含树枝状大分子体系的自组装及基于包结络合作用的超分子多嵌段聚合物研究
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摘要
分子自组装是当今最活跃的科学领域之一，它是实现具有功能单元的多层次有序结构的有效途径，对于揭示生命过程中的各种机制和获得先进功能材料都有着重要的理论意义及应用价值。自上世纪80年代以来，科学家们发现嵌段共聚物在选择性溶剂中的自组装可以形成形态和结构多样的胶束或胶束状聚集体，包括球形、棒状、囊泡状、管状以及复合胶束等。随着研究的不断深入，许多有着复杂结构的大分子被引入到自组装领域研究中。大量的实验事实都证明，组装单元的分子构筑对于自组装过程及其结果都有着巨大的影响。在这些新型的构筑单元中，树枝状大分子，因其具有非常规整、精致的结构且其分子体积、形状和功能可以精确控制，在自组装领域的研究中受到特别的注意。越来越多的实验表明，树枝状大分子在自组装过程中表现出来的行为的确与线性高分子存在着很大的差异。
近年来，我们课题组提出，高分子与高分子之间依靠氢键作用可以形成具有核-壳结构的非共价键合胶束(Non-Covalently Connected Micelle，NCCM)。然而，过去的工作中所选用的组装单元都是线形结构的高分子。考虑到组装单元的构筑上的不同会导致组装行为和组装体形貌及结构的明显差别，本论文的工作致力于应用树枝状大分子作为构筑单元的自组装构建NCCM。论文中，首先，我们将利用Frechet-type扇形树枝状大分子dendron引入到溶液中自组装体系，研究了它与线形高分子在溶液中基于氢键相互作用的自组装行为。然后，又利用液晶树枝状大分子作为结构导向成分，尝试制备了C60的“纳米导线”。最后，我们将研究延伸至基于环糊精和金刚烷之间的包结络合作用获得超分子聚合物的领域。
具体开展了以下几方面的研究工作：
1．)通过收敛法的合成策略，分别合成了焦点具有一个羧基的从一代到四代的Frechet苄醚型dendron，并对其进行了详细的结构表征。另外利用RAFT的方法合成了分子量大约3.6万，且分子量分布很窄(PDI=1.06)的聚4乙烯基吡啶(P4VP)。利用羧基和吡啶基团之间的氢键相互作用，我们实现了该类Dendron和P4VP在共同溶剂(氯仿)中的自组装。发现了组装体的形貌和结构依赖于组装单元的组成。通过调节两种构筑单元的比例，我们分别得到了“西瓜胶束”、大薄壁囊泡和小厚壁囊泡。这些结构和形态是通过SEM，TEM，AFM以及DLS和SLS的研究而确定的。交联薄壁囊泡会提高其强度，可避免其在TEM和SEM制样时的变形和坍塌，从而得到真实的图像。由于两构筑单元之间结构的不对称，使得囊泡的壁内部形成了微相分离的结构，致使该囊泡较之以前所得到的囊泡具有更高级的有序结构。
2．)合成了三代苄醚型dendrimer，并通过傅—克反应和氧化两步反应将其改性为羧基修饰的dendrimer。又用RAFT的方法合成了线形高分子链P2VP。通过羧基和吡啶基之间的氢键相互作用，实现了该改性dendrimer和线形高分子P2VP在选择性溶剂中的自组装。通过调节树枝状大分子和线形高分子的比例，我们不但可以得到典型实心胶束，还可以得到“钵形”胶束。推测该胶束是由于线形高分子P2VP主链塌缩诱导接枝dendrimer进行规则排列形成的。该dendrimer及其组装体可在表面进一步实现多方面的功能化，这将有助于开发出具有应用价值的功能化胶束。
3．)通过Percec扇形树枝分子作为液晶结构导向成分，尝试实现C60的一维规则排列，目的就是想得到具有良好电导性能的C60纳米导线。为此，我们合成了两个Percec扇形树枝分子连接的C60分子。可是由于C60分子的空间位阻的原因，该目标化合物没能具有液晶性质。但有趣的是，将该化合物在HOPG上成膜后却可以得到C60一维排列的规则条纹。经过分析我们判断该条纹结构就是C60纳米导线。在此工作的基础上，我们又设计了以树枝化大分子(Denpol)液晶作为C60载体的策略。这样利用共价键连接的方法克服C60分子位阻效应，从而更有利于实现含C60的液晶。
4．)超分子聚合物是分子组装领域里的重要的研究方向。然而，迄今几乎还没有关于以分子量较小的高分子作为构筑单元合成超分子聚合物的报道。本章中我们首先通过ATRP和click reaction合成了超分子聚合物的组装单元，即含包结络合的主体(环糊精，CD)或客体(金刚烷，Ad)端基的低分子量的Ad-PNIPAm-CD，CD-PNIPAm-CD及Ad-PEG-Ad。通过光散射，NOSEY，荧光光谱表征了超分子的形成。我们还利用了时间停留光谱仪对CD-PNIPAm-CD和Ad-PEG-Ad形成超分子聚合物的过程进行了动力学的研究。发现上述基于端基间的包结络合形成超分子的过程中包含两个阶段，第一个阶段瞬时发生，形成分子量较小的超分子，第二阶段进行较慢，是该分子量较小超分子进一步相互连接为高分子量的超分子的过程。该发现不仅仅对于理解超分子形成的物理过程具有一定理论意义，同时它还将为超分子研究中的高分子合成的分子设计提供指导。
Molecular self-assembly is one of the most active areas in current scientific research. It is a very important and effective way to realize the multi-scale ordered structures containing functional units. Therefore, studies on self-assembly possess tremendous values in both theory and practice in exploring the mechanisms in life processes and preparing advanced functional materials. Since 1980s, scientists have found that block copolymers could self-assemble to micelle or micelle-like aggregates in selective solvents with diverse morphologies such as spheres, rods, vesicles, tubes and compounded micelles etc. Along with the rapid progress of the research, a plenty of new macromolecular building-blocks with sophisticated structures are introduced into the studies of self-assembly. Abundant experimental results concluded that the architecture of the building blocks has obvious impact on the processes and resultant objects of the self-assembly. Among such new-type building blocks, macromolecular dendrimers have drawn special attention since they have regular and diaphanous structures and their molecular volume, shape and functions can be accurately controlled. In fact, more and more experiments reveal that the dendrimers distinguish themselves significantly from the corresponding linear polymers in the self-assembly processes.
In the long-term research of our group on macromolecular self-assembly to construct non-covalent connected micelle (NCCM) via hydrogen bonding, only linear macromolecules as building blocks were used in the past. On the view that molecular architecture of the building blocks could intensively affect the self-assembly behavior and the morphology of the resultant micelles, in this thesis, efforts have been made to use dendrimers and its derivatives as building blocks to construct our NCCM. In the thesis, firstly, we investigated the self-assembly of Frechet-type dendron and linear polymers in solution driven by hydrogen bonding. Afterwards, we tried to acquire C60 "Nanowire" by using liquid crystals of Perece-type dendrons as structural director component. Finally, the research was extended to the field of constructing supramolecular polymers by the inclusion complexion between cyclodextrin and admantane.
This thesis focuses on the following four parts:
1.) The Frechet-type dendrons (G1-G4) with single carboxylic focus were synthesized through the convergent method and characterized in details. Through RAFT method, we acquired P4VP (Mn=36K) with a narrow molecular weight distribution. Self-assembly of the dendrons and P4VP in their common solvent chloroform was realized due to hydrogen-bonding interaction between the carboxyl and pyridine groups. We found that the structure and morphology of the assemblies relied on the composition of the building blocks. By changing the molar ratio of the two building blocks, "watermelon micellers", large thin-shell vesicles and small thick-shell vesicles were attained. Such morphologies were explored and confirmed by SEM, TEM, AFM, DLS and SLS studies. For the thin-shell vesicles, crosslinking the shell could improve the strength and then prevent deformation and collapse of the vesicles during the TEM and SEM sample preparation. Therefore reliable images of the vesicles could be attained. Due to the structural asymmetry of two building blocks, phase separation takes place forming layers in the vesicles shell, thus such vesicles may possess more ordered structure compared to the previously acquired ones.
2.) The third generation dendrimer were synthesized and modified with carboxyl on the surface by means of F-C reaction and oxygenation. Meanwhile, liner polymer P2VP was synthesized by RAFT method. Self-assembly of this modified dendrimer and P2VP in selective solvents due to hydrogen bonding between the carboxyl and pyridine groups were completed. Adjusting the proportion of the dendrimer and liner polymer, we gained typical solid micelles as well as "bowl" micelles. The latter was supposed to form as the collapse of the liner P2VP chains induced grafted dendrimers to take an ordered arrangement. Such assemblies provide broad possibilities for further functionalization on the surface to meet different requirements in a variety of applications.
3.) Taking Percec-type dendron as a liquid-crystal director component, we tried to realize one-dimension regular arrangement of C60 to acquire C60 "Nanowire" with good conductance properties. For this purpose, we synthesized a new compound of C60 connected with two Percec dendrons. But probably due to the steric hindrance of C60, the target compound did not form liquid crystal phase. However, It is interesting that the compound formed long stripes in ordered arrangement on HOPG These stripes can be regarded as C60 nanowires. Based on this work, we designed a new strategy of taking liquid-crystal denpols (dendronazed polymer) as C60 vehicle, i.e. C60 is chemically attached to the denpol chains so that the steric effect could be prevented.
4.) Supramolecular polymers (SupP) have been intensively studied as an important field in molecular assembly. However, few reports on using low-molecular weight polymers as building blocks to construct SupPs. In this chapter we synthesized low-molecular-weight polymers, i.e. Ad-PNIPAm-CD, CD-PNIPAm-CD and Ad-PEG-Ad with end groups of host (CD) and guest (Ad), via ATRP and click reaction. They are used as building blocks to form SupPs driven by the inclusion complexation between the host and guest. The formation of SupPs in solution was studies and characterized by LS, NOSEY, fluorescence spectrum. Particularly, we carried out the kinetic study on the SupP formation from CD-PNIPAm-CD and Ad-PEG-Ad by Stopped-Flow spectroscopy. We found that there are two steps in the formation of the SupPs. In the first step which occurs instantly, relatively low-molecular-weight SupPs formed. Then, in the second step, such formed SupPs connected each other to form much longer SupPs. This finding not only has theoretical significance in understanding the physical process of the formation of SupPs but also provide a guide for designing polymers used for supramolecular studies.
近年来，我们课题组提出，高分子与高分子之间依靠氢键作用可以形成具有核-壳结构的非共价键合胶束(Non-Covalently Connected Micelle，NCCM)。然而，过去的工作中所选用的组装单元都是线形结构的高分子。考虑到组装单元的构筑上的不同会导致组装行为和组装体形貌及结构的明显差别，本论文的工作致力于应用树枝状大分子作为构筑单元的自组装构建NCCM。论文中，首先，我们将利用Frechet-type扇形树枝状大分子dendron引入到溶液中自组装体系，研究了它与线形高分子在溶液中基于氢键相互作用的自组装行为。然后，又利用液晶树枝状大分子作为结构导向成分，尝试制备了C60的“纳米导线”。最后，我们将研究延伸至基于环糊精和金刚烷之间的包结络合作用获得超分子聚合物的领域。
具体开展了以下几方面的研究工作：
1．)通过收敛法的合成策略，分别合成了焦点具有一个羧基的从一代到四代的Frechet苄醚型dendron，并对其进行了详细的结构表征。另外利用RAFT的方法合成了分子量大约3.6万，且分子量分布很窄(PDI=1.06)的聚4乙烯基吡啶(P4VP)。利用羧基和吡啶基团之间的氢键相互作用，我们实现了该类Dendron和P4VP在共同溶剂(氯仿)中的自组装。发现了组装体的形貌和结构依赖于组装单元的组成。通过调节两种构筑单元的比例，我们分别得到了“西瓜胶束”、大薄壁囊泡和小厚壁囊泡。这些结构和形态是通过SEM，TEM，AFM以及DLS和SLS的研究而确定的。交联薄壁囊泡会提高其强度，可避免其在TEM和SEM制样时的变形和坍塌，从而得到真实的图像。由于两构筑单元之间结构的不对称，使得囊泡的壁内部形成了微相分离的结构，致使该囊泡较之以前所得到的囊泡具有更高级的有序结构。
2．)合成了三代苄醚型dendrimer，并通过傅—克反应和氧化两步反应将其改性为羧基修饰的dendrimer。又用RAFT的方法合成了线形高分子链P2VP。通过羧基和吡啶基之间的氢键相互作用，实现了该改性dendrimer和线形高分子P2VP在选择性溶剂中的自组装。通过调节树枝状大分子和线形高分子的比例，我们不但可以得到典型实心胶束，还可以得到“钵形”胶束。推测该胶束是由于线形高分子P2VP主链塌缩诱导接枝dendrimer进行规则排列形成的。该dendrimer及其组装体可在表面进一步实现多方面的功能化，这将有助于开发出具有应用价值的功能化胶束。
3．)通过Percec扇形树枝分子作为液晶结构导向成分，尝试实现C60的一维规则排列，目的就是想得到具有良好电导性能的C60纳米导线。为此，我们合成了两个Percec扇形树枝分子连接的C60分子。可是由于C60分子的空间位阻的原因，该目标化合物没能具有液晶性质。但有趣的是，将该化合物在HOPG上成膜后却可以得到C60一维排列的规则条纹。经过分析我们判断该条纹结构就是C60纳米导线。在此工作的基础上，我们又设计了以树枝化大分子(Denpol)液晶作为C60载体的策略。这样利用共价键连接的方法克服C60分子位阻效应，从而更有利于实现含C60的液晶。
4．)超分子聚合物是分子组装领域里的重要的研究方向。然而，迄今几乎还没有关于以分子量较小的高分子作为构筑单元合成超分子聚合物的报道。本章中我们首先通过ATRP和click reaction合成了超分子聚合物的组装单元，即含包结络合的主体(环糊精，CD)或客体(金刚烷，Ad)端基的低分子量的Ad-PNIPAm-CD，CD-PNIPAm-CD及Ad-PEG-Ad。通过光散射，NOSEY，荧光光谱表征了超分子的形成。我们还利用了时间停留光谱仪对CD-PNIPAm-CD和Ad-PEG-Ad形成超分子聚合物的过程进行了动力学的研究。发现上述基于端基间的包结络合形成超分子的过程中包含两个阶段，第一个阶段瞬时发生，形成分子量较小的超分子，第二阶段进行较慢，是该分子量较小超分子进一步相互连接为高分子量的超分子的过程。该发现不仅仅对于理解超分子形成的物理过程具有一定理论意义，同时它还将为超分子研究中的高分子合成的分子设计提供指导。
Molecular self-assembly is one of the most active areas in current scientific research. It is a very important and effective way to realize the multi-scale ordered structures containing functional units. Therefore, studies on self-assembly possess tremendous values in both theory and practice in exploring the mechanisms in life processes and preparing advanced functional materials. Since 1980s, scientists have found that block copolymers could self-assemble to micelle or micelle-like aggregates in selective solvents with diverse morphologies such as spheres, rods, vesicles, tubes and compounded micelles etc. Along with the rapid progress of the research, a plenty of new macromolecular building-blocks with sophisticated structures are introduced into the studies of self-assembly. Abundant experimental results concluded that the architecture of the building blocks has obvious impact on the processes and resultant objects of the self-assembly. Among such new-type building blocks, macromolecular dendrimers have drawn special attention since they have regular and diaphanous structures and their molecular volume, shape and functions can be accurately controlled. In fact, more and more experiments reveal that the dendrimers distinguish themselves significantly from the corresponding linear polymers in the self-assembly processes.
In the long-term research of our group on macromolecular self-assembly to construct non-covalent connected micelle (NCCM) via hydrogen bonding, only linear macromolecules as building blocks were used in the past. On the view that molecular architecture of the building blocks could intensively affect the self-assembly behavior and the morphology of the resultant micelles, in this thesis, efforts have been made to use dendrimers and its derivatives as building blocks to construct our NCCM. In the thesis, firstly, we investigated the self-assembly of Frechet-type dendron and linear polymers in solution driven by hydrogen bonding. Afterwards, we tried to acquire C60 "Nanowire" by using liquid crystals of Perece-type dendrons as structural director component. Finally, the research was extended to the field of constructing supramolecular polymers by the inclusion complexion between cyclodextrin and admantane.
This thesis focuses on the following four parts:
1.) The Frechet-type dendrons (G1-G4) with single carboxylic focus were synthesized through the convergent method and characterized in details. Through RAFT method, we acquired P4VP (Mn=36K) with a narrow molecular weight distribution. Self-assembly of the dendrons and P4VP in their common solvent chloroform was realized due to hydrogen-bonding interaction between the carboxyl and pyridine groups. We found that the structure and morphology of the assemblies relied on the composition of the building blocks. By changing the molar ratio of the two building blocks, "watermelon micellers", large thin-shell vesicles and small thick-shell vesicles were attained. Such morphologies were explored and confirmed by SEM, TEM, AFM, DLS and SLS studies. For the thin-shell vesicles, crosslinking the shell could improve the strength and then prevent deformation and collapse of the vesicles during the TEM and SEM sample preparation. Therefore reliable images of the vesicles could be attained. Due to the structural asymmetry of two building blocks, phase separation takes place forming layers in the vesicles shell, thus such vesicles may possess more ordered structure compared to the previously acquired ones.
2.) The third generation dendrimer were synthesized and modified with carboxyl on the surface by means of F-C reaction and oxygenation. Meanwhile, liner polymer P2VP was synthesized by RAFT method. Self-assembly of this modified dendrimer and P2VP in selective solvents due to hydrogen bonding between the carboxyl and pyridine groups were completed. Adjusting the proportion of the dendrimer and liner polymer, we gained typical solid micelles as well as "bowl" micelles. The latter was supposed to form as the collapse of the liner P2VP chains induced grafted dendrimers to take an ordered arrangement. Such assemblies provide broad possibilities for further functionalization on the surface to meet different requirements in a variety of applications.
3.) Taking Percec-type dendron as a liquid-crystal director component, we tried to realize one-dimension regular arrangement of C60 to acquire C60 "Nanowire" with good conductance properties. For this purpose, we synthesized a new compound of C60 connected with two Percec dendrons. But probably due to the steric hindrance of C60, the target compound did not form liquid crystal phase. However, It is interesting that the compound formed long stripes in ordered arrangement on HOPG These stripes can be regarded as C60 nanowires. Based on this work, we designed a new strategy of taking liquid-crystal denpols (dendronazed polymer) as C60 vehicle, i.e. C60 is chemically attached to the denpol chains so that the steric effect could be prevented.
4.) Supramolecular polymers (SupP) have been intensively studied as an important field in molecular assembly. However, few reports on using low-molecular weight polymers as building blocks to construct SupPs. In this chapter we synthesized low-molecular-weight polymers, i.e. Ad-PNIPAm-CD, CD-PNIPAm-CD and Ad-PEG-Ad with end groups of host (CD) and guest (Ad), via ATRP and click reaction. They are used as building blocks to form SupPs driven by the inclusion complexation between the host and guest. The formation of SupPs in solution was studies and characterized by LS, NOSEY, fluorescence spectrum. Particularly, we carried out the kinetic study on the SupP formation from CD-PNIPAm-CD and Ad-PEG-Ad by Stopped-Flow spectroscopy. We found that there are two steps in the formation of the SupPs. In the first step which occurs instantly, relatively low-molecular-weight SupPs formed. Then, in the second step, such formed SupPs connected each other to form much longer SupPs. This finding not only has theoretical significance in understanding the physical process of the formation of SupPs but also provide a guide for designing polymers used for supramolecular studies.
引文
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