Thioglycolate de méthyle comme matière première pour la synthèse de beta-alcoxythiophènes

National audienc

3-Alkoxy-4-bromothiophenes: general synthesis of monomers and regio-selective preparation of two dimers

3-Alkoxy-4-bromothiophenes were synthesized in three steps from the readily available methyl 2-carboxylate-3-hydroxythiophene and two isomers of bithiophenes based on the 3-bromo-4-methoxythiophene moiety were regio-selectively prepared. (C) 2011 Elsevier Ltd. All rights reserved

Facile Synthesis of 3-Alkoxy-4-cyanothiophenes As New Building Blocks for Donor−Acceptor Conjugated Systems

International audienc

Evidence for the contribution of sulfur–bromine intramolecular interactions to the self-rigidification of thiophene-based π-conjugated systems

Bithiophene associating 3,4-ethylenedioxythiophene and 3-bromothiophene, and the corresponding polymer exhibit self-rigidified structures of the conjugated backbones resulting from the association of S–Br and S–O non-bonded intramolecular interactions

Efficient synthesis of 3,6-dialkoxythieno[3,2-b]thiophenes as precursors of electrogenerated conjugated polymers

A series of 3,6-dialkoxythieno[3,2-b]thiophenes have been synthesized through three synthetic pathways. Symmetrical derivatives have been obtained from 3,6-dibromothieno[3,2-b]thiophene or by trans-etherification of 3,6-dimethoxythieno[3,2-b]thiophene while unsymmetrical derivatives have been easily prepared from the readily accessible dimethyl 3-hydroxythiophene-2,5-dicarboxylate. These compounds have been used as precursors for electropolymerisation and a first characterisation of the electronic properties of the resulting polymers is presented

Rigid oligomers based on the combination of 3,6-dimethoxythieno[3,2-b]thiophene and 3,4-ethylenedioxythiophene

New oligomers based on the combination of the 3,6-dimethoxythieno[3,2-b]thiophene and 3,4-ethylenedioxythiophene (EDOT) moieties have been prepared and studied by UV–vis spectroscopy and cyclic voltammetry. The use of the intrinsically rigid thienothiophene units in addition to the S⋯O intramolecular interactions leads to planar conformation of the conjugated chains. While the radical cations of oligomers end capped by n-hexyl chains show a tendency to the dimerization, those substituted by n-hexylsulfanyl chains present a high stability

Facile synthesis of 3-substituted thieno[3,2-b]furan derivatives

A facile synthesis of dimethyl 3-hydroxythieno[3,2-b]furan-2,5-dicarboxylate is reported from the available methyl thioglycolate and dimethyl acetylenedicarboxylate starting materials. This compound represents an efficient precursor for the synthesis of 3-substituted thieno[3,2-b]furan derivatives

Electrogenerated Low Band Gap Polymers Based on the 3-Cyano-4-methoxythiophene Building Block

Two position isomers precursors involving 3-cyano-4-methoxythiophene and EDOT (2, 3) have been synthesized. UV−vis and electrochemical data show that the relative position of the methoxy and cyano groups in the structure has dramatic consequences for the reactivity of the precursor and thus for the structure of the resulting polymer. Introduction of the cyano group at the outer β-position of thiophene deactivates the neighboring coupling site, thus leading to the electrodeposition of a material with limited conjugation length. In contrast, when grafted at the inner β-position, the cyano group exerts a stronger effect on the energy gap while the presence of the external methoxy group leads to the straightforward electrodeposition of a low band gap polymer with broad absorption band