Dynamic Knoevenagel Condensation of p-Tolyl Carbenium Cations

We report here that methyl-substituted hexamethoxytrityl (HMT) and the derived trioxatriangulene (TOTA) salts react with aldehydes, forming π-extended tristyryl-substituted HMT and TOTA dyes via a dynamic Knoevenagel condensation. These cations undergo a reversible electrochemical (or chemical) reduction, forming neutral radicals, including the first persistent TOTA radical. This reaction represents a promising platform to generate novel π-conjugated systems.