Synthesis of porphyrins bearing one or two meso substituents

ORGN 649

Masahiko Taniguchi, mttanig@yahoo.com, Dazhong Fan, and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Box 8204, Raleigh, NC 27695-8204

5,15-Disubstituted porphyrins are valuable compounds in bioorganic and materials chemistry.  A new rational synthesis has been developed that employs condensation of a dipyrromethane + a 1,9-disubstituted dipyrromethane derivative affording the zinc porphyrin.  Several C1 synthons have been investigated at the 1,9-positions of the dipyrromethane.  The synthesis is compatible with diverse meso-substituents (e.g., H, alkyl, aryl, ester, acetal) and enables rapid synthesis of trans-AB-, A2-, and A-porphyrins without detectable scrambling.  The synthesis of >50 zinc porphyrins has been surveyed.

 

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005