一种溶解性好的双核配体的合成表征及用于催化甲基丙烯酸甲酯聚合
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摘要
自从Maty]iasezwksi和王锦山首次报道了二联吡啶/Cu体系的原子转移催化聚合之后,关于原子转移自由基聚合(ATRP)的配体的研究一直在进行着,ATRP在获得低分子量分布的聚合产物方面有着其重要的意义,特别是在设计星形聚合物方面有着独特的优势,而且易于操作,选择适当的催化剂配体,可以提高ATRP的活性,并得到分子量分布好的聚合产物,这样的产物在材料的设计方面是有着很重要的作用。寻找合适的高活性催化剂配体,对于ATRP在工业上应用有着很大的价值。
但是目前在催化剂配体的研究当中,合成出的配体具有较大的分子结构,其与金属配位之后的配体在溶剂中存在溶解度低,催化活性较低的缺点。因此,寻找适当的的催化剂使其配合物在溶剂中有较好的溶解度,提高其催化活性是目前研究ATRP的重要工作。
本文以本实验室合成的双-1-苯基-1,3-二酮基苯在无水无氧条件下催化甲基丙烯酸甲酯、苯乙烯能得到分子量分布比较窄的聚合产物的实验为基础,设计并合成了最为简单的1,3-二酮化合物:1,1,2,2-四乙酰基乙烷,并用于反向原子转移催化聚合(RATRP)。由于1,1,2,2-四乙酰基乙烷的结构简单,在各种不同的非质子性溶剂中都有较好的溶解性,且其配合物在一定温度下在这些溶剂中也有较好的溶解度,在一定的条件下其催化甲基丙烯酸甲酯等单体具有较好的催化活性。
实验结果表明,在一定条件下,以1,1,2,2-四乙酰基乙烷/Co和1,1,2,2-四乙酰基乙烷/Ni的催化体系对MMA具有很好的可控性。
Since Matyjasezwksi and Wang JinShan first reported 4,4'-bipyridine/Cu in atom transfer radical polymerization(ATRP),the ligand of ATRP has been engaged in the researches.
ATRP has important significance to obtain low-molecular-weight distribution in the polymer product,especially in the design of star-shaped polymers.Meanwhile,ATRP is easy to operation,and high activity catalyst can improve the atom transfer radical polymerization activity and get good molecular distribution polymerization products.So searching for suitable ligands highly active catalyst for atom transfer radical polymerization in the industrial application is of great value.
However,in the study of ligand catalyst,most ligands synthesised usually have a larger molecular structure or low solubility in the solvent after they coordination with the metal which will influence the activity of the catalyst.Therefore,to find a appropriate solube catalyst in the solvent and enhance its catalytic activity is an important work study in atom transfer catalyzed polymerization.
In this paper,basing on the laboratory work:bi-1-phenyl-1,3-diketone-benzene, which can get a rather narrow molecular weight distribution of polymer products in polymerization of methyl methacrylate and styene,we design and synthesis of the most simple compound:1,1,2,2-tetraacetyl ethane and work for the reverse atom transfer catalyzed polymerization.Because 1,1,2,2-tetraacetyl ethane has a simple structure and good solubility in a variety of non-proton solvents.Their complexes also have good solubility.Experiments show that under certain conditions in the catalytic methyl methacrylate monomer,such as a good catalytic activity.
The experimental results show that under certain conditions,1,1,2,2-tetraacetyl ethane/Co and 1,1,2,2-tetraacetyl ethane/Ni systems have a very good controllable in polymerization of MMA.
但是目前在催化剂配体的研究当中,合成出的配体具有较大的分子结构,其与金属配位之后的配体在溶剂中存在溶解度低,催化活性较低的缺点。因此,寻找适当的的催化剂使其配合物在溶剂中有较好的溶解度,提高其催化活性是目前研究ATRP的重要工作。
本文以本实验室合成的双-1-苯基-1,3-二酮基苯在无水无氧条件下催化甲基丙烯酸甲酯、苯乙烯能得到分子量分布比较窄的聚合产物的实验为基础,设计并合成了最为简单的1,3-二酮化合物:1,1,2,2-四乙酰基乙烷,并用于反向原子转移催化聚合(RATRP)。由于1,1,2,2-四乙酰基乙烷的结构简单,在各种不同的非质子性溶剂中都有较好的溶解性,且其配合物在一定温度下在这些溶剂中也有较好的溶解度,在一定的条件下其催化甲基丙烯酸甲酯等单体具有较好的催化活性。
实验结果表明,在一定条件下,以1,1,2,2-四乙酰基乙烷/Co和1,1,2,2-四乙酰基乙烷/Ni的催化体系对MMA具有很好的可控性。
Since Matyjasezwksi and Wang JinShan first reported 4,4'-bipyridine/Cu in atom transfer radical polymerization(ATRP),the ligand of ATRP has been engaged in the researches.
ATRP has important significance to obtain low-molecular-weight distribution in the polymer product,especially in the design of star-shaped polymers.Meanwhile,ATRP is easy to operation,and high activity catalyst can improve the atom transfer radical polymerization activity and get good molecular distribution polymerization products.So searching for suitable ligands highly active catalyst for atom transfer radical polymerization in the industrial application is of great value.
However,in the study of ligand catalyst,most ligands synthesised usually have a larger molecular structure or low solubility in the solvent after they coordination with the metal which will influence the activity of the catalyst.Therefore,to find a appropriate solube catalyst in the solvent and enhance its catalytic activity is an important work study in atom transfer catalyzed polymerization.
In this paper,basing on the laboratory work:bi-1-phenyl-1,3-diketone-benzene, which can get a rather narrow molecular weight distribution of polymer products in polymerization of methyl methacrylate and styene,we design and synthesis of the most simple compound:1,1,2,2-tetraacetyl ethane and work for the reverse atom transfer catalyzed polymerization.Because 1,1,2,2-tetraacetyl ethane has a simple structure and good solubility in a variety of non-proton solvents.Their complexes also have good solubility.Experiments show that under certain conditions in the catalytic methyl methacrylate monomer,such as a good catalytic activity.
The experimental results show that under certain conditions,1,1,2,2-tetraacetyl ethane/Co and 1,1,2,2-tetraacetyl ethane/Ni systems have a very good controllable in polymerization of MMA.
引文
[1]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,l995,117(20):5614-5615.
[2]Wang J S,Matyjaszewski K.Controlled'7 living"radical polymerization.Halogen atom transfer radical polymerization promoted by a Cu(Ⅰ)/Cu(Ⅱ) redox process[J].Macromolecules,1995,28:7901-7910.
[3]Matyjaszewski K,Gayno r S G,Coca S.U.S.Patent,6538091,2003.
[4]Matyjaszewski K.Current Opinion in Solid State Materials Science[S],1996,1(6):769-776.
[5]Cunningham M F.Living/controlled radical polymerizations in dispersed phase systems Progress in Polymer Science[J],Polymer Science,2002,27(6):1039-1067.
[6]郭清泉,陈焕钦.一种新型自由基聚合:活性/可控自由基聚合[J],高分子材料科学与工程,2003,19(4):56-63.
[7]陈小平,丘坤元.“活性”/控制自由基聚合的研究进展[J],化学进展,2001,13(3):224-233.
[8]Matyaszewski K.Controlling polymer structures by atom transfer radical polymerization and other controlled/living radical polymerizations[Jj.Ma cromole ular Symposia,2003,195(1)55-32.
[9]王艳君,王玉霞,袁才登可逆加成-断裂链转移活性自由基聚合.高分子通报,2003,5(3):57-63.
[10]郭清泉,林淑英,陈焕钦.活性/可控自由基聚合的研究进展,材料科学与工程学报,2003,21(3):13-15.
[11]GeorgesM K,VereginRPN,Kazmaier P M,et al.Polymer science in the 21st century Trends in Polymer Seience[J],Polymer science,1994,2(2):66-72.
[12]Richard P.N.Veregin,Michael K.Georges,Peter M.Kazmaier,Gordon K.Hamer Free radical polymerizations for narrow polydispersity resins:electron spin resonance studies of the kinetics and mechanism,Maeromolecules[J],1993,26(20):5316-5320.
[13]Peter M.Kazmaier,Karen A.Moffat,Michael K.Georges,Richard P.N.Veregin,Gordon K.Hamer Free-Radical Polymerization for Narrow-Polydispersity Resins.Semiempirical Molecular Orbital Calculations as a Criterion for Selecting Stable Free-Radical Reversible Terminators.Macromoleeules,l995,28(6):1841-1846.
[14]S.Richard Turner,Richard W.Blevins Photoinitiated block copolymer formation using dithiocarbamate free radical chemistry[J].Maeromoleeules,1990,23(6):1856-1859.
[15]J.D.Druliner,Living radical polymerization involving oxygen-centered species attached to propagating chain ends[J].Maeromoleeules,1991,24(23):6079-6082.
[16]Mecking,S.;Johnson,L.K.;Wang,L.;Brookhart,M.Mechanistic Studies of the Palladium-Catalyzed Copolymerization of Ethylene and α-Olefins with Methyl Acrylate[J]J.Am.Chem.Soc.1998,120(5):88.
[17]Moineau,G.et.al.Alternative Atom Transfer Radical Polymerization for MMA Using FeCl_3 and AIBN in the Presence of Triphenylphosphine:An Easy Way to Well-Controlled PMMA[J].Macromolecules,1998,31:545.
[18]Pascual etal,Macromolecules,Homogeneous Atom Transfer Radical Polymerization of Styrene Initiated by 1-Chloro-1-phenylehane/Copper(Ⅰ) Chloride/Bipyridine in the Presence of Dimethylformamide[J].1999,32:1432.
[19]Terri J,Desimone J M.Polym PrePr,Degradable Core Cross-Linked Star Polymers via Ring-Opening Polymerization.1998,39(20):824-825.
[20]Lauranence LG,Polym PrePr.RAFT Polymerization of Acrylamide Derivatives Containing 1-Phenylalanine Moiety.1997,24(2):19-26.
[21]何天白,胡汉杰.海外高分子科学的新进展[M].北京:化学工业出版社,2001.
[22]Moineau,Dubois,Jeome,Senninger T,Teyssie P.Alternative Atom Transfer Radical Polymerization for MMA Using FeCl_3 and AIBN in the Presence of Triphenylphosphine:An Easy Way to Well-Controlled PMMA[J].Macromolecules,1998,31:545-547.
[23]Wang W X,Dong Z H,Xia P,Yan D.Reverse atom transfer radical polymerization of methyl acrylate using AIBN as the initiator under heterogeneous conditions[J].Macromol Rapid Commun,1998,19:647-649.
[24]Pattne T E,Matyjszezwski K.Atom transfer radical polymerization and the synthesis of polymeric materials[J].Adv.Materials,1998,10:901-915.
[25]王文新,朱申敏,邰红云.中国化学会1999年高分子学术论文报告会论文集[C].北京:1999.
[26]Qiu J,Gaynor.,Matyjaszewski K.Emulsion polymerization of n-butyl Methacrylate by reverse atom transfer radical polymerization[J].Macromolecules,1999,32:2872-2875.
[27]高楠,张彬,胡春圃.水分散体系中由BPO或KPS引发的苯乙烯反向原子转移自由基聚合[J].高分子学报,2003,5:688-692.
[28]Chen X P.Synthesis of well defined poly(methylmethacrylate) by radical polymerization with a new initiation system TPED/FeCl_3 /PPh_3[J].Macromolecules,1999,32(26):8711-8715.
[29]Chen X P,Qiu K Y.Synthesis of well-defined polystyrene by radicalpolymerization using 1,1,2,2-tetraphenyl-1,2-ethanediol/FeCl_3/PPh_3 initiation system[J].J.Appl.Polym.Sci.,2000,77:1607-1613.
[30]Qin D Q,Qin S H,Qiu K Y.A reverse ATRP process with ahexasubstituted ethane thermal iniferter diethyl 2,3-dicyano-2,3-di(p-tolyl) succinate as the initiator[J].Macromolecules,2000,33(19):6987-6992.
[31]Qin D Q,Qin S H,Qiu K Y.A copper-based reverse ATRP processfor the living radical polymerization of methyl methacrylate[J].J.Appl.Polym.Sci.,2001,81(9):2237-2245.
[32]秦东奇,丘坤元.含有热引发转移终止剂的引发体系在反向原子转移自由基聚合中的应用[J].高分子学报,2001,3:281-287.
[33]Matyjaszewski K,Wang JL,Crimaucl T,shipp D.Controlled/“Living” Atom Transfer Radical Polymerization of Methyl Methacrylate Using Various Initiation Systems[J].Macromolecules,1998,31:1527-1534.
[34]Matyjaszewski K.Emulsion polymerization of n-butyl methacrylate by reverse atom transfer radical polymerization[J].Macromolecules,1999,32:2872-2875.
[35]Chen X P,Qiu K Y.Synthesis of well defined poly(methylmethacrylate) by radical polymerization with a new initiationsystem TPED/FeCl_3PPh_3[J].Macromolecules,1999,32(26):8711-8715.
[36]Chen X P,Qiu K Y.Synthesis of well-defined polystyrene by radical polymerization using 1,1,2,2-tetraphenyl-1,2-ethanediol/FeCl_3/PPh_3initiation system[J].J.Appl.Polym.,Sci.,2000,77:1607-1613.
[37]Feng H K,Dan Y.The research of RATRP of styrene in the microemulsion[J].J.Applied Polymer Science,2006,99(4):1093-1099.
[38]Yi Z,Pan K,Jiang L,et al.Copper-based reverse ATRP process of styrene in mixed solvents[J].European Polymer Journal,2007,43(3):2557-2563.
[39]夏平.反向原子转移自由基聚合的研究AIBN/CuCl_2/bpy引发St聚合[J].湖州师范学院学报,2001,23(3):32-35.
[40]张开,张洪文,李宏途.由AIBN或V50引发的苯乙烯反向原子转移自由基乳液聚合[J].科学通报,2005(50):643-647.
[41]Hua J,Jia B B,Zhong L.Reverse atom transfer radical polymerization of styrene initiated with AIBN/Ni(naph)_2/PPh_3catalyst system[J].合成橡胶工业,2003,26(6):378.
[42]秦东奇,钦曙辉,丘坤元.镍体系(NiCl_2/PPh_3)催化的反向原子自由基聚合[J].高分子学报,2002,2:108-112.
[43]Ludwig B,Tillma E S.Polystyrene end-labeled with 2,7-dibromo2,7-di bromoflu -orene synthesized using an adaptation of reverse atom transfer radical polymerizati -on[J].Macromolecular Chemistry and Physics,2005,2006:2143-2152.
[44]Moineau G,Dubios P,Jerome R.Alternative atom transfer radical polymerization for MMA using FeCl_3 and AIBN in the presence of tiphenylphosphine:An easy way to well-controlled PMMA[J].Macromolecules,1998,31:545-547.
[45]Zhu S M,Yan D Y,Zhang G S.Reverse atom transfer radical polymerization of methyl methacrylate with a new catalytic system,FeCl3/isophthalic acid[J].J.Polym.Sci.Part A:Polym.Chem.,2001,39(6):765-774.
[47]Jousset S,Jian Q,Matyjaszewski K.Atom tansfer radical polymerization of methyl methacrylate in water-borne system[J].Macromolecules,2001,34:6641-6648.
[48]Liu B.The reverse atom transfer radical polymerization of methyl methacrylate in the presence of some polar solvents[J].European Polymer Journal,2001,37:2025-2030.
[49]刘兵,胡春圃.甲基丙烯酸甲酯的反向原子转移自由基聚合反应研究[J].化学学报,2001,59(1):119-123.
[50]李忠辉,张永明,刘燕飞.FeBr_3/Me_6TREN催化MMA反向原子转移自由基聚合研究[J].高等学校化学学报,2005,26:1574-1578.
[51]熊玉兵,樊玲,沈之荃.AIBN/SmCl_3/乳酸体系催化甲基丙烯酸甲酯的反向原子转移自由基聚合[J].高等学校化学学报,2005,26(11):2153-2156.
[52]张颖,张鸿,陈瑾.一种反向原子转移自由基聚合引发体系[J].纪学研究与应用,2006,18(2):143-147.
[53]Guo C D,Teng W R,Wu H X.Synthesis of fullerene-end functionalized poly(methyl methacrylate)via reverse atom transfer radical polymerization[J].Chinese Journal of Chemistry,2005,23:1113-1119.
[54]Ma H Y,Wan X H,Chen X F,et al.Reverse atom transfer radical polymerization of methyl methacrylate in imidazolium ionic liquids[J].Polymer,2003,44(18):5311-5316.
[55]Li N J,Lu J M,Xu Q F.Reverse atom transfer radical polymerization of MMA via immobilized catalysts in imidazolium ionic liquids[J].Journal of Applied Polymer Science,2007,103:3915-3919.
[56]Cheng Z P,Zhu X L,Chen G J,et al.Reverse atom transfer radical solution polymerization of methyl methacrylate under pulsed microwave irradiation[J].Polymer Chemistry,2002,40:3823-3834.
[57]Peng H,Cheng S Y,Feng L X.Properties of poly(n-butylmethacrylate) prepared by reverse atom transfer radical polymerization in an aqueous dispersed system[J].J.Appl.Polym.Sci.,2003,89(6):1542-1547.
[58]Hou C,Jia C N,Wang C H.Copper-Based reverse atom-transfer radical polymerization process for the living radical polymerization of polyaciylonitrile[J].Society of Chemical Industry,2005,55:326-329.
[59]Limer A,Haddleton D M.Reverse atom transfer radical polymerisation(RATRP)of methacrylates using copper(Ⅰ)/ pyridinimine catalysts in conjunction with AIBN[J].European Polymer Journal,2006,42:61-68.
[60]Hou C,Liu J S,Guo Z L.Synthesis of polyacrylonitrilevia reverse ATRP initiated by 1,1,2,2-tetraphenyl-1,2-ethanediol/CuC12/2,2-bipyridine[J].Journal of Applied Polymer Science,2007,103(2):3529-3533.
[61]赵隽颖.水体系丙烯酰胺逆向原子转移自由基聚合研究[D].黑龙江大学学报,2002,13(6):45-48.
[62]张红燕,刘崴崴,王华平.以离子液体为溶剂的原子转移自由基聚合[J].高分子通报,2007(3):17-22.
[63]Benoit D,Chaplinski V,Brashlau R.Development of a universal alkoxyamine for"living"free radical polymerizations[J].J.Am.Chem.Soc,1999,121:3904-3920.
[64]Haddleton D M,Jasieezek C B,HannonMJ,Shooter A[J].Macromolecules,1997,30:2190.
[65]HaddletonDM,Kukulj D,CrossmanMC,etal.Eur.Biometal Derivatives as Catalysts for the Ring-Opening Polymerization of Trimethylene Carbonate.Optimization of the Ca(Ⅱ) Salen Catalyst System.J.Inorg.Chem.1998:1799-1806.
[66]Rachel K.O_Reilly,Vernon C.Gibson,Andrew J.P.White,David J.Williams,Five-coordinate iron(Ⅲ) complexes bearing tridentate nitrogen donor ligands as catalysts for atom transfer radical polymerisation[J].Polyhedron,2004,23:2921-2928.
[67]R.Ferro,S.Milione,T.Caruso,A.Grassi,Iron(Ⅲ)complexes of bidentate nitrogen ligands as catalysts in Reverse Atom Transfer Radical Polymerization of styrene[J].Journal of Molecular Catalysis A:Chemical.molc.ata 2009.3(25).
[68]HouChen,YingLiang et.al.Reverse ATRP of 4-vinylpyridine with Diethyl,3-Dicyano -2,3-Diphenylsuccinate/CuCl2/5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazamacroc yclotetradecane[J].Mater.Sci.Eng.2009.
[69]Andrew J.Clark,Paul Wilson,Copper mediated atom transfer radical cyclisations with AIBN[J].Tetrahedron Letters,2008,49(28):4848-4850
[70]Rossella Ferro,Stefano Milione,Loredana Erra.Synthesis,Characterization and role of a novel dimeric a-diimineiron(Ⅱ) complex in ATRP of styrene[J].Inorganic Chemistry Communications,2008,11:535-538.
[71]K.C.Gupta,Alekha Kumar Sutar,Catalytic activities of Schiff base transition metal complexes,Coordination[J].Chemistry Reviews,2008,252:1420-1450.
[72]Miao Shen,Peng Hao,Wen-Hua Sun,Synthesis,characterization and catalytic behaviors of neutral nickel complexes:Arylnickel N-alkyl-6-(1-(arylimino)ethyl)picolinamide,Journal of Organometallic Chemistry,2008,693:1683-1695.
[73]Timothy E.Patten et.al.Synthesis and characterization of an N-coordinated amidatecopper(Ⅱ) complex of deprotonated N-(2,6-diisopropylphenyl)-2-(bis-(2-pyridylmethyl))aminoethanamide[J],Inorganica Chimica Acta,2008,361:365-372.
[74]张汉青等,含吲哚基新配体催化甲基丙烯酸甲酯的原子转移自由基溶液聚合[J],高分子材料科学与工程,2007,23(2):46-49.
[75]Marc-Stephan Weiser,Rolf Mülhaupt.Cobalt(Ⅱ) octanoate and cobalt(Ⅱ)perfluoroo-ctanoate catalyzed atom transfer radical polymerization of styrene in toluene and fluorous media-Aversatile route to catalyst recycling and oligomer formation[J].Journal of Polymer Science Part A:Polymer Chemistry.2005,43(9):3804-3813.
[76]Rachel K.O'Reilly,Vernon C.Gibson,Vernon C.Gibson,Design of Highly Active Iron-Based Catalysts for Atom Transfer Radical Polymerization:Tridentate Salicylaldiminato Ligands Affording near Ideal Nernstian Behavior[J],J.Am.Chem.Soc,2003,125(15):8450-8451.
[77]Gang Wang,XinLin Zhu,Jian Zhu,ZhenPing Cheng,Iron-Mediated Atom Transfer Radical Polymerization of Styrene with Tris(3,6-dioxaheptyl) Amine as a Ligand,Journal of Polymer Science:Part A:Polymer Chemistry,44(5):483-489.
[78]Xi Zhao,Yanqiong Yu,Shansheng Xu,Baiquan Wang Controlled/“living” radical polymerization of methyl methacrylate catalyzed by CpCo(Ⅰ) complexes conveniently generated from cobaltocene in sit[J],Polymer,2009,50(18):2258-2263.
[79]Yoshihisa Inoue and Krzysztof Matyjaszewski,A Dual Catalyst System for Atom Transfer Radical Polymerization Based on a Halogen-Free Neutral Cu(Ⅰ)Complex[J],Macromolecules,2003,36(2):7432-7438
[80]Huadong Tang,Navamoney Arulsamy,Maciej Radosz,Youqing Shen,Nicolay V.Tsarevsky,Wade A.Braunecker,Wei Tang,andKrzysztof Matyjaszewski,Highly Active Copper-Based Catalyst for Atom Transfer Radical Polymerization,[J].J.Am.Chem.Soc.,2006,128(12):16277-16285
[81]Jianmei Lu,Feng Yan,,John Texter,Advanced applications of ionic liquids in polymer science[J].Progress in Polymer Science,2009,34(2):431-448.
[82]Welton T.Room2temperature ionic liquids.Solvent for synthesis and catalysis[J]. Chem.Rev.,1999,99(8):2071-2083.
[83]Welton T,Wasserscheid P.Ionic liquids in synt hesis[C].Weinheim:Wiley-VCH,2002.
[84]Rogers R,Seddon K.ACS symposium series[C].Washington:American Chemical Society,2002.
[85]Vygodskii Y S,Lozinskaya E I,Shaplov A S.Ionic liquids asnovel promising reaction media for organic and polymer synthesis[J].Polym.Sci.Ser.,2001,43(6):236-251.
[86]Zhao H,Malhotra S W.Application of ionic liquids in organicsynt hesis[J].Aldrichim Acta,2002,35(8):75-83.
[87]Karodia N,Guise S,Newlands C et al.Clean catalysis with ionic solvent s-phosphonium tosylates for hydroformylation[J].Chem.Commun,1998,35(2):2341-2342.
[88]Strehmel V,Laschewsky A,Wetzel H,Gornitz E.Free radical polymerization of n-butyl methacrylate in ionic liquids[J].Macromolecules,2006,39(3):923-30.
[89]Strehmel V.Selection of ionic liquids for free radical polymerization processes[J].Macromol Symp,2001,254(5):25-33.
[90]Thurecht KJ,Gooden,Goel,Tuck,Licence,Irvine.Freeradical polymerization in ionic liquids:the case for a protected radical[J].Macromolecules,2008,41(4),2814-2820.
[91]张红燕,刘葳葳,王华平.以离子液体为溶剂的原子转移自由基聚合[J].高分子通报,2007,3(1):17-22.
[92]何鸣元,戴立益.离子液体与绿色化学[M].化学教学,2002,6(2):123.
1、Yutaka Fukuda,,etal.Observation of t e New k~2C,O:k~22C','O' Coordination Mode of 1,1,2,2-TetraacetyIethanatoLigand in a Dinuclear 1,1,1,5,5,5-Hexafluoro acetylaceto nato Palladium(Ⅱ) Complex[J].Chemistry Letters,2006,35(8).
2、Paul E.Kruger,Tetranuclear copper(Ⅱ) complexes incorporating short and long metal-metal separations:synthesis,structure and magnetism[J].J.Chem.Soc.Dalton Trans.,2000,713-718.
3、ROBERT G.CHARLES Metal Chelate Polymers Derived fromTetraacetylethane[J].Journal of Polymer Science:Part A,1963,1(12),267-276.
4、Tomohiro Koiwa,Synthesis,Characterization,and Detailed Electrochemistry of inuclear Ruthenium(IIIII3) Complexes Bridged by Bisacetylacetonate[J|.Crystal and Molecular Structures of[{Ru(acac)2}2(tae)](acac) 2,4-Pentanedionate Ion,tae)1,1,2,2-Tetraacetylethanate Dianion).Inorg.Chem.,2004,43(20),6215-6223.
5、朱洪友,3,4-二乙酰基-2,5-己二酮的电化学合成及其晶体结构[J],1998,27(1),101-105.
[1]Otsu,T.;Nishikawa,Y.Macromol.Chem.1995,115:278
[2]Nishikawa,Y;Otsu,T.Macromol.Chem.1968,128:276
[3]Endo,K.;Inukai,A.;Otsu,T.Makromol.Chem.phys.1995,196:2065
[4]Endo,K.;Inukai,A.;Otsu,T.Macromol.Chem.Rapid Commun.l994,15(11):893.
[5]贺晓慧,博士论文,中山大学,广州,2004.
[6]Goode,W.E;Owens,F.H;Fellman,R,P.;Snyder,W.H.;Moore,J.E.J.Polym.Sci.1960,46:317
[7]Nishioka,A.;Watanable,H.;Abe,K.;Sono,Y.J.Polym.Sci.l960,48:2
[1]Otsu,T.;Nishikawa,Y.Macromol.Chem.1995,115:278
[2]Nishikawa,Y;Otsu,T.Macromol.Chem.1968,128:276
[3]Endo,K.;Inukai,A.;Otsu,T.Makromol.Chem.phys.1995,196:2065
[4]Endo,K.;Inukai,A.;Otsu,T.Macromol.Chem.Rapid Commun.1994,15(11):893.
[5]贺晓慧,博士论文,中山大学,广州,2004.
[6]Goode,W.E;Owens,F.H;Fellman,R,P.;Snyder,W.H.;Moore,J.E.J.Polym.Sci.1960,46:317
[7]Nishioka,A.;Watanable,H.;Abe,K.;Sono,Y.J.Polym.Sci.1960,48:2
[2]Wang J S,Matyjaszewski K.Controlled'7 living"radical polymerization.Halogen atom transfer radical polymerization promoted by a Cu(Ⅰ)/Cu(Ⅱ) redox process[J].Macromolecules,1995,28:7901-7910.
[3]Matyjaszewski K,Gayno r S G,Coca S.U.S.Patent,6538091,2003.
[4]Matyjaszewski K.Current Opinion in Solid State Materials Science[S],1996,1(6):769-776.
[5]Cunningham M F.Living/controlled radical polymerizations in dispersed phase systems Progress in Polymer Science[J],Polymer Science,2002,27(6):1039-1067.
[6]郭清泉,陈焕钦.一种新型自由基聚合:活性/可控自由基聚合[J],高分子材料科学与工程,2003,19(4):56-63.
[7]陈小平,丘坤元.“活性”/控制自由基聚合的研究进展[J],化学进展,2001,13(3):224-233.
[8]Matyaszewski K.Controlling polymer structures by atom transfer radical polymerization and other controlled/living radical polymerizations[Jj.Ma cromole ular Symposia,2003,195(1)55-32.
[9]王艳君,王玉霞,袁才登可逆加成-断裂链转移活性自由基聚合.高分子通报,2003,5(3):57-63.
[10]郭清泉,林淑英,陈焕钦.活性/可控自由基聚合的研究进展,材料科学与工程学报,2003,21(3):13-15.
[11]GeorgesM K,VereginRPN,Kazmaier P M,et al.Polymer science in the 21st century Trends in Polymer Seience[J],Polymer science,1994,2(2):66-72.
[12]Richard P.N.Veregin,Michael K.Georges,Peter M.Kazmaier,Gordon K.Hamer Free radical polymerizations for narrow polydispersity resins:electron spin resonance studies of the kinetics and mechanism,Maeromolecules[J],1993,26(20):5316-5320.
[13]Peter M.Kazmaier,Karen A.Moffat,Michael K.Georges,Richard P.N.Veregin,Gordon K.Hamer Free-Radical Polymerization for Narrow-Polydispersity Resins.Semiempirical Molecular Orbital Calculations as a Criterion for Selecting Stable Free-Radical Reversible Terminators.Macromoleeules,l995,28(6):1841-1846.
[14]S.Richard Turner,Richard W.Blevins Photoinitiated block copolymer formation using dithiocarbamate free radical chemistry[J].Maeromoleeules,1990,23(6):1856-1859.
[15]J.D.Druliner,Living radical polymerization involving oxygen-centered species attached to propagating chain ends[J].Maeromoleeules,1991,24(23):6079-6082.
[16]Mecking,S.;Johnson,L.K.;Wang,L.;Brookhart,M.Mechanistic Studies of the Palladium-Catalyzed Copolymerization of Ethylene and α-Olefins with Methyl Acrylate[J]J.Am.Chem.Soc.1998,120(5):88.
[17]Moineau,G.et.al.Alternative Atom Transfer Radical Polymerization for MMA Using FeCl_3 and AIBN in the Presence of Triphenylphosphine:An Easy Way to Well-Controlled PMMA[J].Macromolecules,1998,31:545.
[18]Pascual etal,Macromolecules,Homogeneous Atom Transfer Radical Polymerization of Styrene Initiated by 1-Chloro-1-phenylehane/Copper(Ⅰ) Chloride/Bipyridine in the Presence of Dimethylformamide[J].1999,32:1432.
[19]Terri J,Desimone J M.Polym PrePr,Degradable Core Cross-Linked Star Polymers via Ring-Opening Polymerization.1998,39(20):824-825.
[20]Lauranence LG,Polym PrePr.RAFT Polymerization of Acrylamide Derivatives Containing 1-Phenylalanine Moiety.1997,24(2):19-26.
[21]何天白,胡汉杰.海外高分子科学的新进展[M].北京:化学工业出版社,2001.
[22]Moineau,Dubois,Jeome,Senninger T,Teyssie P.Alternative Atom Transfer Radical Polymerization for MMA Using FeCl_3 and AIBN in the Presence of Triphenylphosphine:An Easy Way to Well-Controlled PMMA[J].Macromolecules,1998,31:545-547.
[23]Wang W X,Dong Z H,Xia P,Yan D.Reverse atom transfer radical polymerization of methyl acrylate using AIBN as the initiator under heterogeneous conditions[J].Macromol Rapid Commun,1998,19:647-649.
[24]Pattne T E,Matyjszezwski K.Atom transfer radical polymerization and the synthesis of polymeric materials[J].Adv.Materials,1998,10:901-915.
[25]王文新,朱申敏,邰红云.中国化学会1999年高分子学术论文报告会论文集[C].北京:1999.
[26]Qiu J,Gaynor.,Matyjaszewski K.Emulsion polymerization of n-butyl Methacrylate by reverse atom transfer radical polymerization[J].Macromolecules,1999,32:2872-2875.
[27]高楠,张彬,胡春圃.水分散体系中由BPO或KPS引发的苯乙烯反向原子转移自由基聚合[J].高分子学报,2003,5:688-692.
[28]Chen X P.Synthesis of well defined poly(methylmethacrylate) by radical polymerization with a new initiation system TPED/FeCl_3 /PPh_3[J].Macromolecules,1999,32(26):8711-8715.
[29]Chen X P,Qiu K Y.Synthesis of well-defined polystyrene by radicalpolymerization using 1,1,2,2-tetraphenyl-1,2-ethanediol/FeCl_3/PPh_3 initiation system[J].J.Appl.Polym.Sci.,2000,77:1607-1613.
[30]Qin D Q,Qin S H,Qiu K Y.A reverse ATRP process with ahexasubstituted ethane thermal iniferter diethyl 2,3-dicyano-2,3-di(p-tolyl) succinate as the initiator[J].Macromolecules,2000,33(19):6987-6992.
[31]Qin D Q,Qin S H,Qiu K Y.A copper-based reverse ATRP processfor the living radical polymerization of methyl methacrylate[J].J.Appl.Polym.Sci.,2001,81(9):2237-2245.
[32]秦东奇,丘坤元.含有热引发转移终止剂的引发体系在反向原子转移自由基聚合中的应用[J].高分子学报,2001,3:281-287.
[33]Matyjaszewski K,Wang JL,Crimaucl T,shipp D.Controlled/“Living” Atom Transfer Radical Polymerization of Methyl Methacrylate Using Various Initiation Systems[J].Macromolecules,1998,31:1527-1534.
[34]Matyjaszewski K.Emulsion polymerization of n-butyl methacrylate by reverse atom transfer radical polymerization[J].Macromolecules,1999,32:2872-2875.
[35]Chen X P,Qiu K Y.Synthesis of well defined poly(methylmethacrylate) by radical polymerization with a new initiationsystem TPED/FeCl_3PPh_3[J].Macromolecules,1999,32(26):8711-8715.
[36]Chen X P,Qiu K Y.Synthesis of well-defined polystyrene by radical polymerization using 1,1,2,2-tetraphenyl-1,2-ethanediol/FeCl_3/PPh_3initiation system[J].J.Appl.Polym.,Sci.,2000,77:1607-1613.
[37]Feng H K,Dan Y.The research of RATRP of styrene in the microemulsion[J].J.Applied Polymer Science,2006,99(4):1093-1099.
[38]Yi Z,Pan K,Jiang L,et al.Copper-based reverse ATRP process of styrene in mixed solvents[J].European Polymer Journal,2007,43(3):2557-2563.
[39]夏平.反向原子转移自由基聚合的研究AIBN/CuCl_2/bpy引发St聚合[J].湖州师范学院学报,2001,23(3):32-35.
[40]张开,张洪文,李宏途.由AIBN或V50引发的苯乙烯反向原子转移自由基乳液聚合[J].科学通报,2005(50):643-647.
[41]Hua J,Jia B B,Zhong L.Reverse atom transfer radical polymerization of styrene initiated with AIBN/Ni(naph)_2/PPh_3catalyst system[J].合成橡胶工业,2003,26(6):378.
[42]秦东奇,钦曙辉,丘坤元.镍体系(NiCl_2/PPh_3)催化的反向原子自由基聚合[J].高分子学报,2002,2:108-112.
[43]Ludwig B,Tillma E S.Polystyrene end-labeled with 2,7-dibromo2,7-di bromoflu -orene synthesized using an adaptation of reverse atom transfer radical polymerizati -on[J].Macromolecular Chemistry and Physics,2005,2006:2143-2152.
[44]Moineau G,Dubios P,Jerome R.Alternative atom transfer radical polymerization for MMA using FeCl_3 and AIBN in the presence of tiphenylphosphine:An easy way to well-controlled PMMA[J].Macromolecules,1998,31:545-547.
[45]Zhu S M,Yan D Y,Zhang G S.Reverse atom transfer radical polymerization of methyl methacrylate with a new catalytic system,FeCl3/isophthalic acid[J].J.Polym.Sci.Part A:Polym.Chem.,2001,39(6):765-774.
[47]Jousset S,Jian Q,Matyjaszewski K.Atom tansfer radical polymerization of methyl methacrylate in water-borne system[J].Macromolecules,2001,34:6641-6648.
[48]Liu B.The reverse atom transfer radical polymerization of methyl methacrylate in the presence of some polar solvents[J].European Polymer Journal,2001,37:2025-2030.
[49]刘兵,胡春圃.甲基丙烯酸甲酯的反向原子转移自由基聚合反应研究[J].化学学报,2001,59(1):119-123.
[50]李忠辉,张永明,刘燕飞.FeBr_3/Me_6TREN催化MMA反向原子转移自由基聚合研究[J].高等学校化学学报,2005,26:1574-1578.
[51]熊玉兵,樊玲,沈之荃.AIBN/SmCl_3/乳酸体系催化甲基丙烯酸甲酯的反向原子转移自由基聚合[J].高等学校化学学报,2005,26(11):2153-2156.
[52]张颖,张鸿,陈瑾.一种反向原子转移自由基聚合引发体系[J].纪学研究与应用,2006,18(2):143-147.
[53]Guo C D,Teng W R,Wu H X.Synthesis of fullerene-end functionalized poly(methyl methacrylate)via reverse atom transfer radical polymerization[J].Chinese Journal of Chemistry,2005,23:1113-1119.
[54]Ma H Y,Wan X H,Chen X F,et al.Reverse atom transfer radical polymerization of methyl methacrylate in imidazolium ionic liquids[J].Polymer,2003,44(18):5311-5316.
[55]Li N J,Lu J M,Xu Q F.Reverse atom transfer radical polymerization of MMA via immobilized catalysts in imidazolium ionic liquids[J].Journal of Applied Polymer Science,2007,103:3915-3919.
[56]Cheng Z P,Zhu X L,Chen G J,et al.Reverse atom transfer radical solution polymerization of methyl methacrylate under pulsed microwave irradiation[J].Polymer Chemistry,2002,40:3823-3834.
[57]Peng H,Cheng S Y,Feng L X.Properties of poly(n-butylmethacrylate) prepared by reverse atom transfer radical polymerization in an aqueous dispersed system[J].J.Appl.Polym.Sci.,2003,89(6):1542-1547.
[58]Hou C,Jia C N,Wang C H.Copper-Based reverse atom-transfer radical polymerization process for the living radical polymerization of polyaciylonitrile[J].Society of Chemical Industry,2005,55:326-329.
[59]Limer A,Haddleton D M.Reverse atom transfer radical polymerisation(RATRP)of methacrylates using copper(Ⅰ)/ pyridinimine catalysts in conjunction with AIBN[J].European Polymer Journal,2006,42:61-68.
[60]Hou C,Liu J S,Guo Z L.Synthesis of polyacrylonitrilevia reverse ATRP initiated by 1,1,2,2-tetraphenyl-1,2-ethanediol/CuC12/2,2-bipyridine[J].Journal of Applied Polymer Science,2007,103(2):3529-3533.
[61]赵隽颖.水体系丙烯酰胺逆向原子转移自由基聚合研究[D].黑龙江大学学报,2002,13(6):45-48.
[62]张红燕,刘崴崴,王华平.以离子液体为溶剂的原子转移自由基聚合[J].高分子通报,2007(3):17-22.
[63]Benoit D,Chaplinski V,Brashlau R.Development of a universal alkoxyamine for"living"free radical polymerizations[J].J.Am.Chem.Soc,1999,121:3904-3920.
[64]Haddleton D M,Jasieezek C B,HannonMJ,Shooter A[J].Macromolecules,1997,30:2190.
[65]HaddletonDM,Kukulj D,CrossmanMC,etal.Eur.Biometal Derivatives as Catalysts for the Ring-Opening Polymerization of Trimethylene Carbonate.Optimization of the Ca(Ⅱ) Salen Catalyst System.J.Inorg.Chem.1998:1799-1806.
[66]Rachel K.O_Reilly,Vernon C.Gibson,Andrew J.P.White,David J.Williams,Five-coordinate iron(Ⅲ) complexes bearing tridentate nitrogen donor ligands as catalysts for atom transfer radical polymerisation[J].Polyhedron,2004,23:2921-2928.
[67]R.Ferro,S.Milione,T.Caruso,A.Grassi,Iron(Ⅲ)complexes of bidentate nitrogen ligands as catalysts in Reverse Atom Transfer Radical Polymerization of styrene[J].Journal of Molecular Catalysis A:Chemical.molc.ata 2009.3(25).
[68]HouChen,YingLiang et.al.Reverse ATRP of 4-vinylpyridine with Diethyl,3-Dicyano -2,3-Diphenylsuccinate/CuCl2/5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazamacroc yclotetradecane[J].Mater.Sci.Eng.2009.
[69]Andrew J.Clark,Paul Wilson,Copper mediated atom transfer radical cyclisations with AIBN[J].Tetrahedron Letters,2008,49(28):4848-4850
[70]Rossella Ferro,Stefano Milione,Loredana Erra.Synthesis,Characterization and role of a novel dimeric a-diimineiron(Ⅱ) complex in ATRP of styrene[J].Inorganic Chemistry Communications,2008,11:535-538.
[71]K.C.Gupta,Alekha Kumar Sutar,Catalytic activities of Schiff base transition metal complexes,Coordination[J].Chemistry Reviews,2008,252:1420-1450.
[72]Miao Shen,Peng Hao,Wen-Hua Sun,Synthesis,characterization and catalytic behaviors of neutral nickel complexes:Arylnickel N-alkyl-6-(1-(arylimino)ethyl)picolinamide,Journal of Organometallic Chemistry,2008,693:1683-1695.
[73]Timothy E.Patten et.al.Synthesis and characterization of an N-coordinated amidatecopper(Ⅱ) complex of deprotonated N-(2,6-diisopropylphenyl)-2-(bis-(2-pyridylmethyl))aminoethanamide[J],Inorganica Chimica Acta,2008,361:365-372.
[74]张汉青等,含吲哚基新配体催化甲基丙烯酸甲酯的原子转移自由基溶液聚合[J],高分子材料科学与工程,2007,23(2):46-49.
[75]Marc-Stephan Weiser,Rolf Mülhaupt.Cobalt(Ⅱ) octanoate and cobalt(Ⅱ)perfluoroo-ctanoate catalyzed atom transfer radical polymerization of styrene in toluene and fluorous media-Aversatile route to catalyst recycling and oligomer formation[J].Journal of Polymer Science Part A:Polymer Chemistry.2005,43(9):3804-3813.
[76]Rachel K.O'Reilly,Vernon C.Gibson,Vernon C.Gibson,Design of Highly Active Iron-Based Catalysts for Atom Transfer Radical Polymerization:Tridentate Salicylaldiminato Ligands Affording near Ideal Nernstian Behavior[J],J.Am.Chem.Soc,2003,125(15):8450-8451.
[77]Gang Wang,XinLin Zhu,Jian Zhu,ZhenPing Cheng,Iron-Mediated Atom Transfer Radical Polymerization of Styrene with Tris(3,6-dioxaheptyl) Amine as a Ligand,Journal of Polymer Science:Part A:Polymer Chemistry,44(5):483-489.
[78]Xi Zhao,Yanqiong Yu,Shansheng Xu,Baiquan Wang Controlled/“living” radical polymerization of methyl methacrylate catalyzed by CpCo(Ⅰ) complexes conveniently generated from cobaltocene in sit[J],Polymer,2009,50(18):2258-2263.
[79]Yoshihisa Inoue and Krzysztof Matyjaszewski,A Dual Catalyst System for Atom Transfer Radical Polymerization Based on a Halogen-Free Neutral Cu(Ⅰ)Complex[J],Macromolecules,2003,36(2):7432-7438
[80]Huadong Tang,Navamoney Arulsamy,Maciej Radosz,Youqing Shen,Nicolay V.Tsarevsky,Wade A.Braunecker,Wei Tang,andKrzysztof Matyjaszewski,Highly Active Copper-Based Catalyst for Atom Transfer Radical Polymerization,[J].J.Am.Chem.Soc.,2006,128(12):16277-16285
[81]Jianmei Lu,Feng Yan,,John Texter,Advanced applications of ionic liquids in polymer science[J].Progress in Polymer Science,2009,34(2):431-448.
[82]Welton T.Room2temperature ionic liquids.Solvent for synthesis and catalysis[J]. Chem.Rev.,1999,99(8):2071-2083.
[83]Welton T,Wasserscheid P.Ionic liquids in synt hesis[C].Weinheim:Wiley-VCH,2002.
[84]Rogers R,Seddon K.ACS symposium series[C].Washington:American Chemical Society,2002.
[85]Vygodskii Y S,Lozinskaya E I,Shaplov A S.Ionic liquids asnovel promising reaction media for organic and polymer synthesis[J].Polym.Sci.Ser.,2001,43(6):236-251.
[86]Zhao H,Malhotra S W.Application of ionic liquids in organicsynt hesis[J].Aldrichim Acta,2002,35(8):75-83.
[87]Karodia N,Guise S,Newlands C et al.Clean catalysis with ionic solvent s-phosphonium tosylates for hydroformylation[J].Chem.Commun,1998,35(2):2341-2342.
[88]Strehmel V,Laschewsky A,Wetzel H,Gornitz E.Free radical polymerization of n-butyl methacrylate in ionic liquids[J].Macromolecules,2006,39(3):923-30.
[89]Strehmel V.Selection of ionic liquids for free radical polymerization processes[J].Macromol Symp,2001,254(5):25-33.
[90]Thurecht KJ,Gooden,Goel,Tuck,Licence,Irvine.Freeradical polymerization in ionic liquids:the case for a protected radical[J].Macromolecules,2008,41(4),2814-2820.
[91]张红燕,刘葳葳,王华平.以离子液体为溶剂的原子转移自由基聚合[J].高分子通报,2007,3(1):17-22.
[92]何鸣元,戴立益.离子液体与绿色化学[M].化学教学,2002,6(2):123.
1、Yutaka Fukuda,,etal.Observation of t e New k~2C,O:k~22C','O' Coordination Mode of 1,1,2,2-TetraacetyIethanatoLigand in a Dinuclear 1,1,1,5,5,5-Hexafluoro acetylaceto nato Palladium(Ⅱ) Complex[J].Chemistry Letters,2006,35(8).
2、Paul E.Kruger,Tetranuclear copper(Ⅱ) complexes incorporating short and long metal-metal separations:synthesis,structure and magnetism[J].J.Chem.Soc.Dalton Trans.,2000,713-718.
3、ROBERT G.CHARLES Metal Chelate Polymers Derived fromTetraacetylethane[J].Journal of Polymer Science:Part A,1963,1(12),267-276.
4、Tomohiro Koiwa,Synthesis,Characterization,and Detailed Electrochemistry of inuclear Ruthenium(IIIII3) Complexes Bridged by Bisacetylacetonate[J|.Crystal and Molecular Structures of[{Ru(acac)2}2(tae)](acac) 2,4-Pentanedionate Ion,tae)1,1,2,2-Tetraacetylethanate Dianion).Inorg.Chem.,2004,43(20),6215-6223.
5、朱洪友,3,4-二乙酰基-2,5-己二酮的电化学合成及其晶体结构[J],1998,27(1),101-105.
[1]Otsu,T.;Nishikawa,Y.Macromol.Chem.1995,115:278
[2]Nishikawa,Y;Otsu,T.Macromol.Chem.1968,128:276
[3]Endo,K.;Inukai,A.;Otsu,T.Makromol.Chem.phys.1995,196:2065
[4]Endo,K.;Inukai,A.;Otsu,T.Macromol.Chem.Rapid Commun.l994,15(11):893.
[5]贺晓慧,博士论文,中山大学,广州,2004.
[6]Goode,W.E;Owens,F.H;Fellman,R,P.;Snyder,W.H.;Moore,J.E.J.Polym.Sci.1960,46:317
[7]Nishioka,A.;Watanable,H.;Abe,K.;Sono,Y.J.Polym.Sci.l960,48:2
[1]Otsu,T.;Nishikawa,Y.Macromol.Chem.1995,115:278
[2]Nishikawa,Y;Otsu,T.Macromol.Chem.1968,128:276
[3]Endo,K.;Inukai,A.;Otsu,T.Makromol.Chem.phys.1995,196:2065
[4]Endo,K.;Inukai,A.;Otsu,T.Macromol.Chem.Rapid Commun.1994,15(11):893.
[5]贺晓慧,博士论文,中山大学,广州,2004.
[6]Goode,W.E;Owens,F.H;Fellman,R,P.;Snyder,W.H.;Moore,J.E.J.Polym.Sci.1960,46:317
[7]Nishioka,A.;Watanable,H.;Abe,K.;Sono,Y.J.Polym.Sci.1960,48:2