Self-Accelerating Click Reaction for Cyclic Polymer

As the most straightforward synthetic strategy for cyclic polymers in theory, the traditional homodifunctional bimolecular ring-closure methods showed limited success for preparing pure cyclic polymers in practice even after several decades of development. A breakthrough was achieved in this paper to develop a successful homodifunctional bimolecular ring-closure method using a self-accelerating double strain-promoted azide–alkyne click reaction as the intermolecular and subsequent intramolecular coupling reactions. Because of the self-accelerating property of coupling reaction, this novel approach eliminated the usage of equimolar quantities between telechelic polymers and small molecule linkers, which was the prerequisite of traditional homodifunctional bimolecular ring-closure methods for pure cyclic polymers. More importantly, this approach could use an excess amount of small linkers to increase the intermolecular coupling reaction rate, further resulting in a significantly enhanced preparation efficie...

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

[2]  Takuya Yamamoto,et al.  Cyclic polymers revealing topology effects upon self-assemblies, dynamics and responses. , 2015, Soft matter.

[3]  Takuya Yamamoto,et al.  Folding Construction of a Pentacyclic Quadruply fused Polymer Topology with Tailored kyklo-Telechelic Precursors. , 2015, Angewandte Chemie.

[4]  E. Tillman,et al.  Macrocyclic poly(methyl acrylate) and macrocyclic poly(methyl acrylate-block-styrene) synthesized by radical trap-assisted atom transfer radical coupling , 2015 .

[5]  E. Tillman,et al.  Synthesis of Cyclic Poly(methyl methacrylate) Directly from Dihalogenated Linear Precursors , 2015 .

[6]  Scott M. Grayson,et al.  The Synthesis of Cyclic Poly(ethylene imine) and Exact Linear Analogues: An Evaluation of Gene Delivery Comparing Polymer Architectures. , 2015, Journal of the American Chemical Society.

[7]  R. O’Reilly,et al.  Self-assembly of cyclic polymers , 2015 .

[8]  J. Pomposo,et al.  Zwitterionic Ring-Opening Copolymerization of Tetrahydrofuran and Glycidyl Phenyl Ether with B(C6F5)3 , 2015 .

[9]  G. Tew,et al.  Cyclic polymers as a building block for cyclic brush polymers and gels , 2014 .

[10]  Katsunori Tanaka,et al.  Development of bis-unsaturated ester aldehydes as amino-glue probes: sequential double azaelectrocyclization as a promising strategy for bioconjugation. , 2013, Organic & biomolecular chemistry.

[11]  C. Ladavière,et al.  Ring-opening polymerization with Zn(C6F5)2-based Lewis pairs: original and efficient approach to cyclic polyesters. , 2013, Journal of the American Chemical Society.

[12]  G. Tew,et al.  Metallo-supramolecular cyclic polymers. , 2013, Journal of the American Chemical Society.

[13]  S. Honda,et al.  Tuneable enhancement of the salt and thermal stability of polymeric micelles by cyclized amphiphiles , 2013, Nature Communications.

[14]  A. F. Voter,et al.  Synthesis of Macrocyclic Polymers Formed via Intramolecular Radical Trap-Assisted Atom Transfer Radical Coupling. , 2012, ACS macro letters.

[15]  Zhongfan Jia,et al.  Cyclic polymers: Methods and strategies , 2012 .

[16]  Takuya Yamamoto,et al.  A programmed polymer folding: click and clip construction of doubly fused tricyclic and triply fused tetracyclic polymer topologies. , 2011, Journal of the American Chemical Society.

[17]  B. Wang,et al.  Facile derivatization of azide ions using click chemistry for their sensitive detection with LC-MS. , 2011, Chemical Communications.

[18]  Takuya Yamamoto,et al.  Topological polymer chemistry: a cyclic approach toward novel polymer properties and functions , 2011 .

[19]  Yonggang Yang,et al.  Cyclic polymers with pendent carbazole units: enhanced fluorescence and redox behavior. , 2011, Angewandte Chemie.

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

[21]  Scott M. Grayson,et al.  Cyclic polyesters: synthetic approaches and potential applications , 2011 .

[22]  M. Hagiwara,et al.  Strain-promoted double-click reaction for chemical modification of azido-biomolecules. , 2010, Organic & biomolecular chemistry.

[23]  Qi Meng,et al.  Effective click construction of bridged- and spiro-multicyclic polymer topologies with tailored cyclic prepolymers (kyklo-telechelics). , 2010, Journal of the American Chemical Society.

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

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

[26]  J. Hedrick,et al.  Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts. , 2007, Angewandte Chemie.

[27]  Y. Tezuka,et al.  Construction of Polymeric δ-Graph: A Doubly Fused Tricyclic Topology , 2005 .

[28]  M. Ueda,et al.  Nonstoichiometric polycondensation I. synthesis of polythioether from dibromomethane and 4,4′-thiobisbenzenethiol , 2003 .

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

[30]  H. Oike,et al.  Topological polymer chemistry: systematic classification of nonlinear polymer topologies. , 2001, Journal of the American Chemical Society.

[31]  H. Oike,et al.  Designing Unusual Polymer Topologies by Electrostatic Self-Assembly and Covalent Fixation , 2000 .

[32]  T. Endo,et al.  Significance of Stoichiometric Imbalance in Step Polymerization via Reactive Intermediate , 1999 .

[33]  C. Booth,et al.  Preparation and characterization of cyclic poly(oxypropylene) , 1997 .

[34]  H. Kricheldorf,et al.  Polylactones. 35. Macrocyclic and Stereoselective Polymerization of .beta.-D,L-Butyrolactone with Cyclic Dibutyltin Initiators , 1995 .

[35]  C. Booth,et al.  Cyclisation of poly(ethylene glycol)s and related block copolymers , 1993 .

[36]  Zhongfan Jia,et al.  Synthesis of cyclic polymers via ring closure , 2013 .

[37]  K. Endo.  Synthesis and Properties of Cyclic Polymers , 2008 .

[38]  C. Booth,et al.  Preparation of large cyclic poly(oxyethylene)s , 1996 .