Preparation and Novel Properties of 1,8,9-Tris (seleno) anthracene and the Related Compounds

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1.1,8,9-Tris (phenylseleno) anthracene (1) has been tried to prepare in the reaction of 1,8-bis (phenylseleno) anthracene (2) with various organometallic reagents. The method to prepare 2 from 1,8-bis(phenylseleno) anthraquinone was improved and then it was obtained in good yield.2.1,8-Bis (seleno) naphthalenes, 1- (MeSe) -8- (p-YC_6H_4Se) C_<10>H_6 and 1- [8- (p-YC_6H_4Se) -C_<10>H_6] SeSe [C_<10>H_6 (SeC_6H_4Y-p) -8']-1' (3 and 4, respectively : Y=OMe, Me, H,Cl, Br, COOEt, NO_2), and the related compounds were prepared and their NMR spectra were measured. While the ^<77>Se chemical shifts of the MeSe group were correlated well with those of the p-YC_6H_4Se group in 3, those of the Se-Se group were inversely correlated with those of the p-YC_6H_4Se group in 4. The ^4 (Se, Se) values in 3 and 4 were also correlated, with negative slopes, with the ^<77>Se chemical shifts of the p-YC_6H_4Se groups in 3 and 4, respectively.3.The characters of the charge-transfer of the S-Cl-Cl bond in the formation of H_2SCl_2 (MC) were studied by means of MO calculations : the bond is proposed to be better described by the 3c-4e hypervalent model.4. The redox potentials were measured for the selenides prepared till now in this project.