Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines

Edward A. Cuellar, Tobin J Marks

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Abstract

A straightforward, efficient, and generalizable 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 n-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.

Original languageEnglish
Pages (from-to)3766-3770
Number of pages5
JournalInorganic Chemistry
Volume20
Issue number11
Publication statusPublished - 1981

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solubility
Solubility
Metals
Toluene
synthesis
Nickel
metals
toluene
nickel
Ions
acids
Acids
ions
phthalocyanine
1,2,4-trichlorobenzene

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines. / Cuellar, Edward A.; Marks, Tobin J.

In: Inorganic Chemistry, Vol. 20, No. 11, 1981, p. 3766-3770.

Research output: Contribution to journalArticle

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N2 - A straightforward, efficient, and generalizable 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 n-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.

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