Heteroleptic palladium(II) complexes of dipyrrin-1,9-dione supported by intramolecular hydrogen bonding

Clayton J. Curtis, Elisa Tomat

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

The dipyrrin-1,9-dione framework, which is characteristic of the propentdyopent pigments deriving from heme metabolism, coordinates metal ions as monoanionic bidentate donors. The resulting analogs of dipyrrinato complexes undergo reversible ligand-based reductions, thus showcasing the ability of the dipyrrindione scaffold to act as an electron reservoir. Herein we report the synthesis and characterization of three heteroleptic palladium complexes of the redox-active dipyrrindione ligand. Primary amines were chosen as additional ligands so as to assemble complexes of planar geometries with complementary interligand hydrogen-bonding. Full chemical characterization confirms the hydrogen bonding interactions between the primary amine ligands and the acceptor carbonyl groups on the dipyrrolic ligand. The resulting heteroleptic compounds display reversible one-electron reduction events that are centered on the dipyrrindione ligand as revealed by voltammetry and spectroelectrochemistry data. Within these planar Pd(II) complexes, the propentdyopent motif therefore combines reversible ligand-based redox chemistry with interligand hydrogen bonding in the primary coordination sphere of the metal center.

Original languageEnglish (US)
JournalJournal of Porphyrins and Phthalocyanines
DOIs
StateAccepted/In press - Jan 1 2019

Keywords

  • Dipyrrindione
  • Heteroleptic
  • Hydrogen bonding
  • Palladium
  • Primary amine
  • Propentdyopent

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Heteroleptic palladium(II) complexes of dipyrrin-1,9-dione supported by intramolecular hydrogen bonding'. Together they form a unique fingerprint.

  • Cite this