Transition-Metal Isocorroles as Singlet Oxygen Sensitizers.

Inorg Chem

Department of Chemistry, University of Tromsø, N-9037 Tromsø, Norway.

Published: May 2023

Building on a highly efficient synthesis of pyrrole-appended isocorroles, we have worked out conditions for manganese, palladium, and platinum insertion into free-base 5/10-(2-pyrrolyl)-5,10,15-tris(4-methylphenyl)isocorrole, H[5/10-(2-py)TMePiC]. Platinum insertion proved exceedingly challenging but was finally accomplished with -Pt(PhCN)Cl. All the complexes proved weakly phosphorescent in the near-infrared under ambient conditions, with a maximum phosphorescence quantum yield of 0.1% observed for Pd[5-(2-py)TMePiC]. The emission maximum was found to exhibit a strong metal ion dependence for the 5-regioisomeric complexes but not for the 10-regioisomers. Despite the low phosphorescence quantum yields, all the complexes were found to sensitize singlet oxygen formation with moderate to good efficiency, with singlet oxygen quantum yields ranging over 21-52%. With significant absorption in the near-infrared and good singlet oxygen-sensitizing ability, metalloisocorroles deserve examination as photosensitizers in the photodynamic therapy of cancer and other diseases.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10189730PMC
http://dx.doi.org/10.1021/acs.inorgchem.3c00782DOI Listing

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