Synthesis of new di-(3-indolyl)arenes

1,4-Di-(3-indolyl)benzene 6 and 2,8-di-(3-indolyl)dibenzofuran 12 were synthesized from 1,4-diacetylbenzene and 2,8-diacetyldibenzofuran, respectively, via indole synthetic strategies. Investigation into the acid-catalysed formation of macrocyclic systems from these di-(3-indolyl)arenes led to the development of the 18-membered macrocycle 14 from the diindolylbenzene 6, which was capable of undergoing complexation with nickel(II) ions.