First generation and trapping of a dehydrometallophthalocyanine starting from triazole-functionalized zinc phthalocyanine.
Sergei I. Vagin, Antje Frickenschmidt, Bernd Kammerer, and Michael Hanack
Abstract:
Direct 1N-amination of the triazole-fuzed zinc phthalocyanine and oxidation of the formed amino-derivative resulted in the generation of the very reactive intermediate, the dehydrometallophthalocyanine , which was not known previously. The latter was trapped in situ with different dienes, e.g. furan, tetraphenylcyclopentadienone and anthracene to form corresponding Diels-Alder adducts. The products are characterized by 1H and 13C-dept135 NMR, UV-Vis, MALDI-TOF 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, applicable easily to the micromol scale and important for the design of new interesting Pc-based systems.
Printed in Chemistry - A European Journal, 2005, 11(22), 6568-6573
