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Synthesis 1997; 1997(12): 1399-1404
DOI: 10.1055/s-1997-1363
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Convergent Synthesis of Rigid Macrocycles Containing One or Two Tetrathiafulvalene Units

Klaus B. Simonsen1 , Niels Thorup2 , Jan Becher3
  • 1Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark
  • 2Department of Chemistry, Technical University of Denmark, Building 207, DK-2800 Lyngby, Denmark
  • 3Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark, Fax +45(66)158780
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Publication Date:
31 December 2000 (online)

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The synthesis of rigid tetrathiafulvalenenophanes containing one or two tetrathiafulvalene units is presented, together with a stepwise convergent synthesis of macrocyclic bis-tetrathiafulvalenes via several open dimeric tetrathiafulvalenes. These systems were investigated by cyclic voltammetry, which revealed that intramolecular interaction between the electroactive units only took place if the units were fixed in a rigid conformation. The X-ray structure of 10a confirmed the cis configuration of a concave molecule, which is packed in antiparallel stacks.

tetrathiafulvalenophanes - macrocyclic tetrathiafulvalenes - dimeric donor systems - intramolecular interaction - rigid macrocycles