含醛基聚合物的设计与合成
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摘要
合成具有明确结构的反应性功能聚合物并研究其性能与应用,是高分子科学领域的研究热点之一。近年来随着“活性”/可控自由基聚合以及“点击”化学反应的发展,使得合成具有明确、复杂的结构,确定分子量以及化学组成的功能性聚合物成为可能,同时拓展了聚合物在生物医药、纳米科学等领域的应用。可逆加成-断裂链转移(RAFT)聚合由于具有适用单体范围广泛、聚合反应条件温和等优点,较其它“活性”/可控自由基聚合体系具有更强的分子设计能力。本论文利用RAFT聚合技术,设计、合成并表征了有机/无机杂化功能材料以及嵌段、星形-接枝功能聚合物。研究内容分为四部分:
第一部分描述表面引发RAFT聚合制备反应性、温度响应性Fe3O4超顺磁性纳米粒子。通过RAFT试剂S-十二烷基-S′-(α,α′-二甲基-α〞-乙酸)-三硫代碳酸酯(DDMAT)与油酸稳定化的Fe3O4纳米粒子之间简单的配体交换反应,合成表面锚定有RAFT试剂DDMAT的Fe3O4纳米粒子。以此为RAFT控制剂,在Fe3O4纳米粒子表面上引发异丙基丙烯酰胺(NIPAM)与丙烯醛(Ac)的RAFT共聚合,获得结构明确的以异丙基丙烯酰胺-丙烯醛共聚物为壳、Fe3O4为核具有“核-壳”结构的Poly(NIPAM-co-Ac)-g-Fe3O4杂化纳米粒子。纳米粒子表面聚合物层的分子量随单体转化率线性增加,且分子量分布较窄,具有可控聚合的特征。该纳米粒子能够均匀的分散在水介质中,对外界磁场和温度具有双重响应性,且壳层含有反应性醛基,能够高效的负载和分离模型蛋白-牛血清白蛋白(BSA)。
第二部分讨论反应性、电化学活性两亲嵌段共聚物的合成及其氧化-还原响应性胶束化行为。用PEO大分子RAFT试剂(PEO-DDMAT,由单甲氧基聚环氧乙烷与S-十二烷基-S′-(α,α′-二甲基-α〞-乙酸)-三硫代碳酸酯的酯化反应合成)调控二茂铁甲酸(2-醛基-4-乙烯基)苯酚酯(FVFC)自由基聚合,制备PEO-b-PFVFC两亲性嵌段共聚物。该嵌段共聚物在水溶液中能够自组装形成纳米胶束,所得胶束的粒径随着FVFC段的聚合度增加而增大。以苄氧基胺盐酸盐(BHA)为模型药物分子,通过醛基与氨氧基之间的“点击”反应制备了BHA缀合量不同的PEO-b-PFVFC-BHA缀合物;循环伏安法(CV法)检测缀合物的电化学性能表明其氧化电位随着BHA缀合量的增加而变大,因而能够通过自身氧化电位的变化而检测BHA缀合量。PEO-b-PFVFC-BHA缀合物同样能够在水溶液中自组装形成纳米胶束,通过紫外可见光谱(UV-vis)、动态光散射(DLS)、扫描电镜(SEM)、考察了缀合物胶束对外界化学氧化-还原刺激的响应性。PEO-b-PFVFC能够作为潜在的集药物缀合、检测和氧化还原控制释放物于一体的多功能材料。
第三部分为接枝-星形两亲聚合物合成与表征。以AIBN为引发剂,三硫代碳酸酯DDMAT为链转移剂,在60oC THF中首次实现了苯乙烯(St)与丙烯醛(Ac)的RAFT可控自由基共聚合,得到结构明确、分子量可调的St/Ac共聚物Poly(St-co-Ac)。通过“arm-first”法,用Poly(St-co-Ac)作为大分子RAFT试剂调控二乙烯基苯(DVB)交联反应,获得“臂”带有醛基的星形聚合物Poly(St-co-Ac)m-PolyDVB。该星形聚合物与氨氧基修饰的聚环氧乙烷(PEO-ONH2)通过醛基与氨氧基之间的“点击”化学反应,生成Poly(St-co-Ac)m-g-PEO-PolyDVB星形-接枝共聚物。1H NMR与SEC结果证明Poly(St-co-Ac)m-PolyDVB与PEG-ONH2的反应具有定量性特点。通过偏光显微镜(POM)以及动态光散射(DLS)、透射电镜(TEM)考察了不同的PEO接枝量的Poly(St-co-Ac)m-g-PEO- PolyDVB的结晶性能及其在水中的自组装行为。
第四部分涉及含醛基、可降解两亲嵌段共聚物及其聚合物-缀合物的合成。80oC下丁酮中,在PEO大分子RAFT试剂(PEO-DDMAT)存在下,以过氧化二苯甲酰(BPO)为引发剂,进行4-乙烯基苯甲醛(VBA)与5,6-苯基-2-亚甲基-1,3-二氧七环(BMDO)的RAFT共聚合,获得一系列不同组成、分子量分布相对较窄的两亲性嵌段共聚物PEO-b-(VBA-co-BMDO)。由于BMDO的引入,赋予该两亲性嵌段共聚物具有降解性能。PEO-b-(VBA-co-BMDO)通过主链上的醛基与氨氧基乙酸胆固醇酯发生“点击”反应,生成聚合物-固醇酯缀合物。该缀合物能够在水溶液中自组装形成分散比较均匀的纳米胶束。
Synthesis of well-defined reactive functional polymers is an emerging research area in polymer science. Recent advances in“living”/controlled polymerization and“click”chemistry reaction techniques have facilitated access to synthesize well-defined complex architectures, controlled molecular weights, and precisely composition functional polymers; also expanding their application in biomedical and nanotechnology. Taking advantage of the tolerance to a wide range of monomers and mild reaction conditions, reversible addition-fragmentation chain transfer (RAFT) polymerization appeared to be the most versatile process in term of the architecture design among the“living”/controlled radical polymerization techniques. Herein, a series of novel complex architectures multi-functional materials involving organic/inorganic hybrid nanoparticles, star-graft and block copolymers were prepared by RAFT polymerization. The properties and potential application were also studied. The present dissertation consists of four chapters:
Chapter 1 discribes the synthesis of magnetic, Reactive and thermoresponsive Fe3O4 nanoparticles via surface initiated RAFT copolymerization of N-isopropylacrylamide and acrolein. A RAFT agent was directly anchored onto Fe3O4 nanoparticles in a simple procedure employing a ligand exchange reaction of S-1-dodecyl-S?-(α,α′-dimethyl-α′′-acetic acid)trithiocarbonate (DDMAT) with oleic acid initially present on the surface of pristine Fe3O4 nanoparticles. The RAFT agent-functionalized Fe3O4 nanoparticles were then used for the surface initiated RAFT copolymerization of N-isopropylacrylamide (NIPAM) and acrolein to fabricate structurally well-defined hybrid nanoparticles with reactive and thermoresponsive poly(N-isopropylacrylamide-co-acrolein) shell and magnetic Fe3O4 core. Evidence of a well-controlled surface initiated RAFT copolymerization was gained from a linear increase of number-average molecular weight with overall monomer conversions and relatively narrow molecular weight distributions of the copolymers grown from the nanoparticles. The resulting novel magnetic, reactive and thermoresponsive core-shell nanoparticles exhibited temperature-trigged magnetic separation behavior and high ability to immobilize model protein BSA.
Chapter 2 presents the synthesis of reactive and electrochemical active amphiphilic diblock copolymers and their redox-responsive micelles. Amphiphilic block copolymer with a hydrophilic poly(ethylene oxide) (PEO) block and a hydrophobic block containing the combination of reactive aldehyde and redox-active ferrocene groups was synthesized by RAFT polymerization of our previously designed monomer 2-formal-4-vinylphenyl ferrocenecarboxylate (FVFC) using a monomethoxy-terminated PEO-based macro-chain transfer agent. The structure and self-assembly behaviors of the copolymer were characterized. Aminooxy model drug, O-benzylhydroxylamine (BHA) was then conjugated to PEO-b-PFVFC via oxime linkages, generating PEO-b-PFVFC-BHA conjugate. The electrochemical behaviors of the conjugate were evaluated by cyclic voltammetry. The peak (oxidation or reduction) positions depended on the amount of the conjugated BHA, allowing one to detect quantificationally the conjugated molecules by simply measuring the change in potential response of cyclic voltammogram. Also the redox-responsive micellar properties of the conjugates were investigated by combination of UV-vis spectroscopy and scanning electron microscopy (SEM) and dynamic light scattering (DLS). The resulting PEO-b-PFVFC may combine potential applications such as bioconjugation, electrochemical detection and redox-controlled release of encapsulants.
Chapter 3 focuses on the synthesis and characterization of amphiphilic star-graft copolymer. RAFT copolymerization of styrene (St) and acrolein (Ac) was achieved using AIBN as the initiator and S-1-dodecyl-S?-(α,α′-dimethyl-α′′-acetic acid)trithiocarbonate (DDMAT) as the RAFT agent at 60?C in THF. The polymerization exhibited first-order kinetics and the molecular weight increased linearly with increase of monomer conversion. Well defined aldehyde-functionalized copolymer poly(St-co-Ac) was prepared as characterized with SEC and NMR analysis. Star polymers with aldehyde-functionalized arms were then obtained by RAFT polymerization of divinyl benzene (DVB) using poly(St-co-Ac) as a macro-chain transfer agent (CTA) via arm-first approach. The aldhyde functionalized poly (St-co-Ac)m-polyDVB star polymers were subsequently used to couple the aminooxy-functionalized poly (ethylene oxide) (PEO-ONH2) via aldehyde-aminooxy click reaction, leading to the formation of amphiphilic poly (St-co-Ac)m-g-PEO-polyDVB star-graft copolymer. The crystalline and self-assembly behavior were investigated with polarized optical micrographs (POM) and transmission electron microscopy (TEM), and dynamic light scattering (DLS) respectively.
Chapter 4 is directed to the synthesis of aldehyde-functionalized biodegradable amphiphilic copolymer for bioconjugation. RAFT copolymerization of 4-vinylbenzaldehyde (VBA) and 5,6-benzo-2-methylene-1,3- dioxepane (BMDO) was carried out in 2-butanone at 80oC using AIBN as the initiator and a monomethoxy-terminated PEO-based macro-chain transfer agent . Owing to the incorporation of BMDO units, the obtained PEO-b-(VBA-co-BMDO) block copolymers were degradable. The aldehyde bearing block copolymers could conjugate with aminooxy functionalized cholesterol via oxime linkages to form PEO-b-(VBA-co-BMDO)-cholesterol bioconjugate, which self-assemble into monodispersed nanometers scale micelles in aqueous solution.
第一部分描述表面引发RAFT聚合制备反应性、温度响应性Fe3O4超顺磁性纳米粒子。通过RAFT试剂S-十二烷基-S′-(α,α′-二甲基-α〞-乙酸)-三硫代碳酸酯(DDMAT)与油酸稳定化的Fe3O4纳米粒子之间简单的配体交换反应,合成表面锚定有RAFT试剂DDMAT的Fe3O4纳米粒子。以此为RAFT控制剂,在Fe3O4纳米粒子表面上引发异丙基丙烯酰胺(NIPAM)与丙烯醛(Ac)的RAFT共聚合,获得结构明确的以异丙基丙烯酰胺-丙烯醛共聚物为壳、Fe3O4为核具有“核-壳”结构的Poly(NIPAM-co-Ac)-g-Fe3O4杂化纳米粒子。纳米粒子表面聚合物层的分子量随单体转化率线性增加,且分子量分布较窄,具有可控聚合的特征。该纳米粒子能够均匀的分散在水介质中,对外界磁场和温度具有双重响应性,且壳层含有反应性醛基,能够高效的负载和分离模型蛋白-牛血清白蛋白(BSA)。
第二部分讨论反应性、电化学活性两亲嵌段共聚物的合成及其氧化-还原响应性胶束化行为。用PEO大分子RAFT试剂(PEO-DDMAT,由单甲氧基聚环氧乙烷与S-十二烷基-S′-(α,α′-二甲基-α〞-乙酸)-三硫代碳酸酯的酯化反应合成)调控二茂铁甲酸(2-醛基-4-乙烯基)苯酚酯(FVFC)自由基聚合,制备PEO-b-PFVFC两亲性嵌段共聚物。该嵌段共聚物在水溶液中能够自组装形成纳米胶束,所得胶束的粒径随着FVFC段的聚合度增加而增大。以苄氧基胺盐酸盐(BHA)为模型药物分子,通过醛基与氨氧基之间的“点击”反应制备了BHA缀合量不同的PEO-b-PFVFC-BHA缀合物;循环伏安法(CV法)检测缀合物的电化学性能表明其氧化电位随着BHA缀合量的增加而变大,因而能够通过自身氧化电位的变化而检测BHA缀合量。PEO-b-PFVFC-BHA缀合物同样能够在水溶液中自组装形成纳米胶束,通过紫外可见光谱(UV-vis)、动态光散射(DLS)、扫描电镜(SEM)、考察了缀合物胶束对外界化学氧化-还原刺激的响应性。PEO-b-PFVFC能够作为潜在的集药物缀合、检测和氧化还原控制释放物于一体的多功能材料。
第三部分为接枝-星形两亲聚合物合成与表征。以AIBN为引发剂,三硫代碳酸酯DDMAT为链转移剂,在60oC THF中首次实现了苯乙烯(St)与丙烯醛(Ac)的RAFT可控自由基共聚合,得到结构明确、分子量可调的St/Ac共聚物Poly(St-co-Ac)。通过“arm-first”法,用Poly(St-co-Ac)作为大分子RAFT试剂调控二乙烯基苯(DVB)交联反应,获得“臂”带有醛基的星形聚合物Poly(St-co-Ac)m-PolyDVB。该星形聚合物与氨氧基修饰的聚环氧乙烷(PEO-ONH2)通过醛基与氨氧基之间的“点击”化学反应,生成Poly(St-co-Ac)m-g-PEO-PolyDVB星形-接枝共聚物。1H NMR与SEC结果证明Poly(St-co-Ac)m-PolyDVB与PEG-ONH2的反应具有定量性特点。通过偏光显微镜(POM)以及动态光散射(DLS)、透射电镜(TEM)考察了不同的PEO接枝量的Poly(St-co-Ac)m-g-PEO- PolyDVB的结晶性能及其在水中的自组装行为。
第四部分涉及含醛基、可降解两亲嵌段共聚物及其聚合物-缀合物的合成。80oC下丁酮中,在PEO大分子RAFT试剂(PEO-DDMAT)存在下,以过氧化二苯甲酰(BPO)为引发剂,进行4-乙烯基苯甲醛(VBA)与5,6-苯基-2-亚甲基-1,3-二氧七环(BMDO)的RAFT共聚合,获得一系列不同组成、分子量分布相对较窄的两亲性嵌段共聚物PEO-b-(VBA-co-BMDO)。由于BMDO的引入,赋予该两亲性嵌段共聚物具有降解性能。PEO-b-(VBA-co-BMDO)通过主链上的醛基与氨氧基乙酸胆固醇酯发生“点击”反应,生成聚合物-固醇酯缀合物。该缀合物能够在水溶液中自组装形成分散比较均匀的纳米胶束。
Synthesis of well-defined reactive functional polymers is an emerging research area in polymer science. Recent advances in“living”/controlled polymerization and“click”chemistry reaction techniques have facilitated access to synthesize well-defined complex architectures, controlled molecular weights, and precisely composition functional polymers; also expanding their application in biomedical and nanotechnology. Taking advantage of the tolerance to a wide range of monomers and mild reaction conditions, reversible addition-fragmentation chain transfer (RAFT) polymerization appeared to be the most versatile process in term of the architecture design among the“living”/controlled radical polymerization techniques. Herein, a series of novel complex architectures multi-functional materials involving organic/inorganic hybrid nanoparticles, star-graft and block copolymers were prepared by RAFT polymerization. The properties and potential application were also studied. The present dissertation consists of four chapters:
Chapter 1 discribes the synthesis of magnetic, Reactive and thermoresponsive Fe3O4 nanoparticles via surface initiated RAFT copolymerization of N-isopropylacrylamide and acrolein. A RAFT agent was directly anchored onto Fe3O4 nanoparticles in a simple procedure employing a ligand exchange reaction of S-1-dodecyl-S?-(α,α′-dimethyl-α′′-acetic acid)trithiocarbonate (DDMAT) with oleic acid initially present on the surface of pristine Fe3O4 nanoparticles. The RAFT agent-functionalized Fe3O4 nanoparticles were then used for the surface initiated RAFT copolymerization of N-isopropylacrylamide (NIPAM) and acrolein to fabricate structurally well-defined hybrid nanoparticles with reactive and thermoresponsive poly(N-isopropylacrylamide-co-acrolein) shell and magnetic Fe3O4 core. Evidence of a well-controlled surface initiated RAFT copolymerization was gained from a linear increase of number-average molecular weight with overall monomer conversions and relatively narrow molecular weight distributions of the copolymers grown from the nanoparticles. The resulting novel magnetic, reactive and thermoresponsive core-shell nanoparticles exhibited temperature-trigged magnetic separation behavior and high ability to immobilize model protein BSA.
Chapter 2 presents the synthesis of reactive and electrochemical active amphiphilic diblock copolymers and their redox-responsive micelles. Amphiphilic block copolymer with a hydrophilic poly(ethylene oxide) (PEO) block and a hydrophobic block containing the combination of reactive aldehyde and redox-active ferrocene groups was synthesized by RAFT polymerization of our previously designed monomer 2-formal-4-vinylphenyl ferrocenecarboxylate (FVFC) using a monomethoxy-terminated PEO-based macro-chain transfer agent. The structure and self-assembly behaviors of the copolymer were characterized. Aminooxy model drug, O-benzylhydroxylamine (BHA) was then conjugated to PEO-b-PFVFC via oxime linkages, generating PEO-b-PFVFC-BHA conjugate. The electrochemical behaviors of the conjugate were evaluated by cyclic voltammetry. The peak (oxidation or reduction) positions depended on the amount of the conjugated BHA, allowing one to detect quantificationally the conjugated molecules by simply measuring the change in potential response of cyclic voltammogram. Also the redox-responsive micellar properties of the conjugates were investigated by combination of UV-vis spectroscopy and scanning electron microscopy (SEM) and dynamic light scattering (DLS). The resulting PEO-b-PFVFC may combine potential applications such as bioconjugation, electrochemical detection and redox-controlled release of encapsulants.
Chapter 3 focuses on the synthesis and characterization of amphiphilic star-graft copolymer. RAFT copolymerization of styrene (St) and acrolein (Ac) was achieved using AIBN as the initiator and S-1-dodecyl-S?-(α,α′-dimethyl-α′′-acetic acid)trithiocarbonate (DDMAT) as the RAFT agent at 60?C in THF. The polymerization exhibited first-order kinetics and the molecular weight increased linearly with increase of monomer conversion. Well defined aldehyde-functionalized copolymer poly(St-co-Ac) was prepared as characterized with SEC and NMR analysis. Star polymers with aldehyde-functionalized arms were then obtained by RAFT polymerization of divinyl benzene (DVB) using poly(St-co-Ac) as a macro-chain transfer agent (CTA) via arm-first approach. The aldhyde functionalized poly (St-co-Ac)m-polyDVB star polymers were subsequently used to couple the aminooxy-functionalized poly (ethylene oxide) (PEO-ONH2) via aldehyde-aminooxy click reaction, leading to the formation of amphiphilic poly (St-co-Ac)m-g-PEO-polyDVB star-graft copolymer. The crystalline and self-assembly behavior were investigated with polarized optical micrographs (POM) and transmission electron microscopy (TEM), and dynamic light scattering (DLS) respectively.
Chapter 4 is directed to the synthesis of aldehyde-functionalized biodegradable amphiphilic copolymer for bioconjugation. RAFT copolymerization of 4-vinylbenzaldehyde (VBA) and 5,6-benzo-2-methylene-1,3- dioxepane (BMDO) was carried out in 2-butanone at 80oC using AIBN as the initiator and a monomethoxy-terminated PEO-based macro-chain transfer agent . Owing to the incorporation of BMDO units, the obtained PEO-b-(VBA-co-BMDO) block copolymers were degradable. The aldehyde bearing block copolymers could conjugate with aminooxy functionalized cholesterol via oxime linkages to form PEO-b-(VBA-co-BMDO)-cholesterol bioconjugate, which self-assemble into monodispersed nanometers scale micelles in aqueous solution.
引文
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