Molecule of the Month

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