Efficient synthesis of high-spin meta-para-oligoanilines

A series of oligo(N-methylaniline)s consisting of alternating meta and para substituted benzene rings up to 8 units has been synthesized via palladium-catalyzed coupling reactions. These oligo(N-methylaniline)s can be oxidized reversibly to the corresponding oligo(cation radical)s, which are stable at ambient temperature and possess a high-spin ground state as evidenced by ESR spectroscopy.