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Trimethyltetrathiafulvalene bearing an N-methylpyridinium substituent: Synthesis, crystal structures, and charge transfer properties

Moore, A.J.; Batsanov, A.S.; Bryce, M.R.; Howard, J.A.K.; Khodorkovsky, V.; Shapiro, L.; Shames, A.

Authors

A.J. Moore

V. Khodorkovsky

L. Shapiro

A. Shames



Abstract

The synthesis of 4,4',5-trimethyl-5'-(4-pyridyl)tetrathiafulva- lene (3), has been accomplished by reaction of the stannylated precursor 2 with 4-bromopyridine. Alkylation of 3 affords the N-methylpyridinium salt 4 which displays intramolecular charge transfer properties in solution as deduced from UV/Vis spectra, cyclic voltammetric data, and semiempirical quantum mechanical calculations. The X-ray crystal structures of neutral molecule 3, the salt (4(+))I- and the charge transfer salt (4(+))(2)(TCNQ(3))(2-) are reported. The positive charge in (4(+))I- and (4(+))(2)(TCNQ(3))(2-) is predominantly confined on the pyridinium ring. The structure of (4(+))(2)(TCNQ(3))(2-) comprises segregated stacks of cations and TCNQ radical anions, with the anions overlapping in the usual ring-over-bond fashion. This salt is a semiconductor (sigma (rt) = 10(-2) S cm(-1)).

Citation

Moore, A., Batsanov, A., Bryce, M., Howard, J., Khodorkovsky, V., Shapiro, L., & Shames, A. (2001). Trimethyltetrathiafulvalene bearing an N-methylpyridinium substituent: Synthesis, crystal structures, and charge transfer properties. European Journal of Organic Chemistry, 73-78

Journal Article Type Article
Publication Date 2001-01
Journal European Journal of Organic Chemistry
Print ISSN 1434-193X
Publisher Wiley
Peer Reviewed Peer Reviewed
Issue 1
Pages 73-78
Publisher URL <Go to ISI>://000166489000010