原子转移自由基加成固载化催化剂
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摘要
多卤化物是一种重要的原子转移自由基聚合(ATRP)引发剂,它们能够引发多种单体进行聚合,并可以经过一步或多步反应合成多种结构的聚合物,如嵌段、接枝、星型、超支化聚合物等。如果能够测出多卤化物引发聚合的官能度,将对分子结构设计有重要意义。另一方面,由于过渡金属及其络合物的高催化效率及较低的价格,它们经常被广泛用于原子转移自由基加成(ATRA)和聚合中,但产品后处理较困难。如果能将催化剂通过物理或化学方法负载在某种载体上将可能解决以上问题,使产品与催化剂很好的分离,且还能够达到回收和重复使用的目的。
本论文进行了三部分研究工作,第一部分:通过多步反应对硅胶进行改性合成了一种多齿胺改性硅胶配体,合成过程如下:1)通过γ-氨丙基三甲氧基硅烷(γ-APS)与硅胶表面的硅羟基反应,使硅胶表面带有氨基;2)利用硅胶表面氨基与过量的三羟甲基丙烷三丙烯酸酯(TMPTA)发生Michael加成反应;3)利用二乙烯三胺(DETA)与TMPTA改性硅胶表面未反应的双键发生反应使硅胶表面氨基化;4)最后用丙烯酸正丁酯(BA)与DETA改性硅胶表面氨基充分反应成功合多齿胺改性硅胶配体。通过核磁C~(13)NMR、红外光谱(FTIR)及元素分析(EA)分析表明以上各步反应产物的结构及含氮量。此多齿胺改性硅胶配体被分别多次重复用于四氯化碳与甲基丙烯酸甲酯(MMA),三氯乙酸甲酯与苯乙烯(St)的ATRA反应中,通过气相色谱测定了原料的转化率随时间的变化,且通过核磁~1H NMR测定了产物的纯度,我们还进一步将此种多齿胺改性硅胶配体用于TCPP引发St的ATRP和MMTCB引发MMA的ATRP反应中,通过GPC测定所得聚合物的分子量。结果表明:成功合成了预期的多齿胺改性硅胶,此种配体的含氮量为2.5mmol/g。且此种多齿胺改性硅胶配体是ATRA反应很好的配体。在催化四氯化碳与MMA或三氯乙酸甲酯与St的ATRA反应中,此种配体至少可以重复使用7次,且第一次转化率在40h内可达到80%以上,第7次时仍可达到25%以上。但此种配体在用于ATRP反应时却不具有可控性。第二部分:通过多步反应合成了一种多齿胺改性磁性微球配体,合成过程如下:1)利用传统的共沉淀法合成纳米级的磁性四氧化三铁,并用油酸和十二烷基磺酸钠双层表面活性剂对其进行改性,制备稳定性好,能够很好的分散到极性溶剂中的磁流体。21以磁流体为种子,利用乳液聚合方法,以甲基丙烯酸甲酯和三羟甲基丙烷三丙烯酸酯为原料进行交联共聚而得到了表面带有双键的磁性高分子微球;3)利用二乙烯三胺(DETA)与磁性微球表面的双键发生Michael加成反应使硅胶表面氨基化;4)最后用丙烯酸正丁酯与DETA改性磁性微球表面氨基充分反应成功合成多齿胺改性磁性微球配体。通过表面元素分析(XPS)、红外光谱(FTIR)及元素分析(EA)分析表明以上各步反应产物的结构及含氮量。此多齿胺改性磁微球配体被分别多次重复用于四氯化碳与MMA和三氯乙酸甲酯与St的ATRA反应中,通过气相色谱测定了原料的转化率随时间变化。结果表明:成功合成了预期的多齿胺改性磁性微球,此种配体的含氮量约为1.0mmol/g。且此种多齿胺改性磁性微球是ATRA反应很好的配体。在催化四氯化碳与MMA和三氯乙酸甲酯与St的ATRA反应中,此种配体至少可以重复使用5次,且第一次转化率在40h内可达到80%以上,第5次时仍可达到35%以上。第三部分:以四氯化碳和三氯乙酸甲酯分别与苯乙烯(St)和甲基丙烯酸甲酯(MMA)发生原子转移自由基加成反应,合成了多官能卤化物1-苯基-1,3,3,3-四氯丙烷(TCPP)、2,2,4-三氯-4-苯基丁酸甲酯(MTCPB)、2,4,4,4-四氯-2-甲基丁酸甲酯(MMTCB)和2,2,4-三氯-4-甲基戊二酸二甲酯(DMTCMG),然后分别以TCPP和MTCPB为引发剂、CuCl为催化剂、2,2′-联吡啶为配体,进行St的ATRP反应;以MMTCB和DMTCMG为引发剂、CuCl为催化剂、2,2′-联吡啶为配体,进行MMA的ATRP反应。采用~1HNRM和凝胶渗透色谱(GPC)对聚合物结构和分子量进行分析表征。结果表明:聚合物分子量与单体转化率之间存在较好的线性关系;TCPP和MTCPB都是St的ATRP双官能度引发剂;MMTCB是MMA的单官能度引发剂;DMTCMG引发MMA聚合时官能度为1.5。
The polychloroalkanes is one kind of very important initiator of atom transfer radical polymerization (ATRP). They can initiate many kinds of monomers to synthesize different kinds of architectures via single-step or multistep reaction, such as block, graft, star and hyperbranched Copolymers and so on. If the functionality of the polychloroalkanes in polymerization could be determined clearly, it woulde be important for the design of macromolecular structure. On the other hand, transition metal complex have been widely used because of their good catalytic efficiency for the atom transfer radical addition (ATRA) and ATRP, but the postpurification of the product is difficult. Supporting catalyst on insoluble particles is a possible solution to this problem. Catalysts immobilized on insoluble particles by physics or chemistry method can be easily separated from the reaction mixture and be recycled and reused.
Three part of research works had been carried out in the dissertation. The first part: a kind of multidentate amine modified silica gel was synthesized through the following steps: (1) introduce the amino groups onto the surface of silica-gel by the treatment of surface silanol groups withγ-aminopropyl trimethoxy silane (γ-APS); (2) michael addition of excess trihydroxymethyl propyl triacrylate (TMPTA) to amino groups on the silica gel surface; (3) amidation of the unreacted double bonds of TMPTA on the surface of TMPTA modified silica gel with diethylenetriamine (DETA); (4) the multidentate amine modified silica gel was finally obtained by the reaction of amino groups on the surface of DETA modified silica gel with double bond of butyl acrylate (BA). Their chemical structures were confirmed by C~(13) NMR, infrared spectrum (FTIR) and the nitrogen content in the particles was determined by elemental analysis (EA). Then, the multidentate amine immobilized on silica gel was used as ligand for CuCl in ATRA of CCl_4 with MMA and methyl trichloroacetate with St repeatly. The conversion and purity of the product were determined through the gas chromatography and ~1H NMR respectively. Finally, the multidentate amine immobilized on silica gel was used as ligand for CuCl in ATRP of St initiated by TCPP and MMA initiated by MMTCB. The number average molecular weights of the polymers were determined through GPC. The results indicated that the multidentate amine modified silica gel ligand was synthesized successfully and the nitrogen content of this ligand is 2.5mmol/g. The multidentate amine modified silica gel is good catalytic ligand of ATRA reaction. This kind of ligand have been used seven times in the ATRA reaction of carbon tetrachloride with MMA and the methyl trichloroacetate with St, and the conversion for the first time reached above 80% in 40 hours, when the seventh time still exceeded 25%. But the multidentate amine modified silica gel ligand can not control ATRP reaction well. The second part: a kind of multidentate amine modified magnetic microspheres was synthesized through the following steps: (1) Fe_3O_4 magnetic nanoparticles were synthesized by the chemical co-precipitation and modified by oleic acid and sodium dodecyl sulfonate bilayer surfactants. The stability of the magnetic fluid is very good and can be dispersed well in polarity solvent. (2) The magnetic fluid was as seed and carried on the crossing linking copolymerization of methyl methacrylate(MMA) and trihydroxymethyl propyl triacrylate(TMPTA) through emulsion polymerition obtained the magnetic microspheres with the double bond on the surface. (3) amidation of the double bonds of magnetic microspheres on the surface with diethylenetriamine (DETA); (4) the multidentate amine modified magnetic microspheres was finally obtained by the reaction of amino groups on the surface of DETA modified magnetic microspheres with double bond of butyl acrylate (BA). Their chemical structures were confirmed by XPS, infrared spectrum (FTIR) and the nitrogen content in the particles was determined by elemental analysis (EA). Then, the multidentate amine immobilized on magnetic microspheres was used as ligand for CuCl in ATRA of CCl_4 with MMA and methyl trichloroacetate with St repeatly. The conversion and purity of the product were determined through the gas chromatography respectively. The results indicated that the multidentate amine modified magnetic microspheres ligand was synthesized successfully and the nitrogen content of this ligand is 1.0mmol/g. The multidentate amine modified silica gel is good catalytic ligand of ATRA reaction. This kind of ligand have been used five times in the ATRA reaction of carbon tetrachloride with MMA and the methyl trichloroacetate with St, and the conversion for the first time reached above 80% in 40 hours, when the fifth time still exceeded 35%. The third part: 1,1,1,3-tetrachloro-3-phenylpropane(TCPP), methyl 2,2,4-trichloro-4-phenylbutyrate(MTCPB), methyl 2-methyl-2,4,4,4-tetrarchlorobutyrate(MMTCB) and dimethyl 2,2,4-trichloro-4- methyl -glutarate (DMTCMG) have been synthesized via ATRA from styrene (St) and methyl methacrylate (MMA) with carbon tetrachloride and methyl trichloroacetate respectively. When the TCPP and MTCPB were used as initiators for ATRP of St and the MMTCB and DMTCMG were used as initiators for ATRP of MMA in the presence of the cuprous chloride (CuCl)/ 2, 2'-bipyridine catalyst system respectively, a controlled polymerization process was achieved with the resulting polystyrene (PS) and polymethyl methacrylate (PMMA) having number average molecular weights which increased with monomer conversion and narrow molecular weight distributions. The number average molecular weights and structure of the PS and PMMA characterized by ~1H NMR and gel permeation chromatography (GPC) showed that TCPP and MTCPB both act as bifunctional initiators for the ATRP of St and the functionalities of MMTCB and DMTCMG for the ATRP of MMA were 1.0 and 1.5 respectively.
本论文进行了三部分研究工作,第一部分:通过多步反应对硅胶进行改性合成了一种多齿胺改性硅胶配体,合成过程如下:1)通过γ-氨丙基三甲氧基硅烷(γ-APS)与硅胶表面的硅羟基反应,使硅胶表面带有氨基;2)利用硅胶表面氨基与过量的三羟甲基丙烷三丙烯酸酯(TMPTA)发生Michael加成反应;3)利用二乙烯三胺(DETA)与TMPTA改性硅胶表面未反应的双键发生反应使硅胶表面氨基化;4)最后用丙烯酸正丁酯(BA)与DETA改性硅胶表面氨基充分反应成功合多齿胺改性硅胶配体。通过核磁C~(13)NMR、红外光谱(FTIR)及元素分析(EA)分析表明以上各步反应产物的结构及含氮量。此多齿胺改性硅胶配体被分别多次重复用于四氯化碳与甲基丙烯酸甲酯(MMA),三氯乙酸甲酯与苯乙烯(St)的ATRA反应中,通过气相色谱测定了原料的转化率随时间的变化,且通过核磁~1H NMR测定了产物的纯度,我们还进一步将此种多齿胺改性硅胶配体用于TCPP引发St的ATRP和MMTCB引发MMA的ATRP反应中,通过GPC测定所得聚合物的分子量。结果表明:成功合成了预期的多齿胺改性硅胶,此种配体的含氮量为2.5mmol/g。且此种多齿胺改性硅胶配体是ATRA反应很好的配体。在催化四氯化碳与MMA或三氯乙酸甲酯与St的ATRA反应中,此种配体至少可以重复使用7次,且第一次转化率在40h内可达到80%以上,第7次时仍可达到25%以上。但此种配体在用于ATRP反应时却不具有可控性。第二部分:通过多步反应合成了一种多齿胺改性磁性微球配体,合成过程如下:1)利用传统的共沉淀法合成纳米级的磁性四氧化三铁,并用油酸和十二烷基磺酸钠双层表面活性剂对其进行改性,制备稳定性好,能够很好的分散到极性溶剂中的磁流体。21以磁流体为种子,利用乳液聚合方法,以甲基丙烯酸甲酯和三羟甲基丙烷三丙烯酸酯为原料进行交联共聚而得到了表面带有双键的磁性高分子微球;3)利用二乙烯三胺(DETA)与磁性微球表面的双键发生Michael加成反应使硅胶表面氨基化;4)最后用丙烯酸正丁酯与DETA改性磁性微球表面氨基充分反应成功合成多齿胺改性磁性微球配体。通过表面元素分析(XPS)、红外光谱(FTIR)及元素分析(EA)分析表明以上各步反应产物的结构及含氮量。此多齿胺改性磁微球配体被分别多次重复用于四氯化碳与MMA和三氯乙酸甲酯与St的ATRA反应中,通过气相色谱测定了原料的转化率随时间变化。结果表明:成功合成了预期的多齿胺改性磁性微球,此种配体的含氮量约为1.0mmol/g。且此种多齿胺改性磁性微球是ATRA反应很好的配体。在催化四氯化碳与MMA和三氯乙酸甲酯与St的ATRA反应中,此种配体至少可以重复使用5次,且第一次转化率在40h内可达到80%以上,第5次时仍可达到35%以上。第三部分:以四氯化碳和三氯乙酸甲酯分别与苯乙烯(St)和甲基丙烯酸甲酯(MMA)发生原子转移自由基加成反应,合成了多官能卤化物1-苯基-1,3,3,3-四氯丙烷(TCPP)、2,2,4-三氯-4-苯基丁酸甲酯(MTCPB)、2,4,4,4-四氯-2-甲基丁酸甲酯(MMTCB)和2,2,4-三氯-4-甲基戊二酸二甲酯(DMTCMG),然后分别以TCPP和MTCPB为引发剂、CuCl为催化剂、2,2′-联吡啶为配体,进行St的ATRP反应;以MMTCB和DMTCMG为引发剂、CuCl为催化剂、2,2′-联吡啶为配体,进行MMA的ATRP反应。采用~1HNRM和凝胶渗透色谱(GPC)对聚合物结构和分子量进行分析表征。结果表明:聚合物分子量与单体转化率之间存在较好的线性关系;TCPP和MTCPB都是St的ATRP双官能度引发剂;MMTCB是MMA的单官能度引发剂;DMTCMG引发MMA聚合时官能度为1.5。
The polychloroalkanes is one kind of very important initiator of atom transfer radical polymerization (ATRP). They can initiate many kinds of monomers to synthesize different kinds of architectures via single-step or multistep reaction, such as block, graft, star and hyperbranched Copolymers and so on. If the functionality of the polychloroalkanes in polymerization could be determined clearly, it woulde be important for the design of macromolecular structure. On the other hand, transition metal complex have been widely used because of their good catalytic efficiency for the atom transfer radical addition (ATRA) and ATRP, but the postpurification of the product is difficult. Supporting catalyst on insoluble particles is a possible solution to this problem. Catalysts immobilized on insoluble particles by physics or chemistry method can be easily separated from the reaction mixture and be recycled and reused.
Three part of research works had been carried out in the dissertation. The first part: a kind of multidentate amine modified silica gel was synthesized through the following steps: (1) introduce the amino groups onto the surface of silica-gel by the treatment of surface silanol groups withγ-aminopropyl trimethoxy silane (γ-APS); (2) michael addition of excess trihydroxymethyl propyl triacrylate (TMPTA) to amino groups on the silica gel surface; (3) amidation of the unreacted double bonds of TMPTA on the surface of TMPTA modified silica gel with diethylenetriamine (DETA); (4) the multidentate amine modified silica gel was finally obtained by the reaction of amino groups on the surface of DETA modified silica gel with double bond of butyl acrylate (BA). Their chemical structures were confirmed by C~(13) NMR, infrared spectrum (FTIR) and the nitrogen content in the particles was determined by elemental analysis (EA). Then, the multidentate amine immobilized on silica gel was used as ligand for CuCl in ATRA of CCl_4 with MMA and methyl trichloroacetate with St repeatly. The conversion and purity of the product were determined through the gas chromatography and ~1H NMR respectively. Finally, the multidentate amine immobilized on silica gel was used as ligand for CuCl in ATRP of St initiated by TCPP and MMA initiated by MMTCB. The number average molecular weights of the polymers were determined through GPC. The results indicated that the multidentate amine modified silica gel ligand was synthesized successfully and the nitrogen content of this ligand is 2.5mmol/g. The multidentate amine modified silica gel is good catalytic ligand of ATRA reaction. This kind of ligand have been used seven times in the ATRA reaction of carbon tetrachloride with MMA and the methyl trichloroacetate with St, and the conversion for the first time reached above 80% in 40 hours, when the seventh time still exceeded 25%. But the multidentate amine modified silica gel ligand can not control ATRP reaction well. The second part: a kind of multidentate amine modified magnetic microspheres was synthesized through the following steps: (1) Fe_3O_4 magnetic nanoparticles were synthesized by the chemical co-precipitation and modified by oleic acid and sodium dodecyl sulfonate bilayer surfactants. The stability of the magnetic fluid is very good and can be dispersed well in polarity solvent. (2) The magnetic fluid was as seed and carried on the crossing linking copolymerization of methyl methacrylate(MMA) and trihydroxymethyl propyl triacrylate(TMPTA) through emulsion polymerition obtained the magnetic microspheres with the double bond on the surface. (3) amidation of the double bonds of magnetic microspheres on the surface with diethylenetriamine (DETA); (4) the multidentate amine modified magnetic microspheres was finally obtained by the reaction of amino groups on the surface of DETA modified magnetic microspheres with double bond of butyl acrylate (BA). Their chemical structures were confirmed by XPS, infrared spectrum (FTIR) and the nitrogen content in the particles was determined by elemental analysis (EA). Then, the multidentate amine immobilized on magnetic microspheres was used as ligand for CuCl in ATRA of CCl_4 with MMA and methyl trichloroacetate with St repeatly. The conversion and purity of the product were determined through the gas chromatography respectively. The results indicated that the multidentate amine modified magnetic microspheres ligand was synthesized successfully and the nitrogen content of this ligand is 1.0mmol/g. The multidentate amine modified silica gel is good catalytic ligand of ATRA reaction. This kind of ligand have been used five times in the ATRA reaction of carbon tetrachloride with MMA and the methyl trichloroacetate with St, and the conversion for the first time reached above 80% in 40 hours, when the fifth time still exceeded 35%. The third part: 1,1,1,3-tetrachloro-3-phenylpropane(TCPP), methyl 2,2,4-trichloro-4-phenylbutyrate(MTCPB), methyl 2-methyl-2,4,4,4-tetrarchlorobutyrate(MMTCB) and dimethyl 2,2,4-trichloro-4- methyl -glutarate (DMTCMG) have been synthesized via ATRA from styrene (St) and methyl methacrylate (MMA) with carbon tetrachloride and methyl trichloroacetate respectively. When the TCPP and MTCPB were used as initiators for ATRP of St and the MMTCB and DMTCMG were used as initiators for ATRP of MMA in the presence of the cuprous chloride (CuCl)/ 2, 2'-bipyridine catalyst system respectively, a controlled polymerization process was achieved with the resulting polystyrene (PS) and polymethyl methacrylate (PMMA) having number average molecular weights which increased with monomer conversion and narrow molecular weight distributions. The number average molecular weights and structure of the PS and PMMA characterized by ~1H NMR and gel permeation chromatography (GPC) showed that TCPP and MTCPB both act as bifunctional initiators for the ATRP of St and the functionalities of MMTCB and DMTCMG for the ATRP of MMA were 1.0 and 1.5 respectively.
引文
[1]Curran D P.Comprehensive Organic Synthesis[M].Pergamon:New Youk,1992.
[2]Curran D P.the design and application of free radical chain reactions in organic synshesis,part A[J].Synthesis,1988,6:417-439.
[3]Minisci F.Free-Radical Additions to Olefins in the Presence of Redox Systems[J].Acc Chem Res,1975,8(5):165-171.
[4]Iqbal J,Bhatia B,Nayyar N K.Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis:The Formation of Carbon-Carbon Bonds[J].Chem Rev,1994,94(2):519.
[5]Gossage R A,Van de Kuil L A,Van K G.Diaminoarylnickel(Ⅱ)"Pincer"Complexes:Mechanistic Considerations in the Kharasch Addition Reaction,Controlled Polymerization,and Dendrimeric Transition Metal Catalysts[J]. Acc Chem Res, 1998, 31(7): 423.
[6] Clark A J. Atom transfer radical cyclisation reactions mediated by copper complexes [J]. Chem. Soc. Rev, 2002, 31:1.
[7] Severin K [J]. Curr. Org Chem, 2006, 10: 217-224.
[8] (a) Nonhebel D P, Tedder J M, Walton J C. radicals [M]. Cambridge University Press, 1979; (b) Davies D I, Parrott D J. free radicals in organic synthesis [M], Springer-Verlag, Berlin, 1978; (c) Hay J M. reactive free radicals [M],Academic Press, New York, 1974.
[9] (a) Alexakis A, Commercon A, Coulentianos C, Normant J F.Carbocupration of acetylenic acetals and ketals: synthesis of a-b ethylenic acetals, and of dienals and dienones [J]. Pure Appl Chem, 1983, 55, 1759.; (b) Erdik E. Tetrahedron Report Number 159: Copper(I) catalyzed reactions of organolithiums and Grignard reagents [J]. Tetrahedron, 1984, 40, 641.; (c)Lipshutz B H, Wilhelm R S, Kozlowski J A The chemistry of higher order organocuprates [J]. Tetrahedron, 1984, 40: 5005.
[10] (a) Asscher M, Vosfi D. Chlorine activation by redox transfer. Part II. The addition of carbon tetrachloride to olefins [J]. J Chem Soc, 1963, 1887; (b)Asscher M, Vosfi D. Chlorine-activation by redox-transfer. Part III. The " abnormal" addition of chloroform to olefins [J]. J Chem Soc, 1963: 3921
[11] Asscher M, Vosfi D. Redox transfer. Part V. Elementary steps. The oxidation of ferrous and cuprous chloride by carbon tetrachloride [J]. J Chem Soc, Phys Org, 1968,947
[12] (a) Starks H M. Free Radical Telomerisation [M]. New York: Academic Press, 1974, 96; (b) Bury A, Bougeard P, Corker S J, Michael D J, Michele P.1,3-Migration of a cyano-group in substituted 3-cyanopropyl radicals [J]. J Chem Soc, Perkin Trans 2, 1982, 2: 1367.
[13] Corallo M, Pietrasata Y Telomerisation par catalyse redox—VI: Addition dutetrachlorure de carbone sur des monomeres diethyleniques non conjugues [J].Tetrahedron, 1976, 32: 2295
[14] Bellus D Copper-catalyzed additions of organic polyhalides to olefins: a versatile synthetic tool [J]. Pure &Appl Chem, 1985, 57(12): 1827.
[15] (a) Julia M , Saussine L, Thuillier G L. Addition du chloracetate de methyle sur les olefines [J]. J Organomet Chem, 1979, 174: 359.; (b) Julia M, Thuillier G L,Saussine L.Additions D'α-chloronitriles sur les olefines par catalyse redox[J].J Organomet Chem,1979,177:211
[16]Wang J S,Matyjaszewski K Controlled/"living" radical polymerization,atom transfer radical polymerization in the presence of transition-metal complexes [J].J Am Chem Soc,1995,117:5614.
[17]Wang J S,Matyjaszewski K Controlled/"Living" Radical Polymerization.Halogen Atom Transfer Radical Polymerization Promoted by a Cu(Ⅰ)/Cu(Ⅱ)Redox Process[J].Macromolecules,1995,28(23):7901.
[18]Wang J S,Matyjaszewsky K.Controlled/living radical polymerization.Halogen atom transfer radical polymerization promoted by a Cu(Ⅰ)/Cu(Ⅱ)redox process[J].Macromolecules,1995,28(23):7901.
[19]Kato M,Kamigaito M,Sawamoto M.Polymerization of methyl methacrylate with the carbontetrachloride/dichlorotris(triphenylphosphine)ruthenium(Ⅱ)/methyl aluminium bis(2,6-di-tert-butylphenoxide)initiating system:possibility of living radical polymerization[J].Macromolecules,1995,28(5):1721.
[20]Percec V,Barboiu B."Living" Radical Polymerization of Styrene Initiated by Arenesulfonyl Chlorides and CuI(bpy)nCl[J].Macromolecules,1995,28(23):7970.
[21]袁金颖.原子转移自由基聚合反应在合成预定结构聚合物中的应用[J].高分子材料科学与工程,2003,19(5):1-9
[22]史增谦,刘盈海,李艳香.几种新型有机酸配体和FeCl_2络合催化下的苯乙烯原子转移自由基聚合反应[J].河北大学学报(自然科学版),2004,(2):148.
[23]华曼,陈明清,刘晓亚.原子转移自由基聚合的近期进展研究发展[J].化学世界,2004,2:103.
[24]岳玲,周建华,虎春艳.一种新型用于原子转移自由基聚合过程的Cu(Ⅰ)络合物的研究[J].感光科学与光化学,2005,23(3):183.
[25]Wang Yun Pu,Pei Xiao Wei,He Xiao Yan.Synthesis of well defined,polymer-grained silica nanoparticles via reverse ATRP[J].Eur Polym J,2005,(41):1326.
[26]Nikhil K.Singha,Barteld de Ruiter,Ulrich S.Schubert.Atom Transfer Radical Polymerization of 3-Ethyl-3-(acryloyloxy) methyloxetane [J].Macromolecules, 2005,38(9): 3596.
[27] Sachin Borkar, Ayusman Sen. Novel Fluoroal kene MethylAcrylate Copolymers by Atom Transfer Radical Polymerization [J]. Macromolecules,2005, 38(7): 3029.
[28] Yi Zheng Jin, Chao Gao, Harold W K. Polymer -Grafted Carbon Spheres by Surface- Initiated Atom Transfer Radical Polymerization [J] .Macromol Rapid Commun, 2005, 26: 1133.
[29] Tzong Liu Wang, Yu Zhi Liu, Bo Chang Jeng. The Effect of Initiators Reaction Condi tions on the Polymer Syntheses Atom Transfer Radical Polymerization [J]. J Polym Res, 2005,12: 67.
[30] Jayachandran N. Kizhakkedat hu, Kainthan Rajesh Kumar, Diane Goodman.Synt hesis and characterization of well - defined hydrophilic block copolymer brushes by aqueous ATRP [J]. Polymer, 2005, 45: 7471.
[31] Du Jianzhong, Chen Yongming. Atom Transfer Radical Polymerization of a Reactive Monomer: 3-(Trimethoxysilyl) propyl Methacrylate [J].Macromolecules, 2004, 37: 6322.
[32] Frechet J M J, Leduc M R, Weimer Metal. Living free radical polymerization and dendritic polymers [J]. Am Chem Soc Div Polym Chem Prepr, 1997, 38(1): 756.
[33] Kulprathi Panjas. Separation of citricacid from ferment ation broth with a neutral polymeric adsorbent [P]. US: 4720579, 1988- 01-19.
[34] Gaynor S G, Qiu J, Matyjaszewski K. Controlled/"Living" Radical Polymerization Applied to Water-Borne Systems [J]. Macromolecules, 1998,31(17): 5951
[35] Makino T, Tokunaga E, Hogen E. Controlled atom transfer radical polymeriza-tions of methyl methacrylate under micellar conditions [J]. Polym Prep,1998, 39(1): 288
[36] Kato M, Kamigaito M, Sawamoto M. Polymerization of Methyl Methacrylate with the Carbon Tetrachloride/Dichlorotris-(triphenylphos phine) ruthenium (II)/ Methylaluminum Bis (2,6-di-tert-butylphenoxide) Initiating System:Possibility of Living Radical Polymerization [J]. Macromolecules, 1995,28(5): 1721.
[37]Percec V,Barboiu B."Living" Radical Polymerization of Styrene Initiated by Arenesulfonyl Chlorides and CuI(bpy)nCl[J].Macromolecules,1995,28(23):7970.
[38]Fischer H.J Polym Sci,Part A:Polym.Chem.1999,37:1885-1901.
[39]Borsig E,Lazar M,Capla M.Angew.Makromol.Chem.1969,9,89-95.
[40]Chiefari J,Chong Y K,Ercole F.Macromolecules.1998,31:5559-5562.
[41]Shen Y,Zhu S.Zeng F,.Macromol.Chem Phys.2000,201:1169-1175.
[42]Matyjaszewski K,Paik H j,Zhou P,Diamanti S J.Macromolecules,2001,34:5125-5131.
[43]Patten T E,Matyjaszewski K.Adv Mater.1998,10:901-915.
[44]Gobelt B,Matyjaszewski K.Macromol Chem Phys.2000,201:1619-1624.
[45]Ando T,Kamigaito M,Sawamoto M.Tetrahedron 1997,53:15445-15457.
[46]Cheng G L,Hu C P,Ying S K.J Mol Catal A:Chem.1999,144,357-362.
[47]Percec V,Asandei A D,Asgarzadeh F,Barboiu B,Holerca M N,Grigoras C.J Polym Sci Part A:Polym Chem.2000,38:4353-4361.
[48]Senoo M,Kotani Y,Kamigaito M,Sawamoto M.Macromolecules 1999,32:8005-8009.
[49]Xia J,Matyjaszewski K.Macromolecules.1999,32:2434-2437.
[50]Ando T,Kamigaito M,Sawamoto M.Tetrahedron.1997,53:15445-15457.
[51]Zeng F,Shen Y,Zhu S,Pelton R.Macromolecules.2000,33:1628-1635.
[52]Nishikawa T,Kamigaito M,Sawamoto M.Macromolecules.1999,32,2204-2209.
[53]Wang J L,Grimaud T,Matyjaszewski K.Macromolecules.1997,30:6507-6512.
[54]Neumann A,Keul H,Hocker H.Macromol Chem Phys.2000,201:980-984.
[55]Cheng G L,Hu C P,Ying S K.Macromol.Rapid Commun.1999,20:303-307.
[56]Kwon T S,Kumazawa S,Yokoi T,Kondo S,Kunisada H,Yuki Y J.Macromol Sci Pure Appl Chem.1997,A34:1553-1567.
[57]Nishikawa T,Ando T,Kamigaito M,Sawamoto M.Macromolecules.1997,30:2244-2248.
[58]Reining B,Keul H,Hocker H.Polymer.1999,40:3555-3563.
[59]Matyjaszewski K,Jo S M,Paik H J,Gaynor S G.Macromolecules. 1997,30:6398-6400.
[60]汤志忠,高保娇.原子转移自由基聚合及其研究进展[J].化北工学院学报,2004,25,271.
[61]Sedjo R A,MirousB K,BrittainW J Synthesis of Polystyrene-block-poly (methyl methacrylate)Brushes by Reverse Atom Transfer Radical Polymerization[J].Macromolecules,2000,33(5):1492.
[62]Ejaz M,Yamamoto S,Ohno K Controlled Graft Polymerization of Methyl Methacrylate on Silicon Substrate by the Combined Use of the Langmuir-Blodgett and Atom Transfer Radical Polymerization Techniques[J].Macromolecules,1998,31(17):5934.
[63]Zeng F Q,Shen Y Q,Zhu S P Synthesis and Characterization of Comb-Branched Polyelectrolytes.1.Preparation of Cationic Macromonomer of 2-(Dimethylamino)ethyl Methacrylate by Atom Transfer Radical Polymerization[J].Macromolecules,2000,33(5):1628.
[64]Carrot G,Hilborn J,Hedrick J L Novel Initiators for Atom Transfer Radical and Ring-Opening Polymerization:A New General Method for the Preparation of Thiol-Functional Polymers[J].Macromolecules,1999,32(15):5171.
[65]Heise A,Nyuyen C,Malek R Starlike Polymeric Architectures by Atom Transfer Radical Polymerization:Templates for the Production of Low Dielectric Constant Thin Films[J].Macromolecules,2000,33(7):2346.
[66]魏振平,毛世瑞.比色法与液相色谱法对罗红霉素溶液稳定性研究的比较[J].药学学报,2000,35(11):871.
[67]黄涛主编.有机化学实验[M].北京:高等教育出版社,1998.55.
[68]Burwell R I.Manufacture and properties of erythromycin derivatives[J].Chem Rev,1954,54,635.
[69]Suzuki H.Reaction ofpolysubstituted aromatics.XIX.Chloromethylation with chloro- methyl methyl ether and 60%-fuming sulfuric acid.Simple synthesis of some nitropoly methylbenzyl chlorides and dihalopolymethylbenzyl chlorides.[J].Bull Chem Soci Japan 1970,43.3299.
[70]愈凌中.有机化学中的人名反应[M].北京:科学出版社,1984.62.
[71]乌锡康主编.有机化工废水治理技术[M].北京:化学工业出版社,1997. 374.
[72]德雷兹,范德旺迪伦.碱金属柠檬酸盐的制备方法[P].CN:1035611,1997-08-13.
[73]刘群峰,李思东,何卫东.3-氯-2-氯甲基-1-丙烯引发苯乙烯原子转移自由基聚合的研究[J].高分子学报.2007,6:582.
[74]For a review on radical polymerization,see:Moad G,Solomon D H.The Chemistry of Free Radical Polymerization.Elsevier Science:Oxford,U.K.,1995.
[75](a)Szwarc M Nature 1956,178,1168-1169.
(b)Szwarc M,Levy M,Milkovich R.J Am Chem Soc.1956,78,2656-2657.
[76]Eastmond G C,Webster O W.In New Methods of Polymer Synthesis;Ebdon J R.Ed.Blackie:Glasgow U K.1991:22-75
[77]Aida,T.Prog.Polym.Sci.1994,19,469-528.
[78]Sugimoto H,Inoue S.Adv Polym Sci.1999,146,39-119.
[79]Hirao A,Nakahama S.Acta Polym.1998,49,133-144.
[80](a)Higashimura T,Sawamoto M.Adv Polym Sci.1984,62,49-94.
(b)Sawamoto M.Prog Polym Sci.1991,16,111-172.
(c)Sawamoto M,Kamigaito M.In New Methods of Polymer Science;Ebdon J R,Eastmond G C Eds,Blackie:Glasgow U K,1995;Vol.2,pp 37-68.
[81]Kennedy J P,Ivan B.Designed Polymers by Carbocationic Macromolecular Engineering:Theory and Practice;Hanser:Munich,Germany,1992.
[82]Cationic Polymerizations,Matyjaszewski K Ed,Marcel Dekker:New York,1996.
[83]Yasuda H.Prog Polym Sci.2000,25,573-626.
[84]Mecerreyes D,Jerome R,Dubois Ph.Adv Polym Sci.1999,147,1-59.
[85]Grubbs R,Khosravi E.In Synthesis of Polymers;Schluter,A.D.,Ed.;Materials Science and Technology Series;Wiley-VCH:Weinheim,Germany,1999;pp 65-104.
[86]Sluis M V,Barboiu B,Percec V.Rate enhancement by carboxylate salts in the CuCl,Cu_2O,and Cu(0)catalyzed "living" radical polymerization of BMA initiated with sulfonyl chlorides[J].Macromolecules,1998,31(26):9409.
[87]Percec V,Barboiu B,Neumann A.Metal-catalyzed "living" radical polymerization of styrene initiated with arenesulfonyl chlorides.From heterogeneous to homogeneous catalysis[J].Macromolecules,1996,29(10):3665.
[88]Barboiu B,Percec V,Sluis M V.Self-Regulated Phase Transfer of Cu_2O/bpy,Cu(0)/bpy,and Cu_2O/Cu(0)/bpy Catalyzed "living"Radical polymerization Initiated with Sulfonyl Chlorides[J].Macromolecules,1998,31(12):4053.
[89]Barboiu B,Percec V,Asandei A D.Organocopper-Catalyzed "Living"Radical Polymerization Initiated with Aromatic Sulfonyl halides[J].J.Polym.Sci.Part A:Polym.Chem,2000,38(24):4353.
[90]Patten T E,Matyjaszewski K.Atom Transfer Radical Polymerization and the Synthesis of Polymeric Materials[J].Adv Mater,1998,10:901.
[91]Georges M K,Veregin R P N,Kazmaier P M.Narrow molecular weight resins by a free-radical polymerization process[J].Macromolecules,1993,26(11):2987.
[92]Chiefari J,Chong Y K,Ercole F.Living Free-Radical Polymerization by Reversible Addition-Fragmentation Chain Transfer:The RAFT Process[J].Macromolecules,1998,31(16):5559.
[93]Mayadunne R T A,Rizzardo E,Chiefari J.Living Radical Polymerization with Reversible Addition-Fragmentation Chain Transfer(RAFT Polymerization)Using Dithiocarbamates as Chain Transfer Agents[J].Macromolecules,1999,32(21):6977.
[94]王艳君,王玉霞,袁才登.可逆加成一断裂链转移活性自由基聚合[J].高分子通报,2003,3:57.
[95]Leyden D E,Luttrell H,Preconcentration of trace metals using chelating groups immobilized via silylation[J].Anal Chem,1975,47:1612.
[96]Ulman A.Self-assembled monolayers of alkyltrichiorosilanes:Building blocks for future organic materials[J].Adv Mater,1990,2:573.
[97]Hoom H J,Joode P D,Dijkstra D J,Driessen W L,Kooijman H,Veldman N,Spek A L,Reedijk J.Metal binding affinity of a series ofbisbenzimidazoles immobilized on silica[J].J Mater Chem 1997,7:1747.
[98]Kickelbick G,Paik H J,Matajiszewski K.Immobilization of the Copper Catalyst in Atom Transfer Radical Polymerization[J].Macromolecules,1999,32:2941.
[99]Shen Y Q,Zhu S P,Patten R.Effect of Ligand Spacer on Silica Gel Supported Atom Transfer Radical Polymerization of Methyl Methacrylate [J].Macromolecules, 2001, 34:5812.
[100] Kickelbick G, Paik H J, MatyjaszewskiK. Macromolecules, 1999, 32 (9):2941—2947.
[101] Haddleton D M, Kukulj D, Radigue A P. ABSTR Pap. Am. Chem. S. 1999,217: 170-PMSE Part 2.
[102] Hen S Y Q , Zhu S P, Pelton R. M acromo lecules, 2001, 34 (17): 5812-5818.
[ 103] Haddleton D M, Kukulj D, Duncalf D J. Macromolecules, 1998, 31 (16):5201-5205.
[104] Opstal T, Melis K, Verpoort F. Catal. Lett., 2001, 74 (3-4): 155-159.
[105] Hong S C, MatyjaszewskiK. Macromolecules, 2002, 35 (20): 7592-7605 SEP24.
[106] Shen Y Q, Zhu S P. Aiche Journal, 2002,48 (11):2609- 2619.
[107] Booth R J, Hodges J C. Polymer Supported Quenching Reagents for Parallel Purification [J]. J Am Chem Soc, 1997, 119: 4882.
[108] Haddleton D M, Kukulj D, Radigue A P. Atom transfer polymerization of methyl methacrylate mediated by solid supported copper catalysts [J]. Chem Commun, 1999, 99.
[109] Kickelbick G, Paik H J, Matyjaszewski K. Immobilization of the Copper Catalyst in Atom Transfer Radical Polymerization [J]. Macromolecules, 1999,32:2941.
[110] Kickelbick G, Paik H J, Matyjaszewski K. Macromolecules, 1999, 32 (9):2941-2947.
[111] L iou S, Rademacher J T, Malaba D,. Macromolecules, 2000, 33(12):4295-4296.
[112] Shen Y Q, Zhu S P. Macromolecules, 2001, 34 (25):8603-8609.
[113] Shen Y Q , Zhu S P, Zeng F Q. Macromolecules, 2000, 33 (15): 5427-5431.
[114] Hong S C, Paik H J, Matyjaszewski K. An Immobilized/Soluble Hybrid Catalyst System for Atom Transfer Radical Polymerization [J].Macromolecules, 2001, 34: 5099.
[115] Hong S C, Paik H J, MatyjaszewskiK. Macromolecules, 2001, 34 (15):5099-5102.
[116]Hong S C,Lutz J F,Inoue Y.Macromolecules,2003,36(4):1075-1082.
[117]Hong S C,Matayjaszewski K.Fundamentals of Supported Catalysts for Atom Transfer Radical Polymerization(ATRP)and Application of an Immobilized/Soluble Hybrid Catalyst System to ATRP[J].Macromolecules,2002:35:7592.
[118]Hong S C,Neugebauer D,Inoue Y,Lutz J F,Matyjaszewski K[J].Macromolecules,2003,36:27.
[119]Hong S C,Lutz J F,Inoue Y,Lutz J F,Matyjaszewski K.Preparation of Segmented Copolymers in the Presence of an Immobilized/Soluble Hybrid ATRP Catalyst System[J].Macromolecules,2003,36:1075.
[120]Tsarevsky N V,Bernaerts K V,Dufour B,Prez F E D,Matyjaszewski K.Well-Defined(Co)polymers with 5 Vinyltetrazole Units via Combination of Atom Transfer Radical(Co)polymerization of Acrylonitrile and "Click Chemistry"-Type Postpolymerization Modification[J].Macromolecules,2004,37:9308.
[121]Huang J,Cusick B,Pietrasik J,Wang L,Kowalewski T,Lin Q,Matyjaszewski K.Synthesis and In Situ Atomic Force Microscopy Characterization of Temperature-Responsive Hydrogels Based on Poly(2-(dimethylamino)ethyl methacrylate)Prepared by Atom Transfer Radical Polymerization[J].Langmuir,2007,23:241.
[122]Vijayakumar R,Koltypin Y,Felner I.Sonochemical synthesis and characterization of pure nanometer-sized Fe_3O_4 particles[J].Mater Sci Eng A,2000,286(1):101.
[123]邱星屏.四氧化三铁磁性纳米粒子的合成及表征.厦门大学学报(自然科学版),1999,38(5):711.
[124]Warshawsky D A,Upson W T,Ferrar J.Zerovalent metal polymer composites.Ⅲ.Metallization of metal oxide surfaces with the aid of metallized functional polymer microdispersions[J].Polym Sci Part A,1989(27):3015.
[125]Trau D,Yang W,Seydack M.Nanoencapsulated Microcrys talline Particles for Superamplified Biochemical Assays[J].Anal Chem,2002(74):5480.
[126]Caruso F,Schuler C.Enzyme Multilayers on Colloid Particles:Assembly,Stability,and Enzymatic Activity[J].Langmuir,2000(16):9595.
[127]Jin W,Shi X,Caruso F.High Activity Enzyme Microcrystal Multilayer Films [J].JAm Chem Soc,2001(123):8121.
[128]Mecking S,Thomann R.Core-Shell Microspheres of a Catalytic-ally Active Rhodium Complex Bound to a Polyelectroly e-Coated Latex[J].Adv Mater,2000(12):953.
[129]Yang W J,Trau D,Renneberg R.Layer-by-Layer Construction of Novel Biofunctional Fluorescent Microparticles for Immunoassay Applicati-ons[J].J Colloid Interface Sci.2001,234:356.
[130]Khopade A J,Caruso F.Stepwise Self-Assembled Poly(amidoamine)Dendrimer and Poly(styrenesulfonate)Microcapsules as Sustained Delivery Vehicles[J].Biomacromolecules,2002,3(6):1154.
[131]高道江,赖欣,王建华.磁流体制备技术的现状及展望[J].磁性材料及器件,1998,29(2):20.
[132]齐凤春.磁性液体[J].材料导报,1998,12(2):17.
[133]杨咏来,宁桂玲,吕秉玲.液相法制备纳米粉体时防止团聚方法概述[J].材料导报,1998,12(2):11.
[134]邱广明,孙宗华.水溶性磁流体的制备和性质[J].化学试剂,1993,15(4):234.
[135]刘成林,钟菊花,张兆奎.表面修饰对a-Fe2O_3超微粒光谱特性的影响[J].光谱学与光谱分析,2003,23(1):154.
[136]郑水林,张清辉,李杨.超细氧化铁红颜料的表面改性研究[J].矿冶,2003,12(1):69.
[137]李小娥,郝欣,吕海茹.四氧化三铁磁性超细粉的表面改性[J].无机盐工业,2002,34(5):6.
[138]包建军,刘迪文.铁氧磁流体的微波水热合成、表面修饰和磁性高分子微球的制备[J].高分子材料科学与工程,2003,19(5):204.
[139]王秀宇,杨桂琴,张之圣等.磁流体制备中磁性颗粒的表面处理[J].应用化学,2005,22(5):525.
[140]任欢鱼,庄虹,刘勇健.Fe_3O_4纳米颗粒的表面改性[J].化学研究,2003,14(1):11.
[141]施卫贤,杨俊,王亭杰.磁性Fe_3O_4微粒表面有机改性[J].物理化学学报,2001,17(6):507.
[142]刘峥.Fe_3O_4微粒表面有机改性及其应用研究[J].化工技术与开发,2004,33(3):12.
[143]娄敏毅,王德平,黄文旵.偶联剂修饰纳米微球的制备及其表征[J].上海生物医学工程,2004,25(3):14.
[144]Lifen Shen,Paul E,Laibinis T,Alan Hatton.Aquseous magneticfluids stabilized by surfactant bilayers[J].J Magn Magn Mate,1999,194:37.
[145]蒋新宇,周春山,张俊山.导向药物用纳米Fe_3O_4磁性粒子的制备及表征[J].中南工业大学学报(自然科学版),2003,34(5):516.
[146]安丽娟,李兆强,徐娓.超顺磁性高分子微球的制备与表征[J].高等学校化学学报,2005,26(2):366.
[147]陈晓青,张俊山,杨娟玉.双层表面活性剂分散制备水基磁流体[J].无机化学学报,2003,19(5):547.
[148]Tahsin Bahar,Serdar S,Celibi.Immobilization of glucoamylase on magnetic poly(styrene)particles[J].J Appl Polym Sci,1999,72:69.
[149]Yen.Functionalm agneticm icrosphere.USP4,285,819,1981.
[150]Tricot.Process for the preparation of magnetic beads of vinylaromaticpolymers.USP4,339,337.1982.
[151]Marge.Polyacrolein-typemicrosphere,USP4,783,366,1988.
[152]Tsuruta Meiji.Manufacture of magneticmicrosphere,JP 62204501,1987.
[153]Daniel.Magnetic polymerlatex and preparation process.USP4,358,388.1982.
[154]Charmot.Magnetizable composite microspheres of hydrophobic crosslinked polymer,process for them and their applicationin biology.USP5,356,713.1994.
[155]Solcnee Hajna.Colloidal size hydrophobic polymers particulate having discretepartic lesofan in organicm aterialdi spersedth erein.USP4,421,660.1983.
[156]邱广明,杨春雁,孙宗华.单分散亚微米级磁性微球的合成[J].功能高分子学报,1996,9(4):565.
[157]邱广明,章贤明,孙宗华.磁性聚苯乙烯微球的合成和特性[J].高分子材料科学与工程,1993,(2):38.
[158]Noriko,Yanase,Hiromichi,Noguchi,Hideki Asakura,Preparation of Magnetic Latex Particles by Emulsion Polymerization of Styrene in the Presence of Ferrofluid[J].J Appl Polym Sci,1993,50:765.
[159]Hiromichi Noguchi,Noriko Yanase,Yasuzo Uchida.Preparation and Characterization by Thermal Analysis of Magnetic Latex Particles[J].J Appl Polym Sci,1993,48:1593.
[160]Kondo A,Kamura H,Higashitani K.Development and application of Thermo Sensitive magnetic immuno microsphere for antibody Purication[J].Appl Microbiol biotechnol,1994,41:99.
[161]Hwee Peng Khng,David Cunlife,Stephen Davies.The synthesis of submicron magnetic particles and theirusef or preparative purification of proteins.Biotechnol&bioengineering,1998,60(4):419
[162]邱广明,高晓松,杨春雁.Fe_3O_4/P(St-AA)核一壳复合微球的制备和表征[J].应用化学,1996,13(1):6.
[163]李孝红,孙宗华.磁性高分子微球的合成研究—带醛基磁性高分子微球的合成及表征[J].离子交换与吸附,1996,12(6):486.
[164]李孝红,丁小斌,孙宗华.含羟基磁性高分子微球的合成及表征[J].功能高分子学报,1995,8(1):73.
[165]丁小斌,孙宗华,万国祥.热敏性高分子包裹的磁性微球的合成[J].高分子学报,1998,5:628.
[166]丁小斌,孙宗华,万国祥.热敏型高分子包裹的磁性微球的性质及表征[J].高分子学报,1999,6:674.
[167]Richard.Latex of calibrated mono-disperse magnetizablem icrosphere,process of preparation and use of saidlatexin chemistry orin biology.USP5,976,426.1999.
[168]张津辉,蒋中华,王仁芝.磁性微球的制备,理化性质及初步应用[J].化学通报,1997,9:55.
[169]Rembaum.1.Production ofmonodisperse,polymeficmicrosphere.USP4,929,400.1990.
[170]Ugelstad.Process for preparing magnetic polymer panicles,USP4,774,265,1988.
[1]Pyun J,M atyjaszewski K,Kowalewski T.J.Am.Chem.Soc.2001,123(38):944-9446.
[2]Von Weme T,Patten T E.J Am Chem.Soc.1999,121(32):7409-7410.
[3]Matyjaszewski K,Miller P J.J Pyun.Macromolecules,1999,32(20):6526-6535.
[4](a)Simal F,Sebille S,Demonceau A,Noels A F,Nunez R,Abad M,Teixidor F,Vinas C Radical reactions catalysed by ruthenium(Ⅱ)complexes with anionic carborane phosphine ligands:Kharasch addition to olefins and controlled polymerisation[J].Tetrahedron Lett,2000,41,5347;
(b)Tutusaus O,Vinas C,Nunez R,Teixidor F,Demonceau A,Delfosse S,Noels A F,Mata I.,Molins E.The Modulating Possibilities of Dicarbollide Clusters:Optimizing the Kharasch Catalysts[J].J Am Chem Soc.2003,125(39):11830;
(c)Tutusaus O,Delfosse S,Demonceau A,Noels A F,Vinas C,Teixidor F Kharasch addition catalysed by half-sandwich ruthenium complexes.Enhanced activity of ruthenacarboranes[J].Tetrahedron Lett.2003,44,8421.
[5](a)Tallarico J A,Malnick L M,Snapper M L.New Reactivity from (PCy_3)2Cl_2Ru=CHPh:A Mild Catalyst for Kharasch Additions[J].J Org Chem,1999,64(2):344;
(b)Simal F,Demonceau A,Noels A F Kharasch addition and controlled atom transfer radical polymerisation(ATRP)of vinyl monomers catalysed by Grubbs' ruthenium-carbene complexes[J].Tetrahedron Lett.1999,40,5689.
[6](a)Simal F,Wlodarczak L,Demonceau A,Noels A F Highly efficient Kharasch addition catalysed by RuCI(Cp*)(PPh_3)_2[J].Tetrahedron Lett.2000,41:6071;
(b)Simal F,Wlodarczak L,Demonceau A,Noels A F,New,Highly Efficient Catalyst Precursors for Kharasch Additions- [RuCI(Cp*)(PPh_3)_2]and[RuCl(Ind)(PPh_3)_2][J].Eur J Org Chem,2001,14:2689.
[7]Aurore Richel,Albert Demonceau and Alfred F.Noels Electrochemistry as a correlation tool with the catalytic activities in[RuCl_2(p-cymene)(PAr_3)]-catalysed Kharasch additions[J].Tetrahedron Letters,2006,47:2077.
[8]Clercq B D,Lefebvre F,Verpoort F.Immobilization of multifunctional Schiffbase containing ruthenium complexes on MCM-41[J].Applied Catalysis A:General,2003,247:345.
[9]Clark A J,Geden J V,Thom S Solid-Supported Copper Catalysts for Atom-Transfer Radical Cyclizations:Assessment of Support Type and Ligand Structure on Catalyst Performance in the Synthesis of Nitrogen Heterocycles[J].J Org Chem,2006,71(4):1471.
[10]李忠辉,张永明,刘燕刚,薛敏钊.原子转移自由基聚合及催化剂负载化研究进展.高分子材料科学与工程.2005,21(1),6-10.
[11](a)Kickelbick G,Paik H J,Matyjaszewski K Immobilization of the Copper Catalyst in Atom Transfer Radical Polymerization[J].Macromolecules,1999,32(9):2941;(b)Haddleton D M.Kukulj D,Radigue A P.Atom transfer polymerisation of methyl methacrylate mediated by solid supported copper catalysts[J].Chem Commun,1999,1:99;(c)Shen Y,Zhu S,Zeng F,Pelton R Supported atom transfer radical polymerization of methyl methacrylate mediated by CuBr-tetraethyldiethylenetriamine grafted onto silica gel[J].J Polym Sci Part A:Polym Chem,2001,39,1051;(d)Shen Y,Pelton R.Effect of Ligand Spacer on Silica Gel Supported Atom Transfer Radical Polymerization of Methyl Methacrylate[J].Macromolecules,2001,34(17):5812;(e)Nguyen J V,Jones C W,Design,Behavior,and Recycling of Silica-Supported CuBr-Bipyridine ATRP Catalysts[J].Macromolecules,2004,37(4):1190;(f)Nguyen J V,Jones C W.Effect of the synthetic method and support porosity on the structure and performance of silica-supported CuBr/pyridylmethanimine atom transfer radical polymerization catalysts,Ⅱ.Polymerization of methyl methacrylate[J].J Polym Sci Part A:Polym Chem,2004,42:1384.
[1](a)Kato M,Kamigaito M,Sawamoto M,Higashimura T.Macromolecules 1995,28:1721-1723;(b)Wang J S,Matyjaszewski K.J Am Chem Soc.1995,117:5614-5615.
[2](a)Clark A.J Chem Soc Rev.2002,31:1-11;(b)Eckenhoff W T,Pintauer T.Inorg Chem.2007,46:5844-5846.
[3]Gossage R A,van de Kuil L A,van Koten G.Acc Chem Res.1998,31:423-431.
[4](a)Bellesia F,Forti L,Gallini E.Tetrahedron 54,1998,7849-7856;(b)Severin K.Curr Org Chem.2006,10:217-224.
[5](a)Iqbal J,Bhatia B,Nayyar N K.Chem Rev.1994,94,519-564;(b)Simal E Demonceau A.Noels A F.In Recent Research Developments in Organic Chemistry;Pandalai S G Ed.Transworld Research Network:Trivandrum,1999,3:455-464;(c)Demonceau A,Noels A F.Top Organomet Chem.2004,11:155-171.
[1]Xia J,Matyjaszewski,K.Controlled "Living" radical polymerization.atom transfer radical polymerization catalyzed by copper(Ⅰ)and picolylamine complexes[J].Macromolecules,1999,32:2434.
[2]Wang J S,Matyjaszewsky K.Controlled/living radical polymerization: atom transfer radical polymerization in the presence of transition-metal complexes[J].J Am Chem Soc,1995,117:5614.
[3]Nakagawa Y,Matyjaszewski K Synthesis of Well-Defined Allyl End-Functionalized Polystyrene by Atom Transfer Radical Polymerization with an Allyl Halide Initiator[J].Polym J,1998,30:138.
[4]Matyjaszewski K,Beers K L,Kern A Hydrogels by atom transfer radical polymerization.I.Poly(N-vinylpyrrolidinone-g-styrene)via the macromonomer method[J].J Poly Sci:Part A:Polym Chem,1998,36:823.
[5]石艳,傅志峰,李秉毅,焦书科.温度对RBr/CuBr/2,2′-联吡啶引发的苯乙烯原子转移自由基聚合的影响[J].北京化工大学学报,1998,25(2):16.
[6]Zhang Z,Shi Z and Ying S[J].China Synthetic Rubber Industry,1997,20(5):315
[7]Mitsuru Kato,Masarni Kamigaito,Mitsuo Sawamoto,Toshinobu Higashimura.Polymerization of Methyl Methacrylate withthe Carbon Tetrachloridel Dichlorotris-(triphenylphosphine)ruthedum(Ⅱ)/Methylaluminum Bis(2,6-di-tert-butylphen oxide)initiating System:Possibility of Living Radical Polymerization[J].Macromolecules,1996,28:1721.
[8]Granel C,Dubois Ph,Jerome R,Teyssie Ph.Controlled Radical Polymerization of Methacrylic Monomers in the Presence of a Bis(ortho-chelated)Arylnickel(Ⅱ)Complex and Different Activated Alkyl Halides[J].Macromolecules 1996,29:8576.
[9]Destarac M,Matyjaszewski K,Boutevin B.Polychloroalkane initiators in copper-catalyzed atom transfer radical polymerization of (meth)acrylates[J].Macromolecure Chemistry and Physics,2000,201:265.
[10]Mathias Destarac,Jean Marie Bessiere,Bernard Boutevin.Atom Transfer Radical Polymerization of Styrene Initiated by Polychloroalkanes and Catalyzed by CuC1 / 2,2′-Bipyridine:A Kinetic and Mechanistic Study[J].J Polym Sci Part A:Polym Chemistry,1998,36:2933.
[2]Curran D P.the design and application of free radical chain reactions in organic synshesis,part A[J].Synthesis,1988,6:417-439.
[3]Minisci F.Free-Radical Additions to Olefins in the Presence of Redox Systems[J].Acc Chem Res,1975,8(5):165-171.
[4]Iqbal J,Bhatia B,Nayyar N K.Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis:The Formation of Carbon-Carbon Bonds[J].Chem Rev,1994,94(2):519.
[5]Gossage R A,Van de Kuil L A,Van K G.Diaminoarylnickel(Ⅱ)"Pincer"Complexes:Mechanistic Considerations in the Kharasch Addition Reaction,Controlled Polymerization,and Dendrimeric Transition Metal Catalysts[J]. Acc Chem Res, 1998, 31(7): 423.
[6] Clark A J. Atom transfer radical cyclisation reactions mediated by copper complexes [J]. Chem. Soc. Rev, 2002, 31:1.
[7] Severin K [J]. Curr. Org Chem, 2006, 10: 217-224.
[8] (a) Nonhebel D P, Tedder J M, Walton J C. radicals [M]. Cambridge University Press, 1979; (b) Davies D I, Parrott D J. free radicals in organic synthesis [M], Springer-Verlag, Berlin, 1978; (c) Hay J M. reactive free radicals [M],Academic Press, New York, 1974.
[9] (a) Alexakis A, Commercon A, Coulentianos C, Normant J F.Carbocupration of acetylenic acetals and ketals: synthesis of a-b ethylenic acetals, and of dienals and dienones [J]. Pure Appl Chem, 1983, 55, 1759.; (b) Erdik E. Tetrahedron Report Number 159: Copper(I) catalyzed reactions of organolithiums and Grignard reagents [J]. Tetrahedron, 1984, 40, 641.; (c)Lipshutz B H, Wilhelm R S, Kozlowski J A The chemistry of higher order organocuprates [J]. Tetrahedron, 1984, 40: 5005.
[10] (a) Asscher M, Vosfi D. Chlorine activation by redox transfer. Part II. The addition of carbon tetrachloride to olefins [J]. J Chem Soc, 1963, 1887; (b)Asscher M, Vosfi D. Chlorine-activation by redox-transfer. Part III. The " abnormal" addition of chloroform to olefins [J]. J Chem Soc, 1963: 3921
[11] Asscher M, Vosfi D. Redox transfer. Part V. Elementary steps. The oxidation of ferrous and cuprous chloride by carbon tetrachloride [J]. J Chem Soc, Phys Org, 1968,947
[12] (a) Starks H M. Free Radical Telomerisation [M]. New York: Academic Press, 1974, 96; (b) Bury A, Bougeard P, Corker S J, Michael D J, Michele P.1,3-Migration of a cyano-group in substituted 3-cyanopropyl radicals [J]. J Chem Soc, Perkin Trans 2, 1982, 2: 1367.
[13] Corallo M, Pietrasata Y Telomerisation par catalyse redox—VI: Addition dutetrachlorure de carbone sur des monomeres diethyleniques non conjugues [J].Tetrahedron, 1976, 32: 2295
[14] Bellus D Copper-catalyzed additions of organic polyhalides to olefins: a versatile synthetic tool [J]. Pure &Appl Chem, 1985, 57(12): 1827.
[15] (a) Julia M , Saussine L, Thuillier G L. Addition du chloracetate de methyle sur les olefines [J]. J Organomet Chem, 1979, 174: 359.; (b) Julia M, Thuillier G L,Saussine L.Additions D'α-chloronitriles sur les olefines par catalyse redox[J].J Organomet Chem,1979,177:211
[16]Wang J S,Matyjaszewski K Controlled/"living" radical polymerization,atom transfer radical polymerization in the presence of transition-metal complexes [J].J Am Chem Soc,1995,117:5614.
[17]Wang J S,Matyjaszewski K Controlled/"Living" Radical Polymerization.Halogen Atom Transfer Radical Polymerization Promoted by a Cu(Ⅰ)/Cu(Ⅱ)Redox Process[J].Macromolecules,1995,28(23):7901.
[18]Wang J S,Matyjaszewsky K.Controlled/living radical polymerization.Halogen atom transfer radical polymerization promoted by a Cu(Ⅰ)/Cu(Ⅱ)redox process[J].Macromolecules,1995,28(23):7901.
[19]Kato M,Kamigaito M,Sawamoto M.Polymerization of methyl methacrylate with the carbontetrachloride/dichlorotris(triphenylphosphine)ruthenium(Ⅱ)/methyl aluminium bis(2,6-di-tert-butylphenoxide)initiating system:possibility of living radical polymerization[J].Macromolecules,1995,28(5):1721.
[20]Percec V,Barboiu B."Living" Radical Polymerization of Styrene Initiated by Arenesulfonyl Chlorides and CuI(bpy)nCl[J].Macromolecules,1995,28(23):7970.
[21]袁金颖.原子转移自由基聚合反应在合成预定结构聚合物中的应用[J].高分子材料科学与工程,2003,19(5):1-9
[22]史增谦,刘盈海,李艳香.几种新型有机酸配体和FeCl_2络合催化下的苯乙烯原子转移自由基聚合反应[J].河北大学学报(自然科学版),2004,(2):148.
[23]华曼,陈明清,刘晓亚.原子转移自由基聚合的近期进展研究发展[J].化学世界,2004,2:103.
[24]岳玲,周建华,虎春艳.一种新型用于原子转移自由基聚合过程的Cu(Ⅰ)络合物的研究[J].感光科学与光化学,2005,23(3):183.
[25]Wang Yun Pu,Pei Xiao Wei,He Xiao Yan.Synthesis of well defined,polymer-grained silica nanoparticles via reverse ATRP[J].Eur Polym J,2005,(41):1326.
[26]Nikhil K.Singha,Barteld de Ruiter,Ulrich S.Schubert.Atom Transfer Radical Polymerization of 3-Ethyl-3-(acryloyloxy) methyloxetane [J].Macromolecules, 2005,38(9): 3596.
[27] Sachin Borkar, Ayusman Sen. Novel Fluoroal kene MethylAcrylate Copolymers by Atom Transfer Radical Polymerization [J]. Macromolecules,2005, 38(7): 3029.
[28] Yi Zheng Jin, Chao Gao, Harold W K. Polymer -Grafted Carbon Spheres by Surface- Initiated Atom Transfer Radical Polymerization [J] .Macromol Rapid Commun, 2005, 26: 1133.
[29] Tzong Liu Wang, Yu Zhi Liu, Bo Chang Jeng. The Effect of Initiators Reaction Condi tions on the Polymer Syntheses Atom Transfer Radical Polymerization [J]. J Polym Res, 2005,12: 67.
[30] Jayachandran N. Kizhakkedat hu, Kainthan Rajesh Kumar, Diane Goodman.Synt hesis and characterization of well - defined hydrophilic block copolymer brushes by aqueous ATRP [J]. Polymer, 2005, 45: 7471.
[31] Du Jianzhong, Chen Yongming. Atom Transfer Radical Polymerization of a Reactive Monomer: 3-(Trimethoxysilyl) propyl Methacrylate [J].Macromolecules, 2004, 37: 6322.
[32] Frechet J M J, Leduc M R, Weimer Metal. Living free radical polymerization and dendritic polymers [J]. Am Chem Soc Div Polym Chem Prepr, 1997, 38(1): 756.
[33] Kulprathi Panjas. Separation of citricacid from ferment ation broth with a neutral polymeric adsorbent [P]. US: 4720579, 1988- 01-19.
[34] Gaynor S G, Qiu J, Matyjaszewski K. Controlled/"Living" Radical Polymerization Applied to Water-Borne Systems [J]. Macromolecules, 1998,31(17): 5951
[35] Makino T, Tokunaga E, Hogen E. Controlled atom transfer radical polymeriza-tions of methyl methacrylate under micellar conditions [J]. Polym Prep,1998, 39(1): 288
[36] Kato M, Kamigaito M, Sawamoto M. Polymerization of Methyl Methacrylate with the Carbon Tetrachloride/Dichlorotris-(triphenylphos phine) ruthenium (II)/ Methylaluminum Bis (2,6-di-tert-butylphenoxide) Initiating System:Possibility of Living Radical Polymerization [J]. Macromolecules, 1995,28(5): 1721.
[37]Percec V,Barboiu B."Living" Radical Polymerization of Styrene Initiated by Arenesulfonyl Chlorides and CuI(bpy)nCl[J].Macromolecules,1995,28(23):7970.
[38]Fischer H.J Polym Sci,Part A:Polym.Chem.1999,37:1885-1901.
[39]Borsig E,Lazar M,Capla M.Angew.Makromol.Chem.1969,9,89-95.
[40]Chiefari J,Chong Y K,Ercole F.Macromolecules.1998,31:5559-5562.
[41]Shen Y,Zhu S.Zeng F,.Macromol.Chem Phys.2000,201:1169-1175.
[42]Matyjaszewski K,Paik H j,Zhou P,Diamanti S J.Macromolecules,2001,34:5125-5131.
[43]Patten T E,Matyjaszewski K.Adv Mater.1998,10:901-915.
[44]Gobelt B,Matyjaszewski K.Macromol Chem Phys.2000,201:1619-1624.
[45]Ando T,Kamigaito M,Sawamoto M.Tetrahedron 1997,53:15445-15457.
[46]Cheng G L,Hu C P,Ying S K.J Mol Catal A:Chem.1999,144,357-362.
[47]Percec V,Asandei A D,Asgarzadeh F,Barboiu B,Holerca M N,Grigoras C.J Polym Sci Part A:Polym Chem.2000,38:4353-4361.
[48]Senoo M,Kotani Y,Kamigaito M,Sawamoto M.Macromolecules 1999,32:8005-8009.
[49]Xia J,Matyjaszewski K.Macromolecules.1999,32:2434-2437.
[50]Ando T,Kamigaito M,Sawamoto M.Tetrahedron.1997,53:15445-15457.
[51]Zeng F,Shen Y,Zhu S,Pelton R.Macromolecules.2000,33:1628-1635.
[52]Nishikawa T,Kamigaito M,Sawamoto M.Macromolecules.1999,32,2204-2209.
[53]Wang J L,Grimaud T,Matyjaszewski K.Macromolecules.1997,30:6507-6512.
[54]Neumann A,Keul H,Hocker H.Macromol Chem Phys.2000,201:980-984.
[55]Cheng G L,Hu C P,Ying S K.Macromol.Rapid Commun.1999,20:303-307.
[56]Kwon T S,Kumazawa S,Yokoi T,Kondo S,Kunisada H,Yuki Y J.Macromol Sci Pure Appl Chem.1997,A34:1553-1567.
[57]Nishikawa T,Ando T,Kamigaito M,Sawamoto M.Macromolecules.1997,30:2244-2248.
[58]Reining B,Keul H,Hocker H.Polymer.1999,40:3555-3563.
[59]Matyjaszewski K,Jo S M,Paik H J,Gaynor S G.Macromolecules. 1997,30:6398-6400.
[60]汤志忠,高保娇.原子转移自由基聚合及其研究进展[J].化北工学院学报,2004,25,271.
[61]Sedjo R A,MirousB K,BrittainW J Synthesis of Polystyrene-block-poly (methyl methacrylate)Brushes by Reverse Atom Transfer Radical Polymerization[J].Macromolecules,2000,33(5):1492.
[62]Ejaz M,Yamamoto S,Ohno K Controlled Graft Polymerization of Methyl Methacrylate on Silicon Substrate by the Combined Use of the Langmuir-Blodgett and Atom Transfer Radical Polymerization Techniques[J].Macromolecules,1998,31(17):5934.
[63]Zeng F Q,Shen Y Q,Zhu S P Synthesis and Characterization of Comb-Branched Polyelectrolytes.1.Preparation of Cationic Macromonomer of 2-(Dimethylamino)ethyl Methacrylate by Atom Transfer Radical Polymerization[J].Macromolecules,2000,33(5):1628.
[64]Carrot G,Hilborn J,Hedrick J L Novel Initiators for Atom Transfer Radical and Ring-Opening Polymerization:A New General Method for the Preparation of Thiol-Functional Polymers[J].Macromolecules,1999,32(15):5171.
[65]Heise A,Nyuyen C,Malek R Starlike Polymeric Architectures by Atom Transfer Radical Polymerization:Templates for the Production of Low Dielectric Constant Thin Films[J].Macromolecules,2000,33(7):2346.
[66]魏振平,毛世瑞.比色法与液相色谱法对罗红霉素溶液稳定性研究的比较[J].药学学报,2000,35(11):871.
[67]黄涛主编.有机化学实验[M].北京:高等教育出版社,1998.55.
[68]Burwell R I.Manufacture and properties of erythromycin derivatives[J].Chem Rev,1954,54,635.
[69]Suzuki H.Reaction ofpolysubstituted aromatics.XIX.Chloromethylation with chloro- methyl methyl ether and 60%-fuming sulfuric acid.Simple synthesis of some nitropoly methylbenzyl chlorides and dihalopolymethylbenzyl chlorides.[J].Bull Chem Soci Japan 1970,43.3299.
[70]愈凌中.有机化学中的人名反应[M].北京:科学出版社,1984.62.
[71]乌锡康主编.有机化工废水治理技术[M].北京:化学工业出版社,1997. 374.
[72]德雷兹,范德旺迪伦.碱金属柠檬酸盐的制备方法[P].CN:1035611,1997-08-13.
[73]刘群峰,李思东,何卫东.3-氯-2-氯甲基-1-丙烯引发苯乙烯原子转移自由基聚合的研究[J].高分子学报.2007,6:582.
[74]For a review on radical polymerization,see:Moad G,Solomon D H.The Chemistry of Free Radical Polymerization.Elsevier Science:Oxford,U.K.,1995.
[75](a)Szwarc M Nature 1956,178,1168-1169.
(b)Szwarc M,Levy M,Milkovich R.J Am Chem Soc.1956,78,2656-2657.
[76]Eastmond G C,Webster O W.In New Methods of Polymer Synthesis;Ebdon J R.Ed.Blackie:Glasgow U K.1991:22-75
[77]Aida,T.Prog.Polym.Sci.1994,19,469-528.
[78]Sugimoto H,Inoue S.Adv Polym Sci.1999,146,39-119.
[79]Hirao A,Nakahama S.Acta Polym.1998,49,133-144.
[80](a)Higashimura T,Sawamoto M.Adv Polym Sci.1984,62,49-94.
(b)Sawamoto M.Prog Polym Sci.1991,16,111-172.
(c)Sawamoto M,Kamigaito M.In New Methods of Polymer Science;Ebdon J R,Eastmond G C Eds,Blackie:Glasgow U K,1995;Vol.2,pp 37-68.
[81]Kennedy J P,Ivan B.Designed Polymers by Carbocationic Macromolecular Engineering:Theory and Practice;Hanser:Munich,Germany,1992.
[82]Cationic Polymerizations,Matyjaszewski K Ed,Marcel Dekker:New York,1996.
[83]Yasuda H.Prog Polym Sci.2000,25,573-626.
[84]Mecerreyes D,Jerome R,Dubois Ph.Adv Polym Sci.1999,147,1-59.
[85]Grubbs R,Khosravi E.In Synthesis of Polymers;Schluter,A.D.,Ed.;Materials Science and Technology Series;Wiley-VCH:Weinheim,Germany,1999;pp 65-104.
[86]Sluis M V,Barboiu B,Percec V.Rate enhancement by carboxylate salts in the CuCl,Cu_2O,and Cu(0)catalyzed "living" radical polymerization of BMA initiated with sulfonyl chlorides[J].Macromolecules,1998,31(26):9409.
[87]Percec V,Barboiu B,Neumann A.Metal-catalyzed "living" radical polymerization of styrene initiated with arenesulfonyl chlorides.From heterogeneous to homogeneous catalysis[J].Macromolecules,1996,29(10):3665.
[88]Barboiu B,Percec V,Sluis M V.Self-Regulated Phase Transfer of Cu_2O/bpy,Cu(0)/bpy,and Cu_2O/Cu(0)/bpy Catalyzed "living"Radical polymerization Initiated with Sulfonyl Chlorides[J].Macromolecules,1998,31(12):4053.
[89]Barboiu B,Percec V,Asandei A D.Organocopper-Catalyzed "Living"Radical Polymerization Initiated with Aromatic Sulfonyl halides[J].J.Polym.Sci.Part A:Polym.Chem,2000,38(24):4353.
[90]Patten T E,Matyjaszewski K.Atom Transfer Radical Polymerization and the Synthesis of Polymeric Materials[J].Adv Mater,1998,10:901.
[91]Georges M K,Veregin R P N,Kazmaier P M.Narrow molecular weight resins by a free-radical polymerization process[J].Macromolecules,1993,26(11):2987.
[92]Chiefari J,Chong Y K,Ercole F.Living Free-Radical Polymerization by Reversible Addition-Fragmentation Chain Transfer:The RAFT Process[J].Macromolecules,1998,31(16):5559.
[93]Mayadunne R T A,Rizzardo E,Chiefari J.Living Radical Polymerization with Reversible Addition-Fragmentation Chain Transfer(RAFT Polymerization)Using Dithiocarbamates as Chain Transfer Agents[J].Macromolecules,1999,32(21):6977.
[94]王艳君,王玉霞,袁才登.可逆加成一断裂链转移活性自由基聚合[J].高分子通报,2003,3:57.
[95]Leyden D E,Luttrell H,Preconcentration of trace metals using chelating groups immobilized via silylation[J].Anal Chem,1975,47:1612.
[96]Ulman A.Self-assembled monolayers of alkyltrichiorosilanes:Building blocks for future organic materials[J].Adv Mater,1990,2:573.
[97]Hoom H J,Joode P D,Dijkstra D J,Driessen W L,Kooijman H,Veldman N,Spek A L,Reedijk J.Metal binding affinity of a series ofbisbenzimidazoles immobilized on silica[J].J Mater Chem 1997,7:1747.
[98]Kickelbick G,Paik H J,Matajiszewski K.Immobilization of the Copper Catalyst in Atom Transfer Radical Polymerization[J].Macromolecules,1999,32:2941.
[99]Shen Y Q,Zhu S P,Patten R.Effect of Ligand Spacer on Silica Gel Supported Atom Transfer Radical Polymerization of Methyl Methacrylate [J].Macromolecules, 2001, 34:5812.
[100] Kickelbick G, Paik H J, MatyjaszewskiK. Macromolecules, 1999, 32 (9):2941—2947.
[101] Haddleton D M, Kukulj D, Radigue A P. ABSTR Pap. Am. Chem. S. 1999,217: 170-PMSE Part 2.
[102] Hen S Y Q , Zhu S P, Pelton R. M acromo lecules, 2001, 34 (17): 5812-5818.
[ 103] Haddleton D M, Kukulj D, Duncalf D J. Macromolecules, 1998, 31 (16):5201-5205.
[104] Opstal T, Melis K, Verpoort F. Catal. Lett., 2001, 74 (3-4): 155-159.
[105] Hong S C, MatyjaszewskiK. Macromolecules, 2002, 35 (20): 7592-7605 SEP24.
[106] Shen Y Q, Zhu S P. Aiche Journal, 2002,48 (11):2609- 2619.
[107] Booth R J, Hodges J C. Polymer Supported Quenching Reagents for Parallel Purification [J]. J Am Chem Soc, 1997, 119: 4882.
[108] Haddleton D M, Kukulj D, Radigue A P. Atom transfer polymerization of methyl methacrylate mediated by solid supported copper catalysts [J]. Chem Commun, 1999, 99.
[109] Kickelbick G, Paik H J, Matyjaszewski K. Immobilization of the Copper Catalyst in Atom Transfer Radical Polymerization [J]. Macromolecules, 1999,32:2941.
[110] Kickelbick G, Paik H J, Matyjaszewski K. Macromolecules, 1999, 32 (9):2941-2947.
[111] L iou S, Rademacher J T, Malaba D,. Macromolecules, 2000, 33(12):4295-4296.
[112] Shen Y Q, Zhu S P. Macromolecules, 2001, 34 (25):8603-8609.
[113] Shen Y Q , Zhu S P, Zeng F Q. Macromolecules, 2000, 33 (15): 5427-5431.
[114] Hong S C, Paik H J, Matyjaszewski K. An Immobilized/Soluble Hybrid Catalyst System for Atom Transfer Radical Polymerization [J].Macromolecules, 2001, 34: 5099.
[115] Hong S C, Paik H J, MatyjaszewskiK. Macromolecules, 2001, 34 (15):5099-5102.
[116]Hong S C,Lutz J F,Inoue Y.Macromolecules,2003,36(4):1075-1082.
[117]Hong S C,Matayjaszewski K.Fundamentals of Supported Catalysts for Atom Transfer Radical Polymerization(ATRP)and Application of an Immobilized/Soluble Hybrid Catalyst System to ATRP[J].Macromolecules,2002:35:7592.
[118]Hong S C,Neugebauer D,Inoue Y,Lutz J F,Matyjaszewski K[J].Macromolecules,2003,36:27.
[119]Hong S C,Lutz J F,Inoue Y,Lutz J F,Matyjaszewski K.Preparation of Segmented Copolymers in the Presence of an Immobilized/Soluble Hybrid ATRP Catalyst System[J].Macromolecules,2003,36:1075.
[120]Tsarevsky N V,Bernaerts K V,Dufour B,Prez F E D,Matyjaszewski K.Well-Defined(Co)polymers with 5 Vinyltetrazole Units via Combination of Atom Transfer Radical(Co)polymerization of Acrylonitrile and "Click Chemistry"-Type Postpolymerization Modification[J].Macromolecules,2004,37:9308.
[121]Huang J,Cusick B,Pietrasik J,Wang L,Kowalewski T,Lin Q,Matyjaszewski K.Synthesis and In Situ Atomic Force Microscopy Characterization of Temperature-Responsive Hydrogels Based on Poly(2-(dimethylamino)ethyl methacrylate)Prepared by Atom Transfer Radical Polymerization[J].Langmuir,2007,23:241.
[122]Vijayakumar R,Koltypin Y,Felner I.Sonochemical synthesis and characterization of pure nanometer-sized Fe_3O_4 particles[J].Mater Sci Eng A,2000,286(1):101.
[123]邱星屏.四氧化三铁磁性纳米粒子的合成及表征.厦门大学学报(自然科学版),1999,38(5):711.
[124]Warshawsky D A,Upson W T,Ferrar J.Zerovalent metal polymer composites.Ⅲ.Metallization of metal oxide surfaces with the aid of metallized functional polymer microdispersions[J].Polym Sci Part A,1989(27):3015.
[125]Trau D,Yang W,Seydack M.Nanoencapsulated Microcrys talline Particles for Superamplified Biochemical Assays[J].Anal Chem,2002(74):5480.
[126]Caruso F,Schuler C.Enzyme Multilayers on Colloid Particles:Assembly,Stability,and Enzymatic Activity[J].Langmuir,2000(16):9595.
[127]Jin W,Shi X,Caruso F.High Activity Enzyme Microcrystal Multilayer Films [J].JAm Chem Soc,2001(123):8121.
[128]Mecking S,Thomann R.Core-Shell Microspheres of a Catalytic-ally Active Rhodium Complex Bound to a Polyelectroly e-Coated Latex[J].Adv Mater,2000(12):953.
[129]Yang W J,Trau D,Renneberg R.Layer-by-Layer Construction of Novel Biofunctional Fluorescent Microparticles for Immunoassay Applicati-ons[J].J Colloid Interface Sci.2001,234:356.
[130]Khopade A J,Caruso F.Stepwise Self-Assembled Poly(amidoamine)Dendrimer and Poly(styrenesulfonate)Microcapsules as Sustained Delivery Vehicles[J].Biomacromolecules,2002,3(6):1154.
[131]高道江,赖欣,王建华.磁流体制备技术的现状及展望[J].磁性材料及器件,1998,29(2):20.
[132]齐凤春.磁性液体[J].材料导报,1998,12(2):17.
[133]杨咏来,宁桂玲,吕秉玲.液相法制备纳米粉体时防止团聚方法概述[J].材料导报,1998,12(2):11.
[134]邱广明,孙宗华.水溶性磁流体的制备和性质[J].化学试剂,1993,15(4):234.
[135]刘成林,钟菊花,张兆奎.表面修饰对a-Fe2O_3超微粒光谱特性的影响[J].光谱学与光谱分析,2003,23(1):154.
[136]郑水林,张清辉,李杨.超细氧化铁红颜料的表面改性研究[J].矿冶,2003,12(1):69.
[137]李小娥,郝欣,吕海茹.四氧化三铁磁性超细粉的表面改性[J].无机盐工业,2002,34(5):6.
[138]包建军,刘迪文.铁氧磁流体的微波水热合成、表面修饰和磁性高分子微球的制备[J].高分子材料科学与工程,2003,19(5):204.
[139]王秀宇,杨桂琴,张之圣等.磁流体制备中磁性颗粒的表面处理[J].应用化学,2005,22(5):525.
[140]任欢鱼,庄虹,刘勇健.Fe_3O_4纳米颗粒的表面改性[J].化学研究,2003,14(1):11.
[141]施卫贤,杨俊,王亭杰.磁性Fe_3O_4微粒表面有机改性[J].物理化学学报,2001,17(6):507.
[142]刘峥.Fe_3O_4微粒表面有机改性及其应用研究[J].化工技术与开发,2004,33(3):12.
[143]娄敏毅,王德平,黄文旵.偶联剂修饰纳米微球的制备及其表征[J].上海生物医学工程,2004,25(3):14.
[144]Lifen Shen,Paul E,Laibinis T,Alan Hatton.Aquseous magneticfluids stabilized by surfactant bilayers[J].J Magn Magn Mate,1999,194:37.
[145]蒋新宇,周春山,张俊山.导向药物用纳米Fe_3O_4磁性粒子的制备及表征[J].中南工业大学学报(自然科学版),2003,34(5):516.
[146]安丽娟,李兆强,徐娓.超顺磁性高分子微球的制备与表征[J].高等学校化学学报,2005,26(2):366.
[147]陈晓青,张俊山,杨娟玉.双层表面活性剂分散制备水基磁流体[J].无机化学学报,2003,19(5):547.
[148]Tahsin Bahar,Serdar S,Celibi.Immobilization of glucoamylase on magnetic poly(styrene)particles[J].J Appl Polym Sci,1999,72:69.
[149]Yen.Functionalm agneticm icrosphere.USP4,285,819,1981.
[150]Tricot.Process for the preparation of magnetic beads of vinylaromaticpolymers.USP4,339,337.1982.
[151]Marge.Polyacrolein-typemicrosphere,USP4,783,366,1988.
[152]Tsuruta Meiji.Manufacture of magneticmicrosphere,JP 62204501,1987.
[153]Daniel.Magnetic polymerlatex and preparation process.USP4,358,388.1982.
[154]Charmot.Magnetizable composite microspheres of hydrophobic crosslinked polymer,process for them and their applicationin biology.USP5,356,713.1994.
[155]Solcnee Hajna.Colloidal size hydrophobic polymers particulate having discretepartic lesofan in organicm aterialdi spersedth erein.USP4,421,660.1983.
[156]邱广明,杨春雁,孙宗华.单分散亚微米级磁性微球的合成[J].功能高分子学报,1996,9(4):565.
[157]邱广明,章贤明,孙宗华.磁性聚苯乙烯微球的合成和特性[J].高分子材料科学与工程,1993,(2):38.
[158]Noriko,Yanase,Hiromichi,Noguchi,Hideki Asakura,Preparation of Magnetic Latex Particles by Emulsion Polymerization of Styrene in the Presence of Ferrofluid[J].J Appl Polym Sci,1993,50:765.
[159]Hiromichi Noguchi,Noriko Yanase,Yasuzo Uchida.Preparation and Characterization by Thermal Analysis of Magnetic Latex Particles[J].J Appl Polym Sci,1993,48:1593.
[160]Kondo A,Kamura H,Higashitani K.Development and application of Thermo Sensitive magnetic immuno microsphere for antibody Purication[J].Appl Microbiol biotechnol,1994,41:99.
[161]Hwee Peng Khng,David Cunlife,Stephen Davies.The synthesis of submicron magnetic particles and theirusef or preparative purification of proteins.Biotechnol&bioengineering,1998,60(4):419
[162]邱广明,高晓松,杨春雁.Fe_3O_4/P(St-AA)核一壳复合微球的制备和表征[J].应用化学,1996,13(1):6.
[163]李孝红,孙宗华.磁性高分子微球的合成研究—带醛基磁性高分子微球的合成及表征[J].离子交换与吸附,1996,12(6):486.
[164]李孝红,丁小斌,孙宗华.含羟基磁性高分子微球的合成及表征[J].功能高分子学报,1995,8(1):73.
[165]丁小斌,孙宗华,万国祥.热敏性高分子包裹的磁性微球的合成[J].高分子学报,1998,5:628.
[166]丁小斌,孙宗华,万国祥.热敏型高分子包裹的磁性微球的性质及表征[J].高分子学报,1999,6:674.
[167]Richard.Latex of calibrated mono-disperse magnetizablem icrosphere,process of preparation and use of saidlatexin chemistry orin biology.USP5,976,426.1999.
[168]张津辉,蒋中华,王仁芝.磁性微球的制备,理化性质及初步应用[J].化学通报,1997,9:55.
[169]Rembaum.1.Production ofmonodisperse,polymeficmicrosphere.USP4,929,400.1990.
[170]Ugelstad.Process for preparing magnetic polymer panicles,USP4,774,265,1988.
[1]Pyun J,M atyjaszewski K,Kowalewski T.J.Am.Chem.Soc.2001,123(38):944-9446.
[2]Von Weme T,Patten T E.J Am Chem.Soc.1999,121(32):7409-7410.
[3]Matyjaszewski K,Miller P J.J Pyun.Macromolecules,1999,32(20):6526-6535.
[4](a)Simal F,Sebille S,Demonceau A,Noels A F,Nunez R,Abad M,Teixidor F,Vinas C Radical reactions catalysed by ruthenium(Ⅱ)complexes with anionic carborane phosphine ligands:Kharasch addition to olefins and controlled polymerisation[J].Tetrahedron Lett,2000,41,5347;
(b)Tutusaus O,Vinas C,Nunez R,Teixidor F,Demonceau A,Delfosse S,Noels A F,Mata I.,Molins E.The Modulating Possibilities of Dicarbollide Clusters:Optimizing the Kharasch Catalysts[J].J Am Chem Soc.2003,125(39):11830;
(c)Tutusaus O,Delfosse S,Demonceau A,Noels A F,Vinas C,Teixidor F Kharasch addition catalysed by half-sandwich ruthenium complexes.Enhanced activity of ruthenacarboranes[J].Tetrahedron Lett.2003,44,8421.
[5](a)Tallarico J A,Malnick L M,Snapper M L.New Reactivity from (PCy_3)2Cl_2Ru=CHPh:A Mild Catalyst for Kharasch Additions[J].J Org Chem,1999,64(2):344;
(b)Simal F,Demonceau A,Noels A F Kharasch addition and controlled atom transfer radical polymerisation(ATRP)of vinyl monomers catalysed by Grubbs' ruthenium-carbene complexes[J].Tetrahedron Lett.1999,40,5689.
[6](a)Simal F,Wlodarczak L,Demonceau A,Noels A F Highly efficient Kharasch addition catalysed by RuCI(Cp*)(PPh_3)_2[J].Tetrahedron Lett.2000,41:6071;
(b)Simal F,Wlodarczak L,Demonceau A,Noels A F,New,Highly Efficient Catalyst Precursors for Kharasch Additions- [RuCI(Cp*)(PPh_3)_2]and[RuCl(Ind)(PPh_3)_2][J].Eur J Org Chem,2001,14:2689.
[7]Aurore Richel,Albert Demonceau and Alfred F.Noels Electrochemistry as a correlation tool with the catalytic activities in[RuCl_2(p-cymene)(PAr_3)]-catalysed Kharasch additions[J].Tetrahedron Letters,2006,47:2077.
[8]Clercq B D,Lefebvre F,Verpoort F.Immobilization of multifunctional Schiffbase containing ruthenium complexes on MCM-41[J].Applied Catalysis A:General,2003,247:345.
[9]Clark A J,Geden J V,Thom S Solid-Supported Copper Catalysts for Atom-Transfer Radical Cyclizations:Assessment of Support Type and Ligand Structure on Catalyst Performance in the Synthesis of Nitrogen Heterocycles[J].J Org Chem,2006,71(4):1471.
[10]李忠辉,张永明,刘燕刚,薛敏钊.原子转移自由基聚合及催化剂负载化研究进展.高分子材料科学与工程.2005,21(1),6-10.
[11](a)Kickelbick G,Paik H J,Matyjaszewski K Immobilization of the Copper Catalyst in Atom Transfer Radical Polymerization[J].Macromolecules,1999,32(9):2941;(b)Haddleton D M.Kukulj D,Radigue A P.Atom transfer polymerisation of methyl methacrylate mediated by solid supported copper catalysts[J].Chem Commun,1999,1:99;(c)Shen Y,Zhu S,Zeng F,Pelton R Supported atom transfer radical polymerization of methyl methacrylate mediated by CuBr-tetraethyldiethylenetriamine grafted onto silica gel[J].J Polym Sci Part A:Polym Chem,2001,39,1051;(d)Shen Y,Pelton R.Effect of Ligand Spacer on Silica Gel Supported Atom Transfer Radical Polymerization of Methyl Methacrylate[J].Macromolecules,2001,34(17):5812;(e)Nguyen J V,Jones C W,Design,Behavior,and Recycling of Silica-Supported CuBr-Bipyridine ATRP Catalysts[J].Macromolecules,2004,37(4):1190;(f)Nguyen J V,Jones C W.Effect of the synthetic method and support porosity on the structure and performance of silica-supported CuBr/pyridylmethanimine atom transfer radical polymerization catalysts,Ⅱ.Polymerization of methyl methacrylate[J].J Polym Sci Part A:Polym Chem,2004,42:1384.
[1](a)Kato M,Kamigaito M,Sawamoto M,Higashimura T.Macromolecules 1995,28:1721-1723;(b)Wang J S,Matyjaszewski K.J Am Chem Soc.1995,117:5614-5615.
[2](a)Clark A.J Chem Soc Rev.2002,31:1-11;(b)Eckenhoff W T,Pintauer T.Inorg Chem.2007,46:5844-5846.
[3]Gossage R A,van de Kuil L A,van Koten G.Acc Chem Res.1998,31:423-431.
[4](a)Bellesia F,Forti L,Gallini E.Tetrahedron 54,1998,7849-7856;(b)Severin K.Curr Org Chem.2006,10:217-224.
[5](a)Iqbal J,Bhatia B,Nayyar N K.Chem Rev.1994,94,519-564;(b)Simal E Demonceau A.Noels A F.In Recent Research Developments in Organic Chemistry;Pandalai S G Ed.Transworld Research Network:Trivandrum,1999,3:455-464;(c)Demonceau A,Noels A F.Top Organomet Chem.2004,11:155-171.
[1]Xia J,Matyjaszewski,K.Controlled "Living" radical polymerization.atom transfer radical polymerization catalyzed by copper(Ⅰ)and picolylamine complexes[J].Macromolecules,1999,32:2434.
[2]Wang J S,Matyjaszewsky K.Controlled/living radical polymerization: atom transfer radical polymerization in the presence of transition-metal complexes[J].J Am Chem Soc,1995,117:5614.
[3]Nakagawa Y,Matyjaszewski K Synthesis of Well-Defined Allyl End-Functionalized Polystyrene by Atom Transfer Radical Polymerization with an Allyl Halide Initiator[J].Polym J,1998,30:138.
[4]Matyjaszewski K,Beers K L,Kern A Hydrogels by atom transfer radical polymerization.I.Poly(N-vinylpyrrolidinone-g-styrene)via the macromonomer method[J].J Poly Sci:Part A:Polym Chem,1998,36:823.
[5]石艳,傅志峰,李秉毅,焦书科.温度对RBr/CuBr/2,2′-联吡啶引发的苯乙烯原子转移自由基聚合的影响[J].北京化工大学学报,1998,25(2):16.
[6]Zhang Z,Shi Z and Ying S[J].China Synthetic Rubber Industry,1997,20(5):315
[7]Mitsuru Kato,Masarni Kamigaito,Mitsuo Sawamoto,Toshinobu Higashimura.Polymerization of Methyl Methacrylate withthe Carbon Tetrachloridel Dichlorotris-(triphenylphosphine)ruthedum(Ⅱ)/Methylaluminum Bis(2,6-di-tert-butylphen oxide)initiating System:Possibility of Living Radical Polymerization[J].Macromolecules,1996,28:1721.
[8]Granel C,Dubois Ph,Jerome R,Teyssie Ph.Controlled Radical Polymerization of Methacrylic Monomers in the Presence of a Bis(ortho-chelated)Arylnickel(Ⅱ)Complex and Different Activated Alkyl Halides[J].Macromolecules 1996,29:8576.
[9]Destarac M,Matyjaszewski K,Boutevin B.Polychloroalkane initiators in copper-catalyzed atom transfer radical polymerization of (meth)acrylates[J].Macromolecure Chemistry and Physics,2000,201:265.
[10]Mathias Destarac,Jean Marie Bessiere,Bernard Boutevin.Atom Transfer Radical Polymerization of Styrene Initiated by Polychloroalkanes and Catalyzed by CuC1 / 2,2′-Bipyridine:A Kinetic and Mechanistic Study[J].J Polym Sci Part A:Polym Chemistry,1998,36:2933.