Synthesis of Cationic Polymers Based on Porphyrins for Photoinactivation of Bacteria

SANTAMARINA, SOFÍA C.; HEREDIA, DANIEL A.; DURANTINI, ANDRÉS M.; DURANTINI, EDGARDO N.

Chemistry Proceeding

MDPI - Publisher of Open Access Journals

Año: 2021

2673-4583

5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin (TPPF20) was synthesized by acid catalyzed condensation between pentafluorobenzaldehyde and pyrrole catalyzed by BF3.OEt2 in dichloromethane. Subsequent oxidation reaction with 2,3-dichloro-5,6-dicyano-p-benzoquinone afforded TPPF20 in 38% yield. After was treated with Zn(II) to form the complex ZnTPPF20. This porphyrin can be modified by nucleophilic aromatic substitution (SNAr) with the displacement of the four para-fluoro atoms, then TPPF20 and ZnTPPF20 were reacted with N,N,N′,N′-tetrakis(3-aminopropyl)-1,4-butanediamine as the dendrimeric structure by SNAr to obtain two polymers, PTPPF16 and PZnTPPF16, respectively. The reactions were carried out in N,N-dimethylformamide achieving 100% conversion. The polymers were purified by precipitation in water and washing the solid with petroleum ether. Moreover, spectroscopic and photodynamic studies of polymers indicated that the porphyrin unit retains its properties as PS. Thus, these polymers are an interesting material with potential applications to form photoactive aseptic surfaces.