含侧链多胺准聚轮烷的合成及性质研究
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摘要
葫芦脲因其特殊的结构特征,已成为国内外研究热点,特别是近几年,葫芦脲分子自组装形成轮烷或者准轮烷在分子开关、分子梭、信息存储等方面,以及葫芦脲的主客体化学在生物体和药物缓释等方面都具有潜在价值。本文设计合成了不同结构特征具有葫芦脲结构的准轮烷聚合物,探索了不同聚合物的聚集行为,同时研究了聚合物与DNA的键合作用,并制备了金纳米粒子材料。论文首先综述了葫芦脲及其在多胺聚合物方面的研究应用成果,从而阐明了论文选题的科学意义,并围绕多胺聚合物与葫芦脲的超分子相互作用进行了一系列理论与应用方面的研究。
(1)设计合成了N’-3-乙烯苄基丁二铵盐酸盐与葫芦脲组装轮烷单体,利用带有葫芦脲的N-3-乙烯苄基丁二铵盐酸盐的准聚轮烷单体(3VBCB)以过硫酸钾(KPS)做引发剂,在水溶液中通过自由基聚合生成新型侧链准聚轮烷P3VBCB。其结构通过1HNMR、EA、FT-TR、TGA、DSC和激光光散射进行了表征、测试和分析。同时,通过P3VBCB与DNA在溶液中电泳、UV-Vis、荧光分析发现P3VBCB与DNA存在相互作用,且呈现正相关关系。P3VBCB具有较强破坏DNA双螺旋结构的性质,显示较强的DNA变性剂的特征。
(2)利用准轮烷单体N-3-乙烯苄基丁二铵盐酸盐和葫芦[6]脲合成一种新的准轮烷单体与丙烯酰胺(AM)通过自由基聚合反应制备了具有准轮烷结构的共聚物PAM3VBCB。1H NMR, FTIR,元素分析数据表明葫芦[6]脲穿在了聚合物的侧链上,并没有因为聚合反应而从侧链脱落；TGA和DSC表征数据表明聚合物的热稳定性随着侧链葫芦[6]脲个数的增加而增强,主要是由于随着侧链葫芦[6]脲个数的增加,共聚物的结构刚性增加导致的。DLS数据表明共聚物的水合动力学半径随着共聚物浓度的增加而增加,而且由于随着溶液pH的增加,小分子葫芦[6]脲尿从共聚物侧链的脱落,造成其随着溶液pH的增加而跳跃增加。同时由于葫芦[6]脲的脱落,PAM3VBCB溶液的pH和电导率随着NaOH滴加量的增加而出现跳跃。
(3)制备了单体N'-(乙烯基苄基)-1,4-丁二铵盐酸盐(4VB)和葫芦[6]脲组装合成一种新的准轮烷单体4VBCB,然后在水溶液中用K2S2O8为引发剂通过4VBCB与丙烯酰胺(AM)通过自由基聚合反应制备了带有葫芦[6]脲结构的共聚物PAM4VBCB,并通过1HNMR, FTIR,元素分析,激光光散射,TGA和DSC对其结构进行了表征。TGA和DSC数据表明共聚物的热力学性质随着AM与4VBCB摩尔比的降低而增强,DLS数据表明共聚物的平均水合动力学半径随着共聚物浓度的增加而增加,这是由于侧链准聚轮烷分子间相互作用的结果。PAM4VBCB-4水合动力学半径随着pH升高而突跃增加,这主要因为随着pH升高,准聚轮烷中的葫芦[6]脲脱落。在PAM4VBCB存在下用氯金酸与与硼氢化钠通过水热反应形成金纳米颗粒负载的碳膜复合材料进行研究,通过XRD和TEM研究了金纳米颗粒负载的碳膜复合材料的形貌特征,实验结果表明共聚物PAM4VBCB可以通过简易和对环境友好的条件制备出尺寸在5-25 nm的金纳米颗粒负载的碳膜复合材料。
(4)利用4VBCB与N-异丙基丙烯酰胺(NAM)在水溶液中通过自由基引发的聚合反应制备了具有温敏的含准轮烷结构的共聚物PNAM4VBCB,通过1HNMR, FTIR,元素分析,激光光散射,TGA和DSC对其结构进行了表征。DLS数据显示准轮烷结构的水合动力学半径随着共聚物浓度的增加而增加。通过DLS和UV-Vis研究了共聚物的温敏性,并且它们的相转变温度能够通过调节NAM/4VBCB在共聚物中的摩尔比进行控制。由于随着溶液pH的增加准轮烷结构的小分子葫芦[6]脲脱落,造成PNAM4VBCB溶液的pH和电导率随着pH增加而出现突跃。同时,以PNAM4VBCB为模板用水热合成一步法合成了金纳米颗粒负载的碳膜复合材料。我们通过TEM研究金纳米颗粒负载的碳膜复合材料来探究实验验条件对金纳米颗粒负载情况的影响,实验结果表明金纳米颗粒的尺寸在5-25 nm的,并通过控制实验参数成功的实现了两种形貌的转化
(5)利用一种准轮烷单体4VBCB与N,N—二甲基内烯酰胺(DMAA)通过自由基引发的聚合反应制备了具有准轮烷结构的共聚物PDMAA4VBCB。共聚物的结构通过1HNMR, FTIR,元素分析,扫描电镜进行了表征,采用激光光散射测定了共聚物的分子量。扫描电镜表明随着4VBCB与DMAA的摩尔比例的增加,共聚物形成的小球直径增加。DLS数据还表明共聚准轮烷PDMAA4VBCB具有温度敏感的性质,并且相变温度能够通过调整共聚准轮烷中的DMAA4VBCB摩尔比进行控制。此外,通过控制氯化钙和碳酸钠或者BaCl2和Na2SO4的加入来调节共聚物侧链上的葫芦[6]脲穿环与脱环。
Cucurbit[6]uril is a nonadecacylic cage compound which has a relatively rigid structure with a hollow core and accessible from the exterior by two carbonyl-fringed portals. Taking advantage of this fact, many researchers have studied rotaxane, polyrotaxanes, molecular necklace and molecular switch using cucurbit[n]uril (CB[n]). In this paper, we synthesized some side chain polyrotaxanes with CB[n]. Different polymers were synthesized with different pseudorotaxane monomer and acrylamide et al. Brief research background of this work is introduced, in which the history and recent progress in cucurbituril and polyelectrolytes as well as the application of CB[6] in polyelectrolytes are reviewed from a worldwide angle of view. The objective and the scientific significance of this doctoral dissertation are also pointed out.
(1) A novel side-chain pseudorotaxane monomer N'-(3-vinylbenzyl)-1, 4-diaminobutane dihydrochloride with cucurbit[6]uril threaded (3VBCB) were prepared. We synthesized the side-chain polymers of P3VBCB by free radical polymerization with KPS as initiator in aqueous solution, which was characterized by 1H NMR, FT-IR, elemental analysis, DSC, TGA and static light scattering. At the same time, the interaction between DNA and P3VBCB was studied by gel electrophoresis and UV-Vis.
(2) New copolymers of acrylamide and complex pseudorotaxane monomer N'-(3-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril threaded (3VBCB) were prepared via free radical polymerization in aqueous solution, which were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. The thermal properties of copolymers were studied by TGA and DSC, and the effects of the copolymer concentration and pH on the average hydrodynamic radius (Rh) of the copolymers were studied by DLS. At the same time, the interaction between DNA and PAM3VBCB was studied by gel electrophoresis and UV-Vis.
(3) New side-chain copolymers of acrylamide and complex pseudorotaxane monomer N'-(4-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril threaded (4VBCB) were prepared via free radical polymerization in aqueous solution. The copolymers PAM4VBCB were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. Then the as-obtained copolymer PAM4VBCB, HAuCl4 and NaBH4 were used as reactants to obtain uniform Au NPs/carbon film composites via a hydrothermal process, and through tuning the experimental parameters such as reaction time, pH, quantity of HAuCl4 solution, and so on, Au NPs or Au@ carbon spHere core-shell like structures could also be obtained.
(4) The side-chain copolymers of N-isopropyl acrylamide (NAM) and complex pseudorotaxane monomer N'-(4-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril (CB[6]) threaded (4VBCB) were prepared via free-radical polymerization in aqueous solution. The copolymers with CB[6] (PNAM4VBCB) were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. And both pH and electrical conductivity curves of the solution of PNAM4VBCB-4 have a jump. In addition, the copolymers have thermal sensitivity and their phase-change temperatures could be controlled by adjusting the mole ratio of NAM/4VBCB in the copolymers. At the same time, the as-obtained copolymer PNAM4VBCB, HAuCl4 and NaBH4 were used as reactants to obtain uniform Au NPs/carbon film composites via a hydrothennal process, which was studied by TEM to analyze a distributing of the polymer nano material.
(5) The side-chain copolymers DMAA and complex pseudorotaxane monomer N'-(4-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril (CB[6]) threaded (4VBCB) were prepared via free-radical polymerization in aqueous solution. The copolymers with CB[6] (PDMAA4VBCB) were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. DLS data show that the copolymers have thennal sensitivity and their phase-change temperatures could be controlled by adjusting the mole ratio of DMAA/4VBCB in the copolymers. We can contral on or out of CB[6] in the pendent by controlling CaCl2 & NaCO3 addition, or BaCl2 & Na2SO4 addition.
(1)设计合成了N’-3-乙烯苄基丁二铵盐酸盐与葫芦脲组装轮烷单体,利用带有葫芦脲的N-3-乙烯苄基丁二铵盐酸盐的准聚轮烷单体(3VBCB)以过硫酸钾(KPS)做引发剂,在水溶液中通过自由基聚合生成新型侧链准聚轮烷P3VBCB。其结构通过1HNMR、EA、FT-TR、TGA、DSC和激光光散射进行了表征、测试和分析。同时,通过P3VBCB与DNA在溶液中电泳、UV-Vis、荧光分析发现P3VBCB与DNA存在相互作用,且呈现正相关关系。P3VBCB具有较强破坏DNA双螺旋结构的性质,显示较强的DNA变性剂的特征。
(2)利用准轮烷单体N-3-乙烯苄基丁二铵盐酸盐和葫芦[6]脲合成一种新的准轮烷单体与丙烯酰胺(AM)通过自由基聚合反应制备了具有准轮烷结构的共聚物PAM3VBCB。1H NMR, FTIR,元素分析数据表明葫芦[6]脲穿在了聚合物的侧链上,并没有因为聚合反应而从侧链脱落；TGA和DSC表征数据表明聚合物的热稳定性随着侧链葫芦[6]脲个数的增加而增强,主要是由于随着侧链葫芦[6]脲个数的增加,共聚物的结构刚性增加导致的。DLS数据表明共聚物的水合动力学半径随着共聚物浓度的增加而增加,而且由于随着溶液pH的增加,小分子葫芦[6]脲尿从共聚物侧链的脱落,造成其随着溶液pH的增加而跳跃增加。同时由于葫芦[6]脲的脱落,PAM3VBCB溶液的pH和电导率随着NaOH滴加量的增加而出现跳跃。
(3)制备了单体N'-(乙烯基苄基)-1,4-丁二铵盐酸盐(4VB)和葫芦[6]脲组装合成一种新的准轮烷单体4VBCB,然后在水溶液中用K2S2O8为引发剂通过4VBCB与丙烯酰胺(AM)通过自由基聚合反应制备了带有葫芦[6]脲结构的共聚物PAM4VBCB,并通过1HNMR, FTIR,元素分析,激光光散射,TGA和DSC对其结构进行了表征。TGA和DSC数据表明共聚物的热力学性质随着AM与4VBCB摩尔比的降低而增强,DLS数据表明共聚物的平均水合动力学半径随着共聚物浓度的增加而增加,这是由于侧链准聚轮烷分子间相互作用的结果。PAM4VBCB-4水合动力学半径随着pH升高而突跃增加,这主要因为随着pH升高,准聚轮烷中的葫芦[6]脲脱落。在PAM4VBCB存在下用氯金酸与与硼氢化钠通过水热反应形成金纳米颗粒负载的碳膜复合材料进行研究,通过XRD和TEM研究了金纳米颗粒负载的碳膜复合材料的形貌特征,实验结果表明共聚物PAM4VBCB可以通过简易和对环境友好的条件制备出尺寸在5-25 nm的金纳米颗粒负载的碳膜复合材料。
(4)利用4VBCB与N-异丙基丙烯酰胺(NAM)在水溶液中通过自由基引发的聚合反应制备了具有温敏的含准轮烷结构的共聚物PNAM4VBCB,通过1HNMR, FTIR,元素分析,激光光散射,TGA和DSC对其结构进行了表征。DLS数据显示准轮烷结构的水合动力学半径随着共聚物浓度的增加而增加。通过DLS和UV-Vis研究了共聚物的温敏性,并且它们的相转变温度能够通过调节NAM/4VBCB在共聚物中的摩尔比进行控制。由于随着溶液pH的增加准轮烷结构的小分子葫芦[6]脲脱落,造成PNAM4VBCB溶液的pH和电导率随着pH增加而出现突跃。同时,以PNAM4VBCB为模板用水热合成一步法合成了金纳米颗粒负载的碳膜复合材料。我们通过TEM研究金纳米颗粒负载的碳膜复合材料来探究实验验条件对金纳米颗粒负载情况的影响,实验结果表明金纳米颗粒的尺寸在5-25 nm的,并通过控制实验参数成功的实现了两种形貌的转化
(5)利用一种准轮烷单体4VBCB与N,N—二甲基内烯酰胺(DMAA)通过自由基引发的聚合反应制备了具有准轮烷结构的共聚物PDMAA4VBCB。共聚物的结构通过1HNMR, FTIR,元素分析,扫描电镜进行了表征,采用激光光散射测定了共聚物的分子量。扫描电镜表明随着4VBCB与DMAA的摩尔比例的增加,共聚物形成的小球直径增加。DLS数据还表明共聚准轮烷PDMAA4VBCB具有温度敏感的性质,并且相变温度能够通过调整共聚准轮烷中的DMAA4VBCB摩尔比进行控制。此外,通过控制氯化钙和碳酸钠或者BaCl2和Na2SO4的加入来调节共聚物侧链上的葫芦[6]脲穿环与脱环。
Cucurbit[6]uril is a nonadecacylic cage compound which has a relatively rigid structure with a hollow core and accessible from the exterior by two carbonyl-fringed portals. Taking advantage of this fact, many researchers have studied rotaxane, polyrotaxanes, molecular necklace and molecular switch using cucurbit[n]uril (CB[n]). In this paper, we synthesized some side chain polyrotaxanes with CB[n]. Different polymers were synthesized with different pseudorotaxane monomer and acrylamide et al. Brief research background of this work is introduced, in which the history and recent progress in cucurbituril and polyelectrolytes as well as the application of CB[6] in polyelectrolytes are reviewed from a worldwide angle of view. The objective and the scientific significance of this doctoral dissertation are also pointed out.
(1) A novel side-chain pseudorotaxane monomer N'-(3-vinylbenzyl)-1, 4-diaminobutane dihydrochloride with cucurbit[6]uril threaded (3VBCB) were prepared. We synthesized the side-chain polymers of P3VBCB by free radical polymerization with KPS as initiator in aqueous solution, which was characterized by 1H NMR, FT-IR, elemental analysis, DSC, TGA and static light scattering. At the same time, the interaction between DNA and P3VBCB was studied by gel electrophoresis and UV-Vis.
(2) New copolymers of acrylamide and complex pseudorotaxane monomer N'-(3-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril threaded (3VBCB) were prepared via free radical polymerization in aqueous solution, which were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. The thermal properties of copolymers were studied by TGA and DSC, and the effects of the copolymer concentration and pH on the average hydrodynamic radius (Rh) of the copolymers were studied by DLS. At the same time, the interaction between DNA and PAM3VBCB was studied by gel electrophoresis and UV-Vis.
(3) New side-chain copolymers of acrylamide and complex pseudorotaxane monomer N'-(4-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril threaded (4VBCB) were prepared via free radical polymerization in aqueous solution. The copolymers PAM4VBCB were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. Then the as-obtained copolymer PAM4VBCB, HAuCl4 and NaBH4 were used as reactants to obtain uniform Au NPs/carbon film composites via a hydrothermal process, and through tuning the experimental parameters such as reaction time, pH, quantity of HAuCl4 solution, and so on, Au NPs or Au@ carbon spHere core-shell like structures could also be obtained.
(4) The side-chain copolymers of N-isopropyl acrylamide (NAM) and complex pseudorotaxane monomer N'-(4-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril (CB[6]) threaded (4VBCB) were prepared via free-radical polymerization in aqueous solution. The copolymers with CB[6] (PNAM4VBCB) were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. And both pH and electrical conductivity curves of the solution of PNAM4VBCB-4 have a jump. In addition, the copolymers have thermal sensitivity and their phase-change temperatures could be controlled by adjusting the mole ratio of NAM/4VBCB in the copolymers. At the same time, the as-obtained copolymer PNAM4VBCB, HAuCl4 and NaBH4 were used as reactants to obtain uniform Au NPs/carbon film composites via a hydrothennal process, which was studied by TEM to analyze a distributing of the polymer nano material.
(5) The side-chain copolymers DMAA and complex pseudorotaxane monomer N'-(4-vinylbenzyl)-1,4-diaminobutane dihydrochloride with cucurbit[6]uril (CB[6]) threaded (4VBCB) were prepared via free-radical polymerization in aqueous solution. The copolymers with CB[6] (PDMAA4VBCB) were characterized by 1H NMR, FT-IR, elemental analysis, and static light scattering. DLS data show that the copolymers have thennal sensitivity and their phase-change temperatures could be controlled by adjusting the mole ratio of DMAA/4VBCB in the copolymers. We can contral on or out of CB[6] in the pendent by controlling CaCl2 & NaCO3 addition, or BaCl2 & Na2SO4 addition.
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