基于主客体化学和大分子自组装的响应性功能材料和纳米组装结构
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摘要
大分子自组装是聚合物(或大分子包覆的前躯体)在弱相互作用力(范德华力、氢键、疏水作用、静电相互作用、电荷转移等)的诱导下自发地形成具有规整结构体系的过程。当前,大分子自组装已发展成为构筑新颖结构和新型功能高分子材料的重要途径。主客体相互作用是超分子化学的一种重要形式,是组装过程的主要驱动力。作为第二代主体分子的环糊精(Cyclodextrin)和第四代主体分子的葫芦脲(Cucurbituril)由于其自身独特的性质而备受关注。在水溶液中,环糊精和葫芦脲可以选择性地结合多种有机、无机以及生物分子形成主客体包结络合物。由于环糊精和葫芦脲与一些客体分子及其衍生物的包结络合与客体分子的匹配度(如β-环糊精与金刚烷的匹配度高于偶氮苯)、构象(如偶氮苯)、价态(二茂铁以及联吡啶盐和萘)等密切相关,因此可通过化学诱导、光控或者电化学来控制包结络合物的形成与解离。这些主客体体系在设计、制备刺激响应型功能材料以及超分子纳米器件中具有广阔的发展前景。本论文正由此展开,并主要包含以下四部分内容：
I.具有双重响应性的超分子杂化水凝胶我们首先利用RAFT聚合方法合成了一端为偶氮苯基元、另外一端为温敏性的聚异丙基丙烯酰胺嵌段、中间为亲水的聚N’N-二甲基聚丙烯酰胺的响应性嵌段共聚物(AZO-(PDMA-b-PNIPAM))。在水溶液中,嵌段共聚物可与β-CD@QDs形成由包结络合驱动的“星状”杂化包结络合物(Hybrid inclusion complex,简称HIC),其结构为以纳米粒子为核、聚合物为壳以及最外端为温敏性的PNIPAM嵌段。并利用UV-Vis光谱、TGA、动态光散射以及TEM等表征证明了HIC的结构。当其溶液温度高于LCST时,由于最外端PNIPAM嵌段的疏水聚集,浓度高于7wt%的HIC溶液会形成凝胶。我们利用ARES流变仪系统地研究了凝胶的溶胶-凝胶过程以及凝胶的形成机理。我们得到的凝胶分别由两个独立的交联点来支撑：即AZO-(PDMA-b-PNIPAM)嵌段共聚物端基的偶氮苯与β-CD@QDs纳米粒子表面上环糊精的主客体相互作用和高于LCST时疏水聚集的PNIPAM嵌段。因此,当引入竞争性的主体分子α-环糊精或客体分子金刚烷时及或当体系的的温度降低到LCST对,就能实现凝胶-溶胶的转变,我们还利用流变定量地研究了这两种外界刺激下凝胶-溶胶的转变过程以及解离机理。同时我们还系统地研究了嵌段共聚物的聚合度、嵌段共聚物与纳米粒子的摩尔比等因素对凝胶形成的影响以及不同温度下HIC的荧光性质。
Ⅱ.基于石墨烯的快速响应超分子杂化水凝胶我们以6-单氨基乙Z二胺基-β-环糊精和氧化石墨烯为原料,利用环氧开环反应制备了水溶性的表面p-环糊精修饰的石墨烯(CD-G)。CD-G可与端基含有偶氮苯基元的AZO-(PDMA-b-PNIPAM)嵌段共聚物形成主客体相互作用驱动的“刷状”的杂化石墨烯包结络合物(HGIC),其结构是以无机的片层石墨烯为核,嵌段共聚物为壳,最外端为温敏的PNIPAM嵌段。并利用TGA、UV-Vis光谱、X-光电子能谱,Raman光谱、TEM、AFM等手段对HGIC的结构进行了系统的表征。由于最外端的PNIPAM嵌段的温敏性质,浓度为10wt%的HGIC溶液会在接近溶液的LCST时由于PNIPAM的疏水聚集而迅速地形成超分子复合水凝胶,并利用动态流变以及粘度-温度变化定量地研究了溶胶-凝胶的形成过程以及凝胶的形成机理。同时我们基于一系列不同PDMA嵌段和PNIPAM嵌段的共聚物制备了7种不同的HGIC,考察了粘度-在LCST附近变化,结果表明,随着嵌段共聚物中PDMA与PNIPAM嵌段聚合度比率的增加,相对应的HGIC体系的凝胶点的温度以及粘度拐点的温度也在增加。同时我们发现由相同的嵌段共聚物构筑的HIC与HGIC,在相同的流变测试条件下,HGIC形成凝胶时的速率要远高于HIC,同时凝胶点的温度也远低于HIC,这可能是由于柔性以及超薄的石墨烯片层更有助于3维凝胶网络的形成,进而展示了快速的凝胶形成过程。
Ⅲ.基于葫芦脲的双重包结络合能力的非共价连接胶束我们设计并合成了侧链含有双联吡啶盐基元的亲水性共聚物(P(Mv-co-DMA))(?)口端基含有萘基元的温敏性聚合物聚N-异丙基丙烯酰胺(Np-PNIPAM),当引入葫芦[8]脲后,由于该主体分子可同时包结联吡啶季铵盐和萘两种客体分子,两聚合物会形成由主体分子增强的电荷转移相互作用驱动的超分子接枝聚合物,并利用UV-Vis光谱和ITC证明了其结构的形成。当高于LCST时,由于PNIPAM的温敏性质,形成的接枝聚合物就会自组装形成主体增强的电荷转移相互作用驱动的非共价连接胶束。我们利用动态光散射监视的胶束的形成过程,TEM图像表明形成了直径在200-250nm的球状结构的胶束。在胶束中按照一定的摩尔比加入还原剂连二亚硫酸钠,体系的流体力学半径Rh显著的降低。此部分研究工作还在进行中。
Ⅳ.基于葫芦脲的双重包结络合能力的聚合物水凝胶我们首先设计并合成了三种不同分子量,且侧链含有萘基元的亲水性聚合物(P(NP-co-DMA))以及双联吡啶二聚体,并初步探索了加入葫芦[8]脲后,由包结络合作用引发的超分子水凝胶的形成条件。
Macromolecular self-assembly is the process that polymers (or macromolecules capped precursors) form well-defined structure driven by various weak interactions (van der waal' force, hydrogen-bond, electrostatic interaction, hydrophobic interaction etc). Currently, Macromolecular self-assembly becomes an important approach to construct new structures and new functional materials. Host-guest chemistry is an core contents of supramolecular chemistry, as well as important driving force of self-assembly. As the respective second generation and fourth generation of host molecules, cyclodextrin and cucurbituril have attracted extensive attention due to their unique structure and properties. In aqueous solution, cyclodextrin and cucurbituril can selectively encapsulate different organic molecules, inorganic molecules and biomolecules to form host-guest complexes. Because inclusion complexation between host and guest is greatly dependent on their matching degree (e.g.β-Cyclodextrin is more favorable to form inclusion complexes with adamantane than azobenzene), configuration (e.g. azobenzene), valence state (e.g. ferrocene or viologen and naphthalene) of guest molecules, formation and dissociation of the inclusion complex can be controlled by chemical induction, photo-irradiation or electrochemistry. These inclusion complexation systems have great potentials in designing and preparing stimulated functional materials and supramolecular nano-devices. This thesis majorly starts from this background, and contains four parts as follows:
I. Dual stimuli-responsive hybrid supramolecular hydrogel AZO-(PDMA-b-PNIPAM) block copolymers with azobenzene groups on one end, themo-sensitive PNIPAM block on the other end and hydrophilic PDMA block in the middle were prepared through RAFT polymerization. In aqueous solution, the block copolymer and β-CD@QDs can form novel star-shaped hybrid inclusion complexes (HIC) in which β-CD@QDs nanoparticles is the core and block copolymer is the shell with PNIPAM block as the out layer. The supramolecular structure was confirmed by a combination of techniques, including UV-Vis spectrum, TGA, DLS and TEM. When the solution temperature was heated above LCST, HIC solution with a concentration above7wt%would form hydrogel due to the hydrophobic aggregation of PNIPAM block at the out layer. The sol-gel transition and hydrogel formation mechanism was studied by rheology. The inclusion complexation between azobenzene groups of AZO-(PDMA-b-PNIPAM) block copolymers and cyclodextrin on the surface of β-CD@QDs nanoparticles as well as collapsed PNIPAM domains served as two different and independent crosslinks. Then, gel-sol transition occurred when competitive host or guest, i.e. α-cyclodextrin or adamantane was added or the solution temperature was cooled below LCST of PNIPAM. Furthermore, the mechanism of the gel-sol transition and dissociation mechanism of hydrogel following the two external stimuli were quantitatively studied by rheology. The effects of polymerization degree of block copolymers, molar ratio between block copolymer and β-CD@QDs nanoparticles on hydrogel formation as well as fluorescence properties of HIC at different temperature were also studied.
II. Supramolecular hybrid hydrogel from noncovalently functionalized graphene with block copolymer Water soluble (3-cyclodextrin surface-functionalized graphene was prepared via amine-epoxy reaction from ethylenediamino-(3-cyclodextrin and graphene oxide, which was further noncovalently functionalized with azobenzene-end functionalized AZO-(PDMA-b-PNIPAM) block copolymer to form brush-like hybrid graphene inclusion complexes (HGIC). HGICs have inorganic graphene nonosheets as the core, block copolymer as the shell and PNIPAM block at the out layer. The core and the shell were connected by inclusion complexation. Structure of resulted HGIC was fully characterized by a combination of techniques including TGA, UV-vis spectroscopy, X-ray photoelectron spectroscopy (XPS), Raman spectroscopy, TEM and AFM. The HGIC of10wt%concentration can quickly form supramolecular hybrid hydrogel as a result of aggregation of PNIPAM at the out layer when the temperature was close to its LCST. The sol-gel transition and formation mechanism was investigated by dynamic rheology and viscosity-temperature measurement. Seven different HGICs was prepared through inclusion complexation between CD-G and seven block copolymers with different polymerization degree. Viscous/elastic modulus and viscosity of the HGICs with temperature variation was fully investigated by dynamic rheology and viscosity-temperature measurement. The results show that gel point Tgel and viscosity turning points Tη increased with the ratio of degree of polymerization of PDMA block to PNIPAM block of HGIC superstructure. It was also found the hydrogel formation of HGIC was more quickly than that of HIC and the gelation temperature of HGIC was much lower than that of the HIC when the same temperature increase rate, the same block copolymer (Rm) and the same concentration were used. This may be attributed that the flexible and ultrathin2D planar structure of graphene sheets were more favored in the three-dimensional gel network formation.
III. Noncovalently connected Micelles driven by Host-stabilized charge transfer interaction Hydrophilic copolymer containing two violegen moieties at the side chain (P(Mv-co-DMA)) and naphthalene end functionalized PNIPAM (Np-PNIPAM) was prepared, respectively, which can form graft-like copolymers in the presence of Cucurbit[8]uril. The formation of the copolymer driven by host-stabilized charge transfer interaction was confirmed by UV-Vis spectrum. The resultant copolymers can further self-assemble into non-covalently connected micelles (NCCM) above LCST of PNIPAM chains. Formation of micelle was monitored by DLS and TEM image shows spherical structure with diameter of200-250nm. DLS results also showed that Rh decreased greatly after adding reduced agent. Part work of this chapter is still in process.
IV. Supramolecular hydrogel driven by host-stabilized charge transfer interaction Three different copolymers with naphthalene as the side chain and viologen dimer were designed and prepared. A primary research was performed on the formation of supramolecular hydrogel driven by host-stabilized charge transfer interaction, when the CB[8] was added.
I.具有双重响应性的超分子杂化水凝胶我们首先利用RAFT聚合方法合成了一端为偶氮苯基元、另外一端为温敏性的聚异丙基丙烯酰胺嵌段、中间为亲水的聚N’N-二甲基聚丙烯酰胺的响应性嵌段共聚物(AZO-(PDMA-b-PNIPAM))。在水溶液中,嵌段共聚物可与β-CD@QDs形成由包结络合驱动的“星状”杂化包结络合物(Hybrid inclusion complex,简称HIC),其结构为以纳米粒子为核、聚合物为壳以及最外端为温敏性的PNIPAM嵌段。并利用UV-Vis光谱、TGA、动态光散射以及TEM等表征证明了HIC的结构。当其溶液温度高于LCST时,由于最外端PNIPAM嵌段的疏水聚集,浓度高于7wt%的HIC溶液会形成凝胶。我们利用ARES流变仪系统地研究了凝胶的溶胶-凝胶过程以及凝胶的形成机理。我们得到的凝胶分别由两个独立的交联点来支撑：即AZO-(PDMA-b-PNIPAM)嵌段共聚物端基的偶氮苯与β-CD@QDs纳米粒子表面上环糊精的主客体相互作用和高于LCST时疏水聚集的PNIPAM嵌段。因此,当引入竞争性的主体分子α-环糊精或客体分子金刚烷时及或当体系的的温度降低到LCST对,就能实现凝胶-溶胶的转变,我们还利用流变定量地研究了这两种外界刺激下凝胶-溶胶的转变过程以及解离机理。同时我们还系统地研究了嵌段共聚物的聚合度、嵌段共聚物与纳米粒子的摩尔比等因素对凝胶形成的影响以及不同温度下HIC的荧光性质。
Ⅱ.基于石墨烯的快速响应超分子杂化水凝胶我们以6-单氨基乙Z二胺基-β-环糊精和氧化石墨烯为原料,利用环氧开环反应制备了水溶性的表面p-环糊精修饰的石墨烯(CD-G)。CD-G可与端基含有偶氮苯基元的AZO-(PDMA-b-PNIPAM)嵌段共聚物形成主客体相互作用驱动的“刷状”的杂化石墨烯包结络合物(HGIC),其结构是以无机的片层石墨烯为核,嵌段共聚物为壳,最外端为温敏的PNIPAM嵌段。并利用TGA、UV-Vis光谱、X-光电子能谱,Raman光谱、TEM、AFM等手段对HGIC的结构进行了系统的表征。由于最外端的PNIPAM嵌段的温敏性质,浓度为10wt%的HGIC溶液会在接近溶液的LCST时由于PNIPAM的疏水聚集而迅速地形成超分子复合水凝胶,并利用动态流变以及粘度-温度变化定量地研究了溶胶-凝胶的形成过程以及凝胶的形成机理。同时我们基于一系列不同PDMA嵌段和PNIPAM嵌段的共聚物制备了7种不同的HGIC,考察了粘度-在LCST附近变化,结果表明,随着嵌段共聚物中PDMA与PNIPAM嵌段聚合度比率的增加,相对应的HGIC体系的凝胶点的温度以及粘度拐点的温度也在增加。同时我们发现由相同的嵌段共聚物构筑的HIC与HGIC,在相同的流变测试条件下,HGIC形成凝胶时的速率要远高于HIC,同时凝胶点的温度也远低于HIC,这可能是由于柔性以及超薄的石墨烯片层更有助于3维凝胶网络的形成,进而展示了快速的凝胶形成过程。
Ⅲ.基于葫芦脲的双重包结络合能力的非共价连接胶束我们设计并合成了侧链含有双联吡啶盐基元的亲水性共聚物(P(Mv-co-DMA))(?)口端基含有萘基元的温敏性聚合物聚N-异丙基丙烯酰胺(Np-PNIPAM),当引入葫芦[8]脲后,由于该主体分子可同时包结联吡啶季铵盐和萘两种客体分子,两聚合物会形成由主体分子增强的电荷转移相互作用驱动的超分子接枝聚合物,并利用UV-Vis光谱和ITC证明了其结构的形成。当高于LCST时,由于PNIPAM的温敏性质,形成的接枝聚合物就会自组装形成主体增强的电荷转移相互作用驱动的非共价连接胶束。我们利用动态光散射监视的胶束的形成过程,TEM图像表明形成了直径在200-250nm的球状结构的胶束。在胶束中按照一定的摩尔比加入还原剂连二亚硫酸钠,体系的流体力学半径Rh显著的降低。此部分研究工作还在进行中。
Ⅳ.基于葫芦脲的双重包结络合能力的聚合物水凝胶我们首先设计并合成了三种不同分子量,且侧链含有萘基元的亲水性聚合物(P(NP-co-DMA))以及双联吡啶二聚体,并初步探索了加入葫芦[8]脲后,由包结络合作用引发的超分子水凝胶的形成条件。
Macromolecular self-assembly is the process that polymers (or macromolecules capped precursors) form well-defined structure driven by various weak interactions (van der waal' force, hydrogen-bond, electrostatic interaction, hydrophobic interaction etc). Currently, Macromolecular self-assembly becomes an important approach to construct new structures and new functional materials. Host-guest chemistry is an core contents of supramolecular chemistry, as well as important driving force of self-assembly. As the respective second generation and fourth generation of host molecules, cyclodextrin and cucurbituril have attracted extensive attention due to their unique structure and properties. In aqueous solution, cyclodextrin and cucurbituril can selectively encapsulate different organic molecules, inorganic molecules and biomolecules to form host-guest complexes. Because inclusion complexation between host and guest is greatly dependent on their matching degree (e.g.β-Cyclodextrin is more favorable to form inclusion complexes with adamantane than azobenzene), configuration (e.g. azobenzene), valence state (e.g. ferrocene or viologen and naphthalene) of guest molecules, formation and dissociation of the inclusion complex can be controlled by chemical induction, photo-irradiation or electrochemistry. These inclusion complexation systems have great potentials in designing and preparing stimulated functional materials and supramolecular nano-devices. This thesis majorly starts from this background, and contains four parts as follows:
I. Dual stimuli-responsive hybrid supramolecular hydrogel AZO-(PDMA-b-PNIPAM) block copolymers with azobenzene groups on one end, themo-sensitive PNIPAM block on the other end and hydrophilic PDMA block in the middle were prepared through RAFT polymerization. In aqueous solution, the block copolymer and β-CD@QDs can form novel star-shaped hybrid inclusion complexes (HIC) in which β-CD@QDs nanoparticles is the core and block copolymer is the shell with PNIPAM block as the out layer. The supramolecular structure was confirmed by a combination of techniques, including UV-Vis spectrum, TGA, DLS and TEM. When the solution temperature was heated above LCST, HIC solution with a concentration above7wt%would form hydrogel due to the hydrophobic aggregation of PNIPAM block at the out layer. The sol-gel transition and hydrogel formation mechanism was studied by rheology. The inclusion complexation between azobenzene groups of AZO-(PDMA-b-PNIPAM) block copolymers and cyclodextrin on the surface of β-CD@QDs nanoparticles as well as collapsed PNIPAM domains served as two different and independent crosslinks. Then, gel-sol transition occurred when competitive host or guest, i.e. α-cyclodextrin or adamantane was added or the solution temperature was cooled below LCST of PNIPAM. Furthermore, the mechanism of the gel-sol transition and dissociation mechanism of hydrogel following the two external stimuli were quantitatively studied by rheology. The effects of polymerization degree of block copolymers, molar ratio between block copolymer and β-CD@QDs nanoparticles on hydrogel formation as well as fluorescence properties of HIC at different temperature were also studied.
II. Supramolecular hybrid hydrogel from noncovalently functionalized graphene with block copolymer Water soluble (3-cyclodextrin surface-functionalized graphene was prepared via amine-epoxy reaction from ethylenediamino-(3-cyclodextrin and graphene oxide, which was further noncovalently functionalized with azobenzene-end functionalized AZO-(PDMA-b-PNIPAM) block copolymer to form brush-like hybrid graphene inclusion complexes (HGIC). HGICs have inorganic graphene nonosheets as the core, block copolymer as the shell and PNIPAM block at the out layer. The core and the shell were connected by inclusion complexation. Structure of resulted HGIC was fully characterized by a combination of techniques including TGA, UV-vis spectroscopy, X-ray photoelectron spectroscopy (XPS), Raman spectroscopy, TEM and AFM. The HGIC of10wt%concentration can quickly form supramolecular hybrid hydrogel as a result of aggregation of PNIPAM at the out layer when the temperature was close to its LCST. The sol-gel transition and formation mechanism was investigated by dynamic rheology and viscosity-temperature measurement. Seven different HGICs was prepared through inclusion complexation between CD-G and seven block copolymers with different polymerization degree. Viscous/elastic modulus and viscosity of the HGICs with temperature variation was fully investigated by dynamic rheology and viscosity-temperature measurement. The results show that gel point Tgel and viscosity turning points Tη increased with the ratio of degree of polymerization of PDMA block to PNIPAM block of HGIC superstructure. It was also found the hydrogel formation of HGIC was more quickly than that of HIC and the gelation temperature of HGIC was much lower than that of the HIC when the same temperature increase rate, the same block copolymer (Rm) and the same concentration were used. This may be attributed that the flexible and ultrathin2D planar structure of graphene sheets were more favored in the three-dimensional gel network formation.
III. Noncovalently connected Micelles driven by Host-stabilized charge transfer interaction Hydrophilic copolymer containing two violegen moieties at the side chain (P(Mv-co-DMA)) and naphthalene end functionalized PNIPAM (Np-PNIPAM) was prepared, respectively, which can form graft-like copolymers in the presence of Cucurbit[8]uril. The formation of the copolymer driven by host-stabilized charge transfer interaction was confirmed by UV-Vis spectrum. The resultant copolymers can further self-assemble into non-covalently connected micelles (NCCM) above LCST of PNIPAM chains. Formation of micelle was monitored by DLS and TEM image shows spherical structure with diameter of200-250nm. DLS results also showed that Rh decreased greatly after adding reduced agent. Part work of this chapter is still in process.
IV. Supramolecular hydrogel driven by host-stabilized charge transfer interaction Three different copolymers with naphthalene as the side chain and viologen dimer were designed and prepared. A primary research was performed on the formation of supramolecular hydrogel driven by host-stabilized charge transfer interaction, when the CB[8] was added.
引文
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