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Palladium Complexes of N-Methylcorroles.

Francesco Pizzoli1, Alessandro Mita1, Fabrizio Caroleo1

  • 1Department of Chemical Science and Technologies, University of Rome Tor Vergata, Via della Ricerca Scientifica, 00133, Rome, Italy.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 7, 2023
PubMed
Summary

N-methylation of corrole ligands creates chiral compounds for palladium coordination. These palladium complexes generate singlet oxygen, with enhanced photostability when complexed with human serum albumin (HSA).

Keywords:
chiralitycorrolesluminescencepalladium complexesporphyrinoids

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Area of Science:

  • Coordination Chemistry
  • Organic Synthesis
  • Photochemistry

Background:

  • Corrole ligands are versatile macrocycles with potential applications in catalysis and medicine.
  • Dianionic corrole ligands are desirable for coordinating divalent metal ions like palladium(II).
  • N-alkylation offers a route to modify corrole electronic and structural properties.

Purpose of the Study:

  • To synthesize N-methylated corrole ligands via controlled alkylation.
  • To investigate the coordination of palladium(II) to these modified corroles.
  • To characterize the photophysical properties and reactivity of the resulting palladium complexes, including their behavior in biological media.

Main Methods:

  • N-methylation of corrole using methyl iodide (CH3I).
  • Separation and characterization of regioisomers (N-21 and N-22 methyl derivatives) using chromatography and spectroscopy.
  • Structural analysis via X-ray crystallography.
  • Palladium insertion reactions.
  • Circular Dichroism (ECD) computation for absolute configuration assignment.
  • Photophysical studies including singlet oxygen generation and photobleaching experiments.
  • Complexation with human serum albumin (HSA) and assessment of ROS production mechanisms.

Main Results:

  • Selective N-methylation of corrole was achieved, yielding two regioisomers.
  • Monosubstituted N-methylcorroles successfully coordinated with Pd(II), while dimethylated derivatives did not.
  • X-ray crystallography revealed significant macrocycle distortion in Pd(II) complexes.
  • The Pd(II) complexes generated singlet oxygen but lacked luminescence.
  • Complexation with HSA protected the corroles from photobleaching and altered the ROS generation mechanism from Type II to Type I.

Conclusions:

  • N-methylation provides access to chiral corrole ligands suitable for specific metal coordination.
  • Palladium(II) complexes of N-methylcorroles exhibit interesting photophysical properties and potential for ROS generation.
  • Encapsulation within HSA enhances the stability and modifies the reactivity of these complexes, suggesting potential for biomedical applications.