Display options
Cite
Schmidt EY, Trofimov BA, Mikhaleva AI, et al. Synthesis and optical properties of 2-(benzo[b]thiophene-3-yl)pyrroles and a new BODIPY fluorophore (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene). Chemistry. 2009;15(23):5823-30doi: 10.1002/chem.200802467.
Schmidt, E. Y., Trofimov, B. A., Mikhaleva, A. I., Zorina, N. V., Protzuk, N. I., Petrushenko, K. B., Ushakov, I. A., Dvorko, M. Y., Méallet-Renault, R., Clavier, G., Vu, T. T., Tran, H. T., & Pansu, R. B. (2009). Synthesis and optical properties of 2-(benzo[b]thiophene-3-yl)pyrroles and a new BODIPY fluorophore (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene). Chemistry (Weinheim an der Bergstrasse, Germany), 15(23), 5823-30. https://doi.org/10.1002/chem.200802467
Schmidt, Elena Yu, et al. "Synthesis and optical properties of 2-(benzo[b]thiophene-3-yl)pyrroles and a new BODIPY fluorophore (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene)." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 15,23 (2009): 5823-30. doi: https://doi.org/10.1002/chem.200802467
Schmidt EY, Trofimov BA, Mikhaleva AI, Zorina NV, Protzuk NI, Petrushenko KB, Ushakov IA, Dvorko MY, Méallet-Renault R, Clavier G, Vu TT, Tran HT, Pansu RB. Synthesis and optical properties of 2-(benzo[b]thiophene-3-yl)pyrroles and a new BODIPY fluorophore (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene). Chemistry. 2009 Jun 02;15(23):5823-30. doi: 10.1002/chem.200802467. PMID: 19396897.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2009 Jun 02;15(23):5823-30. doi: 10.1002/chem.200802467.

Synthesis and optical properties of 2-(benzo[b]thiophene-3-yl)pyrroles and a new BODIPY fluorophore (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene).

Chemistry (Weinheim an der Bergstrasse, Germany)

Elena Yu Schmidt, Boris A Trofimov, Al'bina I Mikhaleva, Nadezhda V Zorina, Nadezhda I Protzuk, Konstantin B Petrushenko, Igor A Ushakov, Marina Yu Dvorko, Rachel Méallet-Renault, Gilles Clavier, Thanh Truc Vu, Ha Thanh Thao Tran, Robert B Pansu

Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation.

PMID: 19396897 DOI: 10.1002/chem.200802467

Abstract

2-(Benzo[b]thiophene-3-yl)-1-vinylpyrrole has been synthesized directly from 3-acetylbenzo[b]thiophene oxime and acetylene (flow system, KOH-DMSO, 120 degrees C, 5 h) in 68% yield. Devinylation of the synthesized pyrrole (Hg(OAc)(2), NaBH(4), 50 degrees C) led to the corresponding 2-(benzo[b]thiophene-3-yl)pyrrole in 63% yield. Trifluoroacetylation of both the pyrroles with trifluoroacetic anhydride (80 degrees C, 1 h) gave the corresponding 5-trifluoroacetyl pyrroles in 97% and 76% yields, respectively. 2-(Benzo[b]thiophene-3-yl)pyrrole was reacted subsequently with mesityl aldehyde, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), and BF(3)OEt(2) to afford 4,4-difluoro-3,5-di(benzo[b]thiophene-3-yl)-8-mesityl-4-bora-3a,4a-diaza-s-indacene, a representative of the novel BODIPY fluorophore family (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), in 34% overall yield. The synthesized pyrroles exhibit promising optical properties (absorption and emission spectra, nonlinear optical (NLO) features), superior to existing analogues. The BODIPY fluorophore displays an intense red-shifted fluorescence emission in CH(2)Cl(2) (625 nm, 0.84 fluorescence quantum yield) that is fully preserved in the solid state.

Publication Types