A computational study of sulfur bridged cyclooctatetraenophanes

Scott E. McKay, Robert W. Lashlee, Bryce A. Holthouse, Paul Kiprof

Research output: Contribution to journalArticlepeer-review


Calculations of several thiacyclooctatetraenophanes predicted, as part of their overall geometry, substantial flattening of the cyclooctatetraene (COT) structures relative to the tub conformation generally associated with the COT molecule. The COT structures were approximately parallel to each other and the interplanar distances were predicted to be within 2.787-2.803 Å at the DFT/UB3YLP level of calculation. DFT/UB3LYP optimized geometries afforded significant delocalization of the COT structures in each of the thiacyclooctatetraenophanes. Hartree-Fock (HF) methods and the semi-empirical Austin Model 1 (AM1) method deviated significantly from the DFT/UB3LYP optimized geometries. Cyclooctatetraenes can undergo reversible sizing by oxidation and reduction reactions to form the aromatic dication and aromatic dianion, respectively, which could then be used to prepare molecular backbones for polymeric organometallic molecular wires. The number of bridges and the introduction of the sulfur atom have been investigated to provide disparate synthetic routes.

Original languageEnglish (US)
Pages (from-to)543-548
Number of pages6
JournalJournal of Molecular Graphics and Modelling
Issue number4
StatePublished - Dec 2006

Bibliographical note

Funding Information:
We are grateful to the Petroleum Research Fund administered by the ACS for financial support of this work. We would also like to thank Dr. A. Brown for his helpful comments and we would like to thank the Supercomputing Institute for Digital Simulation and Advanced Computation of the University of Minnesota and the Visualization and Digital Imaging Laboratory at the University of Minnesota Duluth for valuable computer resources.


  • B3LYP
  • Cyclooctatetrene
  • Cyclophanes
  • Delocalization
  • Hartree-Fock
  • Semi-empirical


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