2002 Fiscal Year Final Research Report Summary

Design and Applications of Helical Crystal Spaces by Spontaneous Resolution

Research Project

Project/Area Number	13555251
Research Category	Grant-in-Aid for Scientific Research (B)
Allocation Type	Single-year Grants
Section	展開研究
Research Field	Synthetic chemistry
Research Institution	The University of Tokyo
Principal Investigator	AIDA Takuzo Graduate School of Engineering, Professor, 大学院・工学系研究科, 教授 (00167769)
Project Period (FY)	2001 – 2002
Keywords	Porphyrin / Chirality / Spontaneous Resolution
Research Abstract	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.

(2 results)