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Short Paper | Regular issue | Vol 83, No. 7, 2011, pp.1621-1629
Published online, 12th April, 2011
DOI: 10.3987/COM-11-12191
Synthesis and Properties of anti/syn-Regioisomeric Mixtures of Alkyl-Substituted Tetracenes

Chitoshi Kitamura,* Hiroyuki Kano, Hideki Tsukuda, Takeshi Kawase, Takashi Kobayashi, and Hiroyoshi Naito

*Department of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2201, Japan


We prepared anti/syn-regioisomeric mixtures of alkyl-substituted tetracenes via Diels-Alder reaction between asymmetric furans and 2,6-naphthodiyne synthon. The solid-state color of the mixtures changed before and after recrystallization from Et2O, suggesting a difference in the molecular arrangements dependent on the different alkyl substituents as well as the change in the distribution of the anti/syn regioisomers after recrystallization. Slow evaporation of the recrystallized mixtures produced single crystals suitable for X-ray analysis, which revealed that the anti regioisomer was isolated.