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

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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.