Benzo[c,d]indole-Containing Aza-BODIPY Dyes

Asymmetrization-Induced Solid-State Emission and Aggregation-Induced Emission Enhancement as New Properties of a Well-Known Chromophore

Soji Shimizu, Ai Murayama, Takuya Haruyama, Taku Iino, Shigeki Mori, Hiroyuki Furuta, Nagao Kobayashi

研究成果: ジャーナルへの寄稿記事

25 引用 (Scopus)

抄録

A series of symmetric and asymmetric benzo[c,d]indole-containing aza boron dipyrromethene (aza-BODIPY) compounds was synthesized by a titanium tetrachloride-mediated Schiff-base formation reaction of commercially available benzo[c,d]indole-2(1H)-one and heteroaromatic amines. These aza-BODIPY analogues show different electronic structures from those of regular aza-BODIPYs, with hypsochromic shifts of the main absorption compared to their BODIPY counterparts. In addition to the intense fluorescence in solution, asymmetric compounds exhibited solid-state fluorescence due to significant contribution of the vibronic bands to both absorption and fluorescence as well as reduced fluorescence quenching in the aggregates. Finally, aggregation-induced emission enhancement, which is rare in BODIPY chromophores, was achieved by introducing a nonconjugated moiety into the core structure.

元の言語英語
ページ(範囲)12996-13003
ページ数8
ジャーナルChemistry - A European Journal
21
発行部数37
DOI
出版物ステータス出版済み - 9 1 2015

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Chromophores
Coloring Agents
Agglomeration
Dyes
Fluorescence
Boron compounds
Boron
Schiff Bases
Electronic structure
Amines
Quenching
Titanium
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
indole
dipyrromethene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

これを引用

Benzo[c,d]indole-Containing Aza-BODIPY Dyes : Asymmetrization-Induced Solid-State Emission and Aggregation-Induced Emission Enhancement as New Properties of a Well-Known Chromophore. / Shimizu, Soji; Murayama, Ai; Haruyama, Takuya; Iino, Taku; Mori, Shigeki; Furuta, Hiroyuki; Kobayashi, Nagao.

:: Chemistry - A European Journal, 巻 21, 番号 37, 01.09.2015, p. 12996-13003.

研究成果: ジャーナルへの寄稿記事

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abstract = "A series of symmetric and asymmetric benzo[c,d]indole-containing aza boron dipyrromethene (aza-BODIPY) compounds was synthesized by a titanium tetrachloride-mediated Schiff-base formation reaction of commercially available benzo[c,d]indole-2(1H)-one and heteroaromatic amines. These aza-BODIPY analogues show different electronic structures from those of regular aza-BODIPYs, with hypsochromic shifts of the main absorption compared to their BODIPY counterparts. In addition to the intense fluorescence in solution, asymmetric compounds exhibited solid-state fluorescence due to significant contribution of the vibronic bands to both absorption and fluorescence as well as reduced fluorescence quenching in the aggregates. Finally, aggregation-induced emission enhancement, which is rare in BODIPY chromophores, was achieved by introducing a nonconjugated moiety into the core structure.",
author = "Soji Shimizu and Ai Murayama and Takuya Haruyama and Taku Iino and Shigeki Mori and Hiroyuki Furuta and Nagao Kobayashi",
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T2 - Asymmetrization-Induced Solid-State Emission and Aggregation-Induced Emission Enhancement as New Properties of a Well-Known Chromophore

AU - Shimizu, Soji

AU - Murayama, Ai

AU - Haruyama, Takuya

AU - Iino, Taku

AU - Mori, Shigeki

AU - Furuta, Hiroyuki

AU - Kobayashi, Nagao

PY - 2015/9/1

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N2 - A series of symmetric and asymmetric benzo[c,d]indole-containing aza boron dipyrromethene (aza-BODIPY) compounds was synthesized by a titanium tetrachloride-mediated Schiff-base formation reaction of commercially available benzo[c,d]indole-2(1H)-one and heteroaromatic amines. These aza-BODIPY analogues show different electronic structures from those of regular aza-BODIPYs, with hypsochromic shifts of the main absorption compared to their BODIPY counterparts. In addition to the intense fluorescence in solution, asymmetric compounds exhibited solid-state fluorescence due to significant contribution of the vibronic bands to both absorption and fluorescence as well as reduced fluorescence quenching in the aggregates. Finally, aggregation-induced emission enhancement, which is rare in BODIPY chromophores, was achieved by introducing a nonconjugated moiety into the core structure.

AB - A series of symmetric and asymmetric benzo[c,d]indole-containing aza boron dipyrromethene (aza-BODIPY) compounds was synthesized by a titanium tetrachloride-mediated Schiff-base formation reaction of commercially available benzo[c,d]indole-2(1H)-one and heteroaromatic amines. These aza-BODIPY analogues show different electronic structures from those of regular aza-BODIPYs, with hypsochromic shifts of the main absorption compared to their BODIPY counterparts. In addition to the intense fluorescence in solution, asymmetric compounds exhibited solid-state fluorescence due to significant contribution of the vibronic bands to both absorption and fluorescence as well as reduced fluorescence quenching in the aggregates. Finally, aggregation-induced emission enhancement, which is rare in BODIPY chromophores, was achieved by introducing a nonconjugated moiety into the core structure.

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