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Enhancement of the Photofunction of Phosphorescent Pt(II) Cyclometalated Complexes Driven by Substituents: Solid-State Luminescence and Circularly Polarized Luminescence

  • Tsukasa Usuki
    Tsukasa Usuki
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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  • , 
  • Hikaru Uchida
    Hikaru Uchida
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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  • , 
  • Kenichiro Omoto
    Kenichiro Omoto
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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  • , 
  • Yoshinori Yamanoi*
    Yoshinori Yamanoi
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    *E-mail: [email protected] (Y.Y.).
    More by Yoshinori Yamanoi
    Orcidhttp://orcid.org/0000-0002-6155-2357
  • , 
  • Ayano Yamada
    Ayano Yamada
    Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
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  • , 
  • Munetaka Iwamura
    Munetaka Iwamura
    Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
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    Orcidhttp://orcid.org/0000-0002-4888-9086
  • , 
  • Koichi Nozaki
    Koichi Nozaki
    Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
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  • , and 
  • Hiroshi Nishihara*
    Hiroshi Nishihara
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    *E-mail: [email protected] (H.N.).
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Cite this: J. Org. Chem. 2019, 84, 17, 10749–10756
Publication Date (Web):August 1, 2019
https://doi.org/10.1021/acs.joc.9b01285
Copyright © 2019 American Chemical Society
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    Abstract

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    Ligand functionalization is an attractive strategy for enhancing the performance of metal-based phosphorescent emitters. Here, we report the synthesis and characterization of cyclometalated Pt(II) complexes Pt3 and Pt4 containing organosilyl-substituted (2-(2-thienyl)pyridine) ligands and compare their properties with those of Pt1 (no substituent) and Pt2 (organocarbon substituent). The photophysical characteristics of these molecules, including their absorption and phosphorescence spectra, phosphorescence quantum yield and lifetime, were investigated. The molecular structures were revealed by X-ray diffraction analysis. Under UV light irradiation, Pt2–Pt4 emitted intense orange phosphorescence in the solid state because of the bulkiness of their side chains (up to ΦP: 0.49). Optically pure (−)-(S)Si-Pt4 and (+)-(R)Si-Pt4 were prepared using the optically active ligands (+)-L4 and (−)-L4, respectively. The chiroptical properties of (+)-(R)Si-Pt4, which has an asymmetric silicon atom, were investigated. Circular dichroism and circularly polarized luminescence measurements showed that these structural motifs are suitable for applications in chiroptical phosphorescent materials.

    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.9b01285.

    • HPLC charts of L4 and Pt4, crystallographic data, photophysical characteristics of Pt1–Pt4 in the solid state and in PMMA, absorption and phosphorescence emission spectra, CD and CPL spectra, PXRD, and copies of 1H and 13C{1H} NMR for L3, L4, and Pt2–Pt4 (PDF)

    • X-ray data for Pt2 (CIF)

    • X-ray data for Pt3 (CIF)

    • X-ray data for (+)-(R)Si-Pt4 (CIF)

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