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

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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
JournalChemPlusChem
DOIs
Publication statusAccepted/In press - 2017

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Infrared absorption
Palladium
Absorption spectra
Discrete Fourier transforms
Dimers
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy
Charge transfer
X ray diffraction
carbazole

Keywords

  • Carbazoles
  • Density functional calculations
  • Isophlorins
  • NIR absorption
  • Porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Palladium Complexes of Carbazole-Based Chalcogenaisophlorins: Synthesis, Structure, and Solid-State NIR Absorption Spectra",
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.",
keywords = "Carbazoles, Density functional calculations, Isophlorins, NIR absorption, Porphyrinoids",
author = "Chihiro Maeda and Kazuto Takaishi and Tadashi Ema",
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language = "English",
journal = "ChemPlusChem",
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TY - JOUR

T1 - Palladium Complexes of Carbazole-Based Chalcogenaisophlorins

T2 - Synthesis, Structure, and Solid-State NIR Absorption Spectra

AU - Maeda, Chihiro

AU - Takaishi, Kazuto

AU - Ema, Tadashi

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

KW - Carbazoles

KW - Density functional calculations

KW - Isophlorins

KW - NIR absorption

KW - Porphyrinoids

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