Synthesis of meso-nitrophenylporphyrins covalently linked to a polyphenylene chain bearing methoxy groups

Abstract

A convenient procedure for the synthesis of polyphenylene porphyrin dyads is described. The dyads consist of a meso-nitrophenylporphyrin covalently linked to a polyphenylene chain by an amide bond. The final phenyl group in the chain bears electron donor methoxy groups. The π-conjugated chain was obtained in excellent yield via a Wittig–Horner reaction, which produces a new double bond (E isomer) incorporating either — COOCH 3 or E isomer) incorporating either — CON ( OCH 3)( CH 3) functional groups. Expansion of the conjugated chain involves the reduction of these groups to aldehydes followed by a second Wittig–Horner reaction. 5-(4-Aminophenyl)-10,15,20-tris(4-nitrophenyl)porphyrin was synthesized from meso-(4-nitrophenyl)dipyrromethane. The E isomer) incorporating either — NO 2 groups in para positions of the peripheral phenyl rings give extra electron-withdrawing character to the porphyrin macrocycles. Coupling of the polyphenylene acids with aminoporphyrin results in the desired dyads. These dyads have moieties with different electron donor–acceptor properties. This present strategy may be easily used for preparation of other similar dyad derivatives. These compounds can be suitable for photodynamic therapy.