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Crown ether annelated tetrathiafulvalenes. 2

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  • T.K. Hansen, University of Southern Denmark
  • ,
  • T. Jorgensen, University of Southern Denmark
  • ,
  • F. Jensen
  • P.H. Thygesen, University of Southern Denmark
  • ,
  • K. Christiansen, University of Southern Denmark
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  • M.B. Hursthouse, School of Chemistry and Applied Chemistry
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  • M.E. Harman, School of Chemistry and Applied Chemistry
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  • M.A. Malik, School of Chemistry and Applied Chemistry
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  • B. Girmay, University College of North Wales
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  • A.E. Underbill, University College of North Wales
  • ,
  • M. Begtrup, Danish Farmaceutical University
  • ,
  • J.D. Kilburn, University of Southampton
  • ,
  • K. Belmore, University of Alabama
  • ,
  • P. Roepstorff, University of Southern Denmark
  • ,
  • J. Becher, University of Southern Denmark
A synthetic procedure leading to derivatives of tetrathiafulvalene (TTF) incorporating polyether chains of various lengths, some nitrogen analogs, and a 2,6-bis(methylene)pyridine analog has been developed. These compounds possess cage-type structures which were confirmed by X-ray crystallography in four cases, two of which are reported herein for the first time. Structural and electronic features of these cage molecules were correlated to oxidation potentials by the use of semiempirical methods (MNDO-PM3). An investigation of the alkali metal ion affinity using PDMS revealed that these compounds are poor ligands. Finally, in one case, protonation of the core TTF was studied by NMR.
Original languageEnglish
JournalJournal of Organic Chemistry
Pages (from-to)1359-1366
Number of pages8
Publication statusPublished - 1993
Externally publishedYes

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