一锅法合成两亲性接枝和多嵌段共聚物的研究
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摘要
具有复杂结构共聚物的设计与合成是目前高分子合成化学研究的热点之一在过去十几年中,各种活性聚合技术得到了飞速发展和广泛应用。将多种活性聚合技术与高效的偶合反应相结合,是高分子合成化学中最常用的手段。一锅法技术由于可将多种反应于一锅中进行从而可减少反应纯化等操作而得到越来越多的重视。利用这种方法,可以简便地设计和合成出各种线性和非线性结构(梳型、星型、树枝状、环型等)的共聚物。这些共聚物结构的特殊性使其具有独特的微相形态与自组装行为,并且在化学、材料、物理、生物等领域中有着潜在的用途。
本论文主要利用高效的偶合反应,如"click"化学、原子转移氮氧自由基偶合反应(ATNRC)以及单电子转移氮氧自由基偶合反应(SET-NRC)和活性聚合技术(SET-LRP)进行一锅法反应,结合阴离子聚合、开环聚合(ROP)与原子转移自由基聚合(ATRP)技术,设计合成了具有不同结构的、组分复杂的共聚物。利用1H NMR、SEC、FT-IR等对中间产物和目标聚合物进行了详细的表征,明确了共聚物的结构。本文完成的主要工作如下：
1、通过把ATNRC反应和“click”化学结合,一锅法制备了ABA型嵌段接枝共聚物(PEO-g-PS)-b-(PEO-g-PtBA)-b-(PEO-g-PS)。首先,合成了带有环氧基团的功能性单体4-缩水甘油基-2,2,6,6-四甲基哌啶氮氧自由基(GTEMPO)和1-乙氧基乙基-2,3-环氧丙醚(EEGE),采用阴离子开环聚合的方法,使GTEMPO和EEGE依次与环氧乙烷(EO)进行阴离子开环聚合,得到具有2,2,6,6-四甲基哌啶氮氧自由基(TEMPO)和乙氧基乙基保护羟基的聚环氧乙烷(PEO)主链。通过对共聚物侧基进行一系列的修饰(水解、酯化、叠氮化反应),制得含有多个叠氮和TEMPO侧基的PEO聚合物主链。然后,运用ATRP技术合成含有溴端基的聚丙烯酸叔丁酯(PtBA-Br)。通过选择环氧乙烷(EO)作为小分子“盖帽”试剂,对“活性”聚苯乙烯阴离子进行封端反应,并接着对其端基进行修饰得到含有炔基的聚苯乙烯(PS-Alkyne).最后进行主链与侧链(PtBA-Br, PS-Alkyne)间的‘'click"化学和ATNRC一锅法反应,得到PEO为主链,PS、PtBA为侧链的两亲性ABA型嵌段接枝共聚物。研究了催化剂体系对一锅法反应的影响。
2、在零价铜(Cu(0))/N,N,N',N",N"-五甲基二乙基三胺(PMDETA)的催化下,运用单电子转移活性自由基聚合(SET-LRP)技术和"click"化学,一锅法制备三嵌段共聚物PS-b-PEO-b-PtBA。首先,以2-(1-乙氧基乙氧基)乙氧醇钾作为引发剂,引发环氧乙烷进行阴离子开环聚合,合成带有乙氧基乙基保护羟基与活性羟基的异端功能化聚环氧乙烷。经过一系列端基修饰后,得到含有炔基和溴基团的聚环氧乙烷(Br-PEO-Alkyne).同时运用ATRP技术合成含有溴端基的聚苯乙烯(PS-Br),将溴端基通过亲核取代反应转变为叠氮基团,得到端基为叠氮基团的聚苯乙烯(PS-N3)。在零价铜和PMDETA的存在下,PEO的溴端基按照SET-LRP机理引发丙烯酸叔丁酯(tBA)单体聚合,SET-LRP反应过程中通过SET机理产生的一价铜被直接利用来催化PS的叠氮基团和PEO的炔基团间的"click"偶合反应,最终通过一锅法反应制得三嵌段共聚物PS-b-PEO-b-PtBA。
3、将单电子转移氮氧自由基偶合(SET-NRC)技术和‘"click"化学结合,在零价铜催化下进行一锅法反应,制备三嵌段共聚物。首先制备一系列前驱体,具有TEMPO基团与炔基的异端功能化聚环氧乙烷,端基为溴的聚苯乙烯(PS-Br)和聚丙烯酸叔丁酯(PtBA-Br),端基为叠氮的聚苯乙烯(PS-N3)和聚丙烯酸叔丁酯(PtBA-N3)。然后在这些前驱体间进行一锅法反应：溴基团与氮氧自由基基团间进行SET-NRC偶合反应,接着叠氮与炔基团间进行"click"化学反应。其中引人注目的是SET-NRC反应中产生的一价铜被利用于催化‘'click"化学。为了评估零价铜对此种一锅法反应技术的影响,用不同零价铜(纳米铜、还原铜)进行对比实验,结果发现还原生成的活性比表面积高的零价铜能显著加速SET-NRC和"click"化学的一锅法反应。
The design and synthesis of copolymers with complex architectures are always pursued by polymer chemists. In the past decade, there is tremendous development in controlled polymerization technique. It is the most useful method in polymer synthesis chemistry by combination of the multiple polymerization mechanism and highly efficient coupling methods. One-pot strategy has gained increasing attention in the synthesis of different polymer architectures, because it can reduce the steps of reaction and purification. By means of these methods, a variety of linear and nonlinear (such as comb-shaped, star-shaped, dendritic, cyclic) copolymers are tailored and synthesized. They may show quite different microdomain morphologies in bulk and self-assembly behavior in solution, which have great potential applications in chemistry, materials, physics and biology.
In this thesis, a series of copolymers with complex structures (amphiphilic graft copolymers and triblock copolymers) were synthesized via one-pot strategy by combination of highly efficient coupling reactions ("click" chemistry, ATNRC reaction and SET-NRC reaction) with controlled/"living" polymerization (SET-LRP, anionic polymerization, ROP and ATRP). All the intermediates and target products were characterized by different means such as SEC,1H NMR and FT-IR etc in detail. The main work done in this thesis shows as follows:
1. A new strategy for one-pot preparation of ABA-type block-graft copolymers via a combination of atom transfer nitroxide radical coupling (ATNRC) reaction with "click" chemistry was completed. Firstly, sequential ring-opening polymerization (ROP) of 4-glycidyloxy-2,2,6,6-tetramethyl piperidine-1-oxyl (GTEMPO) and ethoxyethyl glycidyl ether (EEGE) was proceeded for backbone with pended TEMPO and ethoxyethyl-protected hydroxyl groups, which were recovered by hydrolysis and esterified with 2-bromoisobutyryl bromide and subsequently converted into azide groups by NaN3. Then, bromine-containing poly(tert-butyl acrylate) (PtBA-Br) was synthesized by atom transfer radical polymerization (ATRP). Alkyne-containing polystyrene (PS-alkyne) was prepared by capping polystyryl-lithium with ethylene oxide (EO) and subsequent modification by propargyl bromide. Finally, one-pot reaction of "click" chemistry and ATNRC reaction was proceeded simultaneously between backbone and side chains(PtBA-Br, PS-alkyne), and the amphiphilic ABA-type block-graft copolymer with PEO as main chain, PS and PtBA as side chains was obtained. The effects of catalyst systems on the one-pot reaction were discussed.
2. Triblock copolymers of polystyrene-block-poly(ethylene oxide)-block-poly (tert-butyl acrylate) (PS-6-PEO-b-PtBA) were prepared via combination of single electron transfer living radical polymerization (SET-LRP) with "click" chemistry using Cu(0)/N,N,N',N",N"-pentamethyldiethylenetriamine (PMDETA) as catalyst system. Theα,ω-hetero-functionalized PEO with an ethoxyethyl-protected hydroxyl group and an active hydroxyl group was synthesized via anionic ring-opening polymerization (ROP) of ethylene oxide (EO) using potassium 2-(1-ethoxyethoxy) ethoxide as initiator. After further modifications of the end groups, the PEO with alkyne and bromine groups was obtained. Meanwhile, bromine-terminated polystyrene (PS-Br) was synthesized by atom transfer radical polymerization (ATRP), then the bromine end groups were transformed to azide groups by nucleophilic substitution reaction in N, N-dimethylformamide (DMF) in the presence of excessive sodium azide. Lastly, in the presence of Cu(0)/PMDETA, bromine end group of PEO initiated the polymerization of tert-butyl acrylate (tBA) by SET-LRP, the formed Cu(Ⅰ) in situ was used directly to catalyze the "click" coupling between azide group of PS and alkyne group of PEO. Thus the triblock copolymers PS-b-PEO-b-PtBA could be prepared by one-pot strategy.
3. Cu(0) catalyzed one-pot strategy by combination of single electron transfer-nitroxide radical coupling (SET-NRC) reaction with "click" chemistry was carried out in the synthesis of ABC triblock copolymers. Firstly, the precursorsα,ω-heterofunctionalized poly(ethylene oxide) (PEO) with a 2,2,6,6-tetramethyl-piperidine-1-oxyl (TEMPO) group and an alkyne group, polystyrene (PS) and poly(tert-butyl acrylate) (PtBA) with bromine or azide end group, were designed and synthesized respectively. Then the one-pot coupling reactions between these precursors were carried out:The SET-NRC reaction between bromine group and nitroxide radical group, subsequently "click" coupling between azide and alkyne group. It was noticeable that Cu(Ⅰ) generated from Cu(0) by SET mechanism was utilized to catalyze "click" chemistry in situ. In order to estimate the effect of Cu(0) on the one-pot reaction, a comparative analysis was performed in presence of different Cu(0) species(nanosized Cu(0), reduction Cu(0)). The result showed that reduction Cu(0) with more active surface area could accelerate the one-pot reaction of SET-NRC and "click" chemistry significantly.
本论文主要利用高效的偶合反应,如"click"化学、原子转移氮氧自由基偶合反应(ATNRC)以及单电子转移氮氧自由基偶合反应(SET-NRC)和活性聚合技术(SET-LRP)进行一锅法反应,结合阴离子聚合、开环聚合(ROP)与原子转移自由基聚合(ATRP)技术,设计合成了具有不同结构的、组分复杂的共聚物。利用1H NMR、SEC、FT-IR等对中间产物和目标聚合物进行了详细的表征,明确了共聚物的结构。本文完成的主要工作如下：
1、通过把ATNRC反应和“click”化学结合,一锅法制备了ABA型嵌段接枝共聚物(PEO-g-PS)-b-(PEO-g-PtBA)-b-(PEO-g-PS)。首先,合成了带有环氧基团的功能性单体4-缩水甘油基-2,2,6,6-四甲基哌啶氮氧自由基(GTEMPO)和1-乙氧基乙基-2,3-环氧丙醚(EEGE),采用阴离子开环聚合的方法,使GTEMPO和EEGE依次与环氧乙烷(EO)进行阴离子开环聚合,得到具有2,2,6,6-四甲基哌啶氮氧自由基(TEMPO)和乙氧基乙基保护羟基的聚环氧乙烷(PEO)主链。通过对共聚物侧基进行一系列的修饰(水解、酯化、叠氮化反应),制得含有多个叠氮和TEMPO侧基的PEO聚合物主链。然后,运用ATRP技术合成含有溴端基的聚丙烯酸叔丁酯(PtBA-Br)。通过选择环氧乙烷(EO)作为小分子“盖帽”试剂,对“活性”聚苯乙烯阴离子进行封端反应,并接着对其端基进行修饰得到含有炔基的聚苯乙烯(PS-Alkyne).最后进行主链与侧链(PtBA-Br, PS-Alkyne)间的‘'click"化学和ATNRC一锅法反应,得到PEO为主链,PS、PtBA为侧链的两亲性ABA型嵌段接枝共聚物。研究了催化剂体系对一锅法反应的影响。
2、在零价铜(Cu(0))/N,N,N',N",N"-五甲基二乙基三胺(PMDETA)的催化下,运用单电子转移活性自由基聚合(SET-LRP)技术和"click"化学,一锅法制备三嵌段共聚物PS-b-PEO-b-PtBA。首先,以2-(1-乙氧基乙氧基)乙氧醇钾作为引发剂,引发环氧乙烷进行阴离子开环聚合,合成带有乙氧基乙基保护羟基与活性羟基的异端功能化聚环氧乙烷。经过一系列端基修饰后,得到含有炔基和溴基团的聚环氧乙烷(Br-PEO-Alkyne).同时运用ATRP技术合成含有溴端基的聚苯乙烯(PS-Br),将溴端基通过亲核取代反应转变为叠氮基团,得到端基为叠氮基团的聚苯乙烯(PS-N3)。在零价铜和PMDETA的存在下,PEO的溴端基按照SET-LRP机理引发丙烯酸叔丁酯(tBA)单体聚合,SET-LRP反应过程中通过SET机理产生的一价铜被直接利用来催化PS的叠氮基团和PEO的炔基团间的"click"偶合反应,最终通过一锅法反应制得三嵌段共聚物PS-b-PEO-b-PtBA。
3、将单电子转移氮氧自由基偶合(SET-NRC)技术和‘"click"化学结合,在零价铜催化下进行一锅法反应,制备三嵌段共聚物。首先制备一系列前驱体,具有TEMPO基团与炔基的异端功能化聚环氧乙烷,端基为溴的聚苯乙烯(PS-Br)和聚丙烯酸叔丁酯(PtBA-Br),端基为叠氮的聚苯乙烯(PS-N3)和聚丙烯酸叔丁酯(PtBA-N3)。然后在这些前驱体间进行一锅法反应：溴基团与氮氧自由基基团间进行SET-NRC偶合反应,接着叠氮与炔基团间进行"click"化学反应。其中引人注目的是SET-NRC反应中产生的一价铜被利用于催化‘'click"化学。为了评估零价铜对此种一锅法反应技术的影响,用不同零价铜(纳米铜、还原铜)进行对比实验,结果发现还原生成的活性比表面积高的零价铜能显著加速SET-NRC和"click"化学的一锅法反应。
The design and synthesis of copolymers with complex architectures are always pursued by polymer chemists. In the past decade, there is tremendous development in controlled polymerization technique. It is the most useful method in polymer synthesis chemistry by combination of the multiple polymerization mechanism and highly efficient coupling methods. One-pot strategy has gained increasing attention in the synthesis of different polymer architectures, because it can reduce the steps of reaction and purification. By means of these methods, a variety of linear and nonlinear (such as comb-shaped, star-shaped, dendritic, cyclic) copolymers are tailored and synthesized. They may show quite different microdomain morphologies in bulk and self-assembly behavior in solution, which have great potential applications in chemistry, materials, physics and biology.
In this thesis, a series of copolymers with complex structures (amphiphilic graft copolymers and triblock copolymers) were synthesized via one-pot strategy by combination of highly efficient coupling reactions ("click" chemistry, ATNRC reaction and SET-NRC reaction) with controlled/"living" polymerization (SET-LRP, anionic polymerization, ROP and ATRP). All the intermediates and target products were characterized by different means such as SEC,1H NMR and FT-IR etc in detail. The main work done in this thesis shows as follows:
1. A new strategy for one-pot preparation of ABA-type block-graft copolymers via a combination of atom transfer nitroxide radical coupling (ATNRC) reaction with "click" chemistry was completed. Firstly, sequential ring-opening polymerization (ROP) of 4-glycidyloxy-2,2,6,6-tetramethyl piperidine-1-oxyl (GTEMPO) and ethoxyethyl glycidyl ether (EEGE) was proceeded for backbone with pended TEMPO and ethoxyethyl-protected hydroxyl groups, which were recovered by hydrolysis and esterified with 2-bromoisobutyryl bromide and subsequently converted into azide groups by NaN3. Then, bromine-containing poly(tert-butyl acrylate) (PtBA-Br) was synthesized by atom transfer radical polymerization (ATRP). Alkyne-containing polystyrene (PS-alkyne) was prepared by capping polystyryl-lithium with ethylene oxide (EO) and subsequent modification by propargyl bromide. Finally, one-pot reaction of "click" chemistry and ATNRC reaction was proceeded simultaneously between backbone and side chains(PtBA-Br, PS-alkyne), and the amphiphilic ABA-type block-graft copolymer with PEO as main chain, PS and PtBA as side chains was obtained. The effects of catalyst systems on the one-pot reaction were discussed.
2. Triblock copolymers of polystyrene-block-poly(ethylene oxide)-block-poly (tert-butyl acrylate) (PS-6-PEO-b-PtBA) were prepared via combination of single electron transfer living radical polymerization (SET-LRP) with "click" chemistry using Cu(0)/N,N,N',N",N"-pentamethyldiethylenetriamine (PMDETA) as catalyst system. Theα,ω-hetero-functionalized PEO with an ethoxyethyl-protected hydroxyl group and an active hydroxyl group was synthesized via anionic ring-opening polymerization (ROP) of ethylene oxide (EO) using potassium 2-(1-ethoxyethoxy) ethoxide as initiator. After further modifications of the end groups, the PEO with alkyne and bromine groups was obtained. Meanwhile, bromine-terminated polystyrene (PS-Br) was synthesized by atom transfer radical polymerization (ATRP), then the bromine end groups were transformed to azide groups by nucleophilic substitution reaction in N, N-dimethylformamide (DMF) in the presence of excessive sodium azide. Lastly, in the presence of Cu(0)/PMDETA, bromine end group of PEO initiated the polymerization of tert-butyl acrylate (tBA) by SET-LRP, the formed Cu(Ⅰ) in situ was used directly to catalyze the "click" coupling between azide group of PS and alkyne group of PEO. Thus the triblock copolymers PS-b-PEO-b-PtBA could be prepared by one-pot strategy.
3. Cu(0) catalyzed one-pot strategy by combination of single electron transfer-nitroxide radical coupling (SET-NRC) reaction with "click" chemistry was carried out in the synthesis of ABC triblock copolymers. Firstly, the precursorsα,ω-heterofunctionalized poly(ethylene oxide) (PEO) with a 2,2,6,6-tetramethyl-piperidine-1-oxyl (TEMPO) group and an alkyne group, polystyrene (PS) and poly(tert-butyl acrylate) (PtBA) with bromine or azide end group, were designed and synthesized respectively. Then the one-pot coupling reactions between these precursors were carried out:The SET-NRC reaction between bromine group and nitroxide radical group, subsequently "click" coupling between azide and alkyne group. It was noticeable that Cu(Ⅰ) generated from Cu(0) by SET mechanism was utilized to catalyze "click" chemistry in situ. In order to estimate the effect of Cu(0) on the one-pot reaction, a comparative analysis was performed in presence of different Cu(0) species(nanosized Cu(0), reduction Cu(0)). The result showed that reduction Cu(0) with more active surface area could accelerate the one-pot reaction of SET-NRC and "click" chemistry significantly.
引文
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