Construction of Chiral Nano-Space and Functionallization in Organic Zeolites based on Molecular Self-Assembly.

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In this project, to the purpose for the construction of chiral nano-space and functionallization in organic zeolites based on molecular self-sssembly, we studied the following four items. [1]Synthesis of hexaarylbenzenes with various hydrogen bonding groups and their porous hydrogen-bonded network : We prepared hexaarylbenzenes with various hydrogen bonding groups as well as functional groups by the Co-catalyzed cyclotrimerization of diarylacetylenes, as a scaffold of organic zeolites. Hexakis(4-carbamoylphenyl)benzene forms various types of 3-D hydrogen-bonded porous networks, depending on recrystallization conditions. [2]Synthesis of hexa(arylethynyl)benzenes with various functional groups : We prepared alternately functionallized hexa(arylethynyl)benzenes by the double Sonogashira-coupling reactions using 1,3,5-tribromo-2,4,6-triiodobenzene. [3]Synthesis of hexa(arylethynyl)benzanes with chiral groups : We prepared hexa(arylethynyl)benzenes with α-Phenethyloxy group as a chiral group at 1,3,5-positions and with 4-carboxypheny1,4-Pyridyl, or 4-cyanophenyl groups as an interactive group for a network formation at 2,4,6-positions by the reaction mentioned in item-2. We will investigate the functions of these compounds directed towards chiral organic zeolites with chiral hydrogen-bonded o r metal-coordination network. [4]Synthesis of hexaarylbenzenes with amino acids : By the condensation reactions of hexakis(4-carboxyphenyl)benzene or hexakis(4-aminophenyl)benzene, which were prepared by the reaction of item-1, with (L)-alanine Benzyl ester or N-Boc-(L)-alanine, we synthesized hexakis[4-((L)-alanine)phenyl]benzenes with C-or N-terminals, respectively. We will investigate the functions of these compounds directed towards chiral organic zeolites with chiral hydrogen-bonded network.