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cyclotetramerization of the corresponding 3- or 4-
ortho
-carboranylphthalonitriles
at 200
C, in the presence of zinc(II) acetate [
82
,
83
].
The symmetric and octa-anionic phthalocyanine
47
was synthesized in 30%
yield via tetracyclization of the corresponding carborane-containing phthalonitrile
in the presence of DBU and
n
-BuOH at 140
C[
84
]. The carboranylphthalonitrile
was prepared by base-catalyzed aromatic nucleophilic substitution of 4,5-
dichlorophthalonitrile with thiol-carborane.
Phthalocyanines
48
and
49
, as mixtures of regioisomers, bearing four
ortho
-
carboranes were synthesized using the two strategies described above, by fuctional-
ization of a pre-formed macrocycle and by tetramerization of the corresponding
carborane-containing phthalonitriles [
85
]. The former method gave the target
compounds in 13-20% yields while self-condensation of
the phthalonitrile
