17.9.24 Phthalocyanines and Related Compounds (Update 2017)

Abstract

This review updates the original Science of Synthesis chapter (Section 17.9) on phthalocyanines and various ring-fused, ring-contracted, and ring-expanded analogues. It adds some recently published methods, examples, and variations on the synthesis of unsubstituted phthalocyanines and metal phthalocyanines, as well as identically and nonidentically substituted phthalocyanine derivatives. Besides peripheral substitution, axial functionalization is also discussed, but attention is focused only on those methods that represent appreciable progress for a particular type of metal coordination and axial functionalization, provide phthalocyanines with specific features such as chirality, or allow the functionalization of phthalocyanines with entities that are difficult to introduce at the peripheral sites. This account also includes sections on new types of phthalocyanine derivatives and analogues that were not covered in the original chapter, as well as the progress made in the synthesis of some of these families in the decade since 2003.

Key words

phthalocyanines - phthalocyanine–metal complexes - porphyrazines - tetraazaporphyrins - naphthalocyanines - phenanthrenocyanines - triphenylenocyanines - anthracenocyanines - pyrenocyanines - benzoperylenocyanines - helicenocyanines - azulenocyanines - tetraazachlorins - tetraazabacteriochlorins - azaphthalocyanines - triazacorroles - subphthalocyanines - subporphyrazines - superazaporphyrins - pyrenocyanines - phthalonitriles - phthalic anhydrides - phthalic acids - phthalimides - isoindolinediimines - condensation reactions - substituent modification - ligand substitution

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