由苯丙氨酸衍生物凝胶剂形成的超分子有机凝胶及其性能研究
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摘要
近年来,由凝胶因子(Gelator)形成的有机小分子凝胶日益引起人们的关注。这些凝胶因子在分子结构上的共同特点是具有可形成氢键、π-π堆积、配位键等非共价作用的位点,在一定的介质中,凝胶因子分子之间在这些非共价力的作用下自发地聚集、组装成有序的纤维结构,这些纤维能进一步形成缠结的三维网络结构,从而将溶剂小分子锁定在三维网络结构中。由于其性质具有介于固、液体之间这一特性,被广泛应用在催化、纳米材料的模板、药物分子的控制释放载体、手性分离等领域。
本文合成了N-十八烷基-N'-马来酰基-L-苯丙氨酸(ODMA-L-Phe)凝胶因子,对其在有机溶剂中凝胶化性能及自组装机理进行了研究。合成了N-十八烷基丁二酸(ODSA)凝胶因子,并研究了其在可聚合溶剂中的自组装性能。合成了N-十八烷基-N'-丁二酰基-L-丙氨酸(ODSA-L-Ala)、N-十八烷基-N'-马来酰基-L-丙氨酸-N”-偶氮苯(ODSA-L-Ala-AZ)、N-十八烷基-N'-丁二酰基-L-苯丙氨酸(ODSA-L-Phe)凝胶因子,并对它们在有机溶剂中的凝胶性能进行了研究。合成了N-十八烷基马来酸(ODMA)可聚合凝胶因子,利用其在可聚合有机溶剂中的自组装,原位UV固化制备了胆固醇分子印迹聚合物,并考察了其对胆固醇的吸附性能。本论文包括以下主要内容:
(1)由BOC-L-苯丙氨酸、十八胺和马来酸酐为原料,分别经缩合、去保护和酰胺化反应得到N-十八烷基-N'-马来酰基-L-苯丙氨酸可聚合凝胶因子(ODSA-L-Phe)。利用场发射扫描电镜(FE-SEM)、偏光显微镜(POM)对该凝胶因子在溶剂中自组装聚集体形态进行了表征。利用~1H-NMR及园二色谱(CD)对ODSA-L-Phe在有机溶剂中自组装机理进行了研究。
(2)以丁二酸酐、十八胺为原料合成了N-十八烷基丙胺酸(ODSA)凝胶因子。对凝胶因子在可聚合溶剂中的凝胶性能进行了测试。利用偏光显微镜(POM)表征了该凝胶因子在有机溶剂中的聚集形态。并用先凝胶,再在常温下VU聚合的方法制备了苯乙烯-甲基丙烯酸甲酯的共聚物。
(3)合成了N-十八烷基-N′-丁二酰基-L-丙氨酸(ODSA-L-Ala)、N-十八烷基-N′-丁二酰基-L-丙氨酸-N”-偶氮苯(ODSA-L-Ala-AZ)、N-十八烷基-N'-丁二酰基-L-苯丙氨酸(ODSA-L-Phe)凝胶因子系列凝胶因子,并对它们在有机溶剂中的凝胶性能进行了研究。
(4)合成了分子结构中带有双键的N-十八烷基马来酸(ODMA)可聚合凝胶因子。利用该凝胶因子能够在可聚合溶剂,如甲基丙烯酸-β-羟乙酯(HEMA)、甲基丙烯酸(MAA)和二甲基丙烯酸聚乙二醇(200)酯(PEG200DMA)及其混合溶剂中自组装形成稳定的超分子有机凝胶,以3-胆固醇酰氧基-丙酸作为模板分子,在常温下将该凝胶进行原位UV光聚合制备胆固醇分子印迹聚合物。并进一步对该印迹聚合物对胆固醇的吸附进行了研究。
In recent years,supramolecular hydrogels formed by the self-assembly of gelator have received wide interests because of their potential application.Gel aggregates are formed in solvents through intermolecular hydrogen bonding,π-πstacking and other non-covalent bond interations and turn them into macromolecular gel,then solvent molecules are trapped into three-dimension network.Gelators could be applied on catalyzer, nanomaterials,drug carriers and other fields because of its properties between the liquids and solids.
In this paper,several gelators were synthesized,including chrial gelator N-octadecyl-N'-maleoyl-L-phenylalanine(ODMA-L-Phe),polymerizable gelator N-octadecyl maleamic acid(ODMA),gelator N-octadecyl succinic acid(ODSA) and series of gelators based on Phenylalanine or Analine.The mechanism of ODMA-L-Phe self-assembly in organic solvents was investigated using ~1H-NMR and Circular Dichroism (CD).Preparation of cholesteryl-molecular imprinted polymer using ODMA and the adsorption experiments of cholesterol were carded out.The properties of ODSA self-assembly in polymerizable solvents were investigated.The gel properties of the other gelators were characterized also.
This paper are consisted of several sections as the following:
(1)N-octadecyl-N'-maleoyl-L-phenylalanine(ODMA-L-Phe) was synthesized through the condensation,deprotection and acidylation reaction of BOC-L-phenylalanine, octadecylamine and maleic anhydride.ODMA-L-Phe can self-assemble in some organic solvents and turned them into thermally reversible physical supramolecular organogels. The morphology of ODMA-L-Phe aggregates was characterized by polarized optical microscopy(POM) and field emission scanning electron microscope(FE-SEM).The mechanism of ODMA-L-Phe self-assembly in organic solvents was investigated using ~1H-NMR and Circular Dichroism(CD).The results indicated that hydrogen bonding was one of the main driving forces for the self-assembly of ODMA-L-Phe.
(2)Gelator N-octadecyl succinic acid(ODSA) was synthesized from succinic anhydride and octadecylamine by the ring-open reaction.The gel properities of ODSA in several polylymerizable solvents were investigated.The ODSA self-assemble into fibres aggregates in the polymerizable monomer such as styrene,Methyl acrylate,Buthyl acrylate et.al..The morphology of gel aggregates was investigated using POM.
(3)Gelators N-octadecyl-N'-succinic-L-alanine(ODSA-L-Ala),N-octadecyl-N' -succinic -L-alanine-p-aminoazobenzene(ODSA-L-Ala-AZ)and N-octadecyl-N'- succinic -L-alanine(ODSA-L-Phe) were synthesized base on BOC-L-phenylalanine and BOC-L-alanine.The gel properities were investigated in some organic solvents. Suprahydrogel aggregrates were characterized using POM.
(4)Polymerizable gelator N-octadecyl maleamic acid(ODMA) could self-assemble in polymerizable solvent mixture ofβ-hydroxyethyl methacrylate(HEMA),methylacrylic acid(MAA),polyethylene glycol dimethacrylates-200(PEGDMA-200) in the presence of template molecule 3-Cholesteryloxycarbonylbonylpropanoic Acid(COPA),and turned them into thermally reversible stable polymerizable organogels.Organogels were polymerized by in situ UV irradiation and the molecular-imprinting polymers(MIPs) were obtained after removal of the template molecules from polymer through ethanol extracting. Polarized optical microscopy(POM) and field emission scanning electric microscopy (FE-SEM) indicated the aggregates of ODMA were tree branch-like and sheet-like in organogels.The adsorption experiments of cholesterol exhibited that the adsorption equilibrium amount of cholesterol reached 30.2mg/g.The adsorption efficiency of MIPs was found to be dependent on the concentration of the gelator ODMA and template molecule COPA in organogel.
本文合成了N-十八烷基-N'-马来酰基-L-苯丙氨酸(ODMA-L-Phe)凝胶因子,对其在有机溶剂中凝胶化性能及自组装机理进行了研究。合成了N-十八烷基丁二酸(ODSA)凝胶因子,并研究了其在可聚合溶剂中的自组装性能。合成了N-十八烷基-N'-丁二酰基-L-丙氨酸(ODSA-L-Ala)、N-十八烷基-N'-马来酰基-L-丙氨酸-N”-偶氮苯(ODSA-L-Ala-AZ)、N-十八烷基-N'-丁二酰基-L-苯丙氨酸(ODSA-L-Phe)凝胶因子,并对它们在有机溶剂中的凝胶性能进行了研究。合成了N-十八烷基马来酸(ODMA)可聚合凝胶因子,利用其在可聚合有机溶剂中的自组装,原位UV固化制备了胆固醇分子印迹聚合物,并考察了其对胆固醇的吸附性能。本论文包括以下主要内容:
(1)由BOC-L-苯丙氨酸、十八胺和马来酸酐为原料,分别经缩合、去保护和酰胺化反应得到N-十八烷基-N'-马来酰基-L-苯丙氨酸可聚合凝胶因子(ODSA-L-Phe)。利用场发射扫描电镜(FE-SEM)、偏光显微镜(POM)对该凝胶因子在溶剂中自组装聚集体形态进行了表征。利用~1H-NMR及园二色谱(CD)对ODSA-L-Phe在有机溶剂中自组装机理进行了研究。
(2)以丁二酸酐、十八胺为原料合成了N-十八烷基丙胺酸(ODSA)凝胶因子。对凝胶因子在可聚合溶剂中的凝胶性能进行了测试。利用偏光显微镜(POM)表征了该凝胶因子在有机溶剂中的聚集形态。并用先凝胶,再在常温下VU聚合的方法制备了苯乙烯-甲基丙烯酸甲酯的共聚物。
(3)合成了N-十八烷基-N′-丁二酰基-L-丙氨酸(ODSA-L-Ala)、N-十八烷基-N′-丁二酰基-L-丙氨酸-N”-偶氮苯(ODSA-L-Ala-AZ)、N-十八烷基-N'-丁二酰基-L-苯丙氨酸(ODSA-L-Phe)凝胶因子系列凝胶因子,并对它们在有机溶剂中的凝胶性能进行了研究。
(4)合成了分子结构中带有双键的N-十八烷基马来酸(ODMA)可聚合凝胶因子。利用该凝胶因子能够在可聚合溶剂,如甲基丙烯酸-β-羟乙酯(HEMA)、甲基丙烯酸(MAA)和二甲基丙烯酸聚乙二醇(200)酯(PEG200DMA)及其混合溶剂中自组装形成稳定的超分子有机凝胶,以3-胆固醇酰氧基-丙酸作为模板分子,在常温下将该凝胶进行原位UV光聚合制备胆固醇分子印迹聚合物。并进一步对该印迹聚合物对胆固醇的吸附进行了研究。
In recent years,supramolecular hydrogels formed by the self-assembly of gelator have received wide interests because of their potential application.Gel aggregates are formed in solvents through intermolecular hydrogen bonding,π-πstacking and other non-covalent bond interations and turn them into macromolecular gel,then solvent molecules are trapped into three-dimension network.Gelators could be applied on catalyzer, nanomaterials,drug carriers and other fields because of its properties between the liquids and solids.
In this paper,several gelators were synthesized,including chrial gelator N-octadecyl-N'-maleoyl-L-phenylalanine(ODMA-L-Phe),polymerizable gelator N-octadecyl maleamic acid(ODMA),gelator N-octadecyl succinic acid(ODSA) and series of gelators based on Phenylalanine or Analine.The mechanism of ODMA-L-Phe self-assembly in organic solvents was investigated using ~1H-NMR and Circular Dichroism (CD).Preparation of cholesteryl-molecular imprinted polymer using ODMA and the adsorption experiments of cholesterol were carded out.The properties of ODSA self-assembly in polymerizable solvents were investigated.The gel properties of the other gelators were characterized also.
This paper are consisted of several sections as the following:
(1)N-octadecyl-N'-maleoyl-L-phenylalanine(ODMA-L-Phe) was synthesized through the condensation,deprotection and acidylation reaction of BOC-L-phenylalanine, octadecylamine and maleic anhydride.ODMA-L-Phe can self-assemble in some organic solvents and turned them into thermally reversible physical supramolecular organogels. The morphology of ODMA-L-Phe aggregates was characterized by polarized optical microscopy(POM) and field emission scanning electron microscope(FE-SEM).The mechanism of ODMA-L-Phe self-assembly in organic solvents was investigated using ~1H-NMR and Circular Dichroism(CD).The results indicated that hydrogen bonding was one of the main driving forces for the self-assembly of ODMA-L-Phe.
(2)Gelator N-octadecyl succinic acid(ODSA) was synthesized from succinic anhydride and octadecylamine by the ring-open reaction.The gel properities of ODSA in several polylymerizable solvents were investigated.The ODSA self-assemble into fibres aggregates in the polymerizable monomer such as styrene,Methyl acrylate,Buthyl acrylate et.al..The morphology of gel aggregates was investigated using POM.
(3)Gelators N-octadecyl-N'-succinic-L-alanine(ODSA-L-Ala),N-octadecyl-N' -succinic -L-alanine-p-aminoazobenzene(ODSA-L-Ala-AZ)and N-octadecyl-N'- succinic -L-alanine(ODSA-L-Phe) were synthesized base on BOC-L-phenylalanine and BOC-L-alanine.The gel properities were investigated in some organic solvents. Suprahydrogel aggregrates were characterized using POM.
(4)Polymerizable gelator N-octadecyl maleamic acid(ODMA) could self-assemble in polymerizable solvent mixture ofβ-hydroxyethyl methacrylate(HEMA),methylacrylic acid(MAA),polyethylene glycol dimethacrylates-200(PEGDMA-200) in the presence of template molecule 3-Cholesteryloxycarbonylbonylpropanoic Acid(COPA),and turned them into thermally reversible stable polymerizable organogels.Organogels were polymerized by in situ UV irradiation and the molecular-imprinting polymers(MIPs) were obtained after removal of the template molecules from polymer through ethanol extracting. Polarized optical microscopy(POM) and field emission scanning electric microscopy (FE-SEM) indicated the aggregates of ODMA were tree branch-like and sheet-like in organogels.The adsorption experiments of cholesterol exhibited that the adsorption equilibrium amount of cholesterol reached 30.2mg/g.The adsorption efficiency of MIPs was found to be dependent on the concentration of the gelator ODMA and template molecule COPA in organogel.
引文
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