TY - JOUR
T1 - Carbazole-based BODIPYs with ethynyl substituents at the boron center
T2 - Solid-state excimer fluorescence in the VIS/NIR region
AU - Maeda, Chihiro
AU - Nagahata, Keiji
AU - Ema, Tadashi
N1 - Funding Information:
This work was supported by the JSPS KAKENHI Grant Number 15K05427. We thank Prof. A. Osuka and Dr T. Tanaka (Kyoto University) for performing the X-ray diffraction analyses and fluorescence spectroscopy, Prof. K. Matsuda and Dr T. Hirose (Kyoto University) for fluorescence lifetime measurements, and Prof. H. Yorimitsu (Kyoto University) for mass spectroscopy measurements.
Publisher Copyright:
© 2017 The Royal Society of Chemistry.
PY - 2017
Y1 - 2017
N2 - Carbazole-based BODIPYs 1-6 with several different substituents at the boron atom site were synthesized. These dyes fluoresced in the solid state, and 3a with phenylethynyl groups exhibited a red-shifted and broad fluorescence spectrum, which suggested an excimer emission. Its derivatives 3b-n were synthesized, and the relationship between the solid-state emission and crystal packing was investigated. The X-ray crystal structures revealed cofacial dimers that might form excimers. From the structural optimization results, we found that the introduction of mesityl groups hindered intermolecular access and led to reduced interactions between the dimers. In addition, the red-shifted excimer fluorescence suppressed self-absorption, and dyes with ethynyl groups showed solid-state fluorescence in the vis/NIR region.
AB - Carbazole-based BODIPYs 1-6 with several different substituents at the boron atom site were synthesized. These dyes fluoresced in the solid state, and 3a with phenylethynyl groups exhibited a red-shifted and broad fluorescence spectrum, which suggested an excimer emission. Its derivatives 3b-n were synthesized, and the relationship between the solid-state emission and crystal packing was investigated. The X-ray crystal structures revealed cofacial dimers that might form excimers. From the structural optimization results, we found that the introduction of mesityl groups hindered intermolecular access and led to reduced interactions between the dimers. In addition, the red-shifted excimer fluorescence suppressed self-absorption, and dyes with ethynyl groups showed solid-state fluorescence in the vis/NIR region.
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U2 - 10.1039/c7ob01473b
DO - 10.1039/c7ob01473b
M3 - Article
C2 - 28799612
AN - SCOPUS:85030244115
SN - 1477-0520
VL - 15
SP - 7783
EP - 7788
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 37
ER -