A Synthetic Approach to β-Functionalized Naphtho[2,3]porphyrins
Siddhartha Kumar, Whitney A. Webre, Courtney Stewart, Francis D’Souza, Hong Wang
Abstract
A concise synthetic method has been developed to access functionalized naphtho[2,3]porphyrins through combining two sequence reactions involving a Heck–electrocyclization–aromatization sequence and a Wittig–Knovenegal sequence. Using this method, mononaphtho[2,3]porphyrin (NP-1), opp-dinaphtho[2,3]porphyrin (NP-2), and push–pull naphtho[2,3]porphyrin (NP-3) have been prepared. These naphtho[2,3]porphyrins displayed interesting optical and electrochemical properties. Excellent efficiencies of singlet oxygen generation were obtained for these naphtho[2,3]porphyrins.
Topics & Concepts
PorphyrinChemistryAromatizationSequence (biology)Singlet oxygenCombinatorial chemistryWittig reactionElectrochemistryHeck reactionPhotochemistryOxygenOrganic chemistryPalladiumCatalysisElectrodePhysical chemistryBiochemistryPorphyrin and Phthalocyanine ChemistryMetal-Catalyzed Oxygenation MechanismsSupramolecular Chemistry and Complexes