非线性聚合物的“活性”/可控合成及其自组装行为的研究

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英文题名："Living"/Controlled Synthesis of Non-linear Copolymers and Investigation on Their Self-assembly Behaviors 作者：张卫东 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：“活性”/可控自由基聚合 ; 星形杂臂聚合物 ; 两亲性聚合物 ; 自组装 ; “Click ; Chemistry” 英文关键词：“living”/controlled free radical polymerization (LFRP) ; miktoarm amphiphilic star copolymers ; amphiphilic copolymers ; self-assembly ; “click chemistry” 学位年度：2010 导师：朱秀林 ; 张伟 学科代码：070305 学位授予单位：苏州大学 论文提交日期：2010-03-01

摘要

星形(杂臂)聚合物由于其独特的三维结构和性质,近年来备受高分子科学家的关注。相比于同分子量的线性聚合物,星形(杂臂)聚合物表现出几个明显的特点,如紧凑的结构,低的熔融黏度等。传统的星形(杂臂)聚合物的合成主要采用活性阴离子聚合。但是该法操作条件较为苛刻。最近,“活性”/可控自由基聚合的发展极大地方便了精细结构的星形(杂臂)聚合物的合成,如原子转移自由基聚合(ATRP),稳定自由基聚合(SFRP),可逆加成-断裂链转移(RAFT)聚合,单电子转移活性自由基活性聚合(SET-LRP)。一般来讲,单一的一种“活性”/可控自由基聚合技术很难合成星形(杂臂)聚合物。星形(杂臂)聚合物可以采用结合多种“活性”/可控自由基聚合手段,或者结合其它的活性聚合,以及结合“Click Chemistry”来进行设计合成。两亲性聚合物由于在生物,胶体科学以及基因释放等领域具有极大的潜在用途,近来成为高分子研究的热点一个。两亲性共聚物自组装的聚集体形态受到许多因素的影响:如化学结构,聚合物的分子量,链段的序列,链段的相对含量,以及溶剂的性质等。最近的研究发现共聚物的拓扑结构对共聚物自组装聚集体的性质也有很大的影响。
     本论文主要探索了星形(杂臂)聚合物的合成以及他们在自组装方面的一些性质。研究的内容主要包含以下几个方面:
     (1)成功合成了一种新型的三官能团RAFT试剂,1,3,5-苄基三硫代碳酸酯均三嗪(TTA)。研究了以TTA为RAFT试剂,热引发条件下苯乙烯单体的RAFT本体聚合。聚合结果呈现典型的“活性“/可控特征。通过紫外光谱和荧光激发谱图监控了聚合物的水解过程,结果表明聚合物臂数的理论值与实验值基本吻合。以三臂的PS_3为大分子RAFT试剂,N-异丙基丙烯酰胺(NIPAAM)为第二单体,通过RAFT扩链,得到结构规整的两亲性星形共聚物(PS-b-PNIPAAM)_3。通过GPC,1H NMR对共聚物的结构进行了表征。两亲性星形共聚物(PS-b-PNIPAAM)_3在选择性溶剂(DMF/CH_3OH)进行了组装,通过HPPS, TEM对胶束的粒径进行了分析。实验结果表明,组装体(胶束)的尺寸随着亲水链PNIPAAM的相对摩尔含量增加而增大。在水溶液里聚合物的LCST随着疏水链PS的含量的增加而降低。
     (2)成功合成了新型的三官能团引发剂,1-(乙氧基-O-2,2,6,6-四甲基哌啶-1-氧自由基)-3,5二(溴甲基)-2,4,6-三甲基苯(TEMPO-2Br)。使用该引发剂通过三步法设计合成了目标聚合物PS(PNIPAAM-b-P4VP)_2。首次结合SFRP和ATRP成功合成结构和分子量都可控的星形杂臂聚合物(PS(PNIPAAM)_2),然后再通过ATRP的扩链反应合成目标聚合物。即以PS(PNIPAAM)_2为大分子ATRP引发剂,4-乙烯吡啶(4VP)为单体,成功合成了精致的星形杂臂两亲性共聚物PS(PNIPAAM-b-P4VP)_2。同时对两亲性杂臂聚合物PS(PNIPAAM)_2和PS(PNIPAAM-b-P4VP)_2在水溶液里的自组装行为的进行了研究。当4.7 < pH < 3.0时,组装体主要是球形的胶束;但是当1.0 < pH < 3.0时,出现了棒状胶束和球形胶束的聚集体;当pH < 1.0时,球形胶束基本完全消失,仅仅看到一些纳米棒。聚合物PS(PNIPAAM)_2的LCST只有31 oC,而PS(PNIPAAM-b-P4VP)_2的LCST为35 oC。
     (3)结合SET-LRP和RAFT法成功合成了结构规整的pH刺激响应的两亲性星形杂臂聚合物(PAA)_2(PVAc)_2。第一步利用新合成的四官能团的Iniferter试剂,双溴代的黄原酸酯(Xanthate2-Br2),作为SET-LRP的引发剂,以丙酮为溶剂,在Cu(0)的催化下室温聚合丙烯酸叔丁酯(t-BA)得到两臂的聚丙烯酸叔丁酯(PtBA)_2。聚合行为呈现“活性”/可控的特征。聚合物的分子量随单体转化率线性增长。第二步利用(PtBA)_2作为大分子RAFT试剂,RAFT聚合醋酸乙烯酯(VAc)得到A2B2型星形杂臂聚合物(PtBA)_2(PVAc)_2。最后,通过三氟乙酸选择性水解得到目标的两亲性星形杂臂聚合物(PAA)_2(PVAc)_2。通过GPC, 1H NMR和FT-IR对得到的聚合物进行了表征。该聚合物对环境的pH值呈现出良好的刺激响应性。
     (4)结合SET-LRP和RAFT法成功合成了结构规整的两亲性杂臂聚合物(PNIPAAM)3(PVK)。首先利用新合成的新型四官能团的溴代黄原酸酯(Xanthate-Br3)为SET-LRP引发剂,Cu(0)/PMDETA为催化剂,在室温下进行异丙基丙烯酰胺(NIPAAM)的单电子转移活性自由基聚合,得到星形聚异丙基丙烯酰胺(PNIPAAM)3。然后利用(PNIPAAM)3为大分子RAFT试剂,RAFT聚合N-乙烯基咔唑(NVC)单体,得到目标星形杂臂聚合物。通过GPC,1H NMR图谱对聚合物的结构进行了表征。通过DLS,荧光和紫外光谱对聚合物的光学性能进行了研究。结果发现聚合物(PNIPAAM)3(PVK)在水溶液里进行组装后,胶束的尺寸随温度的升高而增加,荧光光谱发现胶束的荧光强度随温度的升高而增大,并且具有可逆性。
     (5)结合SET-LRP和RAFT法成功合成了全亲水性的星形杂臂聚合物(PNIPAAM)_2(PNVP-b-PAA)_2和(PNIPAAM-b-PAA)_2(PNVP)_2。GPC, 1H NMR对聚合物的结构进行了表征。聚合物(PNIPAAM)_2(PNVP-b-PAA)_2在水溶液里可以根据温度,pH值的变化组装成四种不同结构的胶束。而且通过DLS和照片明显看到胶束的之间可以相互转变。
     (6)成功合成了多官能团的偶合试剂,2,4,6-三(间乙炔苯胺)-1,3,5-三嗪(TPTTA)。首先通过ATRP法合成线性聚苯乙烯(PS-Cl)和聚甲基丙烯酸-N,N-二甲氨基乙酯(PDMAEMA-Br)。聚合物通过和叠氮化钠发生亲核取代反应,成功制备了叠氮取代的聚合物PS-N_3和PDMAEMA-N_3。最后利用TPTTA和叠氮封端的线性聚合物(PS-N_3和PDMAEMA-N_3)通过“Click Chemistry”反应制备PS_3和PS(PDMAEMA)_2星形聚合物。1H NMR, FT-IR, UV和GPC详细分析了聚合物的结构。透射电镜TEM证实两亲性星形杂臂聚合物PS(PDMAEMA)_2在水溶液里可以组装成稳定的球形胶束。
     (7)通过SET-RAFT首次成功实现了炔类单体,甲基丙烯酸炔乙酯的“活性”/可控聚合。聚合动力学显示聚合反应为一级反应,而且聚合物的分子量随单体的转化率的增加而线性增长。聚合物的分子量分布指数在可控的范围之内。相比于其它的“活性”/可控自由基聚合方法(ATRP, RAFT和SET-LRP),SET-RAFT聚合甲基丙烯酸炔乙酯的控制性得到了很大程度的提高,主要是由于聚合体系里存在RAFT试剂和原位产生的Cu(II),导致副反应(链终止,链转移反应)的概率降低。同时,结合SET-RAFT聚合和“Click Chemistry”在Cu(0)/PMDETA的催化下,一锅一步法合成了侧链功能化聚合物。
Star (miktoarm) polymers have being gained great attention over the past decades due to their unique three-dimensional shape and properties. Compared with linear polymers, star polymers manifest many advantages, such as lower solution, melt viscosities and so on, due to their compact structures. Traditional strategy for the synthesis of star (miktoarm) block copolymer relies on the well-known anionic polymerization method, however, which required relatively harsh experimental conditions. The recent advances in controlled/“living”free radical polymerization (LFRP), such as, atom transfer radical polymerization (ATRP), stead Free radical polymerization (SFRP), reversible addition-fragmentation chain transfer (RAFT) polymerization, and single-electron transfer mediated living radical polymerization (SET-LRP), facilitated the synthesis of star (miktoarm) block copolymers with predetermined chemical compositions. However, it is also difficult to prepare star (miktoarm) block copolymers by only one LFRP method in some cases. Most recently, the combinations of two or several CRP methods, or combinations of them with other polymerization methods, such as ring opening polymerization (ROP), living anionic polymerization and“Click chemistry”, have been successfully employed to synthesize the star (miktoarm) block copolymers.
     Amphiphilic copolymers have being attracted many interests because of a wide range of potential applications in biology, colloidal science, drug and gene delivery. The aggregated morphology of the self-assembly formed by the amphiphilic copolymers is affected by many factors, such as the chemical structure and molecular weight of the copolymers, the block sequence, the relative lengths of the hydrophobic and hydrophilic blocks, and the nature of solvents. Recent research has suggested that precise nature of the block copolymer chain architectures (linear or nonlinear) also plays an important role in self-assembly behaviors of the block copolymers.
     Our work in this thesis can be summarized as the following:
     (1) The novel trifunctional reversible addition-fragmentation chain transfer (RAFT) agent, tris(1-phenylethyl) 1,3,5-triazine-2,4,6-triyl trithiocarbonate (TTA), was synthesized and used to prepare the three-armed polystyrene (PS_3) via RAFT polymerization of styrene (St) in bulk with thermal initiation. The polymerization kinetic plot was first order and the molecular weights of polymers increased linearly with the monomer conversions, while keeping narrow molecular weight distributions (Mw/Mn≤1.23). The number of arms of PS_3 was analyzed by gel permeation chromatography (GPC), ultraviolet visible (UV-vis) and fluorescence spectra. Furthermore, the three-armed amphiphilic thermosensitive block copolymer, poly(styrene-b-N-isopropylacrylamide)_3 (PS-b-PNIPAAM)_3, with controlled molecular weight and well-defined structure was also successfully prepared via RAFT chain extension method using the obtained three-armed PS as the macro-RAFT agent and N-isopropylacrylamide as the second monomer. The copolymers obtained were characterized by GPC and 1H nuclear magnetic resonance (NMR) spectra. The self-assembly behaviors of the three-armed amphiphilic block copolymers (PS-b-PNIPAAM)_3 in mixed solution (DMF/CH3OH) were also investigated by high performance particle sizes (HPPS) and transmission electron microscopy (TEM). Interestingly, the lower critical solution temperature (LCST) of aqueous solutions of the three-armed amphiphilic block copolymers (PS-b-PNIPAAM)_3 decreased with the increase of relative length of PS in the block copolymers.
     (2) The novel trifunctional initiator, 1-(4-methyleneoxy-2,2,6,6-tetramethylpiperidinoxyl)-3,5-bi(bromomethyl)-2,4,6-trimethylbenzene (TEMPO-2Br), was sucessfully synthesized and used to prepare the miktoarm star amphiphilic poly(styrene)-(poly(N-isopropylacrylamide))_2 (PS(PNIPAAM)_2) via combination of atom transfer radical polymerization (ATRP) and nitroxide-mediated radical polymerization (NMRP) techniques. Furthermore, the star amphiphilic block copolymer, poly(styrene)-(poly(N-isopropylacrylamide-b-4-vinylpyridine))_2 (PS(PNIPAAM-b-P4VP)_2), was also prepared using PS(PNIPAAM)_2 as the macroinitiator and 4-vinylpyridine as the second monomer by ATRP method. The obtained polymers were well-defined with narrow molecular weight distributions (Mw/Mn≤1.29). Meanwhile, the self-assembly behaviors of the miktoarm amphiphilic block copolymers, PS(PNIPAAM)_2 and PS(PNIPAAM-b-P4VP)_2, were also investigated. Interestingly, the aggregate morphology changed from sphere-shape micelles (4.7 < pH < 3.0) to a mixture of spheres and rods (1.0 < pH < 3.0), and rod-shape nanorods formed when pH value was below 1.0. The LCST of PS(PNIPAAM)_2 (pH = 7) was about 31 oC and the LCST of PS(PNIPAAM-b-P4VP)_2 was about 35 oC (pH = 3).
     (3) The pH-responsive amphiphilic A2B2 miktoarm star block copolymer, poly(acrylic acid)_2-poly(vinyl acetate)_2 ((PAA)_2(PVAc)_2), with controlled molecular weight and well-defined structure was successfully synthesized via combination of single-electron transfer mediated living radical polymerization (SET-LRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization methods. Firstly, the precursor two-armed poly(t-butyl acrylate) (PtBA)_2 functionalized with two xanthate groups was prepared by SET-LRP of t-butyl acrylate in acetone at 25 oC using the novel tetrafunctional bromoxanthate (Xanthate2-Br2) as an Iniferter (initiator-transfer agent-terminator) agent. The polymerization behavior showed typical LRP natures by the first-order polymerization kinetics and the linear dependence of molecular weight of the polymer on the monomer conversion. Secondly, the A2B2 miktoarm star block copolymer (PtBA)_2(PVAc)_2 was prepared by RAFT polymerization of VAc using (PtBA-N3)_2(xanthate)_2 obtained as the macro-RAFT agent. Finally, the pH-sensitive A2B2 amphiphilic miktoarm star block copolymer poly(acrylic acid)_2-poly(vinyl acetate)_2 ((PAA)_2(PVAc)_2) was obtained by selectively cleavage of t-butyl esters of (PtBA)_2(PVAc)_2. All the miktoarm star block copolymers were characterized by GPC, 1H NMR and FT-IR spectra. The self-assembly behaviors of the amphiphilic A2B2 miktoarm block copolymers (PAA)_2(PVAc)_2 were also investigated by transmission electron microscopy (TEM).
     (4) A novel amphiphilic A3B miktoarm star copolymer, poly(N-isopropylacrylamide)_3-poly(N-vinylcarbazole) ((PNIPAAM)_3(PVK)), was successfully synthesized by a combination of single-electron transfer living radical polymerization (SET-LRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization. Firstly, the well-defined three-armed poly(N-isopropylacrylamide) (PNIPAAM)_3 was prepared via SET-LRP of N-isopropylacrylamide in acetone at 25 oC using a tetrafunctional bromoxanthate iniferter (Xanthate-Br3) as the initiator and Cu(0)/PMDETA as a catalyst system. Secondly, the target amphiphilic A3B miktoarm star copolymer ((PNIPAAM)_3(PVK)) was prepared via RAFT polymerization of N-vinylcarbazole (NVC) employing (PNIPAAM)_3 as the macro-RAFT agent. The architecture of the amphiphilic A3B miktoarm star copolymers were characterized by GPC, 1H NMR spectra. Furthermore, the fluorescence intensity of micelle increased with the temperature and had a good temperature reversibility, which was investigated by dynamic light scattering (DLS), fluorescent and UV-vis spectra.
     (5) The well-defined miktoarm star terpolymer, poly(N-isopropylacrylamide)_2-poly(N-vinylpyrrolidone-b-acrylic acid)_2 and (poly(N-isopropylacrylamide-b- acrylic acid)_2-poly(N-vinylpyrrolidone)_2, were successfully prepared via a combination of single-electron transfer mediated living radical polymerization (SET-LRP) and RAFT polymerization techniques. All the miktoarm star block copolymers were characterized by GPC, 1H NMR. Interesting, this novel double hydrophilic miktoarm star terpolymer containing pH-responsive PAA and thermo-responsive PNIPAAM segments can self-assemble into four types of micellar aggregates by adjusting solution pH and temperature, the characteristic assembled structures were observed by photo and dynamic light scattering (DLS)。
     (6) Homo/miktoarm star polymers were successfully synthesized via combination of the“arm-first”and“coupling-onto”strategies. Firstly, the multifunctional coupling agent (core), 2, 4, 6-tris(3-ethynylphenyl)-1,3,5-triazine-2,4,6-triamine (TPTTA), was synthesized. Secondly, the linear polystyrene-Cl (PS-Cl) and poly(2-(dimethylamino)ethyl methacrylate)-Br (PDMAEMA-Br) were prepared by atom transfer radical polymerization (ATRP) method. Then, the linear PS-Cl and PDMAEMA-Br chains were modified by a nucleophilic substitution reaction with sodium azide. Finally, homo/miktoarm star polymers PS_3 and PS(PDMAEMA)_2 were designed by click reaction between the core (TPTTA) and the arm precursor (PS-N3 or PDMAEMA-N3). The structures of the PS_3, PS(PDMAEMA)_2 and the precursors were all characterized by 1H NMR, FT-IR, UV and GPC analysis. Moreover, the self-assembly behaviors of the miktoarm amphiphilic copolymer PS(PDMAEMA)_2 was also investigated by transmission electron microscopy (TEM).
     (7) A clickable alkyne monomer, progargyl methacrylate (PgMA), was successfully polymerized in a well-controlled manner via ambient temperature single electron transfer initiation and propagation through the radical addition fragmentation chain transfer (SET-RAFT) method. The living nature of the polymerization was confirmed by the first-order kinetic plots, the linear relationships between molecular weights and the monomer conversions while keeping relatively narrow molecular weight distributions (Mw/Mn≤1.55), and the successful chain-extension with methyl methacrylate (MMA). The better controllability of SET-RAFT than other CRP methods is attributed to the less competitive termination in view of the presence of the chain transfer agent (CTA) as well as the Cu(II) that is generated in situ. Moreover, a one-pot/one-step technique combining SET-RAFT and“click chemistry”methods has been successfully employed to prepare the side-chain functionalized polymers.

引文

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