Synthesis of Conjugated Polymer Based in Zn(II) Porphyrin Bearing Terminal Alkynyl Groups as Photosensitizer

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

Chemistry Proceeding

MDPI - Publisher of Open Access Journals

Año: 2020

2673-4583

5,10,15,20-tetrakis-[4-(ethynyl)phenyl]porphyrin (TEP) was synthesized from the condensationof 4-(ethynyl)benzaldehyde and pyrrole catalyzed by boron trifluoride diethyl etherate indichloromethane (DCM). After oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and purification,TEP was obtained in 34% yield. This porphyrin was metaled with Zn(II) acetate inDCM/methanol to produce the complex ZnTEP in 98% yield. A homocoupling reaction of terminalalkynes of ZnTEP to diynes was used to synthesize conjugated polymer organogel (ZnTEPP). Thereaction was co-catalyzed by PdCl2(PPh3)2 and CuI in tetrahydrofuran. The solvent was evaporatedto obtain xerogel and the SEM images showed microporous structure. In addition, spectroscopicand photodynamic studies of ZnTEPP indicated that the porphyrin unit retains its properties as aphotosensitizer. Thus, this polymer is an interesting material with potential applications in formingphotoactive aseptic surfaces.