ID JOS-acs.langmuir.1c00103
著者：名前 著者：別形式 Miki, Ryotaro / Yamauchi, Tomoya / Kawashima, Kosuke / Egawa, Yuya / Seki, Toshinobu
著者：カナ 著者：所属 城西大学薬学部 / 城西大学薬学部 / 城西大学薬学部 / 城西大学薬学部 / 城西大学薬学部
著者：所属(別形式） Josai University, Faculty of Pharmacy and Pharmaceutical Sciences / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences / Josai University, Faculty of Pharmacy and Pharmaceutical Sciences
著者版フラグ author
出版地 Washington, D.C.
出版者 American Chemical Society
冊子ISSN 07437463
電子ISSN 15205827
掲載誌名 巻 37
号 11
刊行年月 2021-03
開始ページ 3438
終了ページ 3445
コンテンツ作成日 2021-01-12
コンテンツ登録日 2022-03-30
識別番号：DOI info:doi/10.1021/acs.langmuir.1c00103
識別番号：DOI（リンク） PubMed番号 33706516
抄録 We had previously confirmed a glucose-responsive decrease in the viscosity of cetyltrimethylammonium bromide (CTAB) and phenylboronic acid (PBA) wormlike micelle (WLM) systems. However, the mechanisms of the formation of WLMs and the decrease in viscosity with glucose addition have not been determined. In this study, we elucidated the mechanisms using 3-fluorophenylboronic acid (3FPBA) based on 11B NMR and 19F NMR analyses. The system in 60 mM CTAB/60 mM 3FPBA at pH 7.4 demonstrated high viscoelasticity, and the formation of WLMs in the system was confirmed by rheological characteristics. The 11B NMR spectrum at pH 7.4 revealed that 3FPBA existed in a neutral form with sp2-hybridized boron; however, the 11B signal disappeared in the presence of CTAB. In contrast, 19F NMR studies indicated that the quaternary ammonium ion of CTAB interacts with the phenyl group of 3FPBA in the sp2 form via cation-π interactions. PBA derivatives react with various polyols; thus, we investigated the change in the viscous system after the addition of sugar and sugar alcohols. The viscosity of the WLMs decreased with increased polyol concentration, especially those of fructose and mannitol, in which the decrease was apparent at 40-160 mM polyols. The 19F NMR spectra revealed that polyol addition induced decrease in the sp2 form of 3FPBA and increase in the sp3 form of 3FPBA. Based on the results, we propose the following mechanism of the polyol response: (1) The WLMs are stabilized by CTAB and 3FPBA in the sp2 form using cation-π interactions as the driving force. (2) When polyol is added to the system, the sp2 form of 3FPBA decreases and its sp3 form increases. (3) This change means that the structural component of WLMs decreases, which induces the disruption of WLMs, and the viscosity decreases. The formation and deformation mechanisms of the WLMs determined in this study are notable because 3FPBA interacts as a neutral compound, whereas CTAB often interacts with anionic aromatic compounds to form WLMs. Without 19F NMR measurements, these mechanisms would not have been discovered.
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