites were prepared via Hagihara-Sonogashira and Suzuki-Miyaura cross-coupling with ethynyl-terminated tetraphenylsilane and boronic acid-terminated tetraphenylsilane. The chromophores are designed to prevent intermolecular p-p stacking interaction and enhance fluorescence in the solid state. Single crystals of 1a and 2b for X-ray structural analysis were obtained, and weak p-p stacking interactions of the neighboring BODIPY molecules were observed. Spectroscopic properties of all of the dyes in various solvents and in films were investigated. Triphenylsilylphenyl-substituted BODIPYs generally show more pronounced increases in solid-state emission than triphenylsilylphenyl(ethynyl)-substituted BODIPYs. Although the simple BODIPYs do not exhibit any fluorescence in the solid state (F=0), arylsilyl-substituted BODIPYs exhibit weak to moderate solid-state fluorescence with quantum yields of 0.03, 0.07, 0.10, and 0.25. The structure-property relationships were analyzed on the basis of X-ray crystallography, optical spectroscopy, cyclic voltammetry, and theoretical calculations.

Original languageEnglish
Pages (from-to)7852-7861
Number of pages10
JournalChemistry - A European Journal
Volume18
Issue number25
DOIs
Publication statusPublished - 2012 Jun 18
Externally publishedYes

Keywords

  • Boron dipyrromethenes
  • Dyes/pigments
  • Fluorescence
  • Photophysics
  • Solid-state emission

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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