Architecture and Applications of Novel Fluorinated Molecular Assemblies Imparted by the Aggregations of Fluoroalkyl Segments

氟烷基链段聚集体赋予的新型氟化分子组装体的结构和应用

• 批准号: 09650945
• 负责人: SAWADA Hideo
• 金额: $ 2.11万
• 依托单位: Nara National College of Technology
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1997
• 资助国家: 日本
• 起止时间: 1997 至 1999
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09650945/
• 关键词: Aggregation of fluoroalkyl groups; End-capped fluoroalkyl group; Fluorinated oligosurfactant; Aggregates; Solubility; Surface tension; Anti HIV-1 activity; Antibacterial activity; フッ素の凝集; イオン結合; 金属捕捉; ウイルス

It was demonstrated that a series of fluoroalkylated end-capped oligomers containing various functional segments such as carboxy, amide, betaine, and hydroxy groups can be prepared by the use of fluoroalkanoyl peroxides as key intermediates. These thus-obtained fluoroalkylated end-capped oligomers were soluble in water and organic solvents, and were capable of reducing the surface tension of water effectively with a clear break point resembling a CMC, which is almost the same level as that achieved by the usual low molecular weight fluorinated surfactants. This is a unique and interesting feature of our fluoroalkylated end-capped oligo-surfactants. Furthermore, fluoroalkylated end-capped oligomers were suggested to form the molecular assemblies imparted by strong aggregation of the fluoroalkylated end-groups in aqueous solutions, and fluoroalkylated end-capped acrylic acid and sulfonic acid oligomers were also shown to be potent and selective inhibitors of human immunodeficiency virus type 1 (EV-1) in vitro. More interestingly, fluoroalkylated end-capped oligomers containing betaine or hydroxy segments could cause gelation, where the synergistic interactions of both the strong aggregation of the end-capped fluoroalkyl segments and the ionic or hydrogen-bonding interaction are involved in establishing a get network in water and polar organic solvents.

研究表明，以氟烷酰过氧化物为关键中间体，可以合成一系列含有羧基、酰胺基、甜菜碱和羟基等官能团的含氟烷基端基齐聚物。这些端基氟烷基化低聚物可溶于水和有机溶剂，能有效降低水的表面张力，其断裂点类似于CMC，几乎与通常的低相对分子质量含氟表面活性剂所达到的水平相同。这是我们的氟烷基化端基低聚表面活性剂的一个独特而有趣的特征。此外，氟烷基化端基低聚物在水溶液中形成了由氟烷基化端基强烈聚集而形成的分子组装，而氟烷基化端基丙烯酸和磺酸低聚物在体外也被证明是有效的和选择性的人类免疫缺陷病毒1型(EV-1)的抑制剂。更有趣的是，含有甜菜碱或羟基链段的氟烷基化端基齐聚物可以引起凝胶，在水和极性有机溶剂中，端基氟烷基段的强聚集和离子或氢键相互作用的协同作用参与了GET网络的建立。

项目成果

H.Sawada: "Sythesis of Novel Fluoroalkyl End-capped N-Vinyl-2-pyrrolidone-acrylic Acid Co-oligomers by Use of Fluoroalkanoyl Peroxides, and Their Properties"J.Fluorine Chem.. 84. 155-160 (1997)

H.Sawada：“使用氟代烷酰基过氧化物合成新型氟烷基封端的 N-乙烯基-2-吡咯烷酮-丙烯酸共聚低聚物及其性能”J.Fluorine Chem.. 84. 155-160 (1997)

H.Sawada: "Gelation of Fluoroalkylated 2-Acrylamido-2-methylpropanesulfonic Acid Oligomers as Potential for Prevention of HIV-1 Transmission"Polymer. 39. 743-745 (1998)

H.Sawada：“氟烷基化 2-丙烯酰氨基-2-甲基丙磺酸低聚物的凝胶化作为预防 HIV-1 传播的潜力”聚合物。

沢田英夫: "総合論文:フッ素の凝集効果が発現された新しい分子集合体の構築と応用"有機合成化学協会誌. 57. 291-304 (1999)

Hideo Sawada：“综合论文：展示氟聚集效应的新型分子组装体的构建和应用”合成有机化学学会杂志 57. 291-304 (1999)。

H.Sawada: "Account : Architechture and Applications of Novel Self-Assembled Aggregates of Fluoroalkyl-End-Capped Oligomers"J.Fluorine Chem.. 101. 315-324 (2000)

H.Sawada：“帐户：氟烷基封端低聚物的新型自组装聚集体的体系结构和应用”J.Fluorine Chem.. 101. 315-324 (2000)

H.Sawada: "Synthesis and Properties of Fluoroalkylated Oligomers Containing Phosphonium Segments"J.Jpn.Soc.Colour Mater.. 71. 686-692 (1998)

H.Sawada：“含磷链段的氟烷基化低聚物的合成和性能”J.Jpn.Soc.Colour Mater.. 71. 686-692 (1998)