Synthesis of main chain sulfur-containing aliphatic polycarbonates by organocatalytic ring-opening polymerization of macrocyclic carbonates

The first application of organocatalysts is reported to achieve highly active and living ring-opening polymerization (ROP) of thioether-based macrocyclic carbonates for preparing well-defined main chain thioether functional APCs.

[1]  Yan Zhang,et al.  One-shot synthesis and solution properties of ROS/pH responsive methoxy poly(ethylene glycol)-b-polycarbonate , 2019, Polymer Chemistry.

[2]  Wei Tao,et al.  Synthesis of an Oxidation-Sensitive Polyphosphoester Bearing Thioether Group for Triggered Drug Release. , 2019, Biomacromolecules.

[3]  Yan-hong Liu,et al.  Enzymatic synthesis of selenium-containing amphiphilic aliphatic polycarbonate as an oxidation-responsive drug delivery vehicle , 2019, RSC advances.

[4]  F. Wurm,et al.  Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups. , 2018, Chemical Society reviews.

[5]  F. Du,et al.  ROS-responsive poly(ε-caprolactone) with pendent thioether and selenide motifs , 2018 .

[6]  M. Becker,et al.  pH-Responsive, Functionalizable Spyrocyclic Polycarbonate: A Versatile Platform for Biocompatible Nanoparticles. , 2018, Biomacromolecules.

[7]  Fusheng Liu,et al.  Preparation of biorenewable poly(γ-butyrolactone)-b-poly(L-lactide) diblock copolyesters via one-pot sequential metal-free ring-opening polymerization , 2018 .

[8]  F. Du,et al.  ROS-Responsive Chalcogen-Containing Polycarbonates for Photodynamic Therapy. , 2018, Biomacromolecules.

[9]  K. Wooley,et al.  A Vinyl Ether-Functional Polycarbonate as a Template for Multiple Postpolymerization Modifications. , 2018, Macromolecules.

[10]  M. Lang,et al.  Well-Defined Selenium-Containing Aliphatic Polycarbonates via Lipase-Catalyzed Ring-Opening Polymerization of Selenic Macrocyclic Carbonate Monomer. , 2018, ACS macro letters.

[11]  Yan Zhang,et al.  Facile synthesis of ROS-responsive biodegradable main chain poly(carbonate-thioether) copolymers , 2018 .

[12]  Yan Zhang,et al.  A Versatile Strategy to Main Chain Sulfur/Selenium-Functionalized Polycarbonates by Macro-Ring Closure of Diols and Subsequent Ring-Opening Polymerization. , 2018, Chemistry.

[13]  Yu Dai,et al.  Recent development of functional aliphatic polycarbonates for the construction of amphiphilic polymers , 2017 .

[14]  Xin Wang,et al.  Squaramide and amine binary H-bond organocatalysis in polymerizations of cyclic carbonates, lactones, and lactides , 2017 .

[15]  Zhibo Li,et al.  Selective Ring-Opening Polymerization of Non-Strained γ-Butyrolactone Catalyzed by A Cyclic Trimeric Phosphazene Base. , 2017, Angewandte Chemie.

[16]  A. Whittaker,et al.  Synthesis of aliphatic polycarbonates with a tuneable thermal response , 2017 .

[17]  K. Wooley,et al.  Functional Polycarbonate of a d-Glucal-Derived Bicyclic Carbonate via Organocatalytic Ring-Opening Polymerization. , 2017, ACS macro letters.

[18]  Mingyuan Gao,et al.  Nanopolymersomes with an Ultrahigh Iodine Content for High‐Performance X‐Ray Computed Tomography Imaging In Vivo , 2017, Advanced materials.

[19]  Nathaniel H. Park,et al.  Convergent Approach to Boronic Acid Functionalized Polycarbonates: Accessing New Dynamic Material Platforms. , 2017, ACS macro letters.

[20]  N. Hadjichristidis,et al.  Ring-opening polymerization of ω-pentadecalactone catalyzed by phosphazene superbases , 2017 .

[21]  Yi Yan Yang,et al.  Amphiphilic and Hydrophilic Block Copolymers from Aliphatic N-Substituted 8-Membered Cyclic Carbonates: A Versatile Macromolecular Platform for Biomedical Applications. , 2017, Biomacromolecules.

[22]  G. Tew,et al.  Thiol-Ene Step-Growth as a Versatile Route to Functional Polymers. , 2016, Angewandte Chemie.

[23]  Robert J. Ono,et al.  Expanding the Cationic Polycarbonate Platform: Attachment of Sulfonium Moieties by Postpolymerization Ring Opening of Epoxides. , 2016, ACS macro letters.

[24]  H. Frey,et al.  Oxidation-Responsive and "Clickable" Poly(ethylene glycol) via Copolymerization of 2-(Methylthio)ethyl Glycidyl Ether. , 2016, Journal of the American Chemical Society.

[25]  Xiao‐Qi Yu,et al.  Lipase-catalyzed synthesis of oxidation-responsive poly(ethylene glycol)-b-poly(β-thioether ester) amphiphilic block copolymers , 2016 .

[26]  Hans W. Horn,et al.  A Simple and Facile Approach to Aliphatic N-Substituted Functional Eight-Membered Cyclic Carbonates and Their Organocatalytic Polymerization. , 2015, Journal of the American Chemical Society.

[27]  Xinling Wang,et al.  Synthesis and properties of tunable thermoresponsive aliphatic polycarbonate copolymers with oligo ethylene glycol containing thioether and/or sulphone groups , 2015 .

[28]  P. Dubois,et al.  Poly(ω-pentadecalactone)-b-poly(l-lactide) Block Copolymers via Organic-Catalyzed Ring Opening Polymerization and Potential Applications. , 2015, ACS macro letters.

[29]  H. Sardón,et al.  Experimental and computational studies of ring‐opening polymerization of ethylene brassylate macrolactone and copolymerization with ε‐caprolactone and TBD‐guanidine organic catalyst , 2015 .

[30]  Chunsheng Xiao,et al.  Synthesis of thermal and oxidation dual responsive polymers for reactive oxygen species (ROS)-triggered drug release , 2015 .

[31]  P. Datta,et al.  Cooperative Hydrogen-Bond Pairing in Organocatalytic Ring-Opening Polymerization , 2014, Macromolecules.

[32]  H. Sardón,et al.  Organocatalyzed Synthesis of Aliphatic Polyesters from Ethylene Brassylate: A Cheap and Renewable Macrolactone. , 2014, ACS macro letters.

[33]  L. Mespouille,et al.  Implementation of metal-free ring-opening polymerization in the preparation of aliphatic polycarbonate materials , 2014 .

[34]  B. Bibal,et al.  Hydrogen-bonding organocatalysts for ring-opening polymerization , 2014 .

[35]  Zhibo Li,et al.  Oxidation-responsive OEGylated poly-L-cysteine and solution properties studies. , 2014, Biomacromolecules.

[36]  P. Hodge.  Entropically driven ring-opening polymerization of strainless organic macrocycles. , 2014, Chemical reviews.

[37]  D. Mecerreyes,et al.  Acid catalyzed polymerization of macrolactones in bulk and aqueous miniemulsion: Ring opening vs. condensation , 2013 .

[38]  K. Wooley,et al.  Polycarbonates derived from glucose via an organocatalytic approach. , 2013, Journal of the American Chemical Society.

[39]  L. Mespouille,et al.  Synthesis and post-polymerisation modifications of aliphatic poly(carbonate)s prepared by ring-opening polymerisation. , 2013, Chemical Society reviews.

[40]  A. Dove,et al.  Organic Catalysis for Ring-Opening Polymerization. , 2012, ACS macro letters.

[41]  Mpf Mark Pepels,et al.  ω-Pentandecalactone Polymerization and ω-Pentadecalactone/ε-Caprolactone Copolymerization Reactions Using Organic Catalysts , 2012 .

[42]  Xian‐Zheng Zhang,et al.  Construction of functional aliphatic polycarbonates for biomedical applications , 2012 .

[43]  J. Feijen,et al.  Unprecedented Access to Functional Biodegradable Polymers and Coatings , 2011 .

[44]  J. Hedrick,et al.  A simple and efficient synthesis of functionalized cyclic carbonate monomers using a versatile pentafluorophenyl ester intermediate. , 2010, Journal of the American Chemical Society.

[45]  R. Zhuo,et al.  Highly efficient enzymatic catalysis for cyclocarbonate polymerization , 2010 .

[46]  Xiao-hua Luo,et al.  Biocatalytic fabrication of fast-degradable, water-soluble polycarbonate functionalized with tertiary amine groups in backbone. , 2010, Biomacromolecules.

[47]  Yi Yan Yang,et al.  Delivery of anticancer drugs using polymeric micelles stabilized by hydrogen-bonding urea groups. , 2010, Macromolecular rapid communications.

[48]  Alshakim Nelson,et al.  Synthesis of a family of amphiphilic glycopolymers via controlled ring-opening polymerization of functionalized cyclic carbonates and their application in drug delivery. , 2010, Biomaterials.

[49]  K. Toshima,et al.  High-molecular-weight polycarbonates synthesized by enzymatic ROP of a cyclic carbonate as a green process. , 2009, Macromolecular bioscience.

[50]  P. Parzuchowski,et al.  Synthesis of New Glycerol-Based Hyperbranched Polycarbonates , 2008 .

[51]  J. Hedrick,et al.  Tagging alcohols with cyclic carbonate: a versatile equivalent of (meth)acrylate for ring-opening polymerization. , 2008, Chemical communications.

[52]  J. Hedrick,et al.  Organocatalytic ring-opening polymerization. , 2007, Chemical reviews.

[53]  Robert M. Waymouth,et al.  Guanidine and Amidine Organocatalysts for Ring-Opening Polymerization of Cyclic Esters , 2006 .

[54]  David A. Long,et al.  Exploration, Optimization, and Application of Supramolecular Thiourea−Amine Catalysts for the Synthesis of Lactide (Co)polymers , 2006 .

[55]  J. Hedrick,et al.  New Paradigms for Organic Catalysts: The First Organocatalytic Living Polymerization. , 2001, Angewandte Chemie.

[56]  T. Endo,et al.  Synthesis and anionic ring-opening polymerization behavior of amino acid-derived cyclic carbonates , 2001 .

[57]  G. Rokicki.  Aliphatic cyclic carbonates and spiroorthocarbonates as monomers , 2000 .

[58]  H. Kricheldorf,et al.  Polymers of carbonic acid, 21. Ring‐opening polymerization of cyclobis(diethylene glycol carbonate) by means of BuSnCl3, SnOct2 or Bu2SnO as catalysts , 1997 .

[59]  R. Gross,et al.  Synthesis, characterization, and epoxidation of an aliphatic polycarbonate from 2,2-(2-pentene-1,5-diyl)trimethylene carbonate (cHTC) ring-opening polymerization , 1997 .

[60]  H. Höcker,et al.  Synthesis and polymerization of bis(hexamethylene carbonate) and bis(2,2,3,3,4,4,5,5-octafluorohexamethylene carbonate) , 1996 .

[61]  Frank A. Leibfarth,et al.  Organocatalytic ring opening polymerization of trimethylene carbonate. , 2007, Biomacromolecules.