FORMATION OF MOLECULAR ASSEMBLIES REMPONSIVE TO STIMULI AND ENVIRONMENT THROUGH DYNAMIC SELF-ORGANIZATION OF BIOMOLECULE DERIVATIVES

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We focused on the self-assembling abilities of folic acid. We designed and synthesized folic acid derivatives having hexyl, undecyl, or octadecyl substituents for the development of functional thermotropic or lyotropic mesomorphic materials. These compounds showed smectic or discotic liquid crystallinity. Their phase behavior was greatly dependent on the length of the alkyl chains. The formation of smectic and discotic phases is attributable to ribbon-and disk-like aggregation of pterin rings of folic acid derivatives. The adition of sodium triflate or dodecane to a smecitc liquid-crystalline folic acid derivative lead to the change of the hydrogen-bonded pattern from ribbon to disk. These results indicate that the aggregated pattern of the pterin ring in molecular assemblies can be controlled from ribbon to disks by the change of external conditions such as ion-dipole interactions or hydrophhobicity of the medium.