The interactions of β-cyclodextrin (β-CD) with N-phenylphenothiazine (1), N-benzylphenothiazine (2) and N-phenethylphenothiazine (3) were studied by cyclic voltammetry. In aqueous solutions, increasing the amount of β-CD caused negative shifts in the anodic peaks and an increase in the current of the 1/1 +• and 3/3 +• couples owing to the fact that more 1 and 3 were included in the β-CD cavities. However, compound 2 neither gave an anodic nor a cathodic wave in the presence of β-CD because the oxidization reactions on the surface of electrode were controlled by the conformations of the N-substituted phenothiazines in the cavity of β-CD. In 1:9 methanol/water binary solutions, 1 and 3 were investigated by fast scan cyclic voltammetry which showed that the irreversible waves became quasi-reversible waves in the presence of β-CD, confirmed the stabilization of cation radical intermediates by β-CD. The electrochemical and absorption spectral data indicated 1:1 inclusion complex formation of β-CD with 1 and 3 cation radicals in methanol/water binary solutions and the binding constants of 1 +• and 3 +• were very large under this condition.
Research on Chemical Intermediates – Springer Journals
Published: Oct 17, 2004
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