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- Title
Color-Tunable Solid-State Fluorescence Emission from Carbazole-Based BODIPYs.
- Authors
Maeda, Chihiro; Todaka, Takumi; Ueda, Tomomi; Ema, Tadashi
- 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.
- Subjects
CARBAZOLE; THIAZOLES; ORGANOSULFUR compounds; BENZOTHIAZOLE; ISOTHIAZOLE
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 22, p7508
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201505150