title: 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).
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.
authors.affiliation: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation.
authors.forename: Elena Yu
authors.initials: EY
authors.lastname: Schmidt
authors.forename: Boris A
authors.initials: BA
authors.lastname: Trofimov
authors.forename: Al'bina I
authors.initials: AI
authors.lastname: Mikhaleva
authors.forename: Nadezhda V
authors.initials: NV
authors.lastname: Zorina
authors.forename: Nadezhda I
authors.initials: NI
authors.lastname: Protzuk
authors.forename: Konstantin B
authors.initials: KB
authors.lastname: Petrushenko
authors.forename: Igor A
authors.initials: IA
authors.lastname: Ushakov
authors.forename: Marina Yu
authors.initials: MY
authors.lastname: Dvorko
authors.forename: Rachel
authors.initials: R
authors.lastname: Méallet-Renault
authors.forename: Gilles
authors.initials: G
authors.lastname: Clavier
authors.forename: Thanh Truc
authors.initials: TT
authors.lastname: Vu
authors.forename: Ha Thanh Thao
authors.initials: HT
authors.lastname: Tran
authors.forename: Robert B
authors.initials: RB
authors.lastname: Pansu