Article

Journal of inclusion phenomena and macrocyclic chemistry

, Volume 38, Issue 1, pp 199-206

Interplay between Molecular Recognition and Redox Properties: A Theoretical Study of the Inclusion Complexation of β-Cyclodextrin with Phenothiazine and its Radical Cation

  • Lei LiuAffiliated withDepartment of Chemistry, University of Science and Technology of ChinaNational Laboratory of Applied Organic Chemistry, Lanzhou University
  • , Xiao-Song LiAffiliated withDepartment of Chemistry, University of Science and Technology of ChinaNational Laboratory of Applied Organic Chemistry, Lanzhou University
  • , Ting-Wei MuAffiliated withDepartment of Chemistry, University of Science and Technology of ChinaNational Laboratory of Applied Organic Chemistry, Lanzhou University
  • , Qing-Xiang GuoAffiliated withDepartment of Chemistry, University of Science and Technology of ChinaNational Laboratory of Applied Organic Chemistry, Lanzhou University
  • , You-Cheng LiuAffiliated withDepartment of Chemistry, University of Science and Technology of ChinaNational Laboratory of Applied Organic Chemistry, Lanzhou University

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Abstract

The PM3 molecular orbital method was employed in the conformational analysis of the inclusion complexation of β-cyclodextrin with phenothiazine and its radical cation from a complete and unrestricted geometry optimization. Ab initio calculations at the level of HF/3-21G(d) and B3LYP/3-21G(d) were utilized to determine the electronic structures of the host, guest and their complexes. The results indicated that the complexation of β-cyclodextrin with the phenothiazineradical cation was significantly more favorable than that with the neutral one, in good agreement with the experimental observation. The charge-transfer interaction was proposed as a physical reason for such behavior. It is suggested that caution should be given when extrapolating one oxidation state behavior to the supramolecular systems in their other oxidation states.

cyclodextrin inclusion phenothiazine radical cation theoretical study