One-step synthesis and redox properties of dodecahydro-3a,9a-diazaperylene—the most easily oxidized p-phenylenediamine

Abstract

Dodecahydro-3a,9a-diazaperylene (DHDAP) was prepared in one step from p-phenylenediamine and 1-bromo-3-chloropropane, and its first redox potential is 292 mV more negative than the first redox potential of N,N,N',N'-tetramethyl-p-phenylenediamine (TMPD), thus becoming the most easily oxidized p-phenylenediamine homologue.