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Synthesis and Optical Properties of Difluorobora‐ s ‐diazaindacene Dyes with Trifluoromethyl meso‐ Substituents
Author(s) -
Sobenina Lyubov N.,
Petrova Olga V.,
Petrushenko Konstantin B.,
Ushakov Igor A.,
Mikhaleva Albina I.,
MealletRenault Rachel,
Trofimov Boris A.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300212
Subject(s) - chemistry , trifluoromethyl , bodipy , yield (engineering) , condensation , quantum yield , fluorescence , aryl , medicinal chemistry , photochemistry , combinatorial chemistry , organic chemistry , alkyl , physics , materials science , quantum mechanics , metallurgy , thermodynamics
A series of meso ‐CF 3 ‐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).