Chirality Induction Of Benzene Tricarboxamide-linked Zinc Trisporphyrinate By Phenylethylamines

Chiral recognition is one type of important and special molecular recognition. It is one of the vital fundamental processes in natural systems and plays key roles in various fields of science and technology, especially in chirality memory, chirality induction, chirality amplification, and chirality switching.Based on both features of mono-porphyrins and bisporphyrins, we have designed and synthesized a novel trisporphyrin with a benzene tricarboxamide as the linker, and studied its interactions with optical pure monoamine. CD spectra show stoichiometry controlled chirality induction, which is caused by the formation of 1:1, 1:2 and 1:3 complexes. In order to confirm this phenomenon,we have also designed a new triporphyrin [Zn2Ni-1],and measuredits corresponding CD spectra. The 1:3 host-guest complex was also crystallographically characterized. The structure reveals there are multiply intramolecular hydrogen bonds and p-p interactions which could contribute to stabilize the “inside” binding mode.