Issue 5, 2014

A quinoxaline-fused tetrathiafulvalene derivative and its semiconducting charge-transfer salt: synthesis, crystal structures and physical properties

Abstract

A quinoxaline-fused tetrathiafulvalene (TTF) derivative 1 has been synthesized to form a compact and planar π-conjugated donor–acceptor (D–π–A) ensemble, and its single crystal structure has been determined by X-ray diffraction. The inherent redox activity of 1 has been probed by cyclic voltammetry, and UV-vis spectroscopy revealed the typical broad and intense intramolecular charge-transfer (ICT) absorption occurring for such compactly fused D–π–A molecules. Reaction with iodine led to a 2 : 1 semiconducting charge-transfer salt {(1)2I3}, whose single crystal structure investigation, however, underlined the occurrence of a pronounced charge localization in the organic lattice. Consequently, the electrical conductivity of {(1)2I3}, measured by the four contact method on single crystals, gave only a limited value of about 1 × 10−4 Ω−1 cm−1, and the activation energy was determined to be on the order of 470–480 meV.

Graphical abstract: A quinoxaline-fused tetrathiafulvalene derivative and its semiconducting charge-transfer salt: synthesis, crystal structures and physical properties

Supplementary files

Article information

Article type
Paper
Submitted
02 Oct 2013
Accepted
05 Dec 2013
First published
05 Dec 2013

New J. Chem., 2014,38, 2052-2057

Author version available

A quinoxaline-fused tetrathiafulvalene derivative and its semiconducting charge-transfer salt: synthesis, crystal structures and physical properties

Y. Geng, C. Fiolka, K. Krämer, J. Hauser, V. Laukhin, S. Decurtins and S. Liu, New J. Chem., 2014, 38, 2052 DOI: 10.1039/C3NJ01200J

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