First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives : design, synthesis, crystal structures, electronic and electrical properties
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The first charge-transfer complexes of tetrathiafulvalene (1) with 1,2,5-chalcogenadiazole derivatives, i.e. with [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole (2) and 3,4-dicyano-1,2,5-telluradiazole (3), were designed, prepared in the form of air and thermally stable single crystals and structurally defined by X-ray diffraction as 1-2 and 1.3(2), respectively. Starting compound 2 (effective electron acceptor with potentially broad application in the field) was synthesized by a new efficient one-pot method from 3,4-diamino-1,2,5-oxadiazole and disulfur dichloride. The electronic structure of complexes 1.2 and 1.3(2) and thermodynamics of their formation were studied by means of DFT and QTAIM calculations and UV-Vis spectroscopy. The electrical properties of single crystals of the complexes were investigated revealing semiconductor properties with an activation energy of 0.34 eV for 1.2 and 0.40 eV for 1.3(2). Polycrystalline films of the complexes displayed photoconductive effects with increased conductivity under white-light illumination.
Pushkarevsky , N A , Lonchakov , A V , Semenov , N A , Lork , E , Buravov , L I , Konstantinova , L S , Silber , G T , Robertson , N , Gritsan , N P , Rakitin , O A , Woollins , J D , Yagubskii , E B , Beckmann , J & Zibarev , A V 2012 , ' First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives : design, synthesis, crystal structures, electronic and electrical properties ' Synthetic Metals , vol. 162 , no. 24 , pp. 2267-2276 . DOI: 10.1016/j.synthmet.2012.10.026
© 2012 Elsevier B.V. All rights reserved. This is the author’s version of a work that was accepted for publication in Synthetic Metals. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Synthetic Metals, 162, 24, 31 December 2012 DOI 10.1016/j.synthmet.2012.10.026
DescriptionThe authors are grateful to the Royal Society (RS International Joint Project 2010/R3), Deutsche Forschungsgemeinschaft (project 436 RUS 113/967/0-1 R), the Russian Foundation for Basic Research (project 10-03-00735), the Presidium of the Russian Academy of Sciences (projects 7.17, 8.14 and P-8), and to the Siberian Branch of the Russian Academy of Sciences (project 105) for funding.
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