Synthesis of new substituted tetrazines: electrochemical and spectroscopic properties

Abstract

Original tetrazines substituted by heterocyclic rings have been prepared. Their syntheses, as well as their electrochemical and spectroscopic features, are described. Calculations have also been made on the cation radicals, anion radicals and neutral compounds and are in correct agreement with the experimental results. All compounds are electroactive, both in oxidation and reduction, and display two absorption bands in the UV and visible regions of the spectrum. Reduction potentials and maximum wavelengths are correlated with the electron-rich character of the heterocyclic substituent on the tetrazine ring. None of these compounds gives good quality polymers upon electro-oxidation, which was unexpected, especially for the bis(2-pyrrolyl) tetrazine. This latter result can be explained by the occurrence of a self-deprotonation equilibrium in the cation radical.