The oxidative coupling reactions of 6-pentyl-5,11-dihydroindolo[3,2-b]carbazole have been studied and as a result, a number of novel dimers of the indolo[3,2-b]carbazole derivative have been prepared, forming C–C coupled compound 3 when treated with FeCl₃·6H₂O or C–N coupled compounds 4 and 5 when oxidized with air or Pd(OAc)₂, respectively.