A Synthetic Approach to Asymmetric Phthalocyanines with Peripheral Metal-Binding Sites

✍ Scribed by Marco Haas; Shi-Xia Liu; Antonia Neels; Silvio Decurtins

• Book ID: 102170518
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 247 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200600619

✦ Synopsis

Abstract

A phthalonitrile derivative 1, functionalized with two pyridyl groups, undergoes a cyclotetramerization reaction to afford the symmetric metal‐free phthalocyanine 2 with peripheral metal‐binding sites. In view of its insufficient solubility in organic solvents, a synthetic route to asymmetric peripherally octasubstituted Pcs, which contain a combination of 2,3‐di(2‐pyridyl)pyrazino and p‐pentylphenoxy or p‐(tert‐butyl)phenoxy substituent groups, has been developed. The compounds 5–9 were synthesized by a statistical condensation reaction between two different phthalonitriles, and remarkably, all of them have been isolated and characterized as single compounds. For structural characterization, an X‐ray study of the asymmetric Zn phthalocyanine 11 is given. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)