Glaser反应在制备环状聚合物中的应用
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摘要
聚合物的结构与性质之间的关系引起了众多研究者的兴趣。其中,不存在链末端的环状拓扑结构高分子具有不同于直链、支化结构高分子的独特性能,是一类在材料改性、纳米科技和生物医药等领域有着重要应用前景的新型功能聚合物材料,日益受到人们的重视,但其复杂的结构导致它们的合成非常繁琐,并因此束缚了其实际应用。
环状化合物的合成方法之一是应用高效偶联反应使端基官能化的线形前驱体聚合在极稀条件下进行分子内反应成环。利用各种聚合技术以及端基修饰反应,我们可以很容易得到线形前驱体聚合物,因此,选择高效偶联反应对于使用该方法合成环状化合物极为重要。
本课题将有机合成中广泛应用的炔基偶联反应,即Glaser反应,引入到环状聚合物的合成中。Glaser反应是一种高效形成碳键的方法：在一价铜的催化作用下,随着两个氢原子的离去,两个端炔基反应形成二炔键,可在室温下和空气氛围中发生。我们利用该成环技术合成了环状聚环氧乙烷(c-PEO)、环状聚苯乙烯(c-PS)和环状聚环氧乙烷-聚苯乙烯嵌段共聚物(c-PEO-b-PS),说明了该方法在环状聚合物合成中的普适性。我们所取得的主要结果如下：
1.合成了两种单环聚合物：环状聚环氧乙烷(c-PEO)、环状聚苯乙烯(c-PS)。首先,以新戊二醇作为引发剂,在二苯甲基钾(DPMK)的存在下引发环氧乙烷(EO)进行阴离子开环聚合(ROP),用甲醇终止反应,得到两端羟基的线形聚环氧乙烷(α，ω-dihydroxyl PEO);然后,在NaH的作用下,用溴丙炔对PEO进行端基修饰,得到两端为炔丙基的聚环氧乙烷(α,ωo-dipropargyl PEO)；再以吡啶作溶剂,将线形前驱体聚合物溶液以2μm/h的速度滴加到催化剂溶液[Cu(I)Br/PMDETA]中进行成环反应,得到环状产物。在c-PS的合成中,以萘锂为引发剂引发苯乙烯单体进行阴离子聚合,然后用EO作为小分子“盖帽”试剂,对“活性”聚苯乙烯双阴离子进行封端反应,生成了两端均为羟基的聚苯乙烯(a,co-dihydroxylPS),按照与前面同样的方法,将端基转化为炔丙基后进行Glaser成环反应得到环状聚苯乙烯产物。采用GPC、1H NMR、FT-IR和MALDI-TOF MS等手段对中间产物和目标产物进行了详细地表征。
2.合成了环状聚环氧乙烷-聚苯乙烯嵌段共聚物(c-PEO-b-PS)。以α，ω-二羟基聚苯乙烯作为大分子引发剂,在DPMK的存在下利用“活性”羟基引发EO单体进行开环聚合,制备了ABA型三嵌段聚合物,PEO-b-PS-b-PEO,然后将末端羟基转化为炔丙基,得到成环用前驱体聚合物。在成环过程中,改进成环条件,以Cu(I)Br作催化剂、吡啶作溶剂,不加配体(PMDETA),成功得到了环化产物。采用GPC、’H NMR、FT-IR和MALDI-TOF MS等对手段对中间产物和目标产物也进行了详细地表征,发现环化效率接近100%,无分子间缩聚反应副产物出现,因此环状嵌段产物不需要复杂的分离纯化过程。
The relations between structures and properties of polymers have attracted many researchers'attention. Cyclic polymers with "endless" polymer main chains show distinctively unique properties due to their closed ring topology compared to linear and branched ones. As new functional polymers, they could be applied in some important fields, such as material modification, nanotechnology and biological medicine, etc. However, their practical applications are greatly bound by the complicated and tedious synthetic procedure.
Highly-efficient ring-closure technique is one of the synthetic strategies for preparation of cyclic polymers, which involves intra-molecular cyclization of linear precursors with hetero-difunctional or homo-difunctional end groups under high dilute conditions. Functional linear precursors can be easily obtained by different polymerization techniques and end-group modification. Therefore, selecting appropriate cyclization conditions is very important for cyclic polymer preparation.
In this thesis, Glaser coupling reaction is used as cyclization technique to synthesize cyclic polymers. The Cu(I) catalyzed Glaser coupling of terminal alkynes can be conducted at room temperature in air, resulting in the formation of 1,3-diyne. Using this method, we have prepared cyclic poly(ethylene oxide) (c-PEO), cyclic polystyrene (c-PS), and cyclic poly(ethylene oxide)-block-polystyrene (c-PEO-b-PS) indicating that this is an universal method for the synthesis of cyclic polymers. The main results obtained are showed as follows:
1. Two cyclic homo-polymers have been synthesized:c-PEO and c-PS. Firstly, a,co-dihydroxyl PEO were obtained by ring-opening polymerization (ROP) of ethylene oxide (EO) initiated by co-initiator of 2,2-dimethyl-1,3-propanediol and diphenylmethylpotassium (DPMK), terminated by anhydrous methanol. After the reaction between hydroxyl end-groups and propargyl bromide in the presence of NaH,α,ω-dipropargyl PEO were obtained. Then, the linear precursors solution was added dropwise to catalyst solution [Cu(I)Br/N,N,N',N''-pentamethyldiethylenetriamine (PMDETA) dissolved in pyridine] at a rate of 2μmol/h to avoid intermolecular reactions and ensure the purity of cyclic products. c-PS was synthesized using the same manner, except that linear PS was obtained by anionic polymerization initiated by lithium naphthalenide and end-capped with EO. All the intermediates and target products were characterized by GPC、1HNMR、FT-IR and MALDI-TOF MS in detail.
2. Cyclic block copolymer, c-PEO-b-PS, have been designed and synthesized. Firstly,α,ω-dihydroxyl PS were used as macro-initiator in the presence of DPMK to initiate ROP of EO to give the triblock copolymer, poly(ethylene oxide)-block-polystyrene-block-poly(ethylene oxide) (PEO-b-PS-b-PEO). Then, the end hydroxyls were modified to propargyls. In the cyclization process, since pyridine can be acted as ligand, we tried to improve the cyclization condition without adding of PMDETA. It confirmed that the intra-molecular cyclization was also carried out with the efficiency as high as 100%, and no inter-molecular reactions were detected. All the intermediates and target products were characterized by GPC、1H NMR and FT-IR in detail.
环状化合物的合成方法之一是应用高效偶联反应使端基官能化的线形前驱体聚合在极稀条件下进行分子内反应成环。利用各种聚合技术以及端基修饰反应,我们可以很容易得到线形前驱体聚合物,因此,选择高效偶联反应对于使用该方法合成环状化合物极为重要。
本课题将有机合成中广泛应用的炔基偶联反应,即Glaser反应,引入到环状聚合物的合成中。Glaser反应是一种高效形成碳键的方法：在一价铜的催化作用下,随着两个氢原子的离去,两个端炔基反应形成二炔键,可在室温下和空气氛围中发生。我们利用该成环技术合成了环状聚环氧乙烷(c-PEO)、环状聚苯乙烯(c-PS)和环状聚环氧乙烷-聚苯乙烯嵌段共聚物(c-PEO-b-PS),说明了该方法在环状聚合物合成中的普适性。我们所取得的主要结果如下：
1.合成了两种单环聚合物：环状聚环氧乙烷(c-PEO)、环状聚苯乙烯(c-PS)。首先,以新戊二醇作为引发剂,在二苯甲基钾(DPMK)的存在下引发环氧乙烷(EO)进行阴离子开环聚合(ROP),用甲醇终止反应,得到两端羟基的线形聚环氧乙烷(α，ω-dihydroxyl PEO);然后,在NaH的作用下,用溴丙炔对PEO进行端基修饰,得到两端为炔丙基的聚环氧乙烷(α,ωo-dipropargyl PEO)；再以吡啶作溶剂,将线形前驱体聚合物溶液以2μm/h的速度滴加到催化剂溶液[Cu(I)Br/PMDETA]中进行成环反应,得到环状产物。在c-PS的合成中,以萘锂为引发剂引发苯乙烯单体进行阴离子聚合,然后用EO作为小分子“盖帽”试剂,对“活性”聚苯乙烯双阴离子进行封端反应,生成了两端均为羟基的聚苯乙烯(a,co-dihydroxylPS),按照与前面同样的方法,将端基转化为炔丙基后进行Glaser成环反应得到环状聚苯乙烯产物。采用GPC、1H NMR、FT-IR和MALDI-TOF MS等手段对中间产物和目标产物进行了详细地表征。
2.合成了环状聚环氧乙烷-聚苯乙烯嵌段共聚物(c-PEO-b-PS)。以α，ω-二羟基聚苯乙烯作为大分子引发剂,在DPMK的存在下利用“活性”羟基引发EO单体进行开环聚合,制备了ABA型三嵌段聚合物,PEO-b-PS-b-PEO,然后将末端羟基转化为炔丙基,得到成环用前驱体聚合物。在成环过程中,改进成环条件,以Cu(I)Br作催化剂、吡啶作溶剂,不加配体(PMDETA),成功得到了环化产物。采用GPC、’H NMR、FT-IR和MALDI-TOF MS等对手段对中间产物和目标产物也进行了详细地表征,发现环化效率接近100%,无分子间缩聚反应副产物出现,因此环状嵌段产物不需要复杂的分离纯化过程。
The relations between structures and properties of polymers have attracted many researchers'attention. Cyclic polymers with "endless" polymer main chains show distinctively unique properties due to their closed ring topology compared to linear and branched ones. As new functional polymers, they could be applied in some important fields, such as material modification, nanotechnology and biological medicine, etc. However, their practical applications are greatly bound by the complicated and tedious synthetic procedure.
Highly-efficient ring-closure technique is one of the synthetic strategies for preparation of cyclic polymers, which involves intra-molecular cyclization of linear precursors with hetero-difunctional or homo-difunctional end groups under high dilute conditions. Functional linear precursors can be easily obtained by different polymerization techniques and end-group modification. Therefore, selecting appropriate cyclization conditions is very important for cyclic polymer preparation.
In this thesis, Glaser coupling reaction is used as cyclization technique to synthesize cyclic polymers. The Cu(I) catalyzed Glaser coupling of terminal alkynes can be conducted at room temperature in air, resulting in the formation of 1,3-diyne. Using this method, we have prepared cyclic poly(ethylene oxide) (c-PEO), cyclic polystyrene (c-PS), and cyclic poly(ethylene oxide)-block-polystyrene (c-PEO-b-PS) indicating that this is an universal method for the synthesis of cyclic polymers. The main results obtained are showed as follows:
1. Two cyclic homo-polymers have been synthesized:c-PEO and c-PS. Firstly, a,co-dihydroxyl PEO were obtained by ring-opening polymerization (ROP) of ethylene oxide (EO) initiated by co-initiator of 2,2-dimethyl-1,3-propanediol and diphenylmethylpotassium (DPMK), terminated by anhydrous methanol. After the reaction between hydroxyl end-groups and propargyl bromide in the presence of NaH,α,ω-dipropargyl PEO were obtained. Then, the linear precursors solution was added dropwise to catalyst solution [Cu(I)Br/N,N,N',N''-pentamethyldiethylenetriamine (PMDETA) dissolved in pyridine] at a rate of 2μmol/h to avoid intermolecular reactions and ensure the purity of cyclic products. c-PS was synthesized using the same manner, except that linear PS was obtained by anionic polymerization initiated by lithium naphthalenide and end-capped with EO. All the intermediates and target products were characterized by GPC、1HNMR、FT-IR and MALDI-TOF MS in detail.
2. Cyclic block copolymer, c-PEO-b-PS, have been designed and synthesized. Firstly,α,ω-dihydroxyl PS were used as macro-initiator in the presence of DPMK to initiate ROP of EO to give the triblock copolymer, poly(ethylene oxide)-block-polystyrene-block-poly(ethylene oxide) (PEO-b-PS-b-PEO). Then, the end hydroxyls were modified to propargyls. In the cyclization process, since pyridine can be acted as ligand, we tried to improve the cyclization condition without adding of PMDETA. It confirmed that the intra-molecular cyclization was also carried out with the efficiency as high as 100%, and no inter-molecular reactions were detected. All the intermediates and target products were characterized by GPC、1H NMR and FT-IR in detail.
引文
[1]Casassa, E. F., Some Statistical Properties of Flexible Ring Polymers. J. Polym. Sci., Part A:General Papers 1965,3 (2PA):605-&.
[2]Tezuka, Y.; Oike, H., Topological polymer chemistry:Systematic classification of nonlinear polymer topologies. J. Am. Chem. Soc.2001,123 (47):11570-11576.
[3]Laurent, B. A.; Grayson, S. M., Synthetic approaches for the preparation of cyclic polymers. Chem. Soc. Rev.2009,38 (8):2202-2213.
[4]Lepoittevin, B.; Hemery, P., Synthesis of high-molecular-weight cyclic and multicyclic polystyrenes. Polym. Adv. Technol.2002,13 (10-12):771-776.
[5]Geiser, D.; Hocker, H., Synthesis and Investigation of Macrocyclic Polystyrene. Macromolecules 1980,13 (3):653-656.
[6]Roovers, J.; Toporowski, P. M., Synthesis of High Molecular Weight Ring Polystyrenes. Macromolecules 1983,16 (6):843-849.
[7]Ohtani, H.; Kotsuji, H.; Momose, H.; Matsushita, Y.; Noda, I.; Tsuge, S., Ring Structure of Cyclic Poly(2-vinylpyridine) Proved by Pyrolysis-GC/MS. Macromolecules 1999,32 (20):6541-6544.
[8]Ishizu, K.; Kanno, H., Novel Synthesis and Characterization of Cyclic Polystyrenes. Polymer 1996,37 (8):1487-1492.
[9]Ishizu, K.; Ichimura, A., Synthesis of cyclic diblock copolymers by interfacial condensation. Polymer 1998,39 (25):6555-6558.
[10]Yu, G. E.; Sinnathamby, P.; Price, C.; Booth, C., Preparation of large cyclic poly(oxyethylene)s. Chem. Commun.1996, (1):31-32.
[11]Tezuka, Y.; Oike, H., Self-assembly and covalent fixation for topological polymer chemistry. Macromol.Rapid Commun.2001,22 (13):1017-1029.
[12]Oike, H.; Mouri, T.; Tezuka, Y., Efficient polymer cyclization by electrostatic self-assembly and covalent fixation with telechelic poly(tetrahydrofuran) having cyclic ammonium salt groups. Macromolecules 2001,34 (19):6592-6600.
[13]Tezuka, Y.; Mori, K.; Oike, H., Efficient synthesis of cyclic poly(oxyethylene) by electrostatic self-assembly and covalent fixation with telechelic precursor having cyclic ammonium salt groups. Macromolecules 2002,35 (14):5707-5711.
[14]Oike, H.; Washizuka, M.; Tezuka, Y., Designing an "a-ring-with-branches" polymer topology by electrostatic self-assembly and covalent fixation with interiorly functionalized telechelics having cyclic ammonium groups. Macromol.Rapid Commun.2001,22(14):1128-1134.
[15]Tezuka, Y.; Takahashi, N.; Satoh, T.; Adachi, K., Synthesis of polymeric topological isomers having theta-and manacle-constructions with olefinic groups at designated positions. Macromolecules 2007,40:7910-7918.
[16]Adachi, K.; Irie, H.; Sato, T.; Uchibori, A.; Shiozawa, M.; Tezuka, Y., Electrostatic self-assembly and covalent fixation with cationic and anionic telechelic precursors for new loop and branch polymer topologies. Macromolecules 2005,38 (24):10210-10219.
[17]Oike, H.; Uchibori, A.; Tsuchitani, A.; Kim, H. K.; Tezuka, Y., Designing loop and branch polymer topology with cationic star telechelics through effective selection of mono-and difunctional counteranions. Macromolecules 2004,37 (20):7595-7601.
[18]Ishikawa, K.; Yamamoto, T.; Asakawa, M.; Tezuka, Y., Effective Synthesis of Polymer Catenanes by Cooperative Electrostatic/Hydrogen-Bonding Self-Assembly and Covalent Fixation. Macromolecules 2009,43 (1):168-176.
[19]Schulz, M.; Tanner, S.; Barqawi, H.; Binder, W. H., Macrocyclization of Polymers via Ring-Closing Metathesis and Azide/Alkyne-"Click"-Reactions:An Approach to Cyclic Polyisobutylenes. J. Polym. Sci., Part A:Polym. Chem.2010,48 (3):671-680.
[20]Clark, P. G.; Guidry, E. N.; Chan, W. Y.; Steinmetz, W. E.; Grubbs, R. H., Synthesis of a Molecular Charm Bracelet via Click Cyclization and Olefin Metathesis Clipping. J. Am. Chem. Soc.2010,132 (10):3405-3412.
[21]Stanford, M. J.; Pflughaupt, R. L.; Dove, A. P., Synthesis of Stereoregular Cyclic Poly(lactide)s via "Thiol-Ene" Click Chemistry. Macromolecules 2010,43 (16): 6538-6541.
[22]Elmadani, A.; Favier, J. C.; Hemery, P.; Sigwalt, P., Synthesis of Ring-shaped Polyisoprene. Polym. Int.1992,27 (4):353-357.
[23]Schappacher, M.; Deffieux, A., Macromolecular Cavities of Controlled Size.1. Synthesis of Macrotricyclic Poly(chloroethyl vinyl ether)s by Living Cationic Polymerization. Macromolecules 1992,25 (25):6744-6751.
[24]Schappacher, M.; Deffieux, A., Controlled Synthesis of Bicyclic "Eight-Shaped" Poly(chloroethyl vinyl ether)s. Macromolecules 1995,28 (8):2629-2636.
[25]Beinat, S.; Schappacher, M.; Deffieux, A., Linear and Semicyclic Amphiphilic Diblock Copolymers.1. Synthesis and Structural Characterization of Cyclic Diblock Copolymers of Poly(hydroxyethyl vinyl ether) and Linear Polystyrene and Their Linear Homologues. Macromolecules 1996,29 (21):6737-6743.
[26]Riquelurbet, L.; Schappacher, M.; Deffieux, A., A New Strategy for the Synthesis of Cyclic Polystyrenes-Principle and Application. Macromolecules 1994,27 (22): 6318-6324.
[27]Schappacher, M.; Deffieux, A., alpha-acetal-omega-bis(hydroxymethyl) heterodifunctional polystyrene:Synthesis, characterization, and investigation of intramolecular end-to-end ring closure. Macromolecules 2001,34 (17):5827-5832.
[28]Kubo, M.; Hayashi, T.; Kobayashi, H.; Tsuboi, K.; Itoh, T., Synthesis of alpha-Carboxyl, omega-Amino Heterodifunctional Polystyrene and Its Intramolecular Cyclization. Macromolecules 1997,30 (9):2805-2807.
[29]Kubo, M.; Takeuchi, H.; Ohara, T.; Itoh, T.; Nagahata, R., Synthesis of a Well-defined Cyclic Polystyrene via alpha-Carboxyl, omega-Amino Heterodifunctional Polystyrene.J. Polym. Sci., Part A:Polym. Chem.1999,37 (13): 2027-2033.
[30]Kubo, M.; Yamamoto, H.; Uno, T.; Itoh, T.; Sato, H., Synthesis of cyclic poly(methyl methacrylate) by the intramolecular cyclization of alpha-amino, omega-carboxyl heterodifunctional poly(methyl methacrylate). Polym. Bull.2001,47 (1):25-30.
[31]Kubo, M.; Nishigawa, T.; Uno, T.; Itoh, T.; Sato, H., Cyclic polyelectrolyte: Synthesis of cyclic poly(acrylic acid) and cyclic potassium polyacrylate. Macromolecules 2003,36 (24):9264-9266.
[32]Kubo, M.; Hayashi, T.; Kobayashi, H.; Itoh, T., Syntheses of Tadpole-and Eight-shaped Polystyrenes using Cyclic Polystyrene as a Building Block. Macromolecules 1998,31 (4):1053-1057.
[33]Li, H. Y.; Debuigne, A.; Jerome, R.; Lecomte, P., Synthesis of macrocyclic poly(epsilon-caprolactone) by intramolecular cross-linking of unsaturated end groups of chains precyclic by the initiation. Angew. Chem. Int. Ed.2006,45 (14):2264-2267.
[34]Laurent, B. A.; Grayson, S. M., An efficient route to well-defined macrocyclic polymers via "Click" cyclization. J. Am. Chem. Soc.2006,128 (13):4238-4239.
[35]Eugene, D. M.; Grayson, S. M., Efficient preparation of cyclic poly(methyl acrylate)-block-poly(styrene) by combination of atom transfer radical polymerization and click cyclization. Macromolecules 2008,41 (14):5082-5084.
[36]Misaka, H.; Kakuchi, R.; Zhang, C. H.; Sakai, R.; Satoh, T.; Kakuchi, T., Synthesis of Well-Defined Macrocyclic Poly(delta-valerolactone) by "Click Cyclization". Macromolecules 2009,42 (14):5091-5096.
[37]Qiu, X. P.; Tanaka, F.; Winnik, F. M., Temperature-induced phase transition of well-defined cyclic poly(N-isopropylacrylamide)s in aqueous solution. Macromolecules 2007,40:7069-7071.
[38]Xu, J.; Ye, J.; Liu, S. Y, Synthesis of well-defined cyclic poly(N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior. Macromolecules 2007,40 (25):9103-9110.
[39]Ye, J.; Xu, J.; Hu, J. M.; Wang, X. F.; Zhang, G. Z.; Liu, S. Y.; Wu, C., Comparative study of temperature-induced association of cyclic and linear poly(N-isopropylacrylamide) chains in dilute solutions by laser light scattering and stopped-flow temperature jump. Macromolecules 2008,41 (12):4416-4422.
[40]Goldmann, A. S.; Quemener, D.; Millard, P. E.; Davis, T. P.; Stenzel, M. H.; Barner-Kowollik, C.; Muller, A. H. E., Access to cyclic polystyrenes via a combination of reversible addition fragmentation chain transfer (RAFT) polymerization and click chemistry. Polymer 2008,49 (9):2274-2281.
[41]Binauld, S.; Hawker, C. J.; Fleury, E.; Drockenmuller, E., A Modular Approach to Functionalized and Expanded Crown Ether Based Macrocycles Using Click Chemistry. Angew. Chem. Int. Ed.2009,48 (36):6654-6658.
[42]Tezuka, Y.; Komiya, R., Metathesis polymer cyclization with telechelic poly(THF) having allyl groups. Macromolecules 2002,35 (23):8667-8669.
[43]Tezuka, Y.; Ohtsuka, T.; Adachi, K.; Komiya, R.; Ohno, N.; Okui, N., A defect-free ring polymer:Size-controlled cyclic poly(tetrahydrofuran) consisting exclusively of the monomer unit. Macromol.Rapid Commun.2008,29 (14): 1237-1241.
[44]Tezuka, Y.;Komiya, R.; Washizuka, M., Designing 8-shaped polymer topology by metathesis condensation with cyclic poly(THF) precursors having allyl groups. Macromolecules 2003,36(1):12-17.
[45]Tezuka, Y; Ohashi, F., Synthesis of polymeric topological isomers through double metathesis condensation with H-shaped telechelic precursors. Macromol.Rapid Commun.2005,26(8):608-612.
[46]Adachi, K.; Honda, S.; Hayashi, S.; Tezuka, Y, ATRP-RCM Synthesis of Cyclic Diblock Copolymers. Macromolecules 2008,41 (21):7898-7903.
[47]Whittaker, M. R.; Goh, Y. K.; Gemici, H.; Legge, T. M.; Perrier, S.; Monteiro, M. J., Synthesis of monocyclic and linear polystyrene using the reversible coupling/cleavage of thiol/disulfide groups. Macromolecules 2006,39 (26): 9028-9034.
[48]Bielawski, C. W.; Benitez, D.; Grubbs, R. H., An "endless" route to cyclic polymers. Science 2002,297 (5589):2041-2044.
[49]Bielawski, C. W.; Benitez, D.; Grubbs, R. H., Synthesis of cyclic polybutadiene via ring-opening metathesis polymerization:The importance of removing trace linear contaminants. J. Am. Chem. Soc.2003,125 (28):8424-8425.
[50]He, T.; Zheng, G. H.; Pan, C. Y., Synthesis of cyclic polymers and block copolymers by monomer insertion into cyclic initiator by a radical mechanism. Macromolecules 2003,36 (16):5960-5966.
[51]Kudo, H.; Makino, S.; Kameyama, A.; Nishikubo, T., Synthesis of cyclic polymers:Ring-expansion reaction of cyclic S-dithioester with thiiranes. Macromolecules 2005,38 (14):5964-5969.
[52]Kudo, H.; Makino, S.; Nishikubo, T., Synthesis of macrocycles by the ring-crossover reaction of a cyclic dithioester. J. Polym. Sci., Part A:Polym. Chem. 2007,45 (A):680-687.
[53]Kudo, H.; Sato, M.; Wakai, R.; Iwamoto, T.; Nishikubo, T., A novel approach to cyclic polysulfides via the controlled ring-expansion polymerization of cyclic thiourethane with thirianes. Macromolecules 2008,41 (3):521-523.
[54]Shin, E. J.; Jeong, W.; Brown, H. A.; Koo, B. J.; Hedrick, J. L.; Waymouth, R. M., Crystallization of Cyclic Polymers:Synthesis and Crystallization Behavior of High Molecular Weight Cyclic Poly(s-caprolactone)s. Macromolecules 2011:null-null.
[55]Jones, F. R., Cyclics in Styrene-Dimethyl Siloxane Block Copolymers. Eur. Polym. J.1974,10 (3):249-254.
[56]Yin, R.; Hogenesch, T. E., Synthesis and characterization of narrow molecular-weight distribution polystyrene poly(dimethylsiloxane) macrocyclic block-copolymers and their isobaric precursors. Macromolecules 1993,26 (25): 6952-6957.
[57]Yin, R.; Amis, E. J.; Hogenesch, T. E., Synthesis of macrocyclic polystyrene-polydimethylsiloxane block-copolymers. Macromol. Symp.1994,85: 217-238.
[58]Ma, J. J., Synthesis of Well-defined Macrocyclic Block-Copolymers Using Living Coupling Agent Method. Macromol. Symp.1995,91:41-49.
[59]Yu, G. E.; Yang, Z.; Attwood, D.; Price, C.; Booth, C., Association and surface properties of a cyclic block copolymer of ethylene oxide and butylene oxide (Cyclo-B(8)E(42)) in water. Macromolecules 1996,29 (26):8479-8486.
[60]Iatrou, H.; Hadjichristidis, N.; Meier, G.; Frielinghaus, H.; Monkenbusch, M., Synthesis and characterization of model cyclic block copolymers of styrene and butadiene. Comparison of the aggregation phenomena in selective solvents with linear diblock and triblock analogues. Macromolecules 2002,35 (14):5426-5437.
[61]Zhu, Y. Q.; Gido, S. P.; Latrou, H.; Hadjichristidis, N.; Mays, J. W., Microphase separation of cyclic block copolymers of styrene and butadiene and of their corresponding linear triblock copolymers. Macromolecules 2003,36 (1):148-152.
[62]Pantazis, D.; Schulz, D. N.; Hadjichristidis, N., Synthesis of a model cyclic triblock terpolymer of styrene, isoprene, and methyl methacrylate. J. Polym. Sci., Part A:Polym. Chem.2002,40 (10):1476-1483.
[63]Takano, A.; Kadoi, O.; Hirahara, K.; Kawahara, S.; Isono, Y.; Suzuki, J.; Matsushita, Y, Preparation and morphology of ring-shaped polystyrene-block-polyisoprenes. Macromolecules 2003,36 (9):3045-3050.
[64]Cramail, S.; Schappacher, M.; Deffieux, A., Controlled synthesis and solution behavior of macrocyclic poly (styrene)-b-(ethylene oxide) copolymers. Macromol. Chem. Phys.2000,201 (17):2328-2335.
[65]Schappacher, M.; Deffieux, A., Synthesis, characterization, and intramolecular end-to-end ring closure of alpha-isopropylidene 1,1-dihydroxymethyl-omega-diethylacetal polystyrene-block-polyisoprene block copolymers. Macromol. Chem. Phys.2002,203 (17):2463-2469.
[66]Minatti, E.; Borsali, R.; Schappacher, M.;Deffieux, A.; Soldi, V.; Narayanan, T.; Putaux, J. L., Effect of cyclization of polystyrene/polyisoprene block copolymers on their micellar morphology. Macromol.Rapid Commun.2002,23 (16):978-982.
[67]Putaux, J. L.; Minatti, E.; Lefebvre, C.; Borsali, R.; Schappacher, M.; Deffieux, A., Vesicles made of PS-PI cyclic diblock copolymers:In situ freeze-drying cryo-TEM and dynamic light scattering experiments. Faraday Discuss.2005,128: 163-178.
[68]Borsali, R.; Minatti, E.; Putaux, J. L.; Schappacher, M.; Deffieux, A.; Viville, P.; Lazzaroni, R.; Narayanan, T., From "sunflower-like" assemblies toward giant wormlike micelles. Langmuir 2003,19 (1):6-9.
[69]Minatti, E.; Viville, P.; Borsali, R.; Schappacher, M.; Deffieux, A.; Lazzaroni, R., Micellar morphological changes promoted by cyclization of PS-b-PI copolymer:DLS and AFM experiments. Macromolecules 2003,36 (11):4125-4133.
[70]Lecommandoux, S.; Borsali, R.; Schappacher, M.; Deffieux, A.; Narayaman, T.; Rochas, C., Microphase separation of linear and cyclic block copolymers poly(styrene-b-isoprene):SAXS experiments. Macromolecules 2004,37 (5): 1843-1848.
[71]Ouarti, N.; Viville, P.; Lazzaroni, R.; Minatti, E.; Schappacher, M.; Deffieux, A.; Putaux, J. L.; Borsali, R., Micellar aggregation in blends of linear and cyclic poly(styrene-b-isoprene) diblock copolymers. Langmuir 2005,21 (20):9085-9090.
[72]Ouarti, N.; Viville, P.; Lazzaroni, R.; Minatti, E.; Schappacher, M.; Deffieux, A.; Borsali, R., Control of the morphology of linear and cyclic PS-b-PI block copolymer micelles via PS addition. Langmuir 2005,21 (4):1180-1186.
[73]Ge, Z. S.; Zhou, Y. M.; Xu, J.; Liu, H. W.; Chen, D. Y.; Liu, S. Y, High-Efficiency Preparation of Macrocyclic Diblock Copolymers via Selective Click Reaction in Micellar Media. J. Am. Chem. Soc.2009,131 (5):1628-1629.
[74]Shi, G. Y.; Yang, L. P.; Pan, C. Y, Synthesis and characterization of well-defined polystyrene and poly(epsilon-caprolactone) hetero eight-shaped copolymers. J. Polym. Sci., Part A:Polym. Chem.2008,46 (19):6496-6508.
[75]Shi, G. Y.; Pan, C. Y, Synthesis of Well-Defined Figure-of-Eight-Shaped Polymers by a Combination of ATRP and Click Chemistry. Macromol. Rapid Commun. 2008,29(20):1672-1678.
[76]Shi, G. Y.; Tang, X. Z.; Pan, C. Y., Tadpole-shaped amphiphilic copolymers prepared via RAFT polymerization and click reaction. J. Polym. Sci., Part A:Polym. Chem.2008,46 (7):2390-2401.
[77]Li, L. Y.; He, W. D.; Li, J.; Han, S. C.; Sun, X. L.; Zhang, B. Y., Synthesis of Twin-Tail Tadpole-Shaped Hydrophilic Copolymers and Their Thermo-Responsive Behavior. J. Polym. ScI., Part A:Polym. Chem.2009,47 (24):7066-7077.
[78]Dong, Y. Q.; Tong, Y. Y.; Dong, B. T.; Du, F. S.; Li, Z. C., Preparation of Tadpole-Shaped Amphiphilic Cyclic PS-b-linear PEO via ATRP and Click Chemistry. Macromolecules 2009,42 (8):2940-2948.
[79]Shi, G. Y.; Pan, C. Y, An Efficient Synthetic Route to Well-Defined Theta-Shaped Copolymers. J. Polym. Sci., Part A:Polym. Chem.2009,47(10):2620-2630.
[80]Ge, Z. S.; Wang, D.; Zhou, Y. M.; Liu, H. W.; Liu, S. Y., Synthesis of Organic/Inorganic Hybrid Quatrefoil-Shaped Star-Cyclic Polymer Containing a Polyhedral Oligomeric Silsesquioxane Core. Macromolecules 2009,42 (8): 2903-2910.
[81]Li, H. Y.; Riva, R.; Jerome, R.; Lecomte, P., Combination of ring-opening polymerization and "click" chemistry for the synthesis of an amphiphilic tadpole-shaped poly(epsilon-caprolactone) grafted by PEO. Macromolecules 2007,40 (4):824-831.
[82]Tezuka, Y, Topological polymer chemistry by electrostatic self-assembly. J. Polym. Sci., Part A:Polym. Chem.2003,41 (19):2905-2917.
[83]Antonietti, M.; Folsch, K. J., Synthesis and Characterization of 8-Shaped Polystyrene. Makromolekulare Chemie-Rapid Communications 1988,9 (6):423-430.
[84]Li, H. Y.; Riva, R.; Kricheldorf, H. R.; Jerome, R.; Lecomte, P., Synthesis of eight-and star-shaped poly(epsilon-caprolactone)s and their amphiphilic derivatives. Chemistry-a European Journal 2008,14 (1):358-368.
[85]Peng, Y.; Liu, H. W.; Zhang, X. Y.; Liu, S. Y.; Li, Y S., Macrocycle-Terminated Core-Cross-Linked Star Polymers:Synthesis and Characterization. Macromolecules 2009,42 (17):6457-6462.
[86]Ishikawa, K.; Yamamoto, T.; Asakawa, M.; Tezuka, Y., Effective Synthesis of Polymer Catenanes by Cooperative Electrostatic/Hydrogen-Bonding Self-Assembly and Covalent Fixation. Macromolecules 2010,43 (1):168-176.
[87]Sugai, N.; Heguri, H.; Ohta, K.; Meng, Q. Y.; Yamamoto, T.; Tezuka, Y, Effective Click Construction of Bridged-and Spiro-Multicyclic Polymer Topologies with Tailored Cyclic Prepolymers (kyklo-Telechelics). J. Am. Chem. Soc.2010,132 (42): 14790-14802.
[88]Jia, Z. F.; Fu, Q.; Huang, J. L., Synthesis of amphiphilic macrocyclic graft copolymer consisting of a poly(ethylene oxide) ring and multi-polystyrene lateral chains. Macromolecules 2006,39 (16):5190-5193.
[89]Pang, X. C.; Jing, R. K.; Huang, J. L., Synthesis of amphiphilic macrocyclic graft copolymer consisting of a poly(ethylene oxide) ring and multi-poly(epsilon-caprolactone) lateral chains. Polymer 2008,49 (4):893-900.
[90]Li, H. Y.; Jerome, R.; Lecomte, P., Amphiphilic sun-shaped polymers by grafting macrocyclic copolyesters with PEO. Macromolecules 2008,41 (3):650-654.
[91]Schappacher, M.; Deffieux, A., Synthesis of macrocyclic copolymer brushes and their self-assembly into supramolecular tubes. Science 2008,319 (5869):1512-1515.
[92]Deffieux, A.; Schappacher, M., Naturally occurring and synthetic cyclic macromolecules. Cellular and Molecular Life Sciences 2009,66 (15):2599-2602.
[93]Schappacher, M.; Deffieux, A., Imaging of Catenated, Figure-of-Eight, and Trefoil Knot Polymer Rings. Angew. Chem. Int. Ed.2009,48 (32):5930-5933.
[94]Nozaki, T.; Uno, T.; Itoh, T.; Kubo, M, Noncovalent cross-linking of poly(methyl methacrylate) via polypseudorotaxane. Macromolecules 2008,41 (14):5186-5190.
[95]Oike, H.; Mouri, T.; Tezuka, Y., A cyclic macromonomer designed for a novel polymer network architecture having both covalent and physical linkages. Macromolecules 2001,34 (18):6229-6234.
[96]Kubo, M.; Hibino, T.; Tamura, M.; Uno, T.; Itoh, T., Synthesis and copolymerization of cyclic macromonomer based on cyclic polystyrene:Gel formation via chain threading. Macromolecules 2002,35 (15):5816-5820.
[97]Kubo, M.; Kato, N.; Uno, T.; Itoh, T., Preparation of mechanically cross-linked polystyrenes. Macromolecules 2004,57 (8):2762-2765.
[98]Siemsen, P.; Livingston, R. C.; Diederich, F., Acetylenic coupling:A powerful tool in molecular construction. Angew. Chem. Int. Ed.2000,39 (15):2633-2657.
[99]Reppe, W., Athinylierung. Annalen Der Chemie-Justus Liebig 1955,596:1-224.
[100]Eglinton, G; Galbraith, A. R., Cyclic Diynes. Chemistry & Industry 1956, (28):737-738.
[101]Hay, A. S., Oxidative Coupling of Acetylenes. J. Org. Chem.1962,27 (9): 3320-3321.
[102]Chodkiewicz, W.; Cadiot, P., Nouvelle Synthese De Composes Polyacetyleniques Conjugues Symetriques Et Dissymetriques. Comptes Rendus Hebdomadaires Des Seances De L Academie Des Sciences 1955,241 (16): 1055-1057.
[103]Bohlmann, F.; Schonowsky, H.; Grau, G.; Inhoffen, E., Polyacetylenverbindungen.52. Uber Den Mechanismus Der Oxydativen Dimerisierung Von Acetylenverbindungen. Chem. Ber. Recl.1964,97(3):794-&.
[104]Fomina, L.; Vazquez, B.; Tkatchouk, E.; Fomine, S., The Glaser reaction mechanism. A DFT study. Tetrahedron 2002,58(33):6741-6747.
[105]Kijima, M.; Kinoshita, I.; Hiroki, K.; Shirakawa, H.; Yoshikawa, K.; Mishima, Y.; Sasaki, N., Optical properties of conjugated polymers having linear carbon moieties. Current Applied Physics 2002,2 (4):289-294.
[106]Marsden, J. A.; Miller, J. J.; Haley, M. M, Let the best ring win:Selective macrocycle formation through Pd-catalyzed or Cu-mediated alkyne homocoupling. Angew. Chem. Int. Ed. 2004,43 (13):1694-1697.
[107]Fischer, M.; Lieser, G.; Rapp, A.; Schnell, I.; Mamdouh, W.; De Feyter, S.; De Schryver, F. C.; Hoger, S., Shape-persistent macrocycles with intraannular polar groups:Synthesis, liquid crystallinity, and 2D organization. J. Am. Chem. Soc.2004, 126(1):214-222.
[108]Lee, K. S.; Wegner, G, Linear and Cyclic Alkanes (CnH2n+2, CnH2n) with n Greater-than 100-Synthesis and Evidence for Chain-Folding. Makromolekulare Chemie-Rapid Communications 1985,6 (3):203-208.
[109]Beckmann, W.; Doerjer, G.; Logemann, E.; Merkel, C.; Schill, G.; Zurcher, C., Improved Synthesis of Long-Chain 1-Alkynes and Terminal Alkadiynes. Synthesis-Stuttgart 1975, (7):423-425.
[110]Lee, K. S.; Wegner, G.; Hsu, S. L., Vibrational Spectroscopic Studies of Linear and Cyclic Alkanes CnH2n+2prime CnH2n with 24 Less-than-or-Equal-to 288-Chain Folding, Chain Packing and Conformations. Polymer 1987,28 (6):889-896.
[1]Binauld, S.; Hawker, C. J.; Fleury, E.; Drockenmuller, E., A Modular Approach to Functionalized and Expanded Crown Ether Based Macrocycles Using Click Chemistry. Angew. Chem. Int. Ed.2009,48 (36):6654-6658.
[2]Francis, R.; Taton, D.; Logan, J. L.; Masse, P.; Gnanou, Y.; Duran, R. S., Synthesis and surface properties of amphiphilic star-shaped and dendrimer-like copolymers based on polystyrene core and poly(ethylene oxide) corona. Macromolecules 2003,36 (22): 8253-8259.
[3]Wei, J.; Huang, J. L., Synthesis of an amphiphilic star triblock copolymer of polystyrene, poly(ethylene oxide), and polyisoprene using lysine as core molecule. Macromolecules 2005,38 (4):1107-1113.
[4]Gilman, H.; Haubein, A. H., The quantitative analysis of alkyllithium compounds. J. Am. Chem. Soc.1944,66:1515-1516.
[5]Ishizu, K.; Ichimura, A., Synthesis of cyclic diblock copolymers by interfacial condensation. Polymer 1998,39 (25):6555-6558.
[6]Taton, D.; Cloutet, E.; Gnanou, Y., Novel amphiphilic branched copolymers based on polystyrene and poly(ethylene oxide). Macromol. Chem. Phys.1998,199: 2501-2510.
[7]Semlyen, J. A., Cyclic Polymers. Elsevier:New York,1986.
[8]Gan, Y.; Dong, D.; Hogen-Esch, T. E., Effects of Lithium Bromide on the Glass Transition Temperatures of Linear and Macrocyclic Poly(2-vinylpyridine) and Polystyrene. Macromolecules 1995,28 (1):383-385.
[9]Tezuka, Y.; Mori, K.; Oike, H., Efficient synthesis of cyclic poly(oxyethylene) by electrostatic self-assembly and covalent fixation with telechelic precursor having cyclic ammonium salt groups. Macromolecules 2002,35 (14):5707-5711.
[10]Riquelurbet, L.; Schappacher, M.; Deffieux, A., A New Strategy for the Synthesis of Cyclic Polystyrenes-Principle and Application. Macromolecules 1994,27 (22): 6318-6324.
[1]He, T.; Zheng, G. H.; Pan, C. Y., Synthesis of cyclic polymers and block copolymers by monomer insertion into cyclic initiator by a radical mechanism. Macromolecules 2003,36 (16):5960-5966.
[2]Eugene, D. M.; Grayson, S. M., Efficient preparation of cyclic poly(methyl acrylate)-block-poly(styrene) by combination of atom transfer radical polymerization and click cyclization. Macromolecules 2008,41 (14):5082-5084.
[3]Adachi, K.; Honda, S.; Hayashi, S.; Tezuka, Y., ATRP-RCM Synthesis of Cyclic Diblock Copolymers. Macromolecules 2008,41 (21):7898-7903.
[4]Angot, S.; Taton, D.; Gnanou, Y, Amphiphilic Stars and Dendrimer-Like Architectures Based on Poly(Ethylene Oxide) and Polystyrene. Macromolecules 2000, 33 (15):5418-5426.
[5]Roovers, J.; Toporowski, P. M., Synthesis of High Molecular Weight Ring Polystyrenes. Macromolecules 1983,16 (6):843-849.
[6]Riquelurbet, L.; Schappacher, M.; Deffieux, A., A New Strategy for the Synthesis of Cyclic Polystyrenes-Principle and Application. Macromolecules 1994,27 (22): 6318-6324.
[7]Gan, Y.; Dong, D.; Hogen-Esch, T. E., Effects of Lithium Bromide on the Glass Transition Temperatures of Linear and Macrocyclic Poly(2-vinylpyridine) and Polystyrene. Macromolecules 1995,28 (1):383-385.
[8]Ma, J. J., Synthesis of Well-defined Macrocyclic Block-Copolymers Using Living Coupling Agent Method. Macromol Symp.1995,91:41-49.
[9]Lepoittevin, B.; Hemery, P., Synthesis of high-molecular-weight cyclic and multicyclic polystyrenes. Polym. Adv. Technol 2002,13 (10-12):771-776.
[10]Tezuka, Y.; Komiya, R., Metathesis polymer cyclization with telechelic poly(THF) having allyl groups. Macromolecules 2002,35 (23):8667-8669.
[11]Qiu, X. P.; Tanaka, F.; Winnik, F. M., Temperature-induced phase transition of well-defined cyclic poly(N-isopropylacrylamide)s in aqueous solution. Macromolecules 2007,40:7069-7071.
[12]Schappacher, M.; Deffieux, A., Controlled Synthesis of Bicyclic "Eight-Shaped" Poly(chloroethyl vinyl ether)s. Macromolecules 1995,28 (8):2629-2636.
[13]Shi, G. Y.; Pan, C. Y, Synthesis of Weil-Defined Figure-of-Eight-Shaped Polymers by a Combination of ATRP and Click Chemistry. Macromol.Rapid Commun.2008,29 (20):1672-1678.
[14]Shi, G. Y.; Yang, L. P.; Pan, C. Y, Synthesis and characterization of well-defined polystyrene and poly(epsilon-caprolactone) hetero eight-shaped copolymers. J. Polym. Set, Part A:Polym. Chem.2008,46 (19):6496-6508.
[15]Shi, G. Y.; Tang, X. Z.; Pan, C. Y., Tadpole-shaped amphiphilic copolymers prepared via RAFT polymerization and click reaction. J. Polym. Sci., Part A:Polym. Chem.2008,46 (7):2390-2401.
[2]Tezuka, Y.; Oike, H., Topological polymer chemistry:Systematic classification of nonlinear polymer topologies. J. Am. Chem. Soc.2001,123 (47):11570-11576.
[3]Laurent, B. A.; Grayson, S. M., Synthetic approaches for the preparation of cyclic polymers. Chem. Soc. Rev.2009,38 (8):2202-2213.
[4]Lepoittevin, B.; Hemery, P., Synthesis of high-molecular-weight cyclic and multicyclic polystyrenes. Polym. Adv. Technol.2002,13 (10-12):771-776.
[5]Geiser, D.; Hocker, H., Synthesis and Investigation of Macrocyclic Polystyrene. Macromolecules 1980,13 (3):653-656.
[6]Roovers, J.; Toporowski, P. M., Synthesis of High Molecular Weight Ring Polystyrenes. Macromolecules 1983,16 (6):843-849.
[7]Ohtani, H.; Kotsuji, H.; Momose, H.; Matsushita, Y.; Noda, I.; Tsuge, S., Ring Structure of Cyclic Poly(2-vinylpyridine) Proved by Pyrolysis-GC/MS. Macromolecules 1999,32 (20):6541-6544.
[8]Ishizu, K.; Kanno, H., Novel Synthesis and Characterization of Cyclic Polystyrenes. Polymer 1996,37 (8):1487-1492.
[9]Ishizu, K.; Ichimura, A., Synthesis of cyclic diblock copolymers by interfacial condensation. Polymer 1998,39 (25):6555-6558.
[10]Yu, G. E.; Sinnathamby, P.; Price, C.; Booth, C., Preparation of large cyclic poly(oxyethylene)s. Chem. Commun.1996, (1):31-32.
[11]Tezuka, Y.; Oike, H., Self-assembly and covalent fixation for topological polymer chemistry. Macromol.Rapid Commun.2001,22 (13):1017-1029.
[12]Oike, H.; Mouri, T.; Tezuka, Y., Efficient polymer cyclization by electrostatic self-assembly and covalent fixation with telechelic poly(tetrahydrofuran) having cyclic ammonium salt groups. Macromolecules 2001,34 (19):6592-6600.
[13]Tezuka, Y.; Mori, K.; Oike, H., Efficient synthesis of cyclic poly(oxyethylene) by electrostatic self-assembly and covalent fixation with telechelic precursor having cyclic ammonium salt groups. Macromolecules 2002,35 (14):5707-5711.
[14]Oike, H.; Washizuka, M.; Tezuka, Y., Designing an "a-ring-with-branches" polymer topology by electrostatic self-assembly and covalent fixation with interiorly functionalized telechelics having cyclic ammonium groups. Macromol.Rapid Commun.2001,22(14):1128-1134.
[15]Tezuka, Y.; Takahashi, N.; Satoh, T.; Adachi, K., Synthesis of polymeric topological isomers having theta-and manacle-constructions with olefinic groups at designated positions. Macromolecules 2007,40:7910-7918.
[16]Adachi, K.; Irie, H.; Sato, T.; Uchibori, A.; Shiozawa, M.; Tezuka, Y., Electrostatic self-assembly and covalent fixation with cationic and anionic telechelic precursors for new loop and branch polymer topologies. Macromolecules 2005,38 (24):10210-10219.
[17]Oike, H.; Uchibori, A.; Tsuchitani, A.; Kim, H. K.; Tezuka, Y., Designing loop and branch polymer topology with cationic star telechelics through effective selection of mono-and difunctional counteranions. Macromolecules 2004,37 (20):7595-7601.
[18]Ishikawa, K.; Yamamoto, T.; Asakawa, M.; Tezuka, Y., Effective Synthesis of Polymer Catenanes by Cooperative Electrostatic/Hydrogen-Bonding Self-Assembly and Covalent Fixation. Macromolecules 2009,43 (1):168-176.
[19]Schulz, M.; Tanner, S.; Barqawi, H.; Binder, W. H., Macrocyclization of Polymers via Ring-Closing Metathesis and Azide/Alkyne-"Click"-Reactions:An Approach to Cyclic Polyisobutylenes. J. Polym. Sci., Part A:Polym. Chem.2010,48 (3):671-680.
[20]Clark, P. G.; Guidry, E. N.; Chan, W. Y.; Steinmetz, W. E.; Grubbs, R. H., Synthesis of a Molecular Charm Bracelet via Click Cyclization and Olefin Metathesis Clipping. J. Am. Chem. Soc.2010,132 (10):3405-3412.
[21]Stanford, M. J.; Pflughaupt, R. L.; Dove, A. P., Synthesis of Stereoregular Cyclic Poly(lactide)s via "Thiol-Ene" Click Chemistry. Macromolecules 2010,43 (16): 6538-6541.
[22]Elmadani, A.; Favier, J. C.; Hemery, P.; Sigwalt, P., Synthesis of Ring-shaped Polyisoprene. Polym. Int.1992,27 (4):353-357.
[23]Schappacher, M.; Deffieux, A., Macromolecular Cavities of Controlled Size.1. Synthesis of Macrotricyclic Poly(chloroethyl vinyl ether)s by Living Cationic Polymerization. Macromolecules 1992,25 (25):6744-6751.
[24]Schappacher, M.; Deffieux, A., Controlled Synthesis of Bicyclic "Eight-Shaped" Poly(chloroethyl vinyl ether)s. Macromolecules 1995,28 (8):2629-2636.
[25]Beinat, S.; Schappacher, M.; Deffieux, A., Linear and Semicyclic Amphiphilic Diblock Copolymers.1. Synthesis and Structural Characterization of Cyclic Diblock Copolymers of Poly(hydroxyethyl vinyl ether) and Linear Polystyrene and Their Linear Homologues. Macromolecules 1996,29 (21):6737-6743.
[26]Riquelurbet, L.; Schappacher, M.; Deffieux, A., A New Strategy for the Synthesis of Cyclic Polystyrenes-Principle and Application. Macromolecules 1994,27 (22): 6318-6324.
[27]Schappacher, M.; Deffieux, A., alpha-acetal-omega-bis(hydroxymethyl) heterodifunctional polystyrene:Synthesis, characterization, and investigation of intramolecular end-to-end ring closure. Macromolecules 2001,34 (17):5827-5832.
[28]Kubo, M.; Hayashi, T.; Kobayashi, H.; Tsuboi, K.; Itoh, T., Synthesis of alpha-Carboxyl, omega-Amino Heterodifunctional Polystyrene and Its Intramolecular Cyclization. Macromolecules 1997,30 (9):2805-2807.
[29]Kubo, M.; Takeuchi, H.; Ohara, T.; Itoh, T.; Nagahata, R., Synthesis of a Well-defined Cyclic Polystyrene via alpha-Carboxyl, omega-Amino Heterodifunctional Polystyrene.J. Polym. Sci., Part A:Polym. Chem.1999,37 (13): 2027-2033.
[30]Kubo, M.; Yamamoto, H.; Uno, T.; Itoh, T.; Sato, H., Synthesis of cyclic poly(methyl methacrylate) by the intramolecular cyclization of alpha-amino, omega-carboxyl heterodifunctional poly(methyl methacrylate). Polym. Bull.2001,47 (1):25-30.
[31]Kubo, M.; Nishigawa, T.; Uno, T.; Itoh, T.; Sato, H., Cyclic polyelectrolyte: Synthesis of cyclic poly(acrylic acid) and cyclic potassium polyacrylate. Macromolecules 2003,36 (24):9264-9266.
[32]Kubo, M.; Hayashi, T.; Kobayashi, H.; Itoh, T., Syntheses of Tadpole-and Eight-shaped Polystyrenes using Cyclic Polystyrene as a Building Block. Macromolecules 1998,31 (4):1053-1057.
[33]Li, H. Y.; Debuigne, A.; Jerome, R.; Lecomte, P., Synthesis of macrocyclic poly(epsilon-caprolactone) by intramolecular cross-linking of unsaturated end groups of chains precyclic by the initiation. Angew. Chem. Int. Ed.2006,45 (14):2264-2267.
[34]Laurent, B. A.; Grayson, S. M., An efficient route to well-defined macrocyclic polymers via "Click" cyclization. J. Am. Chem. Soc.2006,128 (13):4238-4239.
[35]Eugene, D. M.; Grayson, S. M., Efficient preparation of cyclic poly(methyl acrylate)-block-poly(styrene) by combination of atom transfer radical polymerization and click cyclization. Macromolecules 2008,41 (14):5082-5084.
[36]Misaka, H.; Kakuchi, R.; Zhang, C. H.; Sakai, R.; Satoh, T.; Kakuchi, T., Synthesis of Well-Defined Macrocyclic Poly(delta-valerolactone) by "Click Cyclization". Macromolecules 2009,42 (14):5091-5096.
[37]Qiu, X. P.; Tanaka, F.; Winnik, F. M., Temperature-induced phase transition of well-defined cyclic poly(N-isopropylacrylamide)s in aqueous solution. Macromolecules 2007,40:7069-7071.
[38]Xu, J.; Ye, J.; Liu, S. Y, Synthesis of well-defined cyclic poly(N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior. Macromolecules 2007,40 (25):9103-9110.
[39]Ye, J.; Xu, J.; Hu, J. M.; Wang, X. F.; Zhang, G. Z.; Liu, S. Y.; Wu, C., Comparative study of temperature-induced association of cyclic and linear poly(N-isopropylacrylamide) chains in dilute solutions by laser light scattering and stopped-flow temperature jump. Macromolecules 2008,41 (12):4416-4422.
[40]Goldmann, A. S.; Quemener, D.; Millard, P. E.; Davis, T. P.; Stenzel, M. H.; Barner-Kowollik, C.; Muller, A. H. E., Access to cyclic polystyrenes via a combination of reversible addition fragmentation chain transfer (RAFT) polymerization and click chemistry. Polymer 2008,49 (9):2274-2281.
[41]Binauld, S.; Hawker, C. J.; Fleury, E.; Drockenmuller, E., A Modular Approach to Functionalized and Expanded Crown Ether Based Macrocycles Using Click Chemistry. Angew. Chem. Int. Ed.2009,48 (36):6654-6658.
[42]Tezuka, Y.; Komiya, R., Metathesis polymer cyclization with telechelic poly(THF) having allyl groups. Macromolecules 2002,35 (23):8667-8669.
[43]Tezuka, Y.; Ohtsuka, T.; Adachi, K.; Komiya, R.; Ohno, N.; Okui, N., A defect-free ring polymer:Size-controlled cyclic poly(tetrahydrofuran) consisting exclusively of the monomer unit. Macromol.Rapid Commun.2008,29 (14): 1237-1241.
[44]Tezuka, Y.;Komiya, R.; Washizuka, M., Designing 8-shaped polymer topology by metathesis condensation with cyclic poly(THF) precursors having allyl groups. Macromolecules 2003,36(1):12-17.
[45]Tezuka, Y; Ohashi, F., Synthesis of polymeric topological isomers through double metathesis condensation with H-shaped telechelic precursors. Macromol.Rapid Commun.2005,26(8):608-612.
[46]Adachi, K.; Honda, S.; Hayashi, S.; Tezuka, Y, ATRP-RCM Synthesis of Cyclic Diblock Copolymers. Macromolecules 2008,41 (21):7898-7903.
[47]Whittaker, M. R.; Goh, Y. K.; Gemici, H.; Legge, T. M.; Perrier, S.; Monteiro, M. J., Synthesis of monocyclic and linear polystyrene using the reversible coupling/cleavage of thiol/disulfide groups. Macromolecules 2006,39 (26): 9028-9034.
[48]Bielawski, C. W.; Benitez, D.; Grubbs, R. H., An "endless" route to cyclic polymers. Science 2002,297 (5589):2041-2044.
[49]Bielawski, C. W.; Benitez, D.; Grubbs, R. H., Synthesis of cyclic polybutadiene via ring-opening metathesis polymerization:The importance of removing trace linear contaminants. J. Am. Chem. Soc.2003,125 (28):8424-8425.
[50]He, T.; Zheng, G. H.; Pan, C. Y., Synthesis of cyclic polymers and block copolymers by monomer insertion into cyclic initiator by a radical mechanism. Macromolecules 2003,36 (16):5960-5966.
[51]Kudo, H.; Makino, S.; Kameyama, A.; Nishikubo, T., Synthesis of cyclic polymers:Ring-expansion reaction of cyclic S-dithioester with thiiranes. Macromolecules 2005,38 (14):5964-5969.
[52]Kudo, H.; Makino, S.; Nishikubo, T., Synthesis of macrocycles by the ring-crossover reaction of a cyclic dithioester. J. Polym. Sci., Part A:Polym. Chem. 2007,45 (A):680-687.
[53]Kudo, H.; Sato, M.; Wakai, R.; Iwamoto, T.; Nishikubo, T., A novel approach to cyclic polysulfides via the controlled ring-expansion polymerization of cyclic thiourethane with thirianes. Macromolecules 2008,41 (3):521-523.
[54]Shin, E. J.; Jeong, W.; Brown, H. A.; Koo, B. J.; Hedrick, J. L.; Waymouth, R. M., Crystallization of Cyclic Polymers:Synthesis and Crystallization Behavior of High Molecular Weight Cyclic Poly(s-caprolactone)s. Macromolecules 2011:null-null.
[55]Jones, F. R., Cyclics in Styrene-Dimethyl Siloxane Block Copolymers. Eur. Polym. J.1974,10 (3):249-254.
[56]Yin, R.; Hogenesch, T. E., Synthesis and characterization of narrow molecular-weight distribution polystyrene poly(dimethylsiloxane) macrocyclic block-copolymers and their isobaric precursors. Macromolecules 1993,26 (25): 6952-6957.
[57]Yin, R.; Amis, E. J.; Hogenesch, T. E., Synthesis of macrocyclic polystyrene-polydimethylsiloxane block-copolymers. Macromol. Symp.1994,85: 217-238.
[58]Ma, J. J., Synthesis of Well-defined Macrocyclic Block-Copolymers Using Living Coupling Agent Method. Macromol. Symp.1995,91:41-49.
[59]Yu, G. E.; Yang, Z.; Attwood, D.; Price, C.; Booth, C., Association and surface properties of a cyclic block copolymer of ethylene oxide and butylene oxide (Cyclo-B(8)E(42)) in water. Macromolecules 1996,29 (26):8479-8486.
[60]Iatrou, H.; Hadjichristidis, N.; Meier, G.; Frielinghaus, H.; Monkenbusch, M., Synthesis and characterization of model cyclic block copolymers of styrene and butadiene. Comparison of the aggregation phenomena in selective solvents with linear diblock and triblock analogues. Macromolecules 2002,35 (14):5426-5437.
[61]Zhu, Y. Q.; Gido, S. P.; Latrou, H.; Hadjichristidis, N.; Mays, J. W., Microphase separation of cyclic block copolymers of styrene and butadiene and of their corresponding linear triblock copolymers. Macromolecules 2003,36 (1):148-152.
[62]Pantazis, D.; Schulz, D. N.; Hadjichristidis, N., Synthesis of a model cyclic triblock terpolymer of styrene, isoprene, and methyl methacrylate. J. Polym. Sci., Part A:Polym. Chem.2002,40 (10):1476-1483.
[63]Takano, A.; Kadoi, O.; Hirahara, K.; Kawahara, S.; Isono, Y.; Suzuki, J.; Matsushita, Y, Preparation and morphology of ring-shaped polystyrene-block-polyisoprenes. Macromolecules 2003,36 (9):3045-3050.
[64]Cramail, S.; Schappacher, M.; Deffieux, A., Controlled synthesis and solution behavior of macrocyclic poly (styrene)-b-(ethylene oxide) copolymers. Macromol. Chem. Phys.2000,201 (17):2328-2335.
[65]Schappacher, M.; Deffieux, A., Synthesis, characterization, and intramolecular end-to-end ring closure of alpha-isopropylidene 1,1-dihydroxymethyl-omega-diethylacetal polystyrene-block-polyisoprene block copolymers. Macromol. Chem. Phys.2002,203 (17):2463-2469.
[66]Minatti, E.; Borsali, R.; Schappacher, M.;Deffieux, A.; Soldi, V.; Narayanan, T.; Putaux, J. L., Effect of cyclization of polystyrene/polyisoprene block copolymers on their micellar morphology. Macromol.Rapid Commun.2002,23 (16):978-982.
[67]Putaux, J. L.; Minatti, E.; Lefebvre, C.; Borsali, R.; Schappacher, M.; Deffieux, A., Vesicles made of PS-PI cyclic diblock copolymers:In situ freeze-drying cryo-TEM and dynamic light scattering experiments. Faraday Discuss.2005,128: 163-178.
[68]Borsali, R.; Minatti, E.; Putaux, J. L.; Schappacher, M.; Deffieux, A.; Viville, P.; Lazzaroni, R.; Narayanan, T., From "sunflower-like" assemblies toward giant wormlike micelles. Langmuir 2003,19 (1):6-9.
[69]Minatti, E.; Viville, P.; Borsali, R.; Schappacher, M.; Deffieux, A.; Lazzaroni, R., Micellar morphological changes promoted by cyclization of PS-b-PI copolymer:DLS and AFM experiments. Macromolecules 2003,36 (11):4125-4133.
[70]Lecommandoux, S.; Borsali, R.; Schappacher, M.; Deffieux, A.; Narayaman, T.; Rochas, C., Microphase separation of linear and cyclic block copolymers poly(styrene-b-isoprene):SAXS experiments. Macromolecules 2004,37 (5): 1843-1848.
[71]Ouarti, N.; Viville, P.; Lazzaroni, R.; Minatti, E.; Schappacher, M.; Deffieux, A.; Putaux, J. L.; Borsali, R., Micellar aggregation in blends of linear and cyclic poly(styrene-b-isoprene) diblock copolymers. Langmuir 2005,21 (20):9085-9090.
[72]Ouarti, N.; Viville, P.; Lazzaroni, R.; Minatti, E.; Schappacher, M.; Deffieux, A.; Borsali, R., Control of the morphology of linear and cyclic PS-b-PI block copolymer micelles via PS addition. Langmuir 2005,21 (4):1180-1186.
[73]Ge, Z. S.; Zhou, Y. M.; Xu, J.; Liu, H. W.; Chen, D. Y.; Liu, S. Y, High-Efficiency Preparation of Macrocyclic Diblock Copolymers via Selective Click Reaction in Micellar Media. J. Am. Chem. Soc.2009,131 (5):1628-1629.
[74]Shi, G. Y.; Yang, L. P.; Pan, C. Y, Synthesis and characterization of well-defined polystyrene and poly(epsilon-caprolactone) hetero eight-shaped copolymers. J. Polym. Sci., Part A:Polym. Chem.2008,46 (19):6496-6508.
[75]Shi, G. Y.; Pan, C. Y, Synthesis of Well-Defined Figure-of-Eight-Shaped Polymers by a Combination of ATRP and Click Chemistry. Macromol. Rapid Commun. 2008,29(20):1672-1678.
[76]Shi, G. Y.; Tang, X. Z.; Pan, C. Y., Tadpole-shaped amphiphilic copolymers prepared via RAFT polymerization and click reaction. J. Polym. Sci., Part A:Polym. Chem.2008,46 (7):2390-2401.
[77]Li, L. Y.; He, W. D.; Li, J.; Han, S. C.; Sun, X. L.; Zhang, B. Y., Synthesis of Twin-Tail Tadpole-Shaped Hydrophilic Copolymers and Their Thermo-Responsive Behavior. J. Polym. ScI., Part A:Polym. Chem.2009,47 (24):7066-7077.
[78]Dong, Y. Q.; Tong, Y. Y.; Dong, B. T.; Du, F. S.; Li, Z. C., Preparation of Tadpole-Shaped Amphiphilic Cyclic PS-b-linear PEO via ATRP and Click Chemistry. Macromolecules 2009,42 (8):2940-2948.
[79]Shi, G. Y.; Pan, C. Y, An Efficient Synthetic Route to Well-Defined Theta-Shaped Copolymers. J. Polym. Sci., Part A:Polym. Chem.2009,47(10):2620-2630.
[80]Ge, Z. S.; Wang, D.; Zhou, Y. M.; Liu, H. W.; Liu, S. Y., Synthesis of Organic/Inorganic Hybrid Quatrefoil-Shaped Star-Cyclic Polymer Containing a Polyhedral Oligomeric Silsesquioxane Core. Macromolecules 2009,42 (8): 2903-2910.
[81]Li, H. Y.; Riva, R.; Jerome, R.; Lecomte, P., Combination of ring-opening polymerization and "click" chemistry for the synthesis of an amphiphilic tadpole-shaped poly(epsilon-caprolactone) grafted by PEO. Macromolecules 2007,40 (4):824-831.
[82]Tezuka, Y, Topological polymer chemistry by electrostatic self-assembly. J. Polym. Sci., Part A:Polym. Chem.2003,41 (19):2905-2917.
[83]Antonietti, M.; Folsch, K. J., Synthesis and Characterization of 8-Shaped Polystyrene. Makromolekulare Chemie-Rapid Communications 1988,9 (6):423-430.
[84]Li, H. Y.; Riva, R.; Kricheldorf, H. R.; Jerome, R.; Lecomte, P., Synthesis of eight-and star-shaped poly(epsilon-caprolactone)s and their amphiphilic derivatives. Chemistry-a European Journal 2008,14 (1):358-368.
[85]Peng, Y.; Liu, H. W.; Zhang, X. Y.; Liu, S. Y.; Li, Y S., Macrocycle-Terminated Core-Cross-Linked Star Polymers:Synthesis and Characterization. Macromolecules 2009,42 (17):6457-6462.
[86]Ishikawa, K.; Yamamoto, T.; Asakawa, M.; Tezuka, Y., Effective Synthesis of Polymer Catenanes by Cooperative Electrostatic/Hydrogen-Bonding Self-Assembly and Covalent Fixation. Macromolecules 2010,43 (1):168-176.
[87]Sugai, N.; Heguri, H.; Ohta, K.; Meng, Q. Y.; Yamamoto, T.; Tezuka, Y, Effective Click Construction of Bridged-and Spiro-Multicyclic Polymer Topologies with Tailored Cyclic Prepolymers (kyklo-Telechelics). J. Am. Chem. Soc.2010,132 (42): 14790-14802.
[88]Jia, Z. F.; Fu, Q.; Huang, J. L., Synthesis of amphiphilic macrocyclic graft copolymer consisting of a poly(ethylene oxide) ring and multi-polystyrene lateral chains. Macromolecules 2006,39 (16):5190-5193.
[89]Pang, X. C.; Jing, R. K.; Huang, J. L., Synthesis of amphiphilic macrocyclic graft copolymer consisting of a poly(ethylene oxide) ring and multi-poly(epsilon-caprolactone) lateral chains. Polymer 2008,49 (4):893-900.
[90]Li, H. Y.; Jerome, R.; Lecomte, P., Amphiphilic sun-shaped polymers by grafting macrocyclic copolyesters with PEO. Macromolecules 2008,41 (3):650-654.
[91]Schappacher, M.; Deffieux, A., Synthesis of macrocyclic copolymer brushes and their self-assembly into supramolecular tubes. Science 2008,319 (5869):1512-1515.
[92]Deffieux, A.; Schappacher, M., Naturally occurring and synthetic cyclic macromolecules. Cellular and Molecular Life Sciences 2009,66 (15):2599-2602.
[93]Schappacher, M.; Deffieux, A., Imaging of Catenated, Figure-of-Eight, and Trefoil Knot Polymer Rings. Angew. Chem. Int. Ed.2009,48 (32):5930-5933.
[94]Nozaki, T.; Uno, T.; Itoh, T.; Kubo, M, Noncovalent cross-linking of poly(methyl methacrylate) via polypseudorotaxane. Macromolecules 2008,41 (14):5186-5190.
[95]Oike, H.; Mouri, T.; Tezuka, Y., A cyclic macromonomer designed for a novel polymer network architecture having both covalent and physical linkages. Macromolecules 2001,34 (18):6229-6234.
[96]Kubo, M.; Hibino, T.; Tamura, M.; Uno, T.; Itoh, T., Synthesis and copolymerization of cyclic macromonomer based on cyclic polystyrene:Gel formation via chain threading. Macromolecules 2002,35 (15):5816-5820.
[97]Kubo, M.; Kato, N.; Uno, T.; Itoh, T., Preparation of mechanically cross-linked polystyrenes. Macromolecules 2004,57 (8):2762-2765.
[98]Siemsen, P.; Livingston, R. C.; Diederich, F., Acetylenic coupling:A powerful tool in molecular construction. Angew. Chem. Int. Ed.2000,39 (15):2633-2657.
[99]Reppe, W., Athinylierung. Annalen Der Chemie-Justus Liebig 1955,596:1-224.
[100]Eglinton, G; Galbraith, A. R., Cyclic Diynes. Chemistry & Industry 1956, (28):737-738.
[101]Hay, A. S., Oxidative Coupling of Acetylenes. J. Org. Chem.1962,27 (9): 3320-3321.
[102]Chodkiewicz, W.; Cadiot, P., Nouvelle Synthese De Composes Polyacetyleniques Conjugues Symetriques Et Dissymetriques. Comptes Rendus Hebdomadaires Des Seances De L Academie Des Sciences 1955,241 (16): 1055-1057.
[103]Bohlmann, F.; Schonowsky, H.; Grau, G.; Inhoffen, E., Polyacetylenverbindungen.52. Uber Den Mechanismus Der Oxydativen Dimerisierung Von Acetylenverbindungen. Chem. Ber. Recl.1964,97(3):794-&.
[104]Fomina, L.; Vazquez, B.; Tkatchouk, E.; Fomine, S., The Glaser reaction mechanism. A DFT study. Tetrahedron 2002,58(33):6741-6747.
[105]Kijima, M.; Kinoshita, I.; Hiroki, K.; Shirakawa, H.; Yoshikawa, K.; Mishima, Y.; Sasaki, N., Optical properties of conjugated polymers having linear carbon moieties. Current Applied Physics 2002,2 (4):289-294.
[106]Marsden, J. A.; Miller, J. J.; Haley, M. M, Let the best ring win:Selective macrocycle formation through Pd-catalyzed or Cu-mediated alkyne homocoupling. Angew. Chem. Int. Ed. 2004,43 (13):1694-1697.
[107]Fischer, M.; Lieser, G.; Rapp, A.; Schnell, I.; Mamdouh, W.; De Feyter, S.; De Schryver, F. C.; Hoger, S., Shape-persistent macrocycles with intraannular polar groups:Synthesis, liquid crystallinity, and 2D organization. J. Am. Chem. Soc.2004, 126(1):214-222.
[108]Lee, K. S.; Wegner, G, Linear and Cyclic Alkanes (CnH2n+2, CnH2n) with n Greater-than 100-Synthesis and Evidence for Chain-Folding. Makromolekulare Chemie-Rapid Communications 1985,6 (3):203-208.
[109]Beckmann, W.; Doerjer, G.; Logemann, E.; Merkel, C.; Schill, G.; Zurcher, C., Improved Synthesis of Long-Chain 1-Alkynes and Terminal Alkadiynes. Synthesis-Stuttgart 1975, (7):423-425.
[110]Lee, K. S.; Wegner, G.; Hsu, S. L., Vibrational Spectroscopic Studies of Linear and Cyclic Alkanes CnH2n+2prime CnH2n with 24 Less-than-or-Equal-to 288-Chain Folding, Chain Packing and Conformations. Polymer 1987,28 (6):889-896.
[1]Binauld, S.; Hawker, C. J.; Fleury, E.; Drockenmuller, E., A Modular Approach to Functionalized and Expanded Crown Ether Based Macrocycles Using Click Chemistry. Angew. Chem. Int. Ed.2009,48 (36):6654-6658.
[2]Francis, R.; Taton, D.; Logan, J. L.; Masse, P.; Gnanou, Y.; Duran, R. S., Synthesis and surface properties of amphiphilic star-shaped and dendrimer-like copolymers based on polystyrene core and poly(ethylene oxide) corona. Macromolecules 2003,36 (22): 8253-8259.
[3]Wei, J.; Huang, J. L., Synthesis of an amphiphilic star triblock copolymer of polystyrene, poly(ethylene oxide), and polyisoprene using lysine as core molecule. Macromolecules 2005,38 (4):1107-1113.
[4]Gilman, H.; Haubein, A. H., The quantitative analysis of alkyllithium compounds. J. Am. Chem. Soc.1944,66:1515-1516.
[5]Ishizu, K.; Ichimura, A., Synthesis of cyclic diblock copolymers by interfacial condensation. Polymer 1998,39 (25):6555-6558.
[6]Taton, D.; Cloutet, E.; Gnanou, Y., Novel amphiphilic branched copolymers based on polystyrene and poly(ethylene oxide). Macromol. Chem. Phys.1998,199: 2501-2510.
[7]Semlyen, J. A., Cyclic Polymers. Elsevier:New York,1986.
[8]Gan, Y.; Dong, D.; Hogen-Esch, T. E., Effects of Lithium Bromide on the Glass Transition Temperatures of Linear and Macrocyclic Poly(2-vinylpyridine) and Polystyrene. Macromolecules 1995,28 (1):383-385.
[9]Tezuka, Y.; Mori, K.; Oike, H., Efficient synthesis of cyclic poly(oxyethylene) by electrostatic self-assembly and covalent fixation with telechelic precursor having cyclic ammonium salt groups. Macromolecules 2002,35 (14):5707-5711.
[10]Riquelurbet, L.; Schappacher, M.; Deffieux, A., A New Strategy for the Synthesis of Cyclic Polystyrenes-Principle and Application. Macromolecules 1994,27 (22): 6318-6324.
[1]He, T.; Zheng, G. H.; Pan, C. Y., Synthesis of cyclic polymers and block copolymers by monomer insertion into cyclic initiator by a radical mechanism. Macromolecules 2003,36 (16):5960-5966.
[2]Eugene, D. M.; Grayson, S. M., Efficient preparation of cyclic poly(methyl acrylate)-block-poly(styrene) by combination of atom transfer radical polymerization and click cyclization. Macromolecules 2008,41 (14):5082-5084.
[3]Adachi, K.; Honda, S.; Hayashi, S.; Tezuka, Y., ATRP-RCM Synthesis of Cyclic Diblock Copolymers. Macromolecules 2008,41 (21):7898-7903.
[4]Angot, S.; Taton, D.; Gnanou, Y, Amphiphilic Stars and Dendrimer-Like Architectures Based on Poly(Ethylene Oxide) and Polystyrene. Macromolecules 2000, 33 (15):5418-5426.
[5]Roovers, J.; Toporowski, P. M., Synthesis of High Molecular Weight Ring Polystyrenes. Macromolecules 1983,16 (6):843-849.
[6]Riquelurbet, L.; Schappacher, M.; Deffieux, A., A New Strategy for the Synthesis of Cyclic Polystyrenes-Principle and Application. Macromolecules 1994,27 (22): 6318-6324.
[7]Gan, Y.; Dong, D.; Hogen-Esch, T. E., Effects of Lithium Bromide on the Glass Transition Temperatures of Linear and Macrocyclic Poly(2-vinylpyridine) and Polystyrene. Macromolecules 1995,28 (1):383-385.
[8]Ma, J. J., Synthesis of Well-defined Macrocyclic Block-Copolymers Using Living Coupling Agent Method. Macromol Symp.1995,91:41-49.
[9]Lepoittevin, B.; Hemery, P., Synthesis of high-molecular-weight cyclic and multicyclic polystyrenes. Polym. Adv. Technol 2002,13 (10-12):771-776.
[10]Tezuka, Y.; Komiya, R., Metathesis polymer cyclization with telechelic poly(THF) having allyl groups. Macromolecules 2002,35 (23):8667-8669.
[11]Qiu, X. P.; Tanaka, F.; Winnik, F. M., Temperature-induced phase transition of well-defined cyclic poly(N-isopropylacrylamide)s in aqueous solution. Macromolecules 2007,40:7069-7071.
[12]Schappacher, M.; Deffieux, A., Controlled Synthesis of Bicyclic "Eight-Shaped" Poly(chloroethyl vinyl ether)s. Macromolecules 1995,28 (8):2629-2636.
[13]Shi, G. Y.; Pan, C. Y, Synthesis of Weil-Defined Figure-of-Eight-Shaped Polymers by a Combination of ATRP and Click Chemistry. Macromol.Rapid Commun.2008,29 (20):1672-1678.
[14]Shi, G. Y.; Yang, L. P.; Pan, C. Y, Synthesis and characterization of well-defined polystyrene and poly(epsilon-caprolactone) hetero eight-shaped copolymers. J. Polym. Set, Part A:Polym. Chem.2008,46 (19):6496-6508.
[15]Shi, G. Y.; Tang, X. Z.; Pan, C. Y., Tadpole-shaped amphiphilic copolymers prepared via RAFT polymerization and click reaction. J. Polym. Sci., Part A:Polym. Chem.2008,46 (7):2390-2401.