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Synlett 1999; 1999(4): 397-400
DOI: 10.1055/s-1999-2634
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Novel U-Shaped Bichromophoric Systems for Studying Solvent-Mediated Electron Transfer: Synthesis, X-ray Structure, and Computed Electronic Coupling

Nigel R. Lokan* , Donald C. Craig, Michael N. Paddon-Row
  • *School of Chemistry, University of New South Wales, Sydney, N.S.W., 2052, Australia; Fax +61(2)93 85 61 41; E-mail: m.paddonrow@unsw.edu.au
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Publication Date:
31 December 1999 (online)

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The synthesis of two new rigid U-shaped bichromophoric systems, 5 and 6 containing a dimethoxynaphthalene donor and a dicyanovinyl acceptor is described. X-ray crystallography of the ketone progenitor of 6 revealed inclusion of a solvent molecule within the molecular cavity. Solvent-mediated electronic coupling in the U-shaped systems is predicted to be substantial (260 cm-1 for propane solvent).

Diels-Alder - U-shaped cavities - donor-acceptor - electron transfer - electronic coupling

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