Synthesis and characterization of functionalized ethylenediselenotetrathiafulvalenes: A comparative study with their all-sulfur analogues

Synthesis and Properties of 2-Alkylidene-1,3-dithiolo[4,5-d]-4,5-ethylenediselenotetrathiafulvalene Derivatives and Crystal Structures of Their Cation Radical Salts

“…The triethyl phosphite-mediated cross-coupling reaction of 4,5-ethylenediseleno-1,3-dithiole-2-thione (1) [17] with the ketone 2 [18] afforded phosphonate ester 3 in a 62% yield [19]. MeDTES, EtDTES and CPDTES were synthesized in a 68−86% yield by the Wittig−Horner reaction of 3 with corresponding ketone in the presence of lithium diisopropylamide (LDA) in THF at −78 °C.…”

“…Triethyl phosphite (26 mL) was added to a mixture of 4,5-ethylenediseleno-1,3-dithiole-2-thione (1) [17] (1.00 g, 3.14 mmol) and diethyl (5-oxo-1,3-dithiolo [4,5- [18] (737 mg, 2.23 mmol) in toluene (26 mL), and the solution was stirred at 110 °C for 2 h under argon atmosphere. After cooling to room temperature, the solution was evaporated under reduced pressure to eliminate the solvent and excess of triethyl phosphite.…”

Synthesis Strategies and Chemistry of Nonsymmetrically Substituted Tetrachalcogenafulvalenes

“…Stable organic radicals were also introduced into the TTF skeleton using this route . It is also interesting to note that, using the reduction of bis(carbomethoxy)-TTF ,, into the corresponding hydroxymethyl derivative then converted into the bis(bromomethyl)-TTF 140 by action of PBr 3 , it was possible to link C 60 to TTF , and to build photoactive systems and donor−acceptor molecular entities ,− (Scheme ).

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Bis(vinylenedithio)tetrathiafulvalene analogues of BEDT-TTF

“…TTF-TCNQ, which is metallic under 54 K and known to be the first true one-dimensional synthetic metal, led to the production of superconducting salts based on TTF type donors containing a heteroatom such as sulfur, selenium, oxygen, etc. [ 17 – 20 ]. Among a large number of tetrathiafulvalene analogues, bis(ethyleneditiho)tetrathiafulvalene (BEDT-TTF, 3 ), also known as ET, has been the most studied and has had the largest number of radical cation salts of its CT materials investigated at very low temperature [ 12 , 21 – 24 ].…”