The synthesis of cyclic polymers by olefin metathesis: Achievements and challenges

Cyclic polymers have drawn considerable interest for their peculiar physical properties in comparison to linear polymers, despite their equivalent compositions. Synthetically, cyclic polymers can be accessed through either macrocyclic ring‐closure or by ring‐expansion polymerization, but the main challenge with either method is the production of highly pure cyclic polymer samples. This highlight describes advances in the area of cyclic polymer synthesis, with a particular focus on ring‐expansion metathesis polymerization. Methods for characterizing cyclic polymers and assessing their purity are also discussed in order to emphasize the need for additional robust and reliable methods for synthesizing and studying topologically complex macromolecules. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 228–242

[1]  E. Chen,et al.  A synthetic polymer system with repeatable chemical recyclability , 2018, Science.

[2]  R. Waymouth,et al.  Recent progress on the synthesis of cyclic polymers via ring‐expansion strategies , 2017 .

[3]  M. Ouchi,et al.  Ring-expansion cationic polymerization of vinyl ethers , 2017 .

[4]  M. Ouchi,et al.  A Study on Physical Properties of Cyclic Poly(vinyl ether)s Synthesized via Ring-Expansion Cationic Polymerization , 2017 .

[5]  M. Ouchi,et al.  A convergent approach to ring polymers with narrow molecular weight distributions through post dilution in ring expansion cationic polymerization , 2016 .

[6]  K. Abboud,et al.  Cyclic polymers from alkynes. , 2016, Nature chemistry.

[7]  W. Binder,et al.  Ring expansion-controlled radical polymerization: Synthesis of cyclic polymers and ring component quantification based on SEC–MALS analysis , 2016 .

[8]  Hua Wei,et al.  Recent Progress on Cyclic Polymers: Synthesis, Bioproperties, and Biomedical Applications , 2016 .

[9]  B. Sumerlin,et al.  Introducing "Ynene" Metathesis: Ring-Expansion Metathesis Polymerization Leads to Highly Cis and Syndiotactic Cyclic Polymers of Norbornene. , 2016, Journal of the American Chemical Society.

[10]  F. Fischer,et al.  Initiator Control of Conjugated Polymer Topology in Ring-Opening Alkyne Metathesis Polymerization. , 2016, Journal of the American Chemical Society.

[11]  K. Abboud,et al.  Highly Tactic Cyclic Polynorbornene: Stereoselective Ring Expansion Metathesis Polymerization of Norbornene Catalyzed by a New Tethered Tungsten-Alkylidene Catalyst. , 2016, Journal of the American Chemical Society.

[12]  S. Pun,et al.  ATRP Synthesis of Sunflower Polymers using Cyclic Multimacroinitiators. , 2015, ACS macro letters.

[13]  N. Hosmane,et al.  Advanced Developments in Cyclic Polymers: Synthesis, Applications, and Perspectives , 2015, ChemistryOpen.

[14]  Zhongfan Jia,et al.  Complex polymer topologies built from tailored multifunctional cyclic polymers , 2014 .

[15]  R. Advíncula,et al.  Cyclic polymers and catenanes by atom transfer radical polymerization (ATRP) , 2014 .

[16]  W. Radke.  Polymer separations by liquid interaction chromatography: principles - prospects - limitations. , 2014, Journal of chromatography. A.

[17]  R. Waymouth,et al.  Zwitterionic ring-opening polymerization for the synthesis of high molecular weight cyclic polymers. , 2013, Accounts of chemical research.

[18]  M. Ouchi,et al.  Ring-Expansion Living Cationic Polymerization via Reversible Activation of a Hemiacetal Ester Bond. , 2013, ACS macro letters.

[19]  Y. Tezuka.  Topological Polymer Chemistry:Progress of Cyclic Polymers in Syntheses, Properties and Functions , 2012 .

[20]  Yi Shi,et al.  Synthesis of mikto-topology star polymer containing one cyclic arm , 2012 .

[21]  Junlian Huang,et al.  Synthesis of Amphiphilic Heteroeight-Shaped Polymer Cyclic-[Poly(ethylene oxide)-b-polystyrene]2 via “Click” Chemistry , 2012 .

[22]  G. Tew,et al.  Cyclic Brush Polymers by Combining Ring-Expansion Metathesis Polymerization and the "Grafting from" Technique. , 2012, ACS macro letters.

[23]  Eun Ji Shin,et al.  Zwitterionic copolymerization: synthesis of cyclic gradient copolymers. , 2011, Angewandte Chemie.

[24]  R. Grubbs,et al.  Synthesis and direct imaging of ultrahigh molecular weight cyclic brush polymers. , 2011, Angewandte Chemie.

[25]  Kecheng Zhang,et al.  Universal cyclic polymer templates. , 2011, Journal of the American Chemical Society.

[26]  Sekyung Lee,et al.  Temperature gradient interaction chromatography of polymers: A molecular statistical model. , 2010, Journal of separation science.

[27]  H. Kricheldorf.  Cyclic polymers: Synthetic strategies and physical properties , 2010 .

[28]  F. Szoka,et al.  The influence of polymer topology on pharmacokinetics: differences between cyclic and linear PEGylated poly(acrylic acid) comb polymers. , 2009, Journal of controlled release : official journal of the Controlled Release Society.

[29]  Scott M. Grayson,et al.  Synthetic approaches for the preparation of cyclic polymers. , 2009, Chemical Society reviews.

[30]  Seonyoung Ahn,et al.  Martin's rule for high-performance liquid chromatography retention of polystyrene oligomers. , 2009, Analytical chemistry.

[31]  R. Grubbs,et al.  A direct route to cyclic organic nanostructures via ring-expansion metathesis polymerization of a dendronized macromonomer. , 2009, Journal of the American Chemical Society.

[32]  R. Grubbs,et al.  Ring-expansion metathesis polymerization: catalyst-dependent polymerization profiles. , 2009, Journal of the American Chemical Society.

[33]  D Richter,et al.  Unexpected power-law stress relaxation of entangled ring polymers. , 2008, Nature materials.

[34]  R. Grubbs,et al.  Cyclic ruthenium-alkylidene catalysts for ring-expansion metathesis polymerization. , 2008, Journal of the American Chemical Society.

[35]  F. Tanaka,et al.  Temperature-Induced Phase Transition of Well-Defined Cyclic Poly(N-isopropylacrylamide)s in Aqueous Solution , 2007 .

[36]  Scott M. Grayson,et al.  An efficient route to well-defined macrocyclic polymers via "click" cyclization. , 2006, Journal of the American Chemical Society.

[37]  Y. Matsushita,et al.  Preparation and Characterization of Cyclic Polystyrenes , 2005 .

[38]  T. Chang.  Polymer characterization by interaction chromatography , 2005 .

[39]  V. Arrighi,et al.  On the difference in scattering behavior of cyclic and linear polymers in bulk. , 2005, The Journal of chemical physics.

[40]  Soojin Park,et al.  Characterization of a 4-miktoarm star copolymer of the (PS-b-PI)3 PS type by temperature gradient interaction chromatography , 2003 .

[41]  R. Grubbs,et al.  Synthesis of cyclic polybutadiene via ring-opening metathesis polymerization: the importance of removing trace linear contaminants. , 2003, Journal of the American Chemical Society.

[42]  R. Grubbs,et al.  An "Endless" Route to Cyclic Polymers , 2002, Science.

[43]  M. Pitsikalis,et al.  Polymers with complex architecture by living anionic polymerization. , 2001, Chemical reviews.

[44]  Robert H. Grubbs,et al.  A Versatile Precursor for the Synthesis of New Ruthenium Olefin Metathesis Catalysts , 2001 .

[45]  F. Stelzer,et al.  Comparative investigation of ruthenium-based metathesis catalysts bearing N-heterocyclic carbene (NHC) ligands. , 2001, Chemistry.

[46]  T. Chang,et al.  Liquid chromatography at the critical condition for polyisoprene using a single solvent. , 2001, Analytical chemistry.

[47]  P. Hémery,et al.  New Route to Synthesis of Cyclic Polystyrenes Using Controlled Free Radical Polymerization , 2001 .

[48]  Hyunjung Lee,et al.  Fractionation of Cyclic Polystyrene from Linear Precursor by HPLC at the Chromatographic Critical Condition , 2000 .

[49]  A. Hoveyda,et al.  Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts , 2000 .

[50]  R. Grubbs,et al.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. , 1999, Organic letters.

[51]  H. Ji,et al.  Characterization of Poly(ethylene oxide)-block-poly(l-lactide) by HPLC and MALDI-TOF Mass Spectrometry , 1999 .

[52]  J. P. Harrity,et al.  A Recyclable Ru-Based Metathesis Catalyst , 1999 .

[53]  S. Olesik,et al.  Improvements in polymer characterization by size-exclusion chromatography and liquid chromatography at the critical condition by using enhanced-fluidity liquid mobile phases with packed capillary columns. , 1998, Analytical chemistry.

[54]  K. Hatada,et al.  Separation of Poly(methyl methacrylate)s According to Their Tacticity II. Chromatographic Investigations of Poly(methyl methacrylate)s with Different Tacticity at the Critical Adsorption Point , 1997 .

[55]  Joseph W. Ziller,et al.  A Series of Well‐Defined Metathesis Catalysts–Synthesis of [RuCl2(CHR′)(PR3)2] and Its Reactions , 1995 .

[56]  S. Nguyen,et al.  Ring-opening metathesis polymerization (ROMP) of norbornene by a Group VIII carbene complex in protic media , 1992 .

[57]  M. Sawamoto,et al.  Living cationic polymerization of isobutyl vinyl ether by RCOOH/Lewis acid initiating systems: effects of carboxylate ions and Lewis acid activators , 1991 .

[58]  G. Bazan,et al.  Synthesis of molybdenum imido alkylidene complexes and some reactions involving acyclic olefins , 1990 .

[59]  M. Sawamoto,et al.  Design and initiators of living cationic polymerization of vinyl monomers , 1990 .

[60]  A. Gorshkov,et al.  Applications of the critical phenomena concept in liquid chromatography for functionally type separation of macromolecules , 1985 .

[61]  J. A. Semlyen.  Cyclic polymers , 1981 .

[62]  Jia Huang,et al.  Coil properties of ring‐shaped polymer chains. Theoretical calculation and experimental determination of [η]ring/[η]open , 1980 .

[63]  H. Höcker,et al.  Synthesis and Investigation of Macrocyclic Polystyrene , 1980 .

[64]  R. Schrock,et al.  Preparation and characterization of active niobium, tantalum and tungsten metathesis catalysts , 1980 .

[65]  Homer Jacobson,et al.  Intramolecular Reaction in Polycondensations. I. The Theory of Linear Systems , 1950 .

[66]  E. Chen,et al.  Completely recyclable biopolymers with linear and cyclic topologies via ring-opening polymerization of γ-butyrolactone. , 2016, Nature chemistry.

[67]  R. Grubbs,et al.  The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story. , 2001, Accounts of chemical research.

[68]  C. McEwen,et al.  Instrumental effects in the analysis of polymers of wide polydispersity by MALDI mass spectrometry , 1997 .

[69]  Y. Gallot,et al.  Chromatographic investigations of macromolecules in the critical range of liquid chromatography: 4. Analysis of poly(styrene-b-methyl methacrylate) , 1993 .

[70]  P. Rempp,et al.  Synthesis of ring-shaped macromolecules , 1980 .

[71]  T. Higashimura,et al.  Possible Formation of Living Polymers of p-Methoxystyrene by Iodine , 1977 .