Synthesis of Conjucated pi-Systems for the Elusidation of Biological Functions

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In order to understand the biological function of photosynthetic electron transfer and molecular recognition, we prepared various organic compounds having conjugated pi-system and obtained the following results for photosynthetic electron transfer. 1) By preparing porphyrin-quinone compounds with rigid spacer, the large influence of the orientation of sigma-orbitals of the spacer upon electron transfer has been revealed. 2) By preparing a porphyrin with two quinones, it was concluded that electron transfer rate becomes doubled when there are two electron transfer pathways. 3) Porphyrins linked by a double bond at meso position have been prepared and the relationship between the structure and physical properties has been revealed. 4) A long alkyl chain in which a porphyrin ring is linked at an end and a thiol groupe is connected at the other end has been prepared and the molecule has been self-assembled on gold surface to show redox waves. 5) Porphyrin-linked fullerene was prepared and efficient electron transfer between the redox pair has been observed. In addition, chiral chromogenic crown ethers have been prepared and found that these compounds recognize chiral amines enantioselectively to give different corolation.