Synthesis of porphyrins bearing distinct patterns of C1 substituents

ORGN 552

Zhen Yao, zyao@unity.ncsu.edu, Jayeeta Bhaumik, jbhaumi@unity.ncsu.edu, Dhanalekshmi Savithri, Marcin Ptaszek, mptasze@ncsu.edu, Phillip A. Rodriguez, and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204
The placement of C1 substituents (hydroxymethyl, ester, aldehyde, aminomethyl) at the porphyrin meso- and β-positions affords compact structures with attractive features for applications including self-assembly and bioconjugation. Rational syntheses entail introduction of such substituents into the pyrrole or dipyrromethane precursors to the porphyrins. In this manner, porphyrins bearing alcohol/alcohol, alcohol/ester, aldehyde/ester or aminomethyl/ester substituents have been prepared.