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Inclusion complexation of N-substituted phenothiazines and their radical cations generated electrochemically with β-cyclodextrin

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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.


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