Fluorinated acylthiophenes. Preparation of 5,5'-diheptafluorobutyryl-2,2'-bithiophene via a Grignard coupling reaction

Portnoy, Seymour; Gisser, Henry

doi:10.1021/jo01277a062

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2021

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“…We investigated the influence of stronger electron-withdrawing terminal carbonyl substituents on the spectroscopic properties of oligothiophenes and extended the acylation to perfluorobutyric chloride. 28 No zinc oxide mediated reaction could be observed, and the application of the standard procedure afforded the mono-acylated products for both bisthiophene (4a) and terthiophene (4b) with moderate yields, see Scheme 2. Obviously, activation of perfluoro acid chloride is more difficult, and the electron depletion in the reaction products inhibits a second acylation.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Terminal Terthiophenediones: Fast-Decay Fluorescent Dyes and Their Efficient Syntheses

et al. 2021

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Terminally acylated terthiophenes, in particular, the bis-pivaloyl derivative, were synthesized by Friedel–Crafts acylation with sub-stoichiometric amounts of standard zinc oxide and exhibit strong fluorescence and an ultrafast fluorescence decay of 400 ps. Their high photostability and large Stokes’ shifts are good prerequisites for applications in optical GBit fast data systems such as fiber optics in slip rings.

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Section: ■ Results and Discussionmentioning

confidence: 99%