温度响应性高分子的合成及其胶束化行为研究
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摘要
最近几年来,高分子科学和材料科学的迅猛发展对基础的化学合成技术提出了新的要求,例如可控性,高选择性和高效率等。为适应这种需求而发展起来的活性自由基聚合、开环聚合以及点击反应等引起了国内外高分子化学家及材料化学家的广泛关注。它们不仅为合成各种特殊结构的聚合物,如嵌段、接枝、星形、环形、超支化聚合物提供了有效的科学手段,也为各种有机或无机材料的改性提供了宽广的技术平台。这些合成技术的发展极大地促进了高分子科学和材料科学的发展。本论文在前人研究工作的基础上,在温度响应性高分子的合成、胶束化行为以及碳纳米管的改性方向进行了一些有意义的探索,具体研究内容及结果如下:
1.结合可逆加成-裂解链转移(RAFT)聚合、原子转移自由基聚合(ATRP)以及“click”化学方法,成功合成了聚苯乙烯-聚异丙基丙烯酰胺-聚甲基丙烯酸二甲胺基乙酯(PSt-PNIPAM-PDMAEMA)三杂臂星形共聚物。这种两亲性聚合物可以在水溶液中自组装为以PSt为核、PNIPAM和PDMAEMA链段为壳的胶束。由于PNIPAM和PDMAEMA具有相差较大的低临界溶解温度(LCST),该核壳型胶束表现出双重温度响应性。我们利用动态光散射研究了该胶束温度导致的双重相转变行为。
2.结合ATRP、开环聚合以及“click”化学方法,成功合成了全亲水性聚乙二醇-聚异丙基丙烯酰胺-聚赖氨酸(PEG-PNIPAM-PLys)三杂臂星形共聚物。利用激光光散射仪器和电子显微镜等分析手段,我们研究了该聚合物与聚丙烯酸(PAA)混合形成的聚电解质复合胶束。该胶束以离子键相互作用的PLys/PAA为核,以PEG和PNIPAM链段为壳。动态光散射研究证明该聚电解质复合胶束具有温度响应性。
3.利用可逆加成-断裂-链转移活性聚合(RAFT)成功合成了聚苯乙烯-嵌段-聚异丙基丙烯酰胺(PSt-b-PNIPAM)共聚物,该两亲性聚合物在水中可以自组装为以PSt为核,PNIPAM链为壳的胶束。胶束外壳PNIPAM链端巯基可以与就地还原形成的金纳米粒子进行反应,从而制备出表面键接金纳米粒子的胶束。由于PNIPAM在水溶液中具有温度响应性,因此金纳米粒子可以随着PNIPAM链段的收缩和伸展而改变间距,其紫外吸收性能也随之发生可逆循环变化。
4.通过化学改性,在碳纳米管表面引入氨基,然后引发N~5-苄氧羰基赖氨酸的N~2-羧基-α-氨基酸酐(NCA)单体的开环聚合,成功将聚赖氨酸接枝到碳纳米管表面。利用红外光谱、热失重分析、X-射线光电子能谱、元素分析和高倍电镜表征了该聚赖氨酸接枝的碳纳米管。碳纳米管由于接枝了亲水性聚赖氨酸,其在水溶液中的分散性大大提高。
5.通过丙烯酰化PEG端双键与聚赖氨酸氨基的麦克尔加成反应,成功合成了PLL-g-PEG共聚物;用浓硫酸处理阴离子聚合得到的聚苯乙烯,制备出高磺化度的聚苯乙烯。这两种带相反电荷的聚电解质在磷酸盐缓冲溶液中混合而形成胶束。我们用激光光散射和透射电镜研究了正负电荷混合摩尔比对聚电解质复合胶束形成的影响。
With the development of polymer and material sciences,new requirements for basic synthetic technologies,such as controllabilty,high efficiency,high selectivity etc are presented.According to these requirements,those newly developed techniques,such as controlled free radical polymerization and "click chemistry", have been poured great passion by the scientists.They provided the scientists with powerful methods to synthesize various special-structured polymers as well as various organic & inorganic materials.Smartly application of these techniques in polymer synthesis and material modification is one of the most important topics in the field of chemistry.Based on the research of the precursors,this dissertation describes several interesting research in the synthesis and micellization of polymers, as well as the modification of carbon nanotubes.The main results obtained in this thesis are as follows:
1.Hetero-arm star polymer PSt-PNIPAM-PDMAEMA was synthesized by "clicking" the alkyne group at the junction of PSt-b-PNIPAM diblock copolymer onto the azide end-group of PDMAEMA homopolymer via 1, 3-dipolar cycloaddition.PSt-PNIPAM-PDMAEMA micelles with PSt block as core and PNIPAM and PDMAEMA blocks as shell were formed when adding the copolymer solution in THF into ten folds of water.Lower critical solution temperature(LCST) of PNIPAM and PDMAEMA homopolymer is 32℃for PNIPAM and 40-50℃for PDMAEMA,respectively.Upon continuous heating through their LCSTs,PSt-PNIPAM-PDMAEMA core-shell micelles exhibited two-stage thermally induced collapse.
2.Hetero-arm star polymer PEG-PNIPAM-PLys was synthesized by "clicking" the azide group at the junction of PEG-b-PNIPAM diblock copolymer with the alkyne end-group of poly(L-lysine)(PLys) homopolymer via 1,3-dipolar cyeloaddition.Polyelectrolyte complex(PEC) micelles with the ion-bonded PLys/PAA chains as core and the PEG and PNIPAM chains as shell were formed by mixing the synthesized polymer with poly(acrylic acid)(PAA) in water.Dynamic light scattering(DLS) was used to confirm the thermally induced collapse of the PEC micelles.
3.Poly(styrene-b-N-isopropylaerylamide)(PSt-b-PNIPAM) with dithiobenzoate terminal group was synthesized by reversible addition-fragmentation-transfer polymerization.The dithiobenzoate terminal group was converted into thiol terminal group with NaBH_4,resulting thiol-terminated poly(styrene-b-N-isopropylacrylamide) (PSt-b-PNIPAM-SH).After PSt-b-PNIPAM-SH assembled into core-shell micelles in aqueous solution,gold nanoparticles were in-situ surface-linked onto the micelles through the reduction of gold precursor anions with NaBH_4.Changing the temperature of PSt-b-PNIPAM-Au micelles led to the shrinkage of PNIPAM shell and allowed to tune the distance between gold nanoparticles.Ultraviolet-visible(UV-vis) spectroscopy clearly showed the reversible modulation of UV-vis absorbance of PSt-b-PNIPAM-Au micelles upon heating and cooling.
4.A surface-initiated ring-opening polymerization approach was used to functionalize multiwalled carbon nanotubes(MWNTs) with linear poly(L-lysine) (PLL).The successful grafting was confirmed by Fourier transform infrared spectroscopy,thermal gravimetric analysis,X-ray photoelectron spectroscopy, elemental analyses,high-resolution transmission electron microscopy and field-emission scanning electron microscopy.The as-prepared MWNT-g-PLL exhibited excellent ability to disperse homogeneously in water.
5.PLL-g-PEG compolymer was synthesized by grafting PEG to the chain of PLL via Michael Addition Reaction.Highly sulfonate polystyrene(PSt(SO_3H)) was prepared by treating PSt obtained from anion polymerization with sulfuric acid. Polyelectrolyte complex(PEC) micelles were formed by mixing PLL-g-PEG with highly sulfonated polystyrene in a phosphate buffer solution.The influence of mixing molar ratio to the formation of PEC micelles was studied by Laser light scattering(LLS) and Transmission Electron Microscopy(TEM).
1.结合可逆加成-裂解链转移(RAFT)聚合、原子转移自由基聚合(ATRP)以及“click”化学方法,成功合成了聚苯乙烯-聚异丙基丙烯酰胺-聚甲基丙烯酸二甲胺基乙酯(PSt-PNIPAM-PDMAEMA)三杂臂星形共聚物。这种两亲性聚合物可以在水溶液中自组装为以PSt为核、PNIPAM和PDMAEMA链段为壳的胶束。由于PNIPAM和PDMAEMA具有相差较大的低临界溶解温度(LCST),该核壳型胶束表现出双重温度响应性。我们利用动态光散射研究了该胶束温度导致的双重相转变行为。
2.结合ATRP、开环聚合以及“click”化学方法,成功合成了全亲水性聚乙二醇-聚异丙基丙烯酰胺-聚赖氨酸(PEG-PNIPAM-PLys)三杂臂星形共聚物。利用激光光散射仪器和电子显微镜等分析手段,我们研究了该聚合物与聚丙烯酸(PAA)混合形成的聚电解质复合胶束。该胶束以离子键相互作用的PLys/PAA为核,以PEG和PNIPAM链段为壳。动态光散射研究证明该聚电解质复合胶束具有温度响应性。
3.利用可逆加成-断裂-链转移活性聚合(RAFT)成功合成了聚苯乙烯-嵌段-聚异丙基丙烯酰胺(PSt-b-PNIPAM)共聚物,该两亲性聚合物在水中可以自组装为以PSt为核,PNIPAM链为壳的胶束。胶束外壳PNIPAM链端巯基可以与就地还原形成的金纳米粒子进行反应,从而制备出表面键接金纳米粒子的胶束。由于PNIPAM在水溶液中具有温度响应性,因此金纳米粒子可以随着PNIPAM链段的收缩和伸展而改变间距,其紫外吸收性能也随之发生可逆循环变化。
4.通过化学改性,在碳纳米管表面引入氨基,然后引发N~5-苄氧羰基赖氨酸的N~2-羧基-α-氨基酸酐(NCA)单体的开环聚合,成功将聚赖氨酸接枝到碳纳米管表面。利用红外光谱、热失重分析、X-射线光电子能谱、元素分析和高倍电镜表征了该聚赖氨酸接枝的碳纳米管。碳纳米管由于接枝了亲水性聚赖氨酸,其在水溶液中的分散性大大提高。
5.通过丙烯酰化PEG端双键与聚赖氨酸氨基的麦克尔加成反应,成功合成了PLL-g-PEG共聚物;用浓硫酸处理阴离子聚合得到的聚苯乙烯,制备出高磺化度的聚苯乙烯。这两种带相反电荷的聚电解质在磷酸盐缓冲溶液中混合而形成胶束。我们用激光光散射和透射电镜研究了正负电荷混合摩尔比对聚电解质复合胶束形成的影响。
With the development of polymer and material sciences,new requirements for basic synthetic technologies,such as controllabilty,high efficiency,high selectivity etc are presented.According to these requirements,those newly developed techniques,such as controlled free radical polymerization and "click chemistry", have been poured great passion by the scientists.They provided the scientists with powerful methods to synthesize various special-structured polymers as well as various organic & inorganic materials.Smartly application of these techniques in polymer synthesis and material modification is one of the most important topics in the field of chemistry.Based on the research of the precursors,this dissertation describes several interesting research in the synthesis and micellization of polymers, as well as the modification of carbon nanotubes.The main results obtained in this thesis are as follows:
1.Hetero-arm star polymer PSt-PNIPAM-PDMAEMA was synthesized by "clicking" the alkyne group at the junction of PSt-b-PNIPAM diblock copolymer onto the azide end-group of PDMAEMA homopolymer via 1, 3-dipolar cycloaddition.PSt-PNIPAM-PDMAEMA micelles with PSt block as core and PNIPAM and PDMAEMA blocks as shell were formed when adding the copolymer solution in THF into ten folds of water.Lower critical solution temperature(LCST) of PNIPAM and PDMAEMA homopolymer is 32℃for PNIPAM and 40-50℃for PDMAEMA,respectively.Upon continuous heating through their LCSTs,PSt-PNIPAM-PDMAEMA core-shell micelles exhibited two-stage thermally induced collapse.
2.Hetero-arm star polymer PEG-PNIPAM-PLys was synthesized by "clicking" the azide group at the junction of PEG-b-PNIPAM diblock copolymer with the alkyne end-group of poly(L-lysine)(PLys) homopolymer via 1,3-dipolar cyeloaddition.Polyelectrolyte complex(PEC) micelles with the ion-bonded PLys/PAA chains as core and the PEG and PNIPAM chains as shell were formed by mixing the synthesized polymer with poly(acrylic acid)(PAA) in water.Dynamic light scattering(DLS) was used to confirm the thermally induced collapse of the PEC micelles.
3.Poly(styrene-b-N-isopropylaerylamide)(PSt-b-PNIPAM) with dithiobenzoate terminal group was synthesized by reversible addition-fragmentation-transfer polymerization.The dithiobenzoate terminal group was converted into thiol terminal group with NaBH_4,resulting thiol-terminated poly(styrene-b-N-isopropylacrylamide) (PSt-b-PNIPAM-SH).After PSt-b-PNIPAM-SH assembled into core-shell micelles in aqueous solution,gold nanoparticles were in-situ surface-linked onto the micelles through the reduction of gold precursor anions with NaBH_4.Changing the temperature of PSt-b-PNIPAM-Au micelles led to the shrinkage of PNIPAM shell and allowed to tune the distance between gold nanoparticles.Ultraviolet-visible(UV-vis) spectroscopy clearly showed the reversible modulation of UV-vis absorbance of PSt-b-PNIPAM-Au micelles upon heating and cooling.
4.A surface-initiated ring-opening polymerization approach was used to functionalize multiwalled carbon nanotubes(MWNTs) with linear poly(L-lysine) (PLL).The successful grafting was confirmed by Fourier transform infrared spectroscopy,thermal gravimetric analysis,X-ray photoelectron spectroscopy, elemental analyses,high-resolution transmission electron microscopy and field-emission scanning electron microscopy.The as-prepared MWNT-g-PLL exhibited excellent ability to disperse homogeneously in water.
5.PLL-g-PEG compolymer was synthesized by grafting PEG to the chain of PLL via Michael Addition Reaction.Highly sulfonate polystyrene(PSt(SO_3H)) was prepared by treating PSt obtained from anion polymerization with sulfuric acid. Polyelectrolyte complex(PEC) micelles were formed by mixing PLL-g-PEG with highly sulfonated polystyrene in a phosphate buffer solution.The influence of mixing molar ratio to the formation of PEC micelles was studied by Laser light scattering(LLS) and Transmission Electron Microscopy(TEM).
引文
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