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

Nikolay A. Pushkarevsky, Anton V. Lonchakov, Nikolay A. Semenov, Enno Lork, Lev I. Buravov, Lidia S. Konstantinova, Georg T. Silber, Neil Robertson, Nina P. Gritsan*, Oleg A. Rakitin, J. Derek Woollins, Eduard B. Yagubskii, Jens Beckmann, Andrey V. Zibarev

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2267-2276
Number of pages10
JournalSynthetic Metals
Volume162
Issue number24
DOIs
Publication statusPublished - 31 Dec 2012

Keywords

  • Organic semiconductors
  • Photoconductors
  • Synthesis
  • Crystal structure
  • Quantum chemical calculations
  • Density-functional theory
  • Radical-anion
  • Organic electronics
  • Molecular-structure
  • Excited-states
  • Solar-cells
  • Chemistry
  • Salts
  • TTF
  • Superconductors

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