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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) by 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 is a Chemistry article available to read on EtoBox.
What is 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) about?
## Abstract The light fantastic: Two new 2‐(benzo[__b__]thiophene‐3‐yl)pyrroles have been synthesized, and are shown to exhibit optical properties that are promising for optoelectronic materials and devices such as highly efficient fluorescent sensors (see scheme). In addition a new BODIPY fluorophore, derived from 2‐(benzo[__b__]thiophene‐3‐yl)pyrrole, was also isolated and shows good spectroscopic properties in solution which are fully preserved in the solid state.magnified image 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 °C, 5 h) in 68 % yield. Devinylation of the synthesized pyrrole (Hg(OAc)~2~, NaBH~4~, 50 °C) led to the corresponding 2‐(benzo[__b__]thiophene‐3‐yl)pyrrole in 63 % yield. Trifluoroacetylation of both the pyrroles with trifluoroacetic anhydride (80 °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
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- Author
- 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
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)
- Published
- 2009
- Language
- EN
- Field
- Chemistry (Physical Sciences)