Carbazole-based BODIPYs with ethynyl substituents at the boron center

Solid-state excimer fluorescence in the VIS/NIR region

Chihiro Maeda, Keiji Nagahata, Tadashi Ema

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7783-7788
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number37
DOIs
Publication statusPublished - 2017

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Boron
carbazoles
excimers
boron
Fluorescence
solid state
Dimers
fluorescence
Coloring Agents
dyes
dimers
self absorption
Structural optimization
Crystal structure
X-Rays
Derivatives
X rays
Atoms
Crystals
crystal structure

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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title = "Carbazole-based BODIPYs with ethynyl substituents at the boron center: Solid-state excimer fluorescence in the VIS/NIR region",
abstract = "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.",
author = "Chihiro Maeda and Keiji Nagahata and Tadashi Ema",
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journal = "Organic and Biomolecular Chemistry",
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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

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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