响应性聚合物的合成、组装动力学过程及应用

英文题名：Synthesis, Assembling Kinetics and Applications of Responsive Polymers
作者：王頔
论文级别：博士
学科专业名称：高分子化学与物理
中文关键词：响应性 ; 聚合物 ; 自组装 ; 荧光探针 ; 动力学
英文关键词：Stimuli-Responsive ; Polymer ; Self-Assembly ; Fluorescent Sensor ; Kinetics
学位年度：2011
导师：刘世勇
学科代码：070305
学位授予单位：中国科学技术大学
论文提交日期：2011-05-01

摘要

响应性聚合物由于具有良好的水溶性和可调控表面活性而成为科学研究的热点之一。它一般由化学性质不同的两个或多个嵌段组成。在适当的条件下,每一个嵌段都具有水溶性;但是当受到外界环境的刺激,比如pH值、温度、离子强度、光、电/磁场、生物分子、特殊的分子识别基元发生改变的时候,响应性聚合物会在亲/疏水平衡以及整体的结构上发生显著的变化。正是由于具有这种独特的外部环境响应性,这种聚合物在传感器、药物传输体系、组织工程以及其他生物材料方面等领域中具有重要的应用价值。这篇论文主要集中研究响应性聚合物在传感器方面的应用,同时对响应性聚合物组装过程的动力学进行了初步探讨。具体来说,本论文的工作包括以下几个方面:
     1.通过使用可逆-加成断裂链转移(RAFT)的聚合方法合成了三种不同嵌段比的聚合物:聚甲基丙烯酸缩水甘油酯-b-聚(N-异丙基丙烯酰胺) (PGMA-b-PNIPAM),并研究了它们在水和DMF混合溶剂中的自组装行为。实验结果表明,通过改变亲水段(PNIPAM)和疏水段(PGMA)的长度比例,可以得到不同形貌的组装结果,当亲水段较长时,该两亲性聚合物组装成胶束;当亲水段较短时,则组装成囊泡。同时由于含有PNIPAM嵌段,组装得到的胶束和囊泡均具有温度响应性。
     2.构筑了一种基于温度敏感全亲水性嵌段共聚物的多色荧光比例型pH和温度探针。该嵌段聚合物:聚(N-异丙基丙烯酰胺)-b-聚(寡聚(乙二醇)单甲醚甲基丙烯酸酯) (PNIPAM-b-POEGMA)是通过RAFT的聚合方法合成,使得PNIPAM链段和POEGMA链段分别标记上荧光素异硫氰酸酯(FITC)和具有pH开关荧光发射性质的罗丹明B衍生物单体(RhBAM)。由于FITC的荧光强度会随着pH值的变大而增强,而pH对RhBAM的影响则恰恰相反,使得这种类型的DHBC对pH是超灵敏响应的,在pH变化的时候显示出多色转变,并且这种pH响应的灵敏度在较高的温度下会有进一步的增强。
     3.通过RAFT的聚合方法,合成了分别含有苯硼酸基元和葡萄糖基元的聚(N-异丙基丙烯酰胺)-b-聚(丙烯酰胺基苯硼酸) (PNIPAM-b-PAPBA)和聚(N-异丙基丙烯酰胺)-b-聚(丙烯酰葡萄糖胺) (PNIPAM-b-PAGA)二嵌段聚合物。由于苯硼酸和葡萄糖基元之间在弱碱性条件下(pH 9.3)形成硼酸酯共价键,两种二嵌段聚合物的水溶液混合后能自发形成以PAPBA/PAGA络合物为核,PNIPAM为壳层的高分子复合物胶束。由于硼酸酯共价键在pH值和葡萄糖浓度改变时能可逆形成和断裂,以及胶束PNIPAM壳层的温敏性,所制备的基于苯硼酸/葡萄糖可逆共价键的高分子复合物胶束对pH、葡萄糖和温度具有多重响应性。
     4.通过自由基乳液共聚的方法在温敏性的PNIPAM微凝胶中共价连接能够识别葡萄糖的APBA基团,以及荧光共振能量转移(FRET)给体染料,4-(2-丙烯酰氧基氨乙基)- 7-硝基苯并-2-氧杂-1,3-二唑(NBDAE),和基于罗丹明B的受体染料(RhBEA)。在一定的pH和温度条件下,加热引起的微凝胶塌缩和葡萄糖引起的微凝胶溶胀可以用来调控FRET受体与给体之间的空间距离。通过检测NBDAE和RhBEA之间的FRET效率来监控温度诱导的微凝胶塌缩和葡萄糖诱导的微凝胶溶胀过程。在pH = 8时,P(NIPAM-APBA-NBDAE-RhBEA)微凝胶在37 oC可以作为葡萄糖荧光比率探针,且相比于25 oC时有显著的灵敏度提升。MTT比色实验进一步表明,浓度高达1.6 g/L的温敏性微凝胶仍几乎是没有细胞毒性的。这些结果表明,P(NIPAM-APBA-NBDAE-RhBEA)微凝胶在细胞内条件下可以应用为多功能的检测,细胞成像或控制释放的纳米载体。
     5.采用停流光谱的分析手段研究了聚(乙烯基苯甲酸)-b-聚(N-乙基吗啉甲基丙烯酸酯) (PVBA-b-PMEMA)两性离子聚合物的“Schizophrenic”的胶束化行为。在没有盐存在、高pH值的情况下,该聚合物在水溶液中是单分子溶解的状态,在低pH值的条件下,该聚合物在水溶液中将形成以PVBA为核,PMEMA为壳层的胶束;另一方面,在含有0.8 M Na2SO4存在的情况下,酸性和碱性条件时,该聚合物在水溶液中会分别形成以PVBA为核的胶束和以PMEMA为核的胶束。研究的动力学过程主要包括:pH诱导的PVBA为核的胶束形成与解离的过程;pH = 10状态下盐诱导的PMEMA为核的胶束形成过程,及其稀释诱导的胶束解离过程;0.8 M Na2SO4存在下的PVBA为核的胶束与PMEMA为核的胶束之间结构反转过程。
     6.通过RAFT的聚合方法合成了一种新型的全亲水性嵌段共聚物聚(N-乙基吗啉甲基丙烯酸酯)-b-聚(N-乙烯基苄基吡啶乙磺酸) (PMEMA-b-PSVBP)。该嵌段聚合物两嵌段均具有盐敏的性质。在水溶液中,当Na2SO4的浓度大于0.6 M的时候,PMEMA段就会变的不溶解,而在NaBr > 0.2 M的条件下PSVBP链段可以很好的溶解。通过在水溶液中调节加入的盐的种类和浓度得到三种不同的状态——单链、PMEMA为核的胶束、PSVBP为核的胶束。利用光散射(LLS)和核磁共振H谱(1H NMR)来表征两种胶束的平衡态结构;同时采用停流光谱的技术来研究盐诱导的两种胶束的胶束形成以及结构反转的动力学过程。
Stimuli-responsive polymers have attracted increasing interest due to their ability to undergo reversible or irreversible changes in physical properties and/or chemical structures to an external stimulus including pH, temperature, ionic strength, light irradiation, mechanical forces, electric and magnetic fields, as well as specific analytes and external additives, to name a few, which make them particularly suitable in areas such as drug and gene delivery, tissue engineering, biosensors and separation processes. In this dissertation, applications in sensor based on stimuli-responsive polymers and the kinetics processes for stimuli-responsive polymers self-assembling were investigated in detail. The dissertation includes the following six parts:
     1. The amphiphilic diblock copolymers poly(glycidyl methacrylate)-b-poly(N- isopropyl acrylamide) (PGMA-b-PNIPAM) with three different block ratio were synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. Their self-assembly behavior in mix solution was studied in detail. Experimental results indicate that the amphiphilic diblock copolymer could assemble to form different aggregates due to the block ratio: when the hydrophilic block was long, it would form micelle; while the hydrophilic block was short, it would form vesicle.
     2. Reported the fabrication of thermoresponsive double hydrophilic block copolymer (DHBC)-based highly sensitive ratiometric fluorescent probe for pH and temperature. This type of fluorescent and responsive DHBC, poly(N-isopropylacrylamide)-b-poly(oligo(ethylene glycol) monomethyl ether methacrylate) (PNIPAM-b-POEGMA) was synthesized via RAFT polymerization with the thermoresponsive PNIPAM block and hydrophilic POEGMA block labeled with fluorescein isothiocyanate (FITC) and rhodamine B-based moieties (RhBAM) possessing pH-switchable emission characteristics, respectively. Since the fluorescence intensity of FITC is increased with the increasing pH value, while the influence of pH on RhBAM is quite in opposition, this type DHBC is highly-sensitive to pH exhibiting multicolor-switch when the pH is changed. Moreover, the pH sensitivity can also be enhanced at elevated temperature.
     3. Two types of diblock copolymers containing phenylboronic acid and glucose moieties, respectively, poly(N-isopropylacrylamide)-b-poly(N-acryloyl-3- aminophenylboronic acid) (PNIPAM-b-PAPBA) and poly(N- isopropylacrylamide)-b-poly(acryloyl glucosamine) (PNIPAM-b-PAGA) were synthesized via RAFT polymerization. Due to the formation of borate ester functionalities between phenylboronic acid and glucose moieties under slightly alkaline conditions (pH 9.3), mixed solution of PNIPAM-b-PAPBA and PNIPAM-b-PAGA diblock copolymers can spontaneously form interpolymer complex micelles consisting of PAPBA/PAGA complex cores and PNIPAM coronas. Since the formation/cleavage of borate ester linkages is highly reversible upon the variation of solution pH and glucose concentrations, and the PNIPAM-shell has temperature sensitivity, the obtained interpolymer complex micelles via reversible covalent bond formation between PAPBA and PAGA exhibit multi-responsiveness to pH, glucose, and temperature.
     4. Multifunctional ratiometric probes for glucose and temperatures based on thermoresponsive poly(N-isopropylacrylamide) (PNIPAM) microgels covalently incorporated with glucose-recognizing moieties, N-acryloyl-3- aminophenylboronic acid (APBA), fluorescence resonance energy transfer (FRET) donor dyes, 4-(2-acryloyloxyethylamino)-7-nitro-2,1,3-benzoxadiazole (NBDAE), and rhodamine B-based FRET acceptors (RhBEA) were prepared. P(NIPAM-APBA-NBDAE-RhBEA) microgels containing FRET pairs and APBA were synthesized via free radical emulsion copolymerization. The spatial proximity of FRET donors and acceptors within microgels can be tuned via thermo-induced microgel collapse or glucose-induced microgel swelling at appropriate pH and temperatures, leading to the facile modulation of FRET efficiencies. APBA moieties within P(NIPAM-APBA-NBDAE-RhBEA) microgels can bind with glucose at appropriate pH to form cyclic boronate moieties, which can decrease the pKa of APBA residues and increase the volume phase transition (VPT) temperature of microgels. The gradual addition of glucose into fluorescent microgel dispersions at intermediate temperatures, i.e., between microgel VPT temperatures in the absence and presence of glucose, respectively, can lead to the re-swelling of initially collapsed microgels. Thus, P(NIPAM-APBA-NBDAE-RhBEA) microgels can serve as dual ratiometric fluorescent probes for glucose and temperatures by monitoring the changes in fluorescence emission intensity ratios. Moreover, P(NIPAM-APBA-NBDAE- RhBEA) microgels at pH 8 and 37 oC can serve as a ratiometric fluorescent glucose sensor with improved detection sensitivity as compared to that at 25 oC. MTT assays further revealed that thermoresponsive microgels are almost non-cytotoxic up to a concentration of 1.6 g/L. These results augur well for the application of P(NIPAM-APBA-NBDAE-RhBEA) microgels for multifunctional purposes such as sensing, imaging, and triggered-release nanocarriers under in vivo conditions.
     5. A zwitterionic poly(4-vinylbenzoic acid-b-N-(morpholino)ethyl methacrylate) (PVBA-b-PMEMA) diblock copolymer was prepared. This diblock copolymer exhibit interesting‘schizophrenic’micellization behavior in aqueous solutions. At a low pH value, PVBA-core micelles are formed, while at a high pH value, the diblock copolymer can be dissolved as unimers. In the presence of sufficient Na2SO4, PVBA-core micelles are formed in acidic media and well-defined PMEMA-core micelles are formed in alkaline one. Thus, if dissolved in the presence of 0.8 M Na2SO4, the zwitterionic diblock copolymer can be switched from PVBA-core micelles to PMEMA-core micelles (and vice versa) simply by manipulating the solution pH. The micelle formation and micelle reversion kinetics of this PVBA-b-PMEMA diblock copolymer was studied by making use of a stopped-flow light scattering technique.
     6. A novel sulfobetaine block copolymer, poly(N-(morpholino)ethyl methacrylate)-b-poly(4-(2-sulfoethyl)-1-(4-vinylbenzyl) pyridinium betaine) (PMEMA-b-PSVBP), was synthesized via RAFT polymerization. It exhibits intriguing‘schizophrenic’micellization behavior in aqueous solution, taking advantage of the fact that the PMEMA block gets insoluble at >0.6 M Na2SO4, and the PSVBP block is only molecularly soluble in the presence of >0.2 M NaBr. Thus, PMEMA-core and PSVBP-core micelles can respectively form in aqueous solution due to the selective water solubility of both blocks, depending on the concentration and type of added salts. 1H NMR and laser light scattering (LLS) were employed to characterize the equilibrium structures of the two types of purely salt-induced micelles. Furthermore, the kinetics of the salt-induced formation/dissociation of PMEMA-core and PSVBP-core micelles, and the structural inversion between these two types of micelles were investigated by using stopped-flow apparatus equipped with a light scattering detection.

引文

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