Synthesis and characterization of new polynuclear subphthalocyanine compounds

ORGN 19

Ronald Nohr1, Andreas H. Franz, afranz@pacific.edu1, and Heinz-Peter Schuchmann2. (1) Department of Chemistry, University of the Pacific, 3601 Pacific Avenue, Stockton, CA 95211, (2) Department of Chemistry, Max-Planck Institut fuer Strahlenchemie, Stiftstrasse 34, Muelheim, 45413, Germany
Subphthalocyanines are boron containing aromatic macrocycles composed of three isoindoline groups. These compounds have gained interest for their non-linear optical properties and for their use in the formation of unsymmetrical phthalocyanines via the Kobayashi ring expansion reaction. All subphthalocyanines synthesized to date have utilized ortho-phthalonitriles and/or ortho-naphthalenedicarbonitriles in kinetically controlled reactions producing unmixed and mixed products of the type: A3, A2B, AB2, and B3. We report here the synthesis and characterization of new polynuclear subphthalocyanines from the template cyclization of ortho-anthracenedicarbonitriles and ortho-naphthalenedicarbonitriles. Synthesis of unsymmetrical derivatives, electronic absorption spectra, and mechanistic features highlighting the significant increase in product yield will also be presented.
 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Sunday, 13 March 2005 Convention Center -- Room 11A, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005