𝔖 Bobbio Scriptorium
✦   LIBER   ✦

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)

✍ Scribed 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

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
427 KB
Volume
15
Category
Article
ISSN
0947-6539

No coin nor oath required. For personal study only.

✦ Synopsis

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)‐8‐mesityl‐4‐bora‐3__a__,4__a__‐diaza‐s‐indacene, a representative of the novel BODIPY fluorophore family (BODIPY=4,4‐difluoro‐4‐bora‐3__a__,4__a__‐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.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of 3,5-Di
ChemInform Abstract: Synthesis of 3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY®) Dyes.
✍ L. H. THORESEN; H. KIM; M. B. WELCH; A. BURGHART; K. BURGESS 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 KB 👁 1 views

## Synthesis of 3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY r ) Dyes. -Condensation of arylpyrroles (IV), prepared via Suzuki coupling of arylboronic acids (II) to bromo pyrrole (I), gives highly colored dipyrrolemethenes (VI). Finally, addition of BF 3 -etherate leads to format

ChemInform Abstract: (4,4-Difluoro-4-bor
ChemInform Abstract: (4,4-Difluoro-4-bora-3a,4a-diaza-s-indacen-3-yl)acetaldehyde: Synthesis and Chemical Properties.
✍ Mykola P. Shandura; Viktor P. Yakubovskyi; Yuriy P. Kovtun 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 40 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v