First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties Full article

Journal

Synthetic Metals
ISSN: 0379-6779

Output data

Year: 2012, Volume: 162, Number: 24, Pages: 2267-2276 Pages count : DOI: 10.1016/j.synthmet.2012.10.026

Tags

Organic semiconductors; Photoconductors; Synthesis; Crystal structure; Quantum chemical calculations

Authors

Pushkarevsky Nikolay A. ¹ , Lonchakov Anton V. ^2,3 , Semenov Nikolay A. ⁴ , Lork Enno ⁵ , Buravov Lev I. ⁶ , Konstantinova Lidia S. ⁷ , Silber Georg T. ⁸ , Robertson Neil ⁸ , Gritsan Nina P. ^2,3 , Rakitin Oleg A. ⁷ , Woollins J. Derek ⁹ , Yagubskii Eduard B. ⁶ , Beckmann Jens ⁵ , Zibarev Andrey V. ^3,4

Affiliations

1	(Данные Web of science) Russian Acad Sci, Inst Inorgan Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Inst Chem Kinet & Combust, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Dept Phys, Natl Res Univ, Novosibirsk 630090, Russia
4	(Данные Web of science) Russian Acad Sci, Inst Organ Chem, Novosibirsk 630090, Russia
5	(Данные Web of science) Univ Bremen, Inst Inorgan & Phys Chem, D-28334 Bremen, Germany
6	(Данные Web of science) Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia
7	(Данные Web of science) Russian Acad Sci, Inst Organ Chem, Moscow 119991, Russia
8	(Данные Web of science) Univ Edinburgh, EaStCHEM Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
9	(Данные Web of science) Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland

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. (C) 2012 Elsevier B.V. All rights reserved.

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.
First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

Synthetic Metals. 2012. V.162. N24. P.2267-2276. DOI: 10.1016/j.synthmet.2012.10.026 WOS Scopus

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Dec 1, 2012

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