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

• Published in: Tetrahedron Vol. 75; no. 15; pp. 2330 - 2335
• Main Authors: Inoue, Tsubasa, Moriuchi-Kawakami, Takayo, Kuda, Kentaro, Matsubara, Shota, Fujimori, Keiichi, Moriuchi, Toshiyuki
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 12.04.2019; Elsevier
• Subjects: Alizarin; Chemistry; Chemistry, Organic; CTG derivative; Fluorescence enhancement; Molecular recognition; Physical Sciences; Science & Technology; Selectivity for fluoride ion; Selectivity for fluoride ion; CTG derivative; LHLFPIQXHUNOCI-UHFFFAOYSA-N; Molecular recognition; ZCYYRQFLWXQAMW-UHFFFAOYSA-L; KMPFRDBWDGKCEC-UHFFFAOYSA-N; RIMMVLUOCUWBAQ-UHFFFAOYSA-N; HFFBTZKXYHNMGQ-UHFFFAOYSA-L; Alizarin; Fluorescence enhancement; ACIDS; PROBE
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2019.03.005

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]