Synfacts 2009(7): 0741-0741  
DOI: 10.1055/s-0029-1217218
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Dipole-Dipole Interactions Drive Self-Assembly of Molecular Tweezers

Contributor(s): Timothy M. Swager, Jason R. Cox
A. Lohr, M. Grüne, F. Würthner*
Universität Würzburg, Germany
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22. Juni 2009 (online)


The authors report the synthesis of bis(merocyanine) dyes linked together by either naphthalenedimethylene or dimethylenediphenylmethane spacers. The merocyanine dyes possess large dipole moments (˜17 D) due to a zwitterionic resonance structure (boxed figure). As a result, the molecular tweezers self-assemble into π-stacks exhibiting hypsochromic absorption shifts. The authors report dimerization constants of up to 109 M.