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Solubilities of Organic Semiconductors and Nonsteroidal Anti-inflammatory Drugs in Pure and Mixed Organic Solvents: Measurement and Modeling with Hansen Solubility Parameter
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    Solubilities of Organic Semiconductors and Nonsteroidal Anti-inflammatory Drugs in Pure and Mixed Organic Solvents: Measurement and Modeling with Hansen Solubility Parameter
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    • Yoshihiro Takebayashi*
      Yoshihiro Takebayashi
      Research Institute for Chemical Process Technology, National Institute of Advanced Industrial Science and Technology (AIST), Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
      *Phone: +81-29-861-9272. E-mail: [email protected]
    • Kiwamu Sue
      Kiwamu Sue
      Research Institute for Chemical Process Technology, National Institute of Advanced Industrial Science and Technology (AIST), Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
      More by Kiwamu Sue
    • Takeshi Furuya
      Takeshi Furuya
      Research Institute for Chemical Process Technology, National Institute of Advanced Industrial Science and Technology (AIST), Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
    • Satoshi Yoda
      Satoshi Yoda
      Research Institute for Chemical Process Technology, National Institute of Advanced Industrial Science and Technology (AIST), Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
      More by Satoshi Yoda
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    Journal of Chemical & Engineering Data

    Cite this: J. Chem. Eng. Data 2018, 63, 10, 3889–3901
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    https://doi.org/10.1021/acs.jced.8b00536
    Published September 27, 2018
    Copyright © 2018 American Chemical Society

    Abstract

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    The solubilities of five organic semiconductors and four nonsteroidal anti-inflammatory drugs (NSAIDs) were measured by a static analytical method in a set of seven representative organic solvents at 298.15 K and 0.10 MPa to determine the Hansen solubility parameter (HSP) of the solutes by a quantitative correlation with the extended Hansen model. Solubilities of the organic semiconductors (N,N′-di-1-naphthyl-N,N′-diphenylbenzidine (NPB), 4,4′-bis(9H-carbazol-9-yl)biphenyl (CBP), anthracene, tetracene, and perylene) exhibited similar solvent dependence to each other, increasing in the order of ethanol < acetonitrile < hexane < acetone < carbon tetrachloride < chlorobenzene ≈ chloroform due to the large dispersion parameter δD ≈ 21 and the small polarity and hydrogen bonding parameters (δP, δH) ≈ (5, 5) of the solutes. In contrast, the solubilities of NSAIDs (naproxen, diclofenac, indomethacin, and niflumic acid) were hexane < carbon tetrachloride < acetonitrile ≈ chlorobenzene < ethanol ≈ chloroform < acetone, indicating the smaller δD ≈ 19 and the larger (δP, δH) ≈ (10, 11). The HSP analysis enabled us to estimate the solubilities in other solvents and solvent mixtures; for example, the solubility maximum of indomethacin in the mixtures of ethanol with ethyl acetate, acetone, and acetonitrile was well described by the minimum Hansen distance.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00536.

    • Densities of the saturated solutions, comparison of the solubilities measured in this work and those in literature, and Kamlet–Taft solvatochromic parameters of the acetonitrile + ethanol mixture (PDF)

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    Journal of Chemical & Engineering Data

    Cite this: J. Chem. Eng. Data 2018, 63, 10, 3889–3901
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jced.8b00536
    Published September 27, 2018
    Copyright © 2018 American Chemical Society

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