Triple helical structure constructed by covalent bondings: effective synthesis by a pre-organized partial structure and helicity induced by aromatic–aromatic interactions

Discotic helical macrocycle constructed by aromatic tertiary amide was effectively synthesized using dichlorotriphenylphosphorane as the condensation reagent. The yield was significantly higher when meta-substituted diaminobenzene was used as the linkage for a two 1,3,5-tris(4-carboxyphenyl)benzene moiety than when para-substituted diaminobenzene was used. The yield is thus dependent on whether the pre-organized partial diamide structure suits the construction of the macrocyclic structure.