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Communication | Special issue | Vol 82, No. 2, 2010, pp.1143-1149
Published online, 3rd September, 2010
DOI: 10.3987/COM-10-S(E)96
McMurry Coupling of Diformyldithienylacetylene: Synthesis of [24]-, [36]-, and [48]Annulenes Composed of Thiophene, Acetylene, and Ethylene Units

Masahiko Iyoda,* Pochi Huang, Tomohiko Nishiuchi, Masayoshi Takase, and Tohru Nishinaga

*Graduate School of Science, Tokyo Metropolitan University, 1-1, Minami-ohsawa, Hachioji, Tokyo 192-0364, Japan


The reaction of diformyldithienylacetylene 4 with a McMurry reagent prepared from TiCl4, Zn, and pyridine in THF afforded 24π-dimer 1b (15%), 36π-trimer 2b (13%), and 48π-tetramer 3b (6%). From X-ray analysis, 1b adopts a twisted conformation, although the 1H NMR spectrum of 1b shows a symmetrical structure owing to a rapid conformational change in solution. Absorption and emission spectra, redox properties, and electric conductivities of 1b3b were measured in order to study the structure–property relationship of these macrocyclic systems.