Tetrathiafulvalene Goes Large

  • Author: Asian Journal of Organic Chemistry
  • Published Date: 16 March 2014
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Tetrathiafulvalene Goes Large

Tetrathiafulvalene (TTF), as a π-electron donor, has attracted particular attention within the context of materials chemistry towards molecular (opto)electronics. However, large π-conjugated TTF derivatives with structurally rigid and planar configurations have rarely been studied owing to limited preparative accessibility.

In response to this problem, Shi-Xia Liu and co-workers, Universität Bern, Switzerland, have introduced a concept for the annulation of TTFs to diverse π-electron acceptors by a Schiff base reaction. For instance, direct annulation of two dipyrido[3,2-a:2’,3’-c]phenazine units to the TTF core yields a large π-conjugate as a bridging ligand. Its coordination ability is exemplified by the formation of a stable dinuclear ruthenium (II) complex.

These electrochemically amphoteric compounds exhibit various intense intramolecular charge-transfer absorption bands in different oxidation states. Specifically, an unprecedented TTF•+ radical cation dimerization and oligomerization can be identified upon oxidation of the bridging ligand owing to strong intermolecular π–π interactions.

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Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH