Color-Tunable Solid-State Fluorescence Emission from Carbazole-Based BODIPYs

Chihiro Maeda, Takumi Todaka, Tomomi Ueda, Tadashi Ema

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Several carbazole-based boron dipyrromethene (BODIPY) dyes were synthesized by organometallic approaches. Thiazole, benzothiazole, imidazole, benzimidazole, triazole, and indolone substituents were introduced at the 1-position of the carbazole moiety, and boron complexation of each dipyrrin generated the corresponding compounds 1, 2 a, and 3-6. The properties of these products were investigated by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography, and DFT calculations. These compounds exhibited large Stokes shifts, and compounds 1, 2 a, and 3-5 fluoresced both in solution and in the solid state. Complex 2 a showed the highest fluorescence quantum yield (ΦF) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2 b-f, which had several different substituents, were prepared and the effects of the substituents on the photophysical properties of the compounds were examined. The fluorescence properties showed good correlation with the results of crystal-packing analyses, and the dyes exhibited color-tunable solid-state fluorescence.

Original languageEnglish
Pages (from-to)7508-7513
Number of pages6
JournalChemistry - A European Journal
Volume22
Issue number22
DOIs
Publication statusPublished - May 23 2016

Keywords

  • boron dipyrromethene (BODIPY)
  • carbazoles
  • dyes/pigments
  • fluorescence
  • solid-state emission

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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