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Supramolecular chirogenesis in bis(zinc porphyrin): An absolute configuration probe highly sensitive to guest structure

Org Lett. 2000 Jun 1;2(11):1565-8. doi: 10.1021/ol0000556.

Abstract

The role of the ligand's structure and absolute configuration in the supramolecular chirality induction in achiral bis(zinc porphyrin) has been studied. The amines with bulkier substituents resulted in stronger CD signals due to increased helical displacement in the anti conformer. All the amines with an R absolute configuration gave a negative first Cotton effect and positive second Cotton effect, while the ligands with an S absolute configuration produced CD signals with opposite signs due to formation of the left- and right-handed screw diastereomers, respectively.