Synthesis 2002(9): 1133-1135
DOI: 10.1055/s-2002-32529
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Expanding Tetra[2,3-thienylene]-Based Molecular Muscles to Larger [4n]Annulenes

Michael J. Marsella*, Guangzhe Piao, Fook S. Tham
Department of Chemistry, University of California, Riverside, Riverside, CA 92521-0403, USA
e-Mail: michael.marsella@ucr.edu;
Further Information

Publication History

Received 1 March 2002
Publication Date:
28 June 2002 (online)

Abstract

The synthesis, X-ray structure, and predicted redox-induced conformational dynamics of a thiophene-fused [12]annulene is reported. Regiospecific halogenation of the thiophene ring system and transition-metal catalyzed cross-couplings are key elements in the synthetic strategy. It is predicted (B3LYP/6-31G*) that redox-induced conformational changes yield significant dimensional changes in this annulene, thus establishing it as a candidate for single molecule actuation.

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All calculations were performed using Titan software; Schrödinger, Inc.; 1500 SW First Avenue, Suite 1180, Portland, Oregon 97201, USA

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Crystallographic data has been deposited in the Cambridge Crystallographic Data Centre Database.