“绿色”、高效的ATRP催化体系的构建
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摘要
原子转移自由基聚合（ATRP）的出现为设计合成可控聚合物（可控的分子量和分子量分布）提供了一种简单、高效的方法。目前关于ATRP催化体系的研究热点主要有：（1）基于铁盐催化剂生物毒性小的特点发展高效铁盐催化的ATRP体系；（2）发展简便、低金属盐用量的高效ATRP催化体系；（3）保持控制性的前提下提高聚合反应速率的体系；（4）发展可回收的“绿色”、高效催化体系等方面。这些对ATRP聚合体系的发展都是为了采用高价金属催化并降低最终聚合物中金属盐的残留量来发展“绿色”、高效的ATRP。基于发展“绿色”、高效的ATRP催化体系的重要性，本论文的主要研究内容和结论如下：
(1)2005年，为了降低金属盐的用量，Matyjaszewski课题组成功的发明了相比常规ATRP和反向ATRP有较大优势的高价铜盐催化的电子转移生成催化剂的原子转移自由基聚合（AGET ATRP）技术。尽管铁盐催化剂的控制性相比铜盐和钌盐较差，但铁盐由于其低毒性，丰富性和良好的生物相容性引起了人们广泛的关注。因此基于AGET ATRP技术和高价铁盐催化剂的优势，本论文首先发展了一系列“绿色”、高效铁盐催化下的AGET ATRP。本文第四章成功采用可商品化的配体（三(3,6-二氧杂庚基)胺(TDA-1)）成功地用于铁盐（六水合三氯化铁（FeCl_3·6H_2O））催化的本体或溶液AGET ATRP体系中，反应还可以在空气氛围下直接密封进行，操作非常简便。接着建立了一个无需添加引发剂在一系列的膦配体（三苯基膦（TPP）或者1,4-双(二苯膦基)甲烷（BDPPM））作用铁盐催化的ATRP反应体系。同时对该体系的聚合机理进行了深入的讨论。同时实现了微量FeCl_3·6H_2O为催化剂，咪唑盐（BMIMPF6，BMIMBF_4，OMIMPF6和HMIMPF6）为配体铁盐催化下的高效AGET ATRP反应。最后，基于咪唑盐类配体和其他报道的铁盐配体，采用循环伏安法（CV）系统地考察常见的铁盐催化体系的的反应活性，为选择恰当的铁盐催化体系提供了保障，也为寻找更高效的ATRP催化体系奠定了坚实的基础。
(2)从ATRP通过降低体系中自由基浓度来达到可控聚合的原理可知，与常规的自由基聚合相比，ATRP聚合反应速率较慢，这不利于其工业化生产。因此在维持聚合过程良好控制性的前提下，提高聚合反应的速率变得尤其重要。本文第五章发现催化量的碱（NaOH, Na_3PO_4, NaHCO_3和Na_2CO_3等无机碱；吡啶，三乙胺等有机碱；中性、碱性氧化铝）存在下可以有效地提高铁盐催化AGET ATRP对苯乙烯（St）和甲基丙烯酸甲酯（MMA）单体的聚合速率，同时保持很好的聚合可控性且所有的聚合反应可以在空气氛围下直接密封进行，找到了一种加速ATRP的新方法。所有这些碱在提高聚合速率的同时可获得分子量分布窄的聚合物。碱存在下聚合反应的“活性”/可控特征可以通过扩链反应证明。通过循环伏安法证明了碱存在时对ATRP催化体系的影响。
(3)有机反应中利用温控配体的“温控相转移催化”（TRPTC）特性，成功地解决了水/有机两相体系适用范围受底物水溶性限制的问题。考虑到ATRP反应体系中过渡金属盐/有机配体配合物催化剂和有机配体的相似性，以及ATRP体系中油溶性单体和上述有机合成中水溶性极小的底物的相似性，可以设想如果采用具有温度响应的ATRP有机配体，则可以像在有机合成过程中报道的那样在ATRP过程中实现温控相转移催化过程。本文第六章在水/有机液液两相中，采用含PEG片段的二吡啶胺（PSDL）作为温敏性配体，RAFT试剂作为假卤素引发剂发展了一种可回收利用ATRP催化剂的TRPTC ATRP新方法。反应在90oC时，催化剂可以有效地转移进入有机相催化MMA进行均相反应，反应结束后冷却至室温(25oC)，催化剂从有机相中重新转移回水相中而可控的PMMA聚合物依然留在有机相中从而达到实现分离催化剂的目的。另外，由于TRPTC ATRP在不影响对聚合控制性的前提下，可以成功地在空气（氧气）存在下进行并通过简单的改变温度可实现回收催化剂的目的。
The advent of atom transfer radical polymerization (ATRP) provides a simple way tosynthesize well-defined polymers with controlled molecular weights and narrow molecularweight distributions. Current research of ATRP catalyst system is mainly focused on:(1)developing highly efficient iron-mediated ATRP catalyst system based on itscharacteristics of low toxicity, abundance and biocompatibility;(2) exploring high-activecatalysts to reduce of the amount of transition metal;(3) enhancing polymerization ratewhile maintaining controllability;(4) designing “green”, recyclable and efficient ATRPcatalytic system. These new ATRP techniques for construction of “green” and highlyefficient ATRP catalytic system have been developed by employing higher oxidation statecatalyst (i.e., Cu(II) complex) and reduceing the amount of catalyst. In view of “green” andhighly efficient ATRP, the main contents and conclusions are summarized as follows:
(1) In order to overcome some drawbacks of normal ATRP and reverse ATRP, animproved ATRP technique, copper-mediated activators generated by electron transfer forATRP (AGET ATRP) process, has been developed by Matyjaszewski’s group in2005.Iron has attracted extensive attentions owing to its low toxicity, being readily abundant,and biocompatibility though its complexes are generally considered to be inferior to copperor ruthenium complexes for the control of polymerization. Based on the advantage ofAGET ATRP and iron salts, a series of “green”, efficient iron-mediated AGET ATRP weredeveloped. In chapter Ⅳ, commercially available ligand (tris(3,6-dioxaheptyl)amine,TDA-1) was successfully used for iron(III)-mediated activator generated by electrontransfer atom transfer radical polymerization (AGET ATRP) of St in bulk or solution.Polymerization can also be directly performed in the presence of limited amount of air,which makes operation quite easy. A series of phosphorus-containing ligands wereemployed to establish a novel polymerization system for the iron(III)-mediatedpolymerization of methyl methacrylate (MMA) solely using FeCl_3·6H_2O or FeBr3as thecatalyst without any additional initiators or reducing agents. And the mechanism withoutadditional initiators was discussed in detail. A series of commercially available imidazole salt were used as a novel ligand for activator generated by electron transfer atom transferradical polymerization (AGET ATRP) of MMA in bulk or solution mediated by ppm levelof iron(III) catalyst. Then, values of cyclic voltammetry (CV) for the FeCl_3.6H_2Ocomplexes in the presence of different ligand were measured using acetonitrile as thesolvent to choice highly select efficient catalytic systems, which provides a guildline forselection of proper iron catalysts in application.
(2) Compared with conventional radical polymerization, ATRP shows much slowerpolymerization rate, which is not favourable in commercial process. It becomes animportant goal for chemists to enhance the polymerization rate while keeping goodcontrollability for polymerization. In chapter Ⅴ, we reported that a series of catalyticamounts of base (inorganic bases (i.e., NaOH, Na_3PO_4, NaHCO_3and Na_2CO_3) and organicbases such as pyridine and triethylamine or neutral and basic Al2O_3) can enhance thepolymerization rate of the iron-mediated AGET ATRP of styrene with controlledmolecular weights and molecular weight distributions. It is noted that all thepolymerizations of novel rate-enhancement methods can also be carried out in the presenceof limited amounts of air. The nature of “living”/controlled free radical polymerization inthe presence of base was confirmed by chain extension experiments. Cyclic voltammetry(CV) measuments proves that base play an important role in ATRP catalytic systems.
(3) Thermoregulated phase-transfer catalysis (TRPTC) system based on a cloud pointof nonionic ligands is becoming especially spectacular due to its facile separation just bychanging the temperature of the reaction system, and it has been successfully applied invarious types of organic reactions. Importantly, ATRP reaction system and the oil solublemonomers are similar in the aspects of the transition metal salt, ligand and substrates inorganic reaction, respectively. TRPTC system can be successfully applied in ATRP basedon the samilarlity with a cloud point of nonionic ligands in organic reaction system. Inchapter Ⅵ, a novel strategy via thermoregulated phase-transfer catalysis (TRPTC) toseparate catalyst in aqueous/organic biphasic system has been successfully established in acopper-mediated atom transfer radical polymerization (ATRP) of methyl methacrylate(MMA), using a thermo-responsive PEG-supported dipyridyl ligand (PSDL) as the ligandand RAFT agent as the initiator. The catalyst complex can transfer into the organic phasefrom initial aqueous catalyst solution at the reaction temperature (90oC) to catalyze thehomogeneous polymerization of MMA, then it retransfer into the aqueous solution from the organic phase to separate the catalyst from the polymerization solution once cooled toroom temperature (25oC) while keeping well-controlled product (PMMA) in organic layer.In addition, TRPTC ATRP can be conducted in the presence of a limited amount of air,without sacrificing the controllability over polymerization; in addition the catalyst can berecycled simply yet effectively by changing of the temperature.
(1)2005年，为了降低金属盐的用量，Matyjaszewski课题组成功的发明了相比常规ATRP和反向ATRP有较大优势的高价铜盐催化的电子转移生成催化剂的原子转移自由基聚合（AGET ATRP）技术。尽管铁盐催化剂的控制性相比铜盐和钌盐较差，但铁盐由于其低毒性，丰富性和良好的生物相容性引起了人们广泛的关注。因此基于AGET ATRP技术和高价铁盐催化剂的优势，本论文首先发展了一系列“绿色”、高效铁盐催化下的AGET ATRP。本文第四章成功采用可商品化的配体（三(3,6-二氧杂庚基)胺(TDA-1)）成功地用于铁盐（六水合三氯化铁（FeCl_3·6H_2O））催化的本体或溶液AGET ATRP体系中，反应还可以在空气氛围下直接密封进行，操作非常简便。接着建立了一个无需添加引发剂在一系列的膦配体（三苯基膦（TPP）或者1,4-双(二苯膦基)甲烷（BDPPM））作用铁盐催化的ATRP反应体系。同时对该体系的聚合机理进行了深入的讨论。同时实现了微量FeCl_3·6H_2O为催化剂，咪唑盐（BMIMPF6，BMIMBF_4，OMIMPF6和HMIMPF6）为配体铁盐催化下的高效AGET ATRP反应。最后，基于咪唑盐类配体和其他报道的铁盐配体，采用循环伏安法（CV）系统地考察常见的铁盐催化体系的的反应活性，为选择恰当的铁盐催化体系提供了保障，也为寻找更高效的ATRP催化体系奠定了坚实的基础。
(2)从ATRP通过降低体系中自由基浓度来达到可控聚合的原理可知，与常规的自由基聚合相比，ATRP聚合反应速率较慢，这不利于其工业化生产。因此在维持聚合过程良好控制性的前提下，提高聚合反应的速率变得尤其重要。本文第五章发现催化量的碱（NaOH, Na_3PO_4, NaHCO_3和Na_2CO_3等无机碱；吡啶，三乙胺等有机碱；中性、碱性氧化铝）存在下可以有效地提高铁盐催化AGET ATRP对苯乙烯（St）和甲基丙烯酸甲酯（MMA）单体的聚合速率，同时保持很好的聚合可控性且所有的聚合反应可以在空气氛围下直接密封进行，找到了一种加速ATRP的新方法。所有这些碱在提高聚合速率的同时可获得分子量分布窄的聚合物。碱存在下聚合反应的“活性”/可控特征可以通过扩链反应证明。通过循环伏安法证明了碱存在时对ATRP催化体系的影响。
(3)有机反应中利用温控配体的“温控相转移催化”（TRPTC）特性，成功地解决了水/有机两相体系适用范围受底物水溶性限制的问题。考虑到ATRP反应体系中过渡金属盐/有机配体配合物催化剂和有机配体的相似性，以及ATRP体系中油溶性单体和上述有机合成中水溶性极小的底物的相似性，可以设想如果采用具有温度响应的ATRP有机配体，则可以像在有机合成过程中报道的那样在ATRP过程中实现温控相转移催化过程。本文第六章在水/有机液液两相中，采用含PEG片段的二吡啶胺（PSDL）作为温敏性配体，RAFT试剂作为假卤素引发剂发展了一种可回收利用ATRP催化剂的TRPTC ATRP新方法。反应在90oC时，催化剂可以有效地转移进入有机相催化MMA进行均相反应，反应结束后冷却至室温(25oC)，催化剂从有机相中重新转移回水相中而可控的PMMA聚合物依然留在有机相中从而达到实现分离催化剂的目的。另外，由于TRPTC ATRP在不影响对聚合控制性的前提下，可以成功地在空气（氧气）存在下进行并通过简单的改变温度可实现回收催化剂的目的。
The advent of atom transfer radical polymerization (ATRP) provides a simple way tosynthesize well-defined polymers with controlled molecular weights and narrow molecularweight distributions. Current research of ATRP catalyst system is mainly focused on:(1)developing highly efficient iron-mediated ATRP catalyst system based on itscharacteristics of low toxicity, abundance and biocompatibility;(2) exploring high-activecatalysts to reduce of the amount of transition metal;(3) enhancing polymerization ratewhile maintaining controllability;(4) designing “green”, recyclable and efficient ATRPcatalytic system. These new ATRP techniques for construction of “green” and highlyefficient ATRP catalytic system have been developed by employing higher oxidation statecatalyst (i.e., Cu(II) complex) and reduceing the amount of catalyst. In view of “green” andhighly efficient ATRP, the main contents and conclusions are summarized as follows:
(1) In order to overcome some drawbacks of normal ATRP and reverse ATRP, animproved ATRP technique, copper-mediated activators generated by electron transfer forATRP (AGET ATRP) process, has been developed by Matyjaszewski’s group in2005.Iron has attracted extensive attentions owing to its low toxicity, being readily abundant,and biocompatibility though its complexes are generally considered to be inferior to copperor ruthenium complexes for the control of polymerization. Based on the advantage ofAGET ATRP and iron salts, a series of “green”, efficient iron-mediated AGET ATRP weredeveloped. In chapter Ⅳ, commercially available ligand (tris(3,6-dioxaheptyl)amine,TDA-1) was successfully used for iron(III)-mediated activator generated by electrontransfer atom transfer radical polymerization (AGET ATRP) of St in bulk or solution.Polymerization can also be directly performed in the presence of limited amount of air,which makes operation quite easy. A series of phosphorus-containing ligands wereemployed to establish a novel polymerization system for the iron(III)-mediatedpolymerization of methyl methacrylate (MMA) solely using FeCl_3·6H_2O or FeBr3as thecatalyst without any additional initiators or reducing agents. And the mechanism withoutadditional initiators was discussed in detail. A series of commercially available imidazole salt were used as a novel ligand for activator generated by electron transfer atom transferradical polymerization (AGET ATRP) of MMA in bulk or solution mediated by ppm levelof iron(III) catalyst. Then, values of cyclic voltammetry (CV) for the FeCl_3.6H_2Ocomplexes in the presence of different ligand were measured using acetonitrile as thesolvent to choice highly select efficient catalytic systems, which provides a guildline forselection of proper iron catalysts in application.
(2) Compared with conventional radical polymerization, ATRP shows much slowerpolymerization rate, which is not favourable in commercial process. It becomes animportant goal for chemists to enhance the polymerization rate while keeping goodcontrollability for polymerization. In chapter Ⅴ, we reported that a series of catalyticamounts of base (inorganic bases (i.e., NaOH, Na_3PO_4, NaHCO_3and Na_2CO_3) and organicbases such as pyridine and triethylamine or neutral and basic Al2O_3) can enhance thepolymerization rate of the iron-mediated AGET ATRP of styrene with controlledmolecular weights and molecular weight distributions. It is noted that all thepolymerizations of novel rate-enhancement methods can also be carried out in the presenceof limited amounts of air. The nature of “living”/controlled free radical polymerization inthe presence of base was confirmed by chain extension experiments. Cyclic voltammetry(CV) measuments proves that base play an important role in ATRP catalytic systems.
(3) Thermoregulated phase-transfer catalysis (TRPTC) system based on a cloud pointof nonionic ligands is becoming especially spectacular due to its facile separation just bychanging the temperature of the reaction system, and it has been successfully applied invarious types of organic reactions. Importantly, ATRP reaction system and the oil solublemonomers are similar in the aspects of the transition metal salt, ligand and substrates inorganic reaction, respectively. TRPTC system can be successfully applied in ATRP basedon the samilarlity with a cloud point of nonionic ligands in organic reaction system. Inchapter Ⅵ, a novel strategy via thermoregulated phase-transfer catalysis (TRPTC) toseparate catalyst in aqueous/organic biphasic system has been successfully established in acopper-mediated atom transfer radical polymerization (ATRP) of methyl methacrylate(MMA), using a thermo-responsive PEG-supported dipyridyl ligand (PSDL) as the ligandand RAFT agent as the initiator. The catalyst complex can transfer into the organic phasefrom initial aqueous catalyst solution at the reaction temperature (90oC) to catalyze thehomogeneous polymerization of MMA, then it retransfer into the aqueous solution from the organic phase to separate the catalyst from the polymerization solution once cooled toroom temperature (25oC) while keeping well-controlled product (PMMA) in organic layer.In addition, TRPTC ATRP can be conducted in the presence of a limited amount of air,without sacrificing the controllability over polymerization; in addition the catalyst can berecycled simply yet effectively by changing of the temperature.
引文
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105. Tsarevsky, N. V.; Matyjaszewski, K.“Green” Atom Transfer Radical Polymerization:From Process Design to Preparation of Well-defined Environmentally-friendlyPolymeric Materials. Chem. Rev.2007,107,2270-2299.
106. Tsarevsky, N. V.; Bernaerts, K. V.; Dufour, B.; Du Prez, F. E.; Matyjaszewski, K.Well-defined (Co)Polymers with5-Vinyltetrazole Units via Combination of AtomTransfer Radical (Co)Polymerization of Acrylontrile and “Click Chemistry”-TypePostpolymerization Modification. Macromolecules2004,37,9308-9313.
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108. Qi, K.; Ma, Q.; Remsen, E. E.; Clark, C. G.; Wooley, K. L. Determination of theBioavailability of Biotin Conjugated onto Shell Cross-linked (SCK) Nanoparticles. J.Am. Chem. Soc.2004,126,6599-6607.
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115. Li, M.; Min, K.; Matyjaszewski, K. ATRP in Waterborne Miniemulsion via aSimultaneous Reverse and Normal Initiation Process. Macromolecules2004,37,2106-2112.
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121. Min, K.; Jakubowski, W.; Matyjaszewski, K. AGET ATRP in the Presence of Air inMiniemulsion and in Bulk. Macromol. Rapid Commun.2006,27,594-598.
122. Liu, Y. H.; Miao, X. L.; Zhu, J.; Zhang, Z. B.; Cheng, Z. P. Zhu, X. L.Polymer-Grafted Modification of Activated Carbon by Surface-Initiated AGETATRP. Macromol. Chem. Phys.2012,213,868-877.
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124. Aimi, J.; McCullough, L. A.; Matyjaszewski, K. Synthesis of Poly(vinylacetylene)Block Copolymers by Atom Transfer Radical Polymerization. Macromolecules2008,41,9522-9524.
125. Jakubowski, W; Matyjaszewski, K. Activators Regenerated by Electron Transfer forAtom-Transfer Radical Polymerization of (Meth)acrylates and Related BlockCopolymers. Angew. Chem., Int. Ed.2006,45,4482-4486.
126. Tang, H.; Radosz, M.; Shen, Y. CuBr2/N,N,N′,N′-Tetra[(2-pyridal)methyl]-ethylenediamine/Tertiary Amine as a Highly Active and Versatile Catalyst forAtom-Transfer Radical Polymerization via Activator Generated by Electron Transfer.Macromol. Rapid. Commun.2006,27,1127-1131.
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130. Dong, H. C.; Matyjaszewski, K. ARGET ATRP of2-(Dimethylamino)ethylMethacrylate as an Intrinsic Reducing Agent. Macromolecules2008,41,6868-6870.
131. Hu, Z. Q.; Shen, X. R.; Qiu, H. Y.; Lai, G. Q.; Wu, J. R.; Li, W. Q. AGET ATRP ofMethyl Methacrylate with Poly(ethylene glycol)(PEG) as Solvent and TMEDA asBoth Ligand and Reducing Agent. Eur. Polym. J.2009,45,2313-2318.
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138. Jakubowski, W.; Matyjaszewski, K. New Segmented Copolymers by Combination ofAtom Transfer Radical Polymerization and Ring Opening Polymerization. Macromol.Symp.2006,240,213-223.
139. Wu, D. X.; Yang, Y. F.; Cheng, X. H.; Liu, L.; Tian, J.; Zhao, H. Y. Mixed MolecularBrushes with PLLA and PS Side Chains Prepared by AGET ATRP andRing-Opening Polymerization. Macromolecules2006,39,7513-7519.
140. Wu, D. X.; Zhao, C. Z.; Tian, J.; Zhao, H. Y. Synthesis of PLLA-PEOMAComb-block-comb Type Molecular Brushes Based on AGET ATRP andRing-Opening Polymerization. Polym. Int.2009,58,1335-1340.
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142. Kwiatkowski, P.; Jurczak, J.; Pietrasik, J.; Jakubowski, W.; Mueller, L.;Matyjaszewski, K. High Molecular Weight Polymethacrylates by AGET ATRP underHigh Pressure. Macromolecules2008,41,1067-1069.
143. Kwak, Y. W.; Magenau, A. J. D.; Matyjaszewski, K. ARGET ATRP of MethylAcrylate with Inexpensive Ligands and ppm Concentrations of Catalyst.Macromolecules2011,44,811-819.
144. Qiu, J.; Charleux, B.; Matyjaszewski, K. Controlled/Living Radical Polymerization inAqueous Media: Homogeneous and Heterogeneous Systems. Prog. Polym. Sci.2001,26,2083-2134.
145. Cunningham, M. F. Living/Controlled Radical Polymerizations in Dispersed PhaseSystems. Prog. Polym. Sci.2002,27,1039-1067.
146. Sawamoto, M.; Kamigaito, M. Synthesis of Defined Polymer Architectures.Macromol. Symp.2002,177,17-24.
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