聚乙炔基乙烯的化学改性及聚三唑高分子的合成
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摘要
点击化学的概念自2001年由Sharpless等人提出以来,由于其优异的反应特点而受到广泛关注,相关的研究报道也逐年剧增。随着Hawker等人于2004年将点击1,3-偶极环加成反应引入高分子领域,点击化学的应用范围更加宽广,并对新型高分子材料的合成与改性产生着日益深远的影响。本文将广受欢迎的亚铜催化叠氮/炔1,3-偶极环加成型的点击反应应用于聚合物的化学改性以及新型线性聚合物的合成上,得到一系列在主链或侧链上含有1,2,3-三唑环结构的新型高分子材料,利用FI-IR、~1H NMR、~(19)F NMR、~(13)C NMR等方法对聚合物的结构进行了表征,并对聚合物的溶解性能、热性能、光学性能等进行了研究,对其它物理性质如相对平均分子量及其分布、聚合物形态等进行了测试和分析。全文主要包括以下四个方面的工作。
一、从乙炔单体出发,通过两步反应合成重要单体三甲基硅乙炔,再利用Sonogashira偶联反应合成聚合物单体。单体聚合、去保护基,得到聚乙炔基乙烯。用于化学改性的有机叠氮化物通过卤代烃或甲烷磺酰化物与叠氮钠反应制得。然后利用点击化学方法,在室温下将聚乙炔基乙烯与所制备的有机叠氮化物反应,得到一系列在侧链上含有1,2,3-三唑环的改性高分子材料。
二、合成了双(叠氮化甲基)苯,并设计合成一系列含有双炔基的芳香类炔化物单体,再通过点击环加成聚合反应,得到一系列新型的聚三唑高分子化合物。
三、设计并合成了新型的含酮或砜结构的双叠氮化物,再通过点击环加成聚合反应与先前所制备的双炔类单体进行聚合反应,合成了新型的含酮或砜结构的聚三唑高分子化合物。
四、设计并合成了新型的含有全氟环丁基的芳醚结构的双叠氮单体,再通过点击环加成聚合反应与先前所制备的双炔类单体进行聚合反应,合成了新型的含全氟环丁基的芳醚结构的聚三唑高分子化合物。
There are increasing reports on click chemistry since it was proposed by Sharpless et al in 2001,because it feathers with many excellent reaction properties such as quantitative yields,high tolerance of functional groups,and insensitivity of the reaction to solvents and so on.Since the first report of click chemistry in polymer science by Hawker and co-workers in 2004,the application of click chemistry is extended more broadly,and affects extensively the synthesis and modification of novel polymers.In this dissertation,copper-catalysized azide-alkyne 1,3-dipolar cycloaddition was used for chemical modification of PVacet and for synthesis of novel linear polymers to obtain a series of 1,2,3-triazole rings containing polymers in backbones or side-chains.The structures of these polymers were characterized by FT-IR,~1H NMR,~(13)C NMR and ~(19)F NMR.And their solubility,thermal and optical properties were investigated.In addition,related physical properties such as Mn,Mw, Mw/Mn and mophours were measured and discussed.The main researches include the following four parts.
First,the important monomer TMSA was synthesized through two steps from original material,ethylene.And then,TMSA reacted with bromoethylene by Sonogashira coupling reaction to form TMSA.After polymerization of TMSA,unprotecting, PVacet was prepared.The organic azides were prepared by halgon or methylsulfone reacting with N_aN_3.Finally,PVacet was modified by organic azides through click reaction to yield modified polymers containing 1,2,3-triazole rings in side-chains of polymers.
Secondly,bis(azidomethyl)benzene and aromatic bisalkynes were designed and synthesized.And then a series of novel poly(triazole)s were prepared by click cyclopolymerization between the monomers of bisazides and bisalkynes.
Thirdly,novel bisazides containing ketone or sulfone groups were designed and synthesized,and then a series of novel poly(triazole)s were prepared by click cyclopolymerization with these bisazides and previous bisalkynes.
Finally,novel bisazides containing PFCB were designed and synthesized,and then a series of novel poly(triazole)s were prepared by click cyclopolymerization with these bisazides and previous bisalkynes.
一、从乙炔单体出发,通过两步反应合成重要单体三甲基硅乙炔,再利用Sonogashira偶联反应合成聚合物单体。单体聚合、去保护基,得到聚乙炔基乙烯。用于化学改性的有机叠氮化物通过卤代烃或甲烷磺酰化物与叠氮钠反应制得。然后利用点击化学方法,在室温下将聚乙炔基乙烯与所制备的有机叠氮化物反应,得到一系列在侧链上含有1,2,3-三唑环的改性高分子材料。
二、合成了双(叠氮化甲基)苯,并设计合成一系列含有双炔基的芳香类炔化物单体,再通过点击环加成聚合反应,得到一系列新型的聚三唑高分子化合物。
三、设计并合成了新型的含酮或砜结构的双叠氮化物,再通过点击环加成聚合反应与先前所制备的双炔类单体进行聚合反应,合成了新型的含酮或砜结构的聚三唑高分子化合物。
四、设计并合成了新型的含有全氟环丁基的芳醚结构的双叠氮单体,再通过点击环加成聚合反应与先前所制备的双炔类单体进行聚合反应,合成了新型的含全氟环丁基的芳醚结构的聚三唑高分子化合物。
There are increasing reports on click chemistry since it was proposed by Sharpless et al in 2001,because it feathers with many excellent reaction properties such as quantitative yields,high tolerance of functional groups,and insensitivity of the reaction to solvents and so on.Since the first report of click chemistry in polymer science by Hawker and co-workers in 2004,the application of click chemistry is extended more broadly,and affects extensively the synthesis and modification of novel polymers.In this dissertation,copper-catalysized azide-alkyne 1,3-dipolar cycloaddition was used for chemical modification of PVacet and for synthesis of novel linear polymers to obtain a series of 1,2,3-triazole rings containing polymers in backbones or side-chains.The structures of these polymers were characterized by FT-IR,~1H NMR,~(13)C NMR and ~(19)F NMR.And their solubility,thermal and optical properties were investigated.In addition,related physical properties such as Mn,Mw, Mw/Mn and mophours were measured and discussed.The main researches include the following four parts.
First,the important monomer TMSA was synthesized through two steps from original material,ethylene.And then,TMSA reacted with bromoethylene by Sonogashira coupling reaction to form TMSA.After polymerization of TMSA,unprotecting, PVacet was prepared.The organic azides were prepared by halgon or methylsulfone reacting with N_aN_3.Finally,PVacet was modified by organic azides through click reaction to yield modified polymers containing 1,2,3-triazole rings in side-chains of polymers.
Secondly,bis(azidomethyl)benzene and aromatic bisalkynes were designed and synthesized.And then a series of novel poly(triazole)s were prepared by click cyclopolymerization between the monomers of bisazides and bisalkynes.
Thirdly,novel bisazides containing ketone or sulfone groups were designed and synthesized,and then a series of novel poly(triazole)s were prepared by click cyclopolymerization with these bisazides and previous bisalkynes.
Finally,novel bisazides containing PFCB were designed and synthesized,and then a series of novel poly(triazole)s were prepared by click cyclopolymerization with these bisazides and previous bisalkynes.
引文
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