新型孔材料的合成、结构及其吸附性质的研究
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摘要
有机共轭聚合物是一种新型的多孔材料，具有较大比表面积和良好孔结构性能，在催化化学、环境保护和气体储存等领域有广阔的应用前景，因而得到了广泛的研究与应用。其中芳基炔烃类的有机共轭聚合物含有大范围的π-π共轭体系，具有结构稳定和耐酸碱腐蚀等优点。论文中合成了几类基于Sonogashira-Hagihara反应机理制备的有机共轭聚合物，并且进行了表征分析以及其吸附有机溶剂的应用研究，这些工作将为设计和合成新型多孔材料提供帮助和指导，论文中研究的主要内容及结论概况如下：
1．以1,3,5-三乙炔苯和/或1,4-二乙炔苯为聚合单体制备了一组偶合共轭微孔聚合物(HCMP)。研究结果表明反应物的单体结构和摩尔比对合成样品的比表面积，孔性能有着显著影响。随着1,3,5-三乙炔苯含量的增加，HCMP样品的比表面积和总孔体积也会增加，其吸附有机溶剂的性能越好；然而体系中微孔的孔体积则不断减少，其吸附氢气的能力也随之降低；
2.理想状态卜，1,3,5-三乙炔苯和1,3,5-三溴苯聚合后形成的聚合物是2维有序结构的薄膜结构。但是薄膜材料热力学不稳定，容易发生卷曲或团聚。本文研究发现不同的溶剂对聚合物的形貌有较大的影响。在以甲苯、对二甲苯和间三甲苯为反应溶剂时，分别形成了具有球形、中空管形和片层形的不同形貌的颗粒。不同形貌的聚合物吸附氮气和氢气的性能相近，而吸附有机溶剂的性能相差较大，由于聚合物吸附液体后溶胀效应的影响，片层形的聚合物吸附有机溶剂的性能最好；
3.分别以1,3,5-三乙炔苯和1,4-三溴苯，1，4-二乙炔苯和1,3,5-三溴苯进行反应，合成了具有中空管形结构和平面结构形貌特征的聚合物材料。实验结果表明线性结构1,4-二乙炔苯和平面结构的1,3,5-三乙炔苯在聚合过程中起到了导向剂和模板剂的作用。这两种材料具有较人的比表面积和孔体积，又表现了超强的疏水性质，同时对有机溶剂有良好的吸附性能；
4.1,4-二乙炔苯与1,3,5-三溴苯酚进行反应，合成了高度聚合，具有弹性的聚合物颗粒。1，4-二乙炔苯在聚合过程中起到了导向剂的作用,材料形成了具有中空管形形貌的聚合物颗粒。当这种材料吸附有机溶剂达到饱和后,通过挤压的物理方式将聚合物中的有机物质分离出来,再生方法简单,有良好的应用价值。
Organic conjugated polymers are new porous materials with large surface areas and good porosity. They have found many useful applications in areas such as catalysis, environmental protection, gas storage, and so on, and therefore relevant research has been widely performed. These polymers with phenylene and acetylenyl units possess large π-π interaction systems, and they have many advantages such as structural stability and corrosion resistant of acid-base. This thesis reports the synthesis of several kinds of novel organic conjugated microporous polymers (CMP) based on Sonogashira-Hagihara cross-coupling reactions, and the characterization and the adsorption performance for organic solvents of these samples are studied. Our work will provide useful guidance for the rational design and synthesis of novel porous materials. The main content and conclusions of this thesis are summarized as:
1. A series of homocoupled conjugated microporous polymers (HCMPs) were prepared by cross-coupling polymerization of1,3,5-triethynylbenzene and1,4-diethynylbenzene. Our results show that the structures and molar ratio of monomers has a remarkable influence on the surface area, pore volume, and micropore volume of the as-synthesized HCMP samples. With the increase of molar ratio of1,3,5-triethynylbenzene to1,4-diethynylbenzene, the surface area and total pore volume increased, and this will lead to an increase in their adsorption abilities for organic solvents. However, meanwhile the micropore volume decreased for these HCMP samples, which will result in a decrease of hydrogen sorption ability for HCMPs.
2. Ideally, the polymer prepared by the polymerization of1,3,5-triethynyl-benzene and1,3,5-tribromobenzene shows two-dimensional thin film structure. However, the ultrathin films are thermodynamically unstable, and they tend to roll up or aggregate. Our results show that the reaction solvents have great effect on the morphologies of the polymers. Spherical, tubular and plate-like structures were received during the polymerization by using the toluene, p-xylene, and mesitylene solvents, respectively. The polymers with different morphologies show similar adsorption performance of N2and H2. But the storage capacity for organic solvents is remarkably influenced by CMPs with different morphologies. The plate-like CMP shows best performance for the storage of organic solvents, due to obvious swelling effect.
3. We synthesized CMP with film and nanotube-like morphologies by1,3,5-triethynylbenzene with1,4-dibromobenzene and1,3,5-tribromobenzene with1,4-diethynylbenzene, respectively. Our results show that the linearly1,4-diethynylbenzene and the planar1,3,5-triethynylbenzene played a role of crystallization directing agent and template agent. Both CMP samples demonstrate large BET surface area, pore volumes, and excellent surface superhydrophobicity, and they show good adsorption capacities for organic solvents.
4. The elastic polymer particles with high degree of polymerization were synthesized by1,4-diethynylbenzene and1,3,5-tribromophenol.1,4-diethynylbenzene played a role as directing agents during polymerization, and the polymer particles show the morphology of hollow tubular structure. The organic solvent adsorbed in polymer samples can be separated by squeezing, when the organic solvents reached its saturation state. This physical method is simple and has good applications.
1．以1,3,5-三乙炔苯和/或1,4-二乙炔苯为聚合单体制备了一组偶合共轭微孔聚合物(HCMP)。研究结果表明反应物的单体结构和摩尔比对合成样品的比表面积，孔性能有着显著影响。随着1,3,5-三乙炔苯含量的增加，HCMP样品的比表面积和总孔体积也会增加，其吸附有机溶剂的性能越好；然而体系中微孔的孔体积则不断减少，其吸附氢气的能力也随之降低；
2.理想状态卜，1,3,5-三乙炔苯和1,3,5-三溴苯聚合后形成的聚合物是2维有序结构的薄膜结构。但是薄膜材料热力学不稳定，容易发生卷曲或团聚。本文研究发现不同的溶剂对聚合物的形貌有较大的影响。在以甲苯、对二甲苯和间三甲苯为反应溶剂时，分别形成了具有球形、中空管形和片层形的不同形貌的颗粒。不同形貌的聚合物吸附氮气和氢气的性能相近，而吸附有机溶剂的性能相差较大，由于聚合物吸附液体后溶胀效应的影响，片层形的聚合物吸附有机溶剂的性能最好；
3.分别以1,3,5-三乙炔苯和1,4-三溴苯，1，4-二乙炔苯和1,3,5-三溴苯进行反应，合成了具有中空管形结构和平面结构形貌特征的聚合物材料。实验结果表明线性结构1,4-二乙炔苯和平面结构的1,3,5-三乙炔苯在聚合过程中起到了导向剂和模板剂的作用。这两种材料具有较人的比表面积和孔体积，又表现了超强的疏水性质，同时对有机溶剂有良好的吸附性能；
4.1,4-二乙炔苯与1,3,5-三溴苯酚进行反应，合成了高度聚合，具有弹性的聚合物颗粒。1，4-二乙炔苯在聚合过程中起到了导向剂的作用,材料形成了具有中空管形形貌的聚合物颗粒。当这种材料吸附有机溶剂达到饱和后,通过挤压的物理方式将聚合物中的有机物质分离出来,再生方法简单,有良好的应用价值。
Organic conjugated polymers are new porous materials with large surface areas and good porosity. They have found many useful applications in areas such as catalysis, environmental protection, gas storage, and so on, and therefore relevant research has been widely performed. These polymers with phenylene and acetylenyl units possess large π-π interaction systems, and they have many advantages such as structural stability and corrosion resistant of acid-base. This thesis reports the synthesis of several kinds of novel organic conjugated microporous polymers (CMP) based on Sonogashira-Hagihara cross-coupling reactions, and the characterization and the adsorption performance for organic solvents of these samples are studied. Our work will provide useful guidance for the rational design and synthesis of novel porous materials. The main content and conclusions of this thesis are summarized as:
1. A series of homocoupled conjugated microporous polymers (HCMPs) were prepared by cross-coupling polymerization of1,3,5-triethynylbenzene and1,4-diethynylbenzene. Our results show that the structures and molar ratio of monomers has a remarkable influence on the surface area, pore volume, and micropore volume of the as-synthesized HCMP samples. With the increase of molar ratio of1,3,5-triethynylbenzene to1,4-diethynylbenzene, the surface area and total pore volume increased, and this will lead to an increase in their adsorption abilities for organic solvents. However, meanwhile the micropore volume decreased for these HCMP samples, which will result in a decrease of hydrogen sorption ability for HCMPs.
2. Ideally, the polymer prepared by the polymerization of1,3,5-triethynyl-benzene and1,3,5-tribromobenzene shows two-dimensional thin film structure. However, the ultrathin films are thermodynamically unstable, and they tend to roll up or aggregate. Our results show that the reaction solvents have great effect on the morphologies of the polymers. Spherical, tubular and plate-like structures were received during the polymerization by using the toluene, p-xylene, and mesitylene solvents, respectively. The polymers with different morphologies show similar adsorption performance of N2and H2. But the storage capacity for organic solvents is remarkably influenced by CMPs with different morphologies. The plate-like CMP shows best performance for the storage of organic solvents, due to obvious swelling effect.
3. We synthesized CMP with film and nanotube-like morphologies by1,3,5-triethynylbenzene with1,4-dibromobenzene and1,3,5-tribromobenzene with1,4-diethynylbenzene, respectively. Our results show that the linearly1,4-diethynylbenzene and the planar1,3,5-triethynylbenzene played a role of crystallization directing agent and template agent. Both CMP samples demonstrate large BET surface area, pore volumes, and excellent surface superhydrophobicity, and they show good adsorption capacities for organic solvents.
4. The elastic polymer particles with high degree of polymerization were synthesized by1,4-diethynylbenzene and1,3,5-tribromophenol.1,4-diethynylbenzene played a role as directing agents during polymerization, and the polymer particles show the morphology of hollow tubular structure. The organic solvent adsorbed in polymer samples can be separated by squeezing, when the organic solvents reached its saturation state. This physical method is simple and has good applications.
引文
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