Issue 10, 2002

Synthesis and characterisation of 1,2-difluoro-1,2-bis(5-trimethylsilyl-2-thienyl)ethenes. A new family of conjugated monomers for oxidative polymerisation

Abstract

The synthesis of a series of (E)-1,2-difluoro-1,2-bis(2-thienyl)ethenes (DFDTEs) by low temperature reaction of 2-lithiothiophenes with tetrafluoroethene (TFE) is described. A possible explanation of the mechanism leading to the formation of higher oligomers is also elucidated together with the use of TMS as protecting group to prevent it. All compounds are thoroughly characterised and their E – configuration proved by vibrational spectroscopy. The crystal structure at 120 K of a representative system evidences its essential planarity and suggests significant delocalisation of π-electrons. Fluorine atoms are involved both in short intra- and intermolecular interactions with sulfur atoms and hydrogen atoms, apparently stabilising the planar molecular arrangement.

Graphical abstract: Synthesis and characterisation of 1,2-difluoro-1,2-bis(5-trimethylsilyl-2-thienyl)ethenes. A new family of conjugated monomers for oxidative polymerisation

Supplementary files

Article information

Article type
Paper
Submitted
12 Apr 2002
Accepted
01 Aug 2002
First published
12 Sep 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 1752-1759

Synthesis and characterisation of 1,2-difluoro-1,2-bis(5-trimethylsilyl-2-thienyl)ethenes. A new family of conjugated monomers for oxidative polymerisation

L. Albertin, C. Bertarelli, M. C. Gallazzi, S. V. Meille and S. C. Capelli, J. Chem. Soc., Perkin Trans. 2, 2002, 1752 DOI: 10.1039/B203589H

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