CYCLOBISINTERCALAND MACROCYCLES - SYNTHESIS AND PHYSICOCHEMICAL PROPERTIES OF MACROCYCLIC POLYAMINES CONTAINING 2 CRESCENT-SHAPED DIBENZOPHENANTHROLINE SUBUNITS

A general access to isomeric dibenzo[bj]phenanthrolinedicarboxaldehyde s is described. These pentacyclic planar quinacridine compounds exhibi t crescent-shaped forms that fulfill the geometrical requirements of p roviding broad overlap of nucleobase pairs or triplets. The dialdehyde derivatives have been condensed with various polyamines to give macro cyclic dimeric structures, cyclobisintercalands, of variable size, cha rge, and shape. The related water-soluble monomeric quinacridines were prepared from the dialdehydes by grafting ammonium groups; The physic ochemical properties of the monomeric quinacridines and of the macrocy clic bis-quinacridines have been investigated by spectroscopic methods (UV-vis, fluorescence, NMR). The results show that some of these macr ocyclic compounds could exist as semiclosed conformers suitable to acc ommodate a pair of nucleotides.