具有复杂拓扑结构的两新性环状聚合物合成研究
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摘要
聚合物的结构与性能间的关系一直以来在都在吸引着研究者的兴趣。环形聚合物是一类无端基的特殊拓扑结构聚合物,与相应的线形前驱体相比,具有诸多明显不同的物理化学性能,包括流体力学半径、玻璃化转变温度、本征粘度、临界温度、折光系数、微相分离、溶液中的自组装行为及热稳定性。环形拓扑结构也是自然界中广泛存在的结构之一,生物化学和分子生物学的研究发现在生物体内也存在着一些环形的生物大分子,如环形的DNA、环形多肽以及环形的低聚糖和多糖等。因此,环形聚合物的研究不仅具有重要的理论意义,同时也有助于探索生命的奥秘。但是,相对于对其它拓扑结构的聚合物的研究取得的重大进展,人们对环形聚合物的的研究还很少,主要是由于在环形聚合物的合成方面还存在很大的困难。
本论文利用多种“活性”/可控聚合技术(如阴离子聚合、开环聚合、原子转移自由基聚合(ATRP))以及高效的成环方法(如‘'Click"化学和“Glaser"偶合),设计并合成了一系列拓扑结构新颖的两亲性环形聚合物。本论文完成的主要工作如下：
1、通过阴离子开环聚合、配位开环聚合和"Glaser"偶合相结合,合成了“蝌蚪”形聚合物(l-PCL)-b-(c-PEO)-b-(l-PCL),即在环形PEO的对称部位有两根PCL聚合物链。首先,通过环氧乙烷(EO)单体的两次开环聚合和一系列的端基转化,合成了两端含有炔端基和链中间带有两个羟基的线形PEO。然后,在准高稀的条件下,通过分子内的"Glaser"偶合成环,得到在对称位置带有两个羟基的环形PEO(c-PEO)。最后,用c-PEO上的羟基直接引发己内酯(ε-Cl)单体聚合得到目标聚合物(l-PCL)-b-(c-PEO)-b-(l-PCL).对(l-PCL)-b-(c-PEO)-b-(l-PCL)聚合物在水溶液中的自组装行为与其分子量接近的“π”形结构聚合物(PEO/PCL)-b-PEO-b-(PCL/PEO)进行了对比,前者形成了相互缠绕的纤维状组装体,而后者形成了球形的结构,初步的结果表明环形结构影响了聚合物自组装形成的胶束的形态。
2、通过开环聚合和"Glaser'‘偶合相结合,合成了“蝌蚪”形聚合物c-PEO-(PCL)2,即在环形PEO的同一个位点带两根PCL“尾巴”。首先,链端带有两个炔基、链中间带两个羟基的l-PEO通过季戊四醇半缩醛引发EO聚合及-系列官能团的转化得到。其次,l-PEO分子内的"Glaser"偶合成环得到在环上同一位点具有两个羟基的c-PEO。最后,用c-PEO上的羟基直接引发ε-Cl聚合得到“蝌蚪”形聚合物c-PEO-(PCL)2。
3、通过阴离子开环聚合、ATRP及"Click"化学相结合,合成了“8”字形共聚物([c-(PEO-b-PS)]2),即每个环形单元由具有亲水性的PEO嵌段和疏水性的PS嵌段构成。首先,采用"Core-first"的方法,通过阴离子开环聚合、ATRP和端基转化得到了PEO端基为炔基、PS端基为叠氮的A2B2型四臂星形共聚物(PEO-Alkyne)2-(PS-N3)2。在准高稀的条件下,前驱体(PEO-Alkyne)2-(PS-N3)2的两次“Click'’分子内成环得到“8”字形共聚物([c-(PEO-b-PS)]2)。最后,为了探索拓扑结构对聚合物自组装行为的影响,对“8”字形共聚物([c-(PEO-b-PS)]2)和其四臂星形前驱体(PEO-Alkyne)2-(PS-N3)2在水溶液中的自组装行为进行了对比。结果表明两者在水溶液中都组装成了球形胶束,但是随着拓扑结构从星形到环形的转变,形成胶束的粒径明显增大。
4、通过ATRP和‘'Click"化学、“单电子转移氮氧自由基偶合”(SET-NRC)偶合反应相结合,合成了“太阳”形共聚物c-PHEMA-g-(PS-b-PEO),即在环形主链c-PHEMA上带有高密度接枝的两亲性嵌段PS-b-PEO侧链。首先,用2-溴异丁酸3-三甲基硅基炔丙醇酯引发HEMA进行ATRP聚合,然后再将末端的溴基团转化为叠氮得到一端为炔另一端为叠氮的遥爪聚合物l-HC=C-PHEMA-N3。其次,在准高稀的条件下,l-HC=C-PHEMA-N3的“Click"分子内成环得到c-PHEMA。再次,用2-溴异丁酰溴将c-PHEMA上的羟基溴化后,得到的ATRP大分子引发剂引发St聚合得到PS接枝的“太阳”形聚合物c-PHEMA-g-PS。最后,通过TEMPO-PEO与c-PHEMA-g-PS上的PS侧链的"SET-NRC"偶合,得到两亲性嵌段PS-b-PEO接枝的“太阳”形聚合物c-PHEMA-g-(PS-b-PEO)。
通过多种手段如1HNMR, GPC, FT-IR, MALDI-TOF MS对各种中间产物和目标聚合物的结构进行了详细表征。以期这些聚合物能够作为新模型来探索聚合物结构与性能之间的关系。
Since the polymer's properties are inherently dependent on its architecture, tailored control of polymer architecture has always attracted much attention from polymeric chemists. Because of their unique "endless" topology, cyclic polymers exhibit significant different physical properties in both solution and bulk compared with the linear counterparts, such as higher glass-transition temperature, lower hydrodynamic volume, reduced intrinsic viscosity, higher refractive index. Additionally, cyclic topology is also one of the basic architectures widely spread in the nature. The research in biological chemistry and molecular biology discovered that there were some large cyclic structures in the living body, such as cyclic DNA, cyclic peptides and cyclic oligosaccharides and polysaccharides. Therefore, the study of cyclic polymers not only has important values on thoeiy, but also is helpful for exploring the secret of life. However, compared with the significant development on the study of other complex architectural polymers, cyclic polymer has been less studied due to the synthetic difficulties and lack of the research models.
In this thesis, by combination of several "living"/controlled polymerization techniques with some high efficient cyclization methods, such as "Click" chemistry and "Glaser" coupling, a series of amphiphilic cyclic copolymers with novel architectures have been designed and synthesized. The main works finished in this thesis show as follow:
1. A novel amphiphilic tadpole-shaped copolymer [linear-poly(s-caprolactone)]-b-[cyclic-poly(ethylene oxide)]-b-[linear-poly(ε-caprolactone)][(l-PCL)-b-(c-PEO)-b-(l-PCL)] was synthesized by combination of "Glaser" cyclization with ring-opening polymerization (ROP) mechanism. Firstly, a linear PEO precursor with two terminal alkyne groups and two interior active hydroxyl groups was prepared via successive ROP of EO monomers and a series of functional group transformations. Then, a cyclic PEO precursor with two active hydroxyl groups at the opposite sites was obtained by "Glaser" cyclization in dilute conditions. Finally, the target tadpole-shaped copolymer (l-PCL)-b-(c-PEO)-b-(l-PCL) was obtained by ROP of ε-Cl monomers directly from the opposite active hydroxyl groups on cyclic PEO. The self-assembling behaviours of (l-PCL)-b-(c-PEO)-b-(l-PCL) and their π-shaped analogs of (PEO/PCL)-b-PEO-b-(PCL/PEO) with comparable molecular weight in water were preliminarily investigated. The results showed that the tadpole-shaped copolymers formed intertwined fibril-like micells, however, the π-shaped copolymers formed spherical micells.
2. The tadpole-shaped copolymers [cyclic-poly(ethylene oxide)(PEO)]-b-[linear poly(ε-caprolactone)(PCL)]2[(c-PEO)-b-PCL2] with one PEO ring and two PCL tails were synthesized by combination of "Glaser" coupling with ROP. First, a linear PEO precursor with two terminal alkyne groups and two hydroxyl groups at the chain middle was prepared by ROP of EO monomer and the following transformation of functional groups. Then, cyclic PEO with two hydroxyl groups at the same site was obtained by the "Glaser" cyclization. Finally, the hydroxyl groups on cyclic PEO directly initiated the ROP of ε-CL monomer to produce the target copolymers (c-PEO)-b-PCL2.
3. An amphiphilic hetero eight-shaped copolymer cyclic-[poly (ethylene oxide)-b-polystyrene]2[c-(PEO-b-PS)]2composed of hydrophilic PEO and hydrophobic PS segments was synthesized by combination of "Click" chemistry with anionic ROP and ATRP mechanisms. According to "core-first" strategy, the A2B2star-shaped precursor was obtained by successive ROP of EO, ATRP of styrene and modification of functional groups. Under high dilution condition, the intramolecular cyclization by "Click" chemistry produced the amphiphilic hetero eight-shaped copolymer [c-(PEO-b-PS)]2. The self-assembling behaviors of the obtained eight-shaped copolymers [c-(PEO-b-PS)]2and their four-arm star-shaped precursors (PEO-Alkyne)2-(PS-N3)2were compared. The results revealed that although both of them formed spherical micells in aqueous solution, the sizes of micells increased significantly with the topologies of the copolymers changing from star to cycle.
4. The "sun-shaped" copolymer c-PHEMA-g-(PS-b-PEO) consisting of macrocyclic poly(2-hydroxylethyl methacrylate)(c-PHEMA) as backbone and polystyrene-b-poly(ethylene oxide)(PS-b-PEO) amphiphilic block copolymers as side chains was synthesized by combination of ATRP,"Click" chemistry, and single-electron transfer nitroxide radical coupling (SET-NRC). First, a linear a-alkyne-co-azido heterodifunctional PHEMA was prepared by ATRP of HEMA using3-(trimethylsilyl) propargyl2-bromoisobutyrate as initiator, and then chlorine end groups were transformed to-N3group by nucleophilic substitution reaction in DMF in the presence of an excess of NaN3. The3-trimethylsilyl protective groups could be removed in the presence of tetrabutylammonium fluoride, and the obtained product l-(HC=C-PHEMA-N3) was cyclized by "Click" chemistry in high dilution conditions. The hydroxyl groups on c-PHEMA were transferred into bromine groups by esterification with2-bromoisobutyryl bromide and then initiated the ATRP of styrene to afford the macrocyclic molecular brushes c-PHEMA-g-PS. The PS side chains on c-PHEMA-g-PS were coupled with the TEMPO-PEO to afford the target macrocyclic molecular brushes c-PHEMA-g-(PS-b-PEO) by SET-NRC.
All of the intermerdiates and target copolymers have been characterized in detail by1H NMR, GPC, FT-IR and MALDI-TOF MS. It is expected that all of these amphiphilic cyclic copolymers can be used as novel models to explore the relationship between the polymeric architectures and properties.
本论文利用多种“活性”/可控聚合技术(如阴离子聚合、开环聚合、原子转移自由基聚合(ATRP))以及高效的成环方法(如‘'Click"化学和“Glaser"偶合),设计并合成了一系列拓扑结构新颖的两亲性环形聚合物。本论文完成的主要工作如下：
1、通过阴离子开环聚合、配位开环聚合和"Glaser"偶合相结合,合成了“蝌蚪”形聚合物(l-PCL)-b-(c-PEO)-b-(l-PCL),即在环形PEO的对称部位有两根PCL聚合物链。首先,通过环氧乙烷(EO)单体的两次开环聚合和一系列的端基转化,合成了两端含有炔端基和链中间带有两个羟基的线形PEO。然后,在准高稀的条件下,通过分子内的"Glaser"偶合成环,得到在对称位置带有两个羟基的环形PEO(c-PEO)。最后,用c-PEO上的羟基直接引发己内酯(ε-Cl)单体聚合得到目标聚合物(l-PCL)-b-(c-PEO)-b-(l-PCL).对(l-PCL)-b-(c-PEO)-b-(l-PCL)聚合物在水溶液中的自组装行为与其分子量接近的“π”形结构聚合物(PEO/PCL)-b-PEO-b-(PCL/PEO)进行了对比,前者形成了相互缠绕的纤维状组装体,而后者形成了球形的结构,初步的结果表明环形结构影响了聚合物自组装形成的胶束的形态。
2、通过开环聚合和"Glaser'‘偶合相结合,合成了“蝌蚪”形聚合物c-PEO-(PCL)2,即在环形PEO的同一个位点带两根PCL“尾巴”。首先,链端带有两个炔基、链中间带两个羟基的l-PEO通过季戊四醇半缩醛引发EO聚合及-系列官能团的转化得到。其次,l-PEO分子内的"Glaser"偶合成环得到在环上同一位点具有两个羟基的c-PEO。最后,用c-PEO上的羟基直接引发ε-Cl聚合得到“蝌蚪”形聚合物c-PEO-(PCL)2。
3、通过阴离子开环聚合、ATRP及"Click"化学相结合,合成了“8”字形共聚物([c-(PEO-b-PS)]2),即每个环形单元由具有亲水性的PEO嵌段和疏水性的PS嵌段构成。首先,采用"Core-first"的方法,通过阴离子开环聚合、ATRP和端基转化得到了PEO端基为炔基、PS端基为叠氮的A2B2型四臂星形共聚物(PEO-Alkyne)2-(PS-N3)2。在准高稀的条件下,前驱体(PEO-Alkyne)2-(PS-N3)2的两次“Click'’分子内成环得到“8”字形共聚物([c-(PEO-b-PS)]2)。最后,为了探索拓扑结构对聚合物自组装行为的影响,对“8”字形共聚物([c-(PEO-b-PS)]2)和其四臂星形前驱体(PEO-Alkyne)2-(PS-N3)2在水溶液中的自组装行为进行了对比。结果表明两者在水溶液中都组装成了球形胶束,但是随着拓扑结构从星形到环形的转变,形成胶束的粒径明显增大。
4、通过ATRP和‘'Click"化学、“单电子转移氮氧自由基偶合”(SET-NRC)偶合反应相结合,合成了“太阳”形共聚物c-PHEMA-g-(PS-b-PEO),即在环形主链c-PHEMA上带有高密度接枝的两亲性嵌段PS-b-PEO侧链。首先,用2-溴异丁酸3-三甲基硅基炔丙醇酯引发HEMA进行ATRP聚合,然后再将末端的溴基团转化为叠氮得到一端为炔另一端为叠氮的遥爪聚合物l-HC=C-PHEMA-N3。其次,在准高稀的条件下,l-HC=C-PHEMA-N3的“Click"分子内成环得到c-PHEMA。再次,用2-溴异丁酰溴将c-PHEMA上的羟基溴化后,得到的ATRP大分子引发剂引发St聚合得到PS接枝的“太阳”形聚合物c-PHEMA-g-PS。最后,通过TEMPO-PEO与c-PHEMA-g-PS上的PS侧链的"SET-NRC"偶合,得到两亲性嵌段PS-b-PEO接枝的“太阳”形聚合物c-PHEMA-g-(PS-b-PEO)。
通过多种手段如1HNMR, GPC, FT-IR, MALDI-TOF MS对各种中间产物和目标聚合物的结构进行了详细表征。以期这些聚合物能够作为新模型来探索聚合物结构与性能之间的关系。
Since the polymer's properties are inherently dependent on its architecture, tailored control of polymer architecture has always attracted much attention from polymeric chemists. Because of their unique "endless" topology, cyclic polymers exhibit significant different physical properties in both solution and bulk compared with the linear counterparts, such as higher glass-transition temperature, lower hydrodynamic volume, reduced intrinsic viscosity, higher refractive index. Additionally, cyclic topology is also one of the basic architectures widely spread in the nature. The research in biological chemistry and molecular biology discovered that there were some large cyclic structures in the living body, such as cyclic DNA, cyclic peptides and cyclic oligosaccharides and polysaccharides. Therefore, the study of cyclic polymers not only has important values on thoeiy, but also is helpful for exploring the secret of life. However, compared with the significant development on the study of other complex architectural polymers, cyclic polymer has been less studied due to the synthetic difficulties and lack of the research models.
In this thesis, by combination of several "living"/controlled polymerization techniques with some high efficient cyclization methods, such as "Click" chemistry and "Glaser" coupling, a series of amphiphilic cyclic copolymers with novel architectures have been designed and synthesized. The main works finished in this thesis show as follow:
1. A novel amphiphilic tadpole-shaped copolymer [linear-poly(s-caprolactone)]-b-[cyclic-poly(ethylene oxide)]-b-[linear-poly(ε-caprolactone)][(l-PCL)-b-(c-PEO)-b-(l-PCL)] was synthesized by combination of "Glaser" cyclization with ring-opening polymerization (ROP) mechanism. Firstly, a linear PEO precursor with two terminal alkyne groups and two interior active hydroxyl groups was prepared via successive ROP of EO monomers and a series of functional group transformations. Then, a cyclic PEO precursor with two active hydroxyl groups at the opposite sites was obtained by "Glaser" cyclization in dilute conditions. Finally, the target tadpole-shaped copolymer (l-PCL)-b-(c-PEO)-b-(l-PCL) was obtained by ROP of ε-Cl monomers directly from the opposite active hydroxyl groups on cyclic PEO. The self-assembling behaviours of (l-PCL)-b-(c-PEO)-b-(l-PCL) and their π-shaped analogs of (PEO/PCL)-b-PEO-b-(PCL/PEO) with comparable molecular weight in water were preliminarily investigated. The results showed that the tadpole-shaped copolymers formed intertwined fibril-like micells, however, the π-shaped copolymers formed spherical micells.
2. The tadpole-shaped copolymers [cyclic-poly(ethylene oxide)(PEO)]-b-[linear poly(ε-caprolactone)(PCL)]2[(c-PEO)-b-PCL2] with one PEO ring and two PCL tails were synthesized by combination of "Glaser" coupling with ROP. First, a linear PEO precursor with two terminal alkyne groups and two hydroxyl groups at the chain middle was prepared by ROP of EO monomer and the following transformation of functional groups. Then, cyclic PEO with two hydroxyl groups at the same site was obtained by the "Glaser" cyclization. Finally, the hydroxyl groups on cyclic PEO directly initiated the ROP of ε-CL monomer to produce the target copolymers (c-PEO)-b-PCL2.
3. An amphiphilic hetero eight-shaped copolymer cyclic-[poly (ethylene oxide)-b-polystyrene]2[c-(PEO-b-PS)]2composed of hydrophilic PEO and hydrophobic PS segments was synthesized by combination of "Click" chemistry with anionic ROP and ATRP mechanisms. According to "core-first" strategy, the A2B2star-shaped precursor was obtained by successive ROP of EO, ATRP of styrene and modification of functional groups. Under high dilution condition, the intramolecular cyclization by "Click" chemistry produced the amphiphilic hetero eight-shaped copolymer [c-(PEO-b-PS)]2. The self-assembling behaviors of the obtained eight-shaped copolymers [c-(PEO-b-PS)]2and their four-arm star-shaped precursors (PEO-Alkyne)2-(PS-N3)2were compared. The results revealed that although both of them formed spherical micells in aqueous solution, the sizes of micells increased significantly with the topologies of the copolymers changing from star to cycle.
4. The "sun-shaped" copolymer c-PHEMA-g-(PS-b-PEO) consisting of macrocyclic poly(2-hydroxylethyl methacrylate)(c-PHEMA) as backbone and polystyrene-b-poly(ethylene oxide)(PS-b-PEO) amphiphilic block copolymers as side chains was synthesized by combination of ATRP,"Click" chemistry, and single-electron transfer nitroxide radical coupling (SET-NRC). First, a linear a-alkyne-co-azido heterodifunctional PHEMA was prepared by ATRP of HEMA using3-(trimethylsilyl) propargyl2-bromoisobutyrate as initiator, and then chlorine end groups were transformed to-N3group by nucleophilic substitution reaction in DMF in the presence of an excess of NaN3. The3-trimethylsilyl protective groups could be removed in the presence of tetrabutylammonium fluoride, and the obtained product l-(HC=C-PHEMA-N3) was cyclized by "Click" chemistry in high dilution conditions. The hydroxyl groups on c-PHEMA were transferred into bromine groups by esterification with2-bromoisobutyryl bromide and then initiated the ATRP of styrene to afford the macrocyclic molecular brushes c-PHEMA-g-PS. The PS side chains on c-PHEMA-g-PS were coupled with the TEMPO-PEO to afford the target macrocyclic molecular brushes c-PHEMA-g-(PS-b-PEO) by SET-NRC.
All of the intermerdiates and target copolymers have been characterized in detail by1H NMR, GPC, FT-IR and MALDI-TOF MS. It is expected that all of these amphiphilic cyclic copolymers can be used as novel models to explore the relationship between the polymeric architectures and properties.
引文
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