Design and Applications of Helical Crystal Spaces by Spontaneous Resolution

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Spontaneous resolution was found to occur for hydrogen-bonded complexes between chiral saddle-shaped porphyrins and 4-Br manderic acid. Ethyl 2-methylbutyrate, which was used as a chiral solvent for the crystallization, was enantioselectively included within helical spaces of the crystals with 50% enantiomeric excess. The inclusion of ethyl 2-methylbutyrate was also observed under vapor conditions with the same enantioselectivity and enantiomeric excess.Novel porphyrin dimer and columnar assemblies, which were partially detected by CSI-MS measurements, were prepared from pyridine-attached saddle-shaped porphyrins and palladium or platinum complexes, in order to design novel chiral spaces and reaction fields. These supramolecular assemblies show enhanced CD activity upon interaction with optically active manderic acid compared with monomenc reference, suggesting that the chiral informations of porphyrin/manderic acid complexes transfer to the neighboring saddle prphyrins via rigid linkers.