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 language | English |
|---|---|
| Pages (from-to) | 3766-3770 |
| Number of pages | 5 |
| Journal | Inorganic Chemistry |
| Volume | 20 |
| Issue number | 11 |
| Publication status | Published - 1981 |
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- Inorganic Chemistry
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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 journal › Article
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TY - JOUR
T1 - Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines
AU - Cuellar, Edward A.
AU - Marks, Tobin J
PY - 1981
Y1 - 1981
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.
AB - 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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M3 - Article
VL - 20
SP - 3766
EP - 3770
JO - Inorganic Chemistry
JF - Inorganic Chemistry
SN - 0020-1669
IS - 11
ER -