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Shimizu S, Murayama A, Haruyama T, et al. 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. Chemistry. 2015;21(37):12996-3003doi: 10.1002/chem.201501464.
Shimizu, S., Murayama, A., Haruyama, T., Iino, T., Mori, S., Furuta, H., & Kobayashi, N. (2015). 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. Chemistry (Weinheim an der Bergstrasse, Germany), 21(37), 12996-3003. https://doi.org/10.1002/chem.201501464
Shimizu, Soji, et al. "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." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,37 (2015): 12996-3003. doi: https://doi.org/10.1002/chem.201501464
Shimizu S, Murayama A, Haruyama T, Iino T, Mori S, Furuta H, Kobayashi N. 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. Chemistry. 2015 Sep 07;21(37):12996-3003. doi: 10.1002/chem.201501464. Epub 2015 Jul 17. PMID: 26212774.
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Chemistry. 2015 Sep 07;21(37):12996-3003. doi: 10.1002/chem.201501464. Epub 2015 Jul 17.

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.

Chemistry (Weinheim an der Bergstrasse, Germany)

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

Affiliations

  1. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395 (Japan). [email protected].
  2. Center for Molecular Systems (CMS), Kyushu University, Fukuoka 819-0395 (Japan). [email protected].
  3. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan).
  4. Division of Material Science, Advanced Research Support Center, Ehime University, Matsuyama 790-8577 (Japan).
  5. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395 (Japan).
  6. Center for Molecular Systems (CMS), Kyushu University, Fukuoka 819-0395 (Japan).
  7. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan). [email protected].
  8. Faculty of Textile Science and Technology, Shinshu University, Ueda 386-8567 (Japan). [email protected].

PMID: 26212774 DOI: 10.1002/chem.201501464

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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: aggregation; dyes/pigments; fluorescence; nitrogen heterocycles; solid-state emission

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