Revisiting the stability of hexacenes

Abstract

The Strating-Zwanenberg photodecarbonylation was used to prepare hexacene (1). Compound 1 was found to be extremely unstable in solution, undergoing dimerization and oxidation. However, when generated in a polymer matrix, 1 survived for more than 12 h under ambient conditions. Hexacenes substituted at the 6 and 15 positions with the phenyl, p-tert-butylphenyl, and mesityl groups were synthesized using the quinone reduction method, but these compounds were also shown to be unstable in solution.