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Synthesis of nitroxide-functionalized phthalocyanines |
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| Authors: | Anthony G.M. Barrett Andrew J.P. White Aaron S. Micallef |
| Affiliation: | a Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, England b Centre for Magnetic Resonance, University of Queensland, St Lucia, Queensland 4072, Australia c Synthesis and Molecular Recognition Program, Faculty of Science, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia |
| Abstract: | A nitroxide-functionalized phthalonitrile and a diimino-isoindoline were prepared via Pd(0)-catalyzed cyanation from the corresponding dibromide and subsequent addition of ammonia, without interference from the radical moieties. The structures of these radicals were confirmed by single-crystal X-ray structure determinations. Metal-templated macrocyclization of these species under standard Linstead conditions or in 2-(dimethylamino)ethanol at reflux gave the corresponding metallated and free-base phthalocyanines, which were characterized using UV-vis, FTIR and EPR spectroscopy as well as mass spectrometry. |
| Keywords: | Phthalocyanine Nitroxide Linstead macrocyclization UV-vis spectra EPR |
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