Synthesis and Evaluation of Chiral Compounds for Third Nonlinear Optics

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Chiral compounds have different refractive indices for left and right circularly rotated lights, and hence they show optical rotation proportional to the value n_L-n_R. When a intense linearly polarized light travels through a chiral material, it induces nonlinear optical rotation of the polarization plane. These chiral compounds can be used as photonics device. We have made exploatory studies of chiral pi-electron compounds suitable for such purpose and got the results described below.(1)The exciton coupling mechanism of chiral cyanin dye was theoretically clarified by the MO calculation.(2)The chiral probe of camphoresultamuseful for enantioresolution of carboxylic acids and X-ray determination of their absolute stereochemistry was developed. The method was applied to various chiral carboxylic acids.(3)The absolute stereochemistry of some chiral cyclophane compounds previously determined was revised.(4)The absolute configuration of a cage molecule was determined by the theoretical calculation of CD spectra.(5)The chiral cyclophane with a side chain containing oxygen atoms was enantioresolved and its absolute configuration was determined by the camphorsultam/X-ray method.(6)We succeeded in enantioresolution of monoterpenes by the chiral host-guest complex crystallization method.(7)The absolute stereostructure of double Michael product was determined by the camphoresultam/X-ray method.(8)The chiral phthalic acid amide method useful for anantioresolution of alcohols and determination of their absolute configuration by the X-ray method was developed and applied to various alcohols.(9)It was established that the exciton chirality method was applicable to acyclic dibenzoates to determine their absolute configuration.(10)The absolute configuration of unique chiral [6.6] vespirene compounds were determined by the X-ray method.