A straightforward, efficient, and generalizadle synthesis of symmetrically substituted 2, 3, 9, 10, 16, 17, 23, 24-octaalkylphthalocyanines and uranyl 2, 3, 9, 10, 16, 17, 23, 24, 30, 31 -decaalkylsuperphthalocyaninates from o-dialkylbenzenes is described. For phthalocyanines, the approach is illustrated for methyl and zi-butyl substituents, and both metal-free and nickel complexes are reported. Uranyl superphthalocyanines have been prepared with methyl and n-butyl substituents. The new complexes have been characterized by a variety of chemical and physicochemical methods. Quantitative determination of the solubilities of substituted and unsubstituted phthalocyanine and superphthalocyanine complexes in both 1, 2, 4-trichlorobenzene and toluene demonstrates decreasing solubility in the order (4, 5-Bu2)5SPcUO2 > (4-Me)5SPcUO2 > (4, 5-Me2)5SPcUO2 > SPcUO2 > (4-Me)4PcH2 > Ni(4, 5-Bu2)Pc > Ni(4, 5-Me2)4Pc > NiPc. Attempts to displace the uranyl ion from (4, 5-R2)5SPcUO2 with acids or Cu(OAc)2 lead to the formation of (4, 5-R2)4PcH2 or Cu(4, 5-R2)4Pc, respectively.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Inorganic Chemistry