The Synthesis of Some Phthalocyanines and Napthalocyanines Derived from Sterically Hindered Phenols

✍ Scribed by Matthew Brewis; Guy J. Clarkson; Paul Humberstone; Saad Makhseed; Neil B. McKeown

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 198 KB
• Volume: 4
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/(sici)1521-3765(19980904)4:9<1633::aid-chem1633>3.0.co;2-o

✦ Synopsis

The synthesis of a number of phthalocyanines (Pcs) and naphthalocyanines (NPcs) bearing bulky substituents is described. Precursors are prepared by using a nucleophilic aromatic substitution reaction between a sterically hindered phenol and 4-nitrophthalonitrile, 3-nitrophthalonitrile or 6-fluoro-2,3-napthalonitrile. Thus, Pcs and NPcs derived from 2,6-diisopropylphe-nol, 3,5-di-tert-butylphenol and 2,6-diphenylphenol possess substituents that are forced by steric constraints to adopt a non-planar conformation which enhances the solubility of the macrocycle.

In particular, the Pc derived from 2,6-ditert-butyl-4-methylphenol displays exceptional solubility and a reduced tendency to aggregate in solution. 2,6-Ditert-butylphenol reacts as a carbon nucleophile to produce biphenyl phthalonitrile precursors to Pcs containing redox-active phenolic substituents.