M. Jubault

2-Mono or 2,3-Bis(hydroxymethyl)-6,7-ethylenedithio-tetrathiafulvalenes: New potential precursors of organic metals endowed with hydrogen bonds

Abstract The syntheses of new π-unsymmetrical donors of the TTF family having half moiety of bis(ethylenedithio)-TTF (BEDT-TTF) and half moiety of TTF substituted with one (or two) hydroxymethyl group(s) are described. Their good π-donating ability is demonstrated by cyclic voltammetry.

2,5-Bis(1,4-dithiafulven-6-yl) furans, thiophenes and N-methyl pyrroles as extended analogues of tetrathiafulvalene

Abstract The title compounds are synthesized by Wittig or Wittig-Horner reactions between the corresponding furan, thiopen and N-methyl-pyrrole-2,5-dicarbaldehydes and P-reagents W or P bearing the 1,3-dithiol-2-ylidene moiety adequately substituted at the 4,5-positions; thanks to usual and thin layer cyclic voltammetry, they are shown to possess good π-donor abilities.

The bis-linking of tetrathiafulvalene (TTF) to C60: Towards the control of electron transfer between π-donors and C60

The bis-linking of a tetrathiafulvalene (TTF) to C60 is carried out by [4+2] Diels-Alder cycloaddition of C60 to the 2,3-dimethylene-TTF 2, this transient diene being generated by KI-[18]crown-6 mediated dibromine reductive elimination of the 2,3-bis(bromomethyl)TTF 3. The C60-TTF target cycloadduct 1a is charaterized by spectroscopy and electrochemical study.

Extended analogues of tetrathiafulvalene (TTF): 1,2-bis, 1,4-bis and 1,2,4,5-tetrakis(1,4-dithiafulven-6-yl) benzenes; Synthesis and π-donor abilities.

Abstract The title compounds are prepared by Wittig or Wittig-Horner reactions between the corresponding benzenes di- and tetracarbaldehydes and the P-reagents W or P bearing the 1,3-dithiol-2-ylidene moiety; among them, the tetrakis(dithiafulvenyl)benzene 3c is shown by cyclic voltammetry to possess the best π-donor character and, also, is chemically or electrochemically oxidized.

Tetraformyltetrathiafulvalene (TFTTF) and acetals, precursors of polyfunctionalized TTFs.

Abstract A short synthesis of 1,3-dithiol-2-thiones bearing two aldehyde functionalities, free and/or masked as diethylacetals is described. They are shown to be convenient precursors for synthesizing di- and tetraformyl-TTF. When submitted to four-fold nucleophilic attacks, the latter readily affords new substituted derivatives such as the bis-(pyridazino)-TTF 8 , the tetrakis-(hydroxymethyl)-TTF 9 and the tetravinylic-TTF 10 whose π-donor ability has been characterized.

Oxidative dimerization of 2-(1,4-dithiafulven-6-yl)thiophenes: an alternative route towards extensively π-conjugated tetrathiafulvalene analogs

Abstract Extended tetrathiafulvalene analogs with dienic or bithienylic conjugated spacers have been synthesized by oxidative dimerization of 1,4-dithiafulvenylthiophenes.

In the search of an electron transfer between π-donors and C60: the bis-linking of tetrathiafulvalene (TTF) to C60

Abstract In order to realize the bis-linking of tetrathiafulvalene (TTF) to one or two C 60 , and to reach the dyad compounds 1 and 2 , the [4 + 2] Diels-Alder reactions of C 60 with orthoquinodimethanic derivatives of 1,3-dithioles 5a,b or TTF 9 are studied.

Acid mediated intramolecular cyclization of π-donors bearing two vicinal “cis”-branched, 1,4-dithiafulven-6-yl substituents on a CC bond

Abstract Cis-ethylenic analogues 1 and ortho-benzenic analogues 2 of TTF undergo a rapid acid mediated intrmolecular cyclization into two the corresponding cycloisomers 1′ and 2′ whose structures are confirmed by X-ray diffraction; as shown by cyclic Voltammetry, compounds 1 may act as convenient precursors of organic metals.

2,5-bis(1,4-dithiafulven-6-yl) substituted furans, thiophenes and N-methyl pyrroles as precursors for organic metals

Abstract New heterocyclic π-electron donors are synthetized by Wittig or Wittig-Horner reactions between the corresponding furan, thiophen and N-methyl pyrrole 2,5-dicarbaldehydes and the P-reagents W or P bearing the 1,3-dithiol-2-ylidene moiety adequately substituted at the 4,5-positions; thanks to usual and thin layer cyclic voltammetry, they are shown to possess good π-donor abilities.

Synthesis and electrochemical properties of fused [3,4]furano-tetrathiafulvalenes

Abstract The synthesis of the first fused [3,4]furano-TTFs has been accomplished starting from the 4-formyl-5-diethoxymethyl-2-thioxo-1,3-dithiole. Two routes have been explored involving either the furan ring or the TTF core. In particular, the first proceeds via the new [3,4]furano-2-thioxo-1,3-dithiole.