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Synthesis 2005(19): 3437-3445  
DOI: 10.1055/s-2005-918468
PAPER
© Georg Thieme Verlag Stuttgart · New York

Template-Directed Syntheses of Configurable and Reconfigurable Molecular Switches

Yi Liu, Sourav Saha, Scott A. Vignon, Amar H. Flood, J. Fraser Stoddart*
California NanoSystems Institute and Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue­, Los Angeles, CA 90095-1569, USA
Fax: +1(310)2061843; e-Mail: stoddart@chem.ucla.edu;
Further Information

Publication History

Received 15 September 2005
Publication Date:
14 November 2005 (online)

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Abstract

Two self-complexing compounds based on donor-acceptor interactions, one comprised of a π-electron-deficient cyclobis(paraquat-p-phenylene) (CBPQT4+) ring attached to a side-arm component containing π-electron-rich tetrathiafulvalene (TTF) and 1,5-dioxynaphthalene (DNP) units, and the other comprised of a CBPQT4+ ring carrying two side-arms, one containing a TTF unit and the other a DNP unit have been synthesized. 1H NMR spectroscopy and UV/Vis spectroelectrochemistry have revealed that, while the latter compound behaves as a reconfigurable redox-active molecular switch involving only the side-arm containing the TTF unit in a self-complexing role with the CBPQT4+ ring (the side-arm containing the DNP unit is essentially a ‘spectator’), the former compound behaves as a molecular switch that is reversible and reconfigurable when its starting self-complexing conformation is retained, but becomes only configurable and irreversible when the self-complexing conformation is partially transformed into ‘uncomplexed’ conformation on oxidation of the TTF unit.

Key words

molecular recognition - redox reactions - self-assembly - spectroelectrochemistry - templation

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