Synthesis of novel phenanthrolines and phthalocyanines

ORGN 366

Chandima Abeywickrama and A. D. Baker. Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30, Kissena Blvd, Flushing, NY 11367
Planar molecules containing extensive networks of pi electrons hold a central role in theory and have numerous applications. Of particular interest to this group are molecules of this type that contain diimine moieties that can bind metal ions. Our interest stems from the observation that such compounds, and their metal complexes intercalate between the base pairs in Deoxyribonucleic acid (DNA) and that the phenanthroline analogues can also serve as the precursors for the synthesis of much larger planar pi systems such as novel phthalocyanies and a unique group of cross shaped polymers based on phthalocyanine building blocks. We will describe approaches to the synthesis of several new phenanthroline derivatives using a variety of strategies including tandem coupling and intramolecular acyloin condensations, and the use of suitable dicyano phenanthroline derivatives for the fabrication of highly symmetric phthalocyanines