Norbornadiene Dicarboxylic Acid EsterおよびCyclopentadienone Dimerの合成と光化学反応

概要

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Methyl ester (3b), ethyl ester (3c) of bicyclo [2,2,1] hepta-2,5-diene-2,3-dicarboxylic acid and 5,6,8,9-tetraphenyl tricyclo [5,2,1,0^2,6] deca-4,8-diene-3,10-dione (6), which are effective to store solar energy in their chemical strain structures, were synthesized in yields of 85.5%, 84.1% and 69.4% respectively, and their photochemical behaviors were investigated by measuring absorption and emission spectra. It is found by NMR, IR analysis and m. p. measurements that cage compounds corresponding to the initial compounds are directly produced by irradiation of UV light. Measurements of quantum efficiency indicate that ethyl ester of norbornadiene dicarboxylate is converted to the cage compound more effectively than that of methyl ester. The difference in the efficiencies between both compounds is well fitted with the result of emission fluorescent intensities. The quantum efficiency of the cage compound from cyclopentadienone dimer was observed to be relatively low. The emission studies of cyclopentadienone dimer and the resulted cage compound suggest that an intermediate compound should exist during irradiation of UV light.
東海大学の論文