New Unsymmetrically Benzene-Fused Bis (Tetrathiafulvalene): Synthesis, Characterization, Electrochemical Properties and Electrical Conductivity of Their Materials

Abstract

The synthesis of new unsymmetrically benzene-fused bis (tetrathiafulvalene) has been carried out by a cross-coupling reaction of the respective 4,5-dialkyl-1,3-dithiole- 2-selenone 6–9 with 2-(4-(p-nitrophenyl)-1,3-dithiole-2-ylidene)-1,3,5,7-tetrathia-s-indacene- 6-one 5 prepared by olefination of 4-(p-nitrophenyl)-1,3-dithiole-2-selenone 3 and 1,3,5,7-tetrathia-s-indacene-2,6-dione 4. The conversion of the nitro moiety 10a–d to amino 11a–d then dibenzylamine 12a–d groups respectively used reduction and alkylation methods. The electron donor ability of these new compounds has been measured by cyclic voltammetry (CV) technique. Charge transfer complexes with tetracyanoquino-dimethane (TCNQ) were prepared by chemical redox reactions. The complexes have been proven to give conducting materials.

Bis(vinylenedithio)tetrathiafulvalene analogues of BEDT-TTF

“…In order to improve the properties of TTF type materials, various methods have been applied, including extension of π-conjugation through double bonds [ 25 – 30 ] and fused aromatic rings [ 31 – 34 ] and the construction of molecules having acceptor substituents [ 35 – 37 ]. Generally, all these modifications served to produce molecules with better conjugation and improved S···S intermolecular and C–H···anion interactions in determining the solid state properties [ 35 – 37 ].…”

“…Recently, TTF and analogues have received widespread attention involving the development of new materials by using various anions to form different charge transfer salts. The physical and electronic properties of their solid states were investigated [ 13 , 25 , 47 – 49 ].…”

Studies on Chemical Reactivity of <i>p</i>-aminophenyl Benzene-Fused Bis Tetrathiafulvalenes Through Quantum Chemical Approaches

“…In a previous work [14], we have described the synthesis of new serie of p-aminophenyl benzene-fused bis tetrathiafulvalenes 1-4 indicated in Scheme 1. The synthesis of these electron donors was carried out using a reduction reaction.…”