Download PDF
Synthesis 2005(13): 2157-2160  
DOI: 10.1055/s-2005-869997
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Approach to New Vinylogous Tetrathiafulvalene (TTF) Derivatives: 2,3-Bis(1,3-dithiole-2-ylidene)succinonitriles

Chunyang Jiaa, Shi-Xia Liu*a, Antonia Neelsb, Helen Stoeckli-Evansb, Silvio Decurtins*a
a Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland
Fax: +41(31)6313995; e-Mail: decurtins@iac.unibe.ch;
b Institut de Chimie, Université de Neuchâtel, Av. de Bellevaux 51, 2007 Neuchâtel, Switzerland
Further Information

Publication History

Received 22 December 2004
Publication Date:
13 July 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

A new approach to vinylogous TTF derivatives 5 via an alkyne-coupling reaction is reported. Their fundamental redox behavior has been studied. A proposed reaction mechanism, which accounts for the formation of compounds 5 is discussed.

Key words

cycloadditions - substituent effects - sulfur - synthesis - vinylogous tetrathiafulvalene

7

Slow evaporation of the solution of 5b in CH2Cl2 gave single crystals suitable for X-ray diffraction measurement. Crystal data for compound 5b: C14H12N2S8, MW = 464, monoclinic, C 2, a = 16.527 (2), b = 5.2211 (6), c = 12.897 (2) Å; β = 118.955 (13)°, V = 973.8 (2) Å3, T = 153 (2) K, Z = 2, Dc = 1.585 g·cm-3, µ = 0.917 mm-1, λ = 0.71073 Å, F(000) = 476, independent reflections (R int = 0.1017), 3870 reflections collected; refinement method, full-matrix least-squares refinement on F2; goodness-of-fit on F 2 = 0.761; Final R indices [I > 2σ(I)] R1 = 0.048, wR2 = 0.118.