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Synthesis and Optical Properties of Difluorobora-s-diazaindacene Dyes with Trifluoromethyl meso-Substituents

Lyubov N. Sobenina, Olga V. Petrova, Konstantin B. Petrushenko, Igor A. Ushakov, Albina I. Mikhaleva, Rachel Meallet-Renault, Boris A. Trofimov, Eur. J. Org. Chem. 2013, 4107-4118.

FA series of meso-CF3-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes with aryl and hetaryl substituents at the C-3 and C-5 positions, both symmetric and asymmetric, have been synthesized in 36-90% yields by a new strategy involving as the key step the condensation of 2,2,2-trifluoro-1-(5-arylpyrrol-2-yl)-1-ethanols with diverse 2-arylpyrroles. The starting 2,2,2-trifluoro-1-(5-arylpyrrol-2-yl)-1-ethanols are easily prepared by reduction of the available 2-trifluoroacetyl-5-arylpyrroles. The synthesized dyes fluoresce in a longer wavelength region (626-698 nm) with high quantum yield (0.84-0.99).

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Publication

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Paru le 15 mai 2013

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DOI: 10.1002/ejoc.201300212