Synthesis and Some Properties of Aryl‐ and Aryloxy‐Substituted Phthalocyanines and Their Metal Complexes: A Comparison with Porphyrazine and Naphthalocyanine Analogues

Abstract

Abstract The preparation of new octakis[ m‐ (trifluoromethyl)phenyl]‐ and octakis[ m ‐(trifluoromethyl)phenoxy]phthalocyanines ( 6a and 6b ) and their complexes with magnesium ( 5a , 5b ) and indium ( 7a , 7b ) is described. Their spectroscopic properties and solubilities are discussed in relation to those of metal‐free and metallated octakis[ m ‐(trifluoromethyl)phenyl]porphyrazine, as well as those of metal m ‐(trifluoromethyl)phenyl‐ and m ‐(trifluoromethyl)phenoxy‐substituted 2,3‐naphthalocyanines. A drastic decrease in the solubilities of the metal‐free phthalocyanines in CH 2 Cl 2 was observed on comparing them with m ‐CF 3 ‐phenyl‐substituted porphyrazine. However, their solubilities in THF were high enough for NMR spectra to be recorded. Insertion of (chloro)indium into the cavities of these phthalocyanines noticeably enhances the solubilization of the macrocycles, including in CH 2 Cl 2 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)