Molecular recognition by a novel boronate-containing CTG derivative for hydroxyanthraquinones

C3-functionalized cyclotriguaiacylene (CTG) derivatives were employed in the development of highly selective recognition compounds due to their unique molecular structures. Here, a novel C3-functionalized CTG containing boronate (PPB-CTG) was synthesized and its molecular recognition ability for hyd...

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Bibliographic Details
Published in:Tetrahedron 2019-04, Vol.75 (15), p.2330-2335
Main Authors: Inoue, Tsubasa, Moriuchi-Kawakami, Takayo, Kuda, Kentaro, Matsubara, Shota, Fujimori, Keiichi, Moriuchi, Toshiyuki
Format: Article
Language:English
Subjects:
Alizarin
CTG derivative
Fluorescence enhancement
Molecular recognition
Selectivity for fluoride ion
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Summary:C3-functionalized cyclotriguaiacylene (CTG) derivatives were employed in the development of highly selective recognition compounds due to their unique molecular structures. Here, a novel C3-functionalized CTG containing boronate (PPB-CTG) was synthesized and its molecular recognition ability for hydroxyanthraquinones was investigated by fluorescence spectroscopy. The addition of the synthesized PPB-CTG led to a large increase in the fluorescence intensity of only alizarin and not 1-hydroxyanthraquinone, 2-hydroxyanthraquinone nor quinizarin. It was, thus, suggested that the cyclotriveratrylene (CTV) structure plays an important role in the recognition ability toward alizarin since the mono-phenyl boronate compound (m-TPBAP) showed poor fluorescence properties toward alizarin. Moreover, it was found that the 1:1 mixture of PPB-CTG and alizarin was effective as a fluorescence-enhanced probe toward fluoride ions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.03.005