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Int. J. Mol. Sci. 2014, 15(3), 4550-4564; doi:10.3390/ijms15034550
Article

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

1,* , 1
, 2
, 3
 and 4
1 Laboratory of Aquatic and Terrestrial Ecosystems, Organic and Bioorganic Chemistry Group, University of Mohammed Cherif Mesaadia, Souk Ahras 41000, Algeria 2 Laboratory of Organic Materials and Heterochemistry, University of Tebessa, Constantine Road, Tebessa 12000, Algeria 3 Laboratory of Molecular and Thio-Organic Chemistry, UMR CNRS 6507, INC3M, FR 3038, Labex EMC3, ENSICAEN & University of Caen, Caen 14050, France 4 Department of Applied Chemistry, Graduate School of Science and Engineering, Ehine University, 3 Bunkyo-cho, Matsuyama, Ehine 790-8577, Japan
* Author to whom correspondence should be addressed.
Received: 19 February 2014 / Revised: 7 March 2014 / Accepted: 10 March 2014 / Published: 17 March 2014
(This article belongs to the Section Material Sciences and Nanotechnology)
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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 69 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 10ad to amino 11ad then dibenzylamine 12ad 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.
Keywords: conductivity; redox potentials; organic materials; tetrathiafulvalenes conductivity; redox potentials; organic materials; tetrathiafulvalenes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Abbaz, T.; Bendjeddou, A.; Gouasmia, A.; Villemin, D.; Shirahata, T. New Unsymmetrically Benzene-Fused Bis (Tetrathiafulvalene): Synthesis, Characterization, Electrochemical Properties and Electrical Conductivity of Their Materials. Int. J. Mol. Sci. 2014, 15, 4550-4564.

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