含偶氮电光生色团的螺旋聚乙炔的合成及性能研究
摘要
取代聚炔主链具有交替单双键,使其具有半导体、高气体渗透性、非线性光学、液晶性能、螺旋结构等特殊性质,一些手性侧基取代的聚乙炔因其螺旋构象而具有大的光学螺旋,呈现出强的圆二色谱(CD)信号。含偶氮苯的高分子材料有很多光学应用,如在全息数字存储领域有潜在应用价值,吸引了众多关注。目前已经有很多关于含偶氮聚合物具有光敏、光控开关、光学存储、液晶等特殊性质的报道。因此,将偶氮类生色团引入到聚乙炔中,制备得到新型的偶氮类螺旋聚合物,此类聚乙炔材料将表现出一系列特殊的光学活性、液晶性、分子识别性等。
本论文主要分成四章,第一章综述了螺旋聚乙炔及含偶氮生色团高分子材料的结构特性,各种制备方法及其应用前景,如其在非线性光学材料、液晶材料方面的应用研究进展,并简要介绍了本文的研究内容和创新点。
第二章合成了七种新颖的Y型含偶氮苯生色团的乙炔衍生物单体(M1-M7)。其合成路线是通过：酯化,重氮化偶联,酰胺化等一系列反应步骤完成的。通过红外、核磁、紫外、质谱、元素分析对单体的结构进行了表征。这七种新颖的单体的结构区别是通过改变Y型分子的两个分支上官能团结构来实现的,希望通过此对比来进一步研究它们的结构对其聚合物性能的影响。在分子的结构方面,我们引入手性分子L-丙氨酸,并利用酰胺基团引入氢键,从而为进一步研究氢键作用、手性结构对于聚乙炔螺旋构象及聚合物性能的影响打下基础。
第三章即采用双降冰片烯二氯化二铑和三乙胺的催化体系,将所有制备得到的乙炔衍生物单体进行聚合,制备得到含偶氮电光生色团的聚乙炔,并通过红外,核磁,紫外,凝胶渗透色谱(GPC),圆二色光谱,热重,差示量热扫描(DSC),等手段对该系列聚乙炔的结构和性能进行了表征。
第四章对论文进行了一个概要的总结,并对该课题今后研究的内容和方向进行了展望。
Azobenzene is a well-known photo responsive chromophore that undergoes reversible photoisomerization between trans and cis forms. Polymers carrying azobenzene moieties have attracted much attention due to their unique properties, which allow various photonic applications such as holographic and digital storage of information. There have been many reports concerning polymers carrying azobenzene moieties displaying photoresponsive, photoswitchable, optical memories, and liquid crystalline properties.On the other hand, substituted polyacetylenes possess alternating double bonds in the main chain, which endows them with unique properties such as semiconductivity, high gas permeability, nonlinear optical properties, formation of ferroelectric liquid crystals, and helical structures.Some polyacetylenes substituted with chiral side chains exhibit strong circular dichroism (CD) signals and large optical rotations based on the helical conformation, It is expected that azobenzene-containing helical polyacetylenes will combine these characteristics together and lead to the development of new functional materials, Such polyacetylene material will show a series of special optical activity of liquid crystal, molecular recognition and so on.
The thesis consists of four chapters:Chapter One reviews the structural characteristics, the various preparation methods, application prospects about helical polyacetylenes and the liquid crystal polymers containing azo in side-chain, especially the research of application at non-linear optical materials and liquid crystal materials was introduced.The content and feature of the thesis were pointed out.
Chapter two reported seven novel Y-containing azobenzene chromophore side alkynyl monomers (M1-M7). The synthetic route is carried out by esterification, diazotization coupling, amidation and a series of reaction steps. The monomer structure was characterized by IR, NMR, UV, etc.. The seven creative monomer's difference was realized by changing the Functional group of Y-type molecular, By comparing them, we can understand how the structure affects the properties of them. In the molecular structure, we introduce chiral molecules L-alanine, and use the introduction of amide groups to get hydrogen bond, Lay the foundation for further study of that by contrast with and without hydrogen bonds and by whether they contain chiral structure to study their effects on property of their polymer.
Chapter three reported that a series of propargyl derivatives monomer was polymerized by [Rh(nbd)Cl]2 and Et3N catalyst System. This catalyst system has a good effect to keep main chain cis-trans conformation. IR, NMR, UV, circular dichroism spectroscopy, thermogravimetry, differential scanning calorimetry, GPC were used to investigate the nature of this series of polyacetylene, and also the impact of structure to the poylmers were stuied.
Chapter four gave a simple conclusion of the thesis, and the subject's research content in aftertime and the outlook of future research were reviewed.
本论文主要分成四章,第一章综述了螺旋聚乙炔及含偶氮生色团高分子材料的结构特性,各种制备方法及其应用前景,如其在非线性光学材料、液晶材料方面的应用研究进展,并简要介绍了本文的研究内容和创新点。
第二章合成了七种新颖的Y型含偶氮苯生色团的乙炔衍生物单体(M1-M7)。其合成路线是通过：酯化,重氮化偶联,酰胺化等一系列反应步骤完成的。通过红外、核磁、紫外、质谱、元素分析对单体的结构进行了表征。这七种新颖的单体的结构区别是通过改变Y型分子的两个分支上官能团结构来实现的,希望通过此对比来进一步研究它们的结构对其聚合物性能的影响。在分子的结构方面,我们引入手性分子L-丙氨酸,并利用酰胺基团引入氢键,从而为进一步研究氢键作用、手性结构对于聚乙炔螺旋构象及聚合物性能的影响打下基础。
第三章即采用双降冰片烯二氯化二铑和三乙胺的催化体系,将所有制备得到的乙炔衍生物单体进行聚合,制备得到含偶氮电光生色团的聚乙炔,并通过红外,核磁,紫外,凝胶渗透色谱(GPC),圆二色光谱,热重,差示量热扫描(DSC),等手段对该系列聚乙炔的结构和性能进行了表征。
第四章对论文进行了一个概要的总结,并对该课题今后研究的内容和方向进行了展望。
Azobenzene is a well-known photo responsive chromophore that undergoes reversible photoisomerization between trans and cis forms. Polymers carrying azobenzene moieties have attracted much attention due to their unique properties, which allow various photonic applications such as holographic and digital storage of information. There have been many reports concerning polymers carrying azobenzene moieties displaying photoresponsive, photoswitchable, optical memories, and liquid crystalline properties.On the other hand, substituted polyacetylenes possess alternating double bonds in the main chain, which endows them with unique properties such as semiconductivity, high gas permeability, nonlinear optical properties, formation of ferroelectric liquid crystals, and helical structures.Some polyacetylenes substituted with chiral side chains exhibit strong circular dichroism (CD) signals and large optical rotations based on the helical conformation, It is expected that azobenzene-containing helical polyacetylenes will combine these characteristics together and lead to the development of new functional materials, Such polyacetylene material will show a series of special optical activity of liquid crystal, molecular recognition and so on.
The thesis consists of four chapters:Chapter One reviews the structural characteristics, the various preparation methods, application prospects about helical polyacetylenes and the liquid crystal polymers containing azo in side-chain, especially the research of application at non-linear optical materials and liquid crystal materials was introduced.The content and feature of the thesis were pointed out.
Chapter two reported seven novel Y-containing azobenzene chromophore side alkynyl monomers (M1-M7). The synthetic route is carried out by esterification, diazotization coupling, amidation and a series of reaction steps. The monomer structure was characterized by IR, NMR, UV, etc.. The seven creative monomer's difference was realized by changing the Functional group of Y-type molecular, By comparing them, we can understand how the structure affects the properties of them. In the molecular structure, we introduce chiral molecules L-alanine, and use the introduction of amide groups to get hydrogen bond, Lay the foundation for further study of that by contrast with and without hydrogen bonds and by whether they contain chiral structure to study their effects on property of their polymer.
Chapter three reported that a series of propargyl derivatives monomer was polymerized by [Rh(nbd)Cl]2 and Et3N catalyst System. This catalyst system has a good effect to keep main chain cis-trans conformation. IR, NMR, UV, circular dichroism spectroscopy, thermogravimetry, differential scanning calorimetry, GPC were used to investigate the nature of this series of polyacetylene, and also the impact of structure to the poylmers were stuied.
Chapter four gave a simple conclusion of the thesis, and the subject's research content in aftertime and the outlook of future research were reviewed.
引文
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