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化学进展 2019, Vol. 31 Issue (1): 110-120 DOI: 10.7536/PC180535 前一篇   后一篇

• 综述 •

有机硅合成新方法

王灯旭1,2,**(), 曹金风2, 韩栋栋2, 李文思2, 冯圣玉1,2,**()   

  1. 1. 山东大学国家胶体材料工程技术研究中心 济南 250100
    2. 山东大学化学与化工学院 特种功能聚集体材料教育部重点实验室 济南 250100
  • 收稿日期:2018-05-27 修回日期:2018-07-02 出版日期:2019-01-15 发布日期:2018-12-07
  • 通讯作者: 王灯旭, 冯圣玉
  • 基金资助:
    国家自然科学基金项目(21502105); 国家自然科学基金项目(21774070); 山东省自主创新基金项目资助(2017CXGC1112)
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Novel Organosilicon Synthetic Methodologies

Dengxu Wang1,2,**(), Jinfeng Cao2, Dongdong Han2, Wensi Li2, Shengyu Feng1,2,**()   

  1. 1. National Engineering Technology Research Center for Colloidal Materials, Shandong University, Jinan 250100, China
    2. Key Laboratory of Special Functional Aggregated Materials of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China
  • Received:2018-05-27 Revised:2018-07-02 Online:2019-01-15 Published:2018-12-07
  • Contact: Dengxu Wang, Shengyu Feng
  • About author:
    ** Corresponding author e-mail: (Dengxu Wang);
    (Shengyu Feng)
  • Supported by:
    The work was supported by the National Natural Science Foundation of China(21502105); The work was supported by the National Natural Science Foundation of China(21774070); The Fund for Shandong Province Major Scientific and Technological Innovation Projects(2017CXGC1112)

有机硅材料作为一类具有独特优异性能的新材料,已成为化学和材料领域的重点研究方向之一。本文综述了近年来国内外有机硅合成的新方法,主要包括炔基-叠氮环加成反应、巯基-双键反应和胺-烯迈克尔加成反应等,重点介绍各种合成方法的优势及在制备新型功能化的有机硅化合物、有机硅聚合物及有机硅弹性体等中的应用,并对未来有机硅合成方法的发展方向进行了展望。

关键词： 有机硅合成, 点击化学, 炔基-叠氮反应, 巯基-双键反应, 胺-烯迈克尔加成反应

Organosilicon materials as a novel class of functional materials with unique properties have become one of the most important research fields in chemistry and material sciences. The present review summarizes novel synthetic methodologies, including alkynyl-azide cycloaddition reaction, thiol-ene reaction and amine-ene Michael addition reaction, for organosilicon synthesis. In particular, the advantages of these strategies and their applications in novel functional organosilicon compounds, organosilicon polymers and organosilicon elastomers are introduced. Finally, the trend and future prospects of novel synthetic strategies for organosilicon synthesis will be presented.

Key words: organosilicon synthesis, click chemistry, alkynyl-azide reaction, thiol-ene reaction, amine-ene Michael addition reaction
()
图式1 通过CuAAC反应制备硅烷偶联剂,其中L为连接单元,function为功能性单元[10,11,12]
Scheme 1 Synthetic routes of silane coupling agents by CuAAC reactions. L is the linker and Functions is functional unit[10,11,12]
图式2 通过CuAAC反应制备功能化二硅氧烷和聚硅氧烷[15]
Scheme 2 Synthetic routes of functional disiloxanes and polysiloxanes by CuAAC reactions[15]
图式3 通过CuAAC点击化学反应制备有机硅弹性体[18]。(A)2 mm厚× 9 cm有机硅弹性膜;(B)1 cm × 5 mm厚有机硅弹性体
Scheme 3 Synthesis of organosilicon elastomers by CuAAC click reaction[18]. (A) 2 mm thick ×9 cm silicone film; (B) 1 cm × 5 mm thick silicone elastomer. Reproduced from Ref. [18] with permission. Copyright 2009, American Chemical Society
图式4 通过CuAAC反应制备基于聚硅氧烷-聚乙烯砜的复合材料及在碱性条件下的分解示意图[20]
Scheme 4 Synthesis of polysiloxane-poly(olefin sulfone) compositions by CuAAC reaction and their decomposition via unzipping of POS when exposed to base. Reproduced from Ref.[20] with permission. Copyright 2010, American Chemical Society.
图式5 通过CuAAC反应制备有机硅σ-π共轭聚合物[23, 24]
Scheme 5 Synthesis of organosilicon σ-π conjugated polymers via CuAAC reactions[23, 24]
图式6 巯基-双键反应机理:(A)自由基反应机理;(B) Michael加成反应机理
Scheme 6 Mechanism of thiol-ene reactions. (A) Mechanism of free radical reaction; (B) Mechanism of Michael addition reaction
图式7 通过巯基-双键反应制备功能化聚硅氧烷[30]
Scheme 7 Synthesis of functional polysiloxanes via thiol-ene reaction[30]
图式8 通过巯基-双键反应制备有机硅超支化聚合物[34]
Scheme 8 Synthesis of organosilicon hyperbranced polymers via thiol-ene reaction[34]
图式9 通过巯基-双键反应修饰硅橡胶表面[48]
Scheme 9 Modifying the surface of silicone rubbers. Reproduced from Ref. [48] with permission. Copyright 2013, American Chemical Society
图式10 通过胺烯反应制备功能化硅烷。(a)基于(γ-哌嗪基丙基)甲基二甲氧基硅烷;(b)基于3-氨丙基三乙氧基硅烷[51]
Scheme 10 Synthesis of functional silanes via amine-ene reaction derived from [3-(1-piperazinyl)propyl]methyl- dimethoxysilane (a) and 3-aminopropyltriethoxylsilane (b)[51]
图式11 通过胺-烯反应合成温度响应性聚硅氧烷(a)[53]和温度、光双重响应性聚硅氧烷(b)[55]
Scheme 11 Synthesis of temperature responsive polysiloxane (a)[53] and temperature and light dual-responsive polysiloxane (b)[55]
图式12 基于胺-烯反应制备硅橡胶[58]
Scheme 12 Synthesis of silicone rubber via amine-ene reaction[58]
图式13 通过胺-烯反应制备蒽修饰的聚硅氧烷及弹性体的制备[61]
Scheme 13 Synthesis of anthracene-modified polysiloxane by amine-ene reaction and the formation of elastomers[61]
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摘要

有机硅合成新方法