UV–vis absorption and fluorescence spectra, solvatochromism, and application to pH sensors of novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome

Masaki Matsui, Takaya Yamamoto, Kenta Kakitani, Siddanagouda Biradar, Yasuhiro Kubota, Kazumasa Funabiki

    抄録

    Novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome have been synthesized. The UV–vis absorption maximum in dichloromethane was in the order of the auxochrome: NEt2 (Rhodamine B, 558 nm) < 2-thienyl (569 nm) < 5-thieno[3,2-b]thienyl (608 nm). These new xanthene dyes colored only in non-hydrogen-bond accepting solvents such as chloroform and dichloromethane. The lactone precursors of the thienyl and thieno[3,2-b]thienyl derivatives colored by adding strong acids whose pKa value is lower than −2.2 and 0.23, respectively, whereas that of rhodamine B colored by adding weak acids whose pKa value is lower than 4.7. These results originate from less stability of colored cationic dyes by the heteroaromatics than by the diethylamino auxochrome.

    本文言語英語
    ページ(範囲)533-540
    ページ数8
    ジャーナルDyes and Pigments
    139
    DOI
    ジャーナル掲載日出版済み - 2017 4 1

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    Dyes
    Xanthenes
    Dichloromethane
    Acids
    pH sensors
    Chemical bonds
    Chlorine compounds
    Fluorescence
    Derivatives

    Keywords

      ASJC Scopus subject areas

      • Chemical Engineering(all)
      • Process Chemistry and Technology

      これを引用

      UV–vis absorption and fluorescence spectra, solvatochromism, and application to pH sensors of novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome. / Matsui, Masaki; Yamamoto, Takaya; Kakitani, Kenta; Biradar, Siddanagouda; Kubota, Yasuhiro; Funabiki, Kazumasa.

      :: Dyes and Pigments, 巻 139, 01.04.2017, p. 533-540.

      研究成果: ジャーナルへの寄稿記事

      Matsui, Masaki; Yamamoto, Takaya; Kakitani, Kenta; Biradar, Siddanagouda; Kubota, Yasuhiro; Funabiki, Kazumasa / UV–vis absorption and fluorescence spectra, solvatochromism, and application to pH sensors of novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome.

      :: Dyes and Pigments, 巻 139, 01.04.2017, p. 533-540.

      研究成果: ジャーナルへの寄稿記事

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      keywords = "Auxochrome, DFT calculations, Solvatochromism, UV–Vis absorption spectrum, Xanthene dye, π-Excess heteroaromatic ring",
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      AU - Matsui,Masaki

      AU - Yamamoto,Takaya

      AU - Kakitani,Kenta

      AU - Biradar,Siddanagouda

      AU - Kubota,Yasuhiro

      AU - Funabiki,Kazumasa

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      N2 - Novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome have been synthesized. The UV–vis absorption maximum in dichloromethane was in the order of the auxochrome: NEt2 (Rhodamine B, 558 nm) < 2-thienyl (569 nm) < 5-thieno[3,2-b]thienyl (608 nm). These new xanthene dyes colored only in non-hydrogen-bond accepting solvents such as chloroform and dichloromethane. The lactone precursors of the thienyl and thieno[3,2-b]thienyl derivatives colored by adding strong acids whose pKa value is lower than −2.2 and 0.23, respectively, whereas that of rhodamine B colored by adding weak acids whose pKa value is lower than 4.7. These results originate from less stability of colored cationic dyes by the heteroaromatics than by the diethylamino auxochrome.

      AB - Novel xanthene dyes having thienyl and thieno[3,2-b]thienyl rings as auxochrome have been synthesized. The UV–vis absorption maximum in dichloromethane was in the order of the auxochrome: NEt2 (Rhodamine B, 558 nm) < 2-thienyl (569 nm) < 5-thieno[3,2-b]thienyl (608 nm). These new xanthene dyes colored only in non-hydrogen-bond accepting solvents such as chloroform and dichloromethane. The lactone precursors of the thienyl and thieno[3,2-b]thienyl derivatives colored by adding strong acids whose pKa value is lower than −2.2 and 0.23, respectively, whereas that of rhodamine B colored by adding weak acids whose pKa value is lower than 4.7. These results originate from less stability of colored cationic dyes by the heteroaromatics than by the diethylamino auxochrome.

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      KW - DFT calculations

      KW - Solvatochromism

      KW - UV–Vis absorption spectrum

      KW - Xanthene dye

      KW - π-Excess heteroaromatic ring

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