Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 11, Issue 22, Pages 6568-6573Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200500705
Keywords
cycloaddition; dehydrometallopthalocyanine; phthalocyanines; spectroscopic properties; zinc
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Direct 1N-amination of the triazole-fused zinc phthalocyanine 2 and oxidation of the formed amino derivative 3 resulted in the generation of the very reactive intermediate, the dehydrometallophthalocyanine 4, which was not known previously. The latter was trapped in situ with different dienes, for example, furan, tetraphenylcyclopentadienone, and anthracene to form the corresponding Diels-Alder adducts. The products were characterized by H-1 and C-13-dept135 NMR, and UV/Vis spectroscopy, MALDI-TOF mass spectrometry, and elemental analysis, which are fully in agreement with their structure. The developed synthetic procedure opens a simple and versatile pathway towards unsymmetrical peripheral modification of phthalocyanines, which is readily applicable to the micromol scale and is important for the design of new interesting Pc-based systems.
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