Effect of alkoxy side chain length on the solid-state fluorescence behaviour of bisazomethine dyes possessing dipropylamino terminal group

Hyung Wook Yu, Byung Soon Kim, Shinya Matsumoto

    抄録

    A study was conducted on the optical properties of alkoxy-substituted bisazomethine dyes possessing a dipropylamino terminal group in solution and the solid state. All of the derivatives had similar optical properties in chloroform solution, showing weak fluorescence quantum yield of 5%. In the solid state, the fluorescence behaviour was found to be dependent on the length of the alkoxy side chain. The solid-state fluorescence intensity of the derivatives with the short alkoxy side chains (methoxy, propoxy, and butoxy) was rather low compared to that of the other derivatives in the near-infrared region. However, in the case of the derivatives with the ethoxy side chain the red solid-state fluorescence quantum efficiency improved to 13% at around 700 nm. On the other hand, the derivatives with the middle (pentyloxy to octyloxy) to long (dodecyloxy, hexadecyloxy, and eicosanoxy) alkoxy side chains emitted at around 680 nm, producing enhanced red fluorescence compared to that of the chloroform solution. In particular, the derivative with the hexyloxy side chain showed the highest fluorescence quantum efficiency of over 20% in the solid state. To determine the influence of the alkoxy side chain length on the observed solid-state fluorescence behaviour, X-ray structure analysis was carried out focusing on the molecular arrangement of bisazomethine dyes in crystals. The crystal structures were analysed based on the molecular arrangements of their geometrical characteristics. The result indicated that their solid-state fluorescence depends on the relative positional relationship of the neighbouring molecules and the intermolecular distance resulting from the alkoxy side chain length.

    本文言語英語
    ページ(範囲)131-139
    ページ数9
    ジャーナルDyes and Pigments
    136
    DOI
    ジャーナル掲載日出版済み - 2017 1 1

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    Fluorescence
    Derivatives
    Chain length
    Dyes
    Chlorine compounds
    Quantum efficiency
    Optical properties
    Quantum yield
    Crystal structure
    Infrared radiation
    X rays
    Crystals
    Molecules

    Keywords

      ASJC Scopus subject areas

      • Chemical Engineering(all)
      • Process Chemistry and Technology

      これを引用

      Effect of alkoxy side chain length on the solid-state fluorescence behaviour of bisazomethine dyes possessing dipropylamino terminal group. / Yu, Hyung Wook; Kim, Byung Soon; Matsumoto, Shinya.

      :: Dyes and Pigments, 巻 136, 01.01.2017, p. 131-139.

      研究成果: ジャーナルへの寄稿記事

      Yu, Hyung Wook; Kim, Byung Soon; Matsumoto, Shinya / Effect of alkoxy side chain length on the solid-state fluorescence behaviour of bisazomethine dyes possessing dipropylamino terminal group.

      :: Dyes and Pigments, 巻 136, 01.01.2017, p. 131-139.

      研究成果: ジャーナルへの寄稿記事

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      title = "Effect of alkoxy side chain length on the solid-state fluorescence behaviour of bisazomethine dyes possessing dipropylamino terminal group",
      keywords = "Bisazomethine dye, Crystal structure, Near-infrared fluorescence, Solid-state fluorescence, Substituent effects",
      author = "Yu, {Hyung Wook} and Kim, {Byung Soon} and Shinya Matsumoto",
      year = "2017",
      month = "1",
      doi = "10.1016/j.dyepig.2016.08.043",
      volume = "136",
      pages = "131--139",
      journal = "Dyes and Pigments",
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      TY - JOUR

      T1 - Effect of alkoxy side chain length on the solid-state fluorescence behaviour of bisazomethine dyes possessing dipropylamino terminal group

      AU - Yu,Hyung Wook

      AU - Kim,Byung Soon

      AU - Matsumoto,Shinya

      PY - 2017/1/1

      Y1 - 2017/1/1

      N2 - A study was conducted on the optical properties of alkoxy-substituted bisazomethine dyes possessing a dipropylamino terminal group in solution and the solid state. All of the derivatives had similar optical properties in chloroform solution, showing weak fluorescence quantum yield of 5%. In the solid state, the fluorescence behaviour was found to be dependent on the length of the alkoxy side chain. The solid-state fluorescence intensity of the derivatives with the short alkoxy side chains (methoxy, propoxy, and butoxy) was rather low compared to that of the other derivatives in the near-infrared region. However, in the case of the derivatives with the ethoxy side chain the red solid-state fluorescence quantum efficiency improved to 13% at around 700 nm. On the other hand, the derivatives with the middle (pentyloxy to octyloxy) to long (dodecyloxy, hexadecyloxy, and eicosanoxy) alkoxy side chains emitted at around 680 nm, producing enhanced red fluorescence compared to that of the chloroform solution. In particular, the derivative with the hexyloxy side chain showed the highest fluorescence quantum efficiency of over 20% in the solid state. To determine the influence of the alkoxy side chain length on the observed solid-state fluorescence behaviour, X-ray structure analysis was carried out focusing on the molecular arrangement of bisazomethine dyes in crystals. The crystal structures were analysed based on the molecular arrangements of their geometrical characteristics. The result indicated that their solid-state fluorescence depends on the relative positional relationship of the neighbouring molecules and the intermolecular distance resulting from the alkoxy side chain length.

      AB - A study was conducted on the optical properties of alkoxy-substituted bisazomethine dyes possessing a dipropylamino terminal group in solution and the solid state. All of the derivatives had similar optical properties in chloroform solution, showing weak fluorescence quantum yield of 5%. In the solid state, the fluorescence behaviour was found to be dependent on the length of the alkoxy side chain. The solid-state fluorescence intensity of the derivatives with the short alkoxy side chains (methoxy, propoxy, and butoxy) was rather low compared to that of the other derivatives in the near-infrared region. However, in the case of the derivatives with the ethoxy side chain the red solid-state fluorescence quantum efficiency improved to 13% at around 700 nm. On the other hand, the derivatives with the middle (pentyloxy to octyloxy) to long (dodecyloxy, hexadecyloxy, and eicosanoxy) alkoxy side chains emitted at around 680 nm, producing enhanced red fluorescence compared to that of the chloroform solution. In particular, the derivative with the hexyloxy side chain showed the highest fluorescence quantum efficiency of over 20% in the solid state. To determine the influence of the alkoxy side chain length on the observed solid-state fluorescence behaviour, X-ray structure analysis was carried out focusing on the molecular arrangement of bisazomethine dyes in crystals. The crystal structures were analysed based on the molecular arrangements of their geometrical characteristics. The result indicated that their solid-state fluorescence depends on the relative positional relationship of the neighbouring molecules and the intermolecular distance resulting from the alkoxy side chain length.

      KW - Bisazomethine dye

      KW - Crystal structure

      KW - Near-infrared fluorescence

      KW - Solid-state fluorescence

      KW - Substituent effects

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      T2 - Dyes and Pigments

      JF - Dyes and Pigments

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