Radicals and Radical Ions Derived from Indole, Indole-3-carbinol and Diindolylmethane

The primary products, i.e., the radical cations and radicals obtained on oxidation of the glucobrassicin metabolites (and dietary supplements), indole-3-carbinol (I3C) and diindolylmethane (DIM), and those from parent indole (I) are characterized in an ionic liquid and in Ar matrices. The radical cations of I and I3C are stable toward (photo)deprotonation under these conditions, but the resulting radicals can be generated by UV-photolysis of the neutral precursors. Two types of radicals, obtained by loss of hydrogen from N- and C-atoms, respectively, are found for I3C and DIM.