A nucleophilic aromatic substitution reaction between a sterically hindered phenol and 4-nitrophthalonitrile, 3-nitrophthalonitrile or 6-fluoro-2,3-napthalonitrile has been used to prepare precursors for the synthesis of a number of phthalocyanines, such as 1, and naphthalocyanines bearing bulky substituents.
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Brewis et al. (1998) studied this question.