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

Chihiro Maeda, Takumi Todaka, Tomomi Ueda, Tadashi Ema

Research output: Contribution to journalArticle

20 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, 2a, 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, 2a, and 3-5 fluoresced both in solution and in the solid state. Complex 2a showed the highest fluorescence quantum yield (ΦF) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2b-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
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - 2016

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Boron
Fluorescence
Color
Coloring Agents
Dyes
Thiazoles
Triazoles
X ray crystallography
Fluorescence spectroscopy
Organometallics
Quantum yield
Ultraviolet spectroscopy
Complexation
Discrete Fourier transforms
Cyclic voltammetry
Crystals
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
carbazole
benzothiazole

Keywords

  • Boron dipyrromethene (BODIPY)
  • Carbazoles
  • Dyes/pigments
  • Fluorescence
  • Solid-state emission

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Color-Tunable Solid-State Fluorescence Emission from Carbazole-Based BODIPYs. / Maeda, Chihiro; Todaka, Takumi; Ueda, Tomomi; Ema, Tadashi.

In: Chemistry - A European Journal, 2016.

Research output: Contribution to journalArticle

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