Palladium Complexes of Carbazole-Based Chalcogenaisophlorins: Synthesis, Structure, and Solid-State NIR Absorption Spectra

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3 Citations (Scopus)

Abstract

Annulation reactions of the butadiyne-bridged carbazole dimer 1 produced carbazole-based chalcogenaisophlorins 2–4, which were transformed into the corresponding palladium complexes 2Pd–4Pd. The structures were characterized by NMR spectroscopy and X-ray diffraction analysis. Metallation fixed the structures which displayed weak antiaromatic character derived from the 20π isophlorin framework. These complexes showed weak near-infrared (NIR) absorption typical for antiaromatic porphyrinoids in solution. In addition, 2Pd and 3Pd showed relatively strong solid-state NIR absorption. X-ray diffraction analyses of 2Pd and 3Pd revealed trimeric and dimeric stacked layered structures, respectively, and DFT calculations suggest that the solid-state NIR absorption is ascribed to intermolecular charge transfer.

Original languageEnglish
Pages (from-to)1368-1371
Number of pages4
JournalChemPlusChem
Volume82
Issue number12
DOIs
Publication statusPublished - Dec 2017

Keywords

  • NIR absorption
  • carbazoles
  • density functional calculations
  • isophlorins
  • porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)

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