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

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)533-540
    Number of pages8
    JournalDyes and Pigments
    Volume139
    DOIs
    StatePublished - 2017 Apr 1

    Fingerprint

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

    Keywords

    • Auxochrome
    • DFT calculations
    • Solvatochromism
    • UV–Vis absorption spectrum
    • Xanthene dye
    • π-Excess heteroaromatic ring

    ASJC Scopus subject areas

    • Chemical Engineering(all)
    • Process Chemistry and Technology

    Cite this

    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.

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

    Research output: Contribution to journalArticle

    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.

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

    Research output: Contribution to journalArticle

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