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Progress in Chemistry 2019, Vol. 31 Issue (1): 110-120 DOI: 10.7536/PC180535 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
  • 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)
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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
Scheme 1 Synthetic routes of silane coupling agents by CuAAC reactions. L is the linker and Functions is functional unit[10,11,12]
Scheme 2 Synthetic routes of functional disiloxanes and polysiloxanes by CuAAC reactions[15]
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
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.
Scheme 5 Synthesis of organosilicon σ-π conjugated polymers via CuAAC reactions[23, 24]
Scheme 6 Mechanism of thiol-ene reactions. (A) Mechanism of free radical reaction; (B) Mechanism of Michael addition reaction
Scheme 7 Synthesis of functional polysiloxanes via thiol-ene reaction[30]
Scheme 8 Synthesis of organosilicon hyperbranced polymers via thiol-ene reaction[34]
Scheme 9 Modifying the surface of silicone rubbers. Reproduced from Ref. [48] with permission. Copyright 2013, American Chemical Society
Scheme 10 Synthesis of functional silanes via amine-ene reaction derived from [3-(1-piperazinyl)propyl]methyl- dimethoxysilane (a) and 3-aminopropyltriethoxylsilane (b)[51]
Scheme 11 Synthesis of temperature responsive polysiloxane (a)[53] and temperature and light dual-responsive polysiloxane (b)[55]
Scheme 12 Synthesis of silicone rubber via amine-ene reaction[58]
Scheme 13 Synthesis of anthracene-modified polysiloxane by amine-ene reaction and the formation of elastomers[61]
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