Organometallic-mediated radical (co)polymerization of γ‑methylene-γ-butyrolactone: access to pH-responsive poly(vinyl alcohol) derivatives

Wang, Zhuoqun; Poli, Rinaldo; Detrembleur, Christophe; Debuigne, Antoine

doi:10.1021/acs.macromol.9b01838

Article (Scientific journals)

Organometallic-mediated radical (co)polymerization of γ‑methylene-γ-butyrolactone: access to pH-responsive poly(vinyl alcohol) derivatives

Wang, Zhuoqun; Poli, Rinaldo; Detrembleur, Christophe et al.

2019 • In Macromolecules, 52 (22), p. 8976-8988

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/241308

DOI
10.1021/acs.macromol.9b01838

Files (2)Send to Details Statistics Bibliography Similar publications

Files

Full Text

Wang Z 2019 Macromolecules 52, 8976.pdf

Publisher postprint (2.26 MB)

Request a copy

Annexes

Wang Z 2019 Macromolecules 52, 8976 Supp Info.pdf

Publisher postprint (2.21 MB)

Supporting Informations

Request a copy

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Keywords :

radical polymerization; cobalt-mediated radical polymerization (CMRP); methylene lactone; vinyl acetate

Abstract :

[en] Conjugated vinyl lactones commonly serve as precursors of polymers with pendant cyclic esters, which can undergo several chemical modifications. They have notably been copolymerized with “more activated monomers” like (meth)acrylates. By contrast, the radical polymerization of nonconjugated methylene lactone analogues has been disregarded as well as their copolymerization with “less-activated monomers” such as acyclic vinyl esters. The present work explores the conventional radical polymerization and the reversible deactivation radical polymerization of γ-methylene-γ-butyrolactone (γMγBL) and its copolymerization with vinyl acetate (VAc). Statistical P(γMγBL-co-VAc) copolymers with predictable molar mass, low dispersity, and precise compositions were notably achieved by organometallic-mediated radical polymerization based on cobalt complexes via both reversible termination, also referred to as reversible chain deactivation, and degenerative chain-transfer pathways. Upon hydrolysis, these γMγBL-containing (co)polymers release one alcohol moiety and one carboxylic group per repeating unit, leading to unprecedented carboxylic acid-functionalized poly(vinyl alcohol) derivatives. A preliminary study emphasizes the pH responsiveness of the latter in water.

Research Center/Unit :

Center for Education and Research on Macromolecules (CERM)
Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit

Disciplines :

Materials science & engineering
Chemistry

Author, co-author :

Wang, Zhuoqun ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium

Poli, Rinaldo; University of Toulouse, CNRS, Laboratoire de Chimie de Coordination, France > Institut Universitaire de France, Paris, France

Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium

Debuigne, Antoine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium

Language :

English

Title :

Organometallic-mediated radical (co)polymerization of γ‑methylene-γ-butyrolactone: access to pH-responsive poly(vinyl alcohol) derivatives

Publication date :

26 November 2019

Journal title :

Macromolecules

ISSN :

0024-9297

eISSN :

1520-5835

Publisher :

American Chemical Society (ACS), United States - District of Columbia

Volume :

Issue :

Pages :

8976-8988

Peer reviewed :

Peer Reviewed verified by ORBi

Name of the research project :

The Excellence of Science (EOS) program; The NECOPOL project

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique
FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen

Available on ORBi :

since 14 November 2019

Statistics

Number of views

171 (18 by ULiège)

Number of downloads

8 (3 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

Gowda, R. R.; Chen, E. Y.-X. Sustainable Polymers from Biomass-Derived α-Methylene-γ-Butyrolactones. Encyclopedia of Polymer Science and Technology, 4 th ed.; Wiley, 2014; Vol. 8, pp 235-271.
Gowda, R. R.; Chen, E. Y.-X. Synthesis of β-methyl-α-methylene-γ-butyrolactone from biorenewable itaconic acid. Org. Chem. Front. 2014, 1, 230-234, 10.1039/c3qo00089c
Manzer, L. E. Catalytic Synthesis of α-Methylene-γ-Valerolactone »: a Biomass-Derived Acrylic Monomer. Appl. Catal., A 2004, 272, 249-256, 10.1016/j.apcata.2004.05.048
Tang, X.; Hong, M.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y.-X. The Quest for Converting Biorenewable Bifunctional α-Methylene-γ-butyrolactone into Degradable and Recyclable Polyester: Controlling Vinyl-Addition/Ring-Opening/Cross-Linking Pathways. J. Am. Chem. Soc. 2016, 138, 14326-14337, 10.1021/jacs.6b07974
Hong, M.; Chen, E. Y.-X. Coordination Ring-Opening Copolymerization of Naturally Renewable α-Methylene-γ-butyrolactone into Unsaturated Polyesters. Macromolecules 2014, 47, 3614-3624, 10.1021/ma5007717
Danko, M.; Basko, M.; Ďurkáčová, S.; Duda, A.; Mosnáček, J. Functional Polyesters with Pendant Double Bonds Prepared by Coordination-Insertion and Cationic Ring-Opening Copolymerizations of ϵ-Caprolactone with Renewable Tulipalin A. Macromolecules 2018, 51, 3582-3596, 10.1021/acs.macromol.8b00456
Miyake, G. M.; Zhang, Y.; Chen, E. Y.-X. Living Polymerization of Naturally Renewable Butyrolactone-Based Vinylidene Monomers by Ambiphilic Silicon Propagators. Macromolecules 2010, 43, 4902-4908, 10.1021/ma100615t
Hu, L.; He, J.; Zhang, Y.; Chen, E. Y.-X. Living Group Transfer Polymerization of Renewable α-Methylene-γ-butyrolactones Using Al(C6F5)3 Catalyst. Macromolecules 2018, 51, 1296-1307, 10.1021/acs.macromol.7b02647
Hu, Y.; Gustafson, L. O.; Zhu, H.; Chen, E. Y.-X. Anionic Polymerization of MMA and Renewable Methylene Butyrolactones by Resorbable Potassium Salts. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2008-2017, 10.1002/pola.24628
Zhang, Y.; Miyake, G. M.; Chen, E. Y.-X. Alane-Based Classical and Frustrated Lewis Pairs in Polymer Synthesis: Rapid Polymerization of MMA and Naturally Renewable Methylene Butyrolactones into High-Molecular-Weight Polymers. Angew. Chem., Int. Ed. 2010, 49, 10158-10162, 10.1002/anie.201005534
Zhang, Y.; Miyake, G. M.; John, M. G.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y.-X. Lewis Pair Polymerization by Classical and Frustrated Lewis Pairs: Acid, Base and Monomer Scope and Polymerization Mechanism. Dalton Trans. 2012, 41, 9119, 10.1039/c2dt30427a
Chen, J.; Chen, E. Reactivity of Amine/E(C6F5)3 (E = B, Al) Lewis Pairs toward Linear and Cyclic Acrylic Monomers: Hydrogenation vs. Polymerization. Molecules 2015, 20, 9575-9590, 10.3390/molecules20069575
Zhang, Y.; Schmitt, M.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y. Organocatalytic Conjugate-Addition Polymerization of Linear and Cyclic Acrylic Monomers by N-Heterocyclic Carbenes: Mechanisms of Chain Initiation, Propagation, and Termination. J. Am. Chem. Soc. 2013, 135, 17925-17942, 10.1021/ja4088677
He, J.; Zhang, Y.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y.-X. Chain Propagation and Termination Mechanisms for Polymerization of Conjugated Polar Alkenes by [Al]-Based Frustrated Lewis Pairs. Macromolecules 2014, 47, 7765-7774, 10.1021/ma5019389
Chen, X.; Caporaso, L.; Cavallo, L.; Chen, E. Y.-X. Stereoselectivity in Metallocene-Catalyzed Coordination Polymerization of Renewable Methylene Butyrolactones: From Stereo-random to Stereo-perfect Polymers. J. Am. Chem. Soc. 2012, 134, 7278-7281, 10.1021/ja301811s
Miyake, G. M.; Newton, S. E.; Mariott, W. R.; Chen, E. Y.-X. Coordination Polymerization of Renewable Butyrolactone-Based Vinyl Monomers by Lanthanide and Early Metal Catalysts. Dalton Trans. 2010, 39, 6710-6718, 10.1039/c001909g
Hu, Y.; Wang, X.; Chen, Y.; Caporaso, L.; Cavallo, L.; Chen, E. Y.-X. Rare-Earth Half-Sandwich Dialkyl and Homoleptic Trialkyl Complexes for Rapid and Stereoselective Polymerization of a Conjugated Polar Olefin. Organometallics 2013, 32, 1459-1465, 10.1021/om301128g
Hu, Y.; Xu, X.; Zhang, Y.; Chen, Y.; Chen, E. Y.-X. Polymerization of Naturally Renewable Methylene Butyrolactones by Half-Sandwich Indenyl Rare Earth Metal Dialkyls with Exceptional Activity. Macromolecules 2010, 43, 9328-9336, 10.1021/ma101901y
Akkapeddi, M. K. Poly(α-methylene-γ-butyrolactone)Synthesis, Configurational Structure, and Properties. Macromolecules 1979, 12, 546-551, 10.1021/ma60070a002
Vobecka, Z.; Wei, C.; Tauer, K.; Esposito, D. Poly(α-methylene-γ-valerolactone) 1. Sustainable monomer synthesis and radical polymerization studies. Polymer 2015, 74, 262-271, 10.1016/j.polymer.2015.04.074
Pittman, C. U.; Lee, H. Radical-Initiated Polymerization of β-Methyl-α-Methylene-γ-Butyrolactone. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1759-1777, 10.1002/pola.10719
Akkapeddi, M. K. The free radical copolymerization characteristics of α-methylene γ-butyrolactone. Polymer 1979, 20, 1215-1216, 10.1016/0032-3861(79)90145-9
Yoon, K.; Jung, D.; Lee, S.; Lee, S.; Choi, S.; Woo, S.; Moon, J. Novel 193nm Photoresist Based on Olefin-Containing Lactones. Proceedings of the SPIE, 2001; Vol. 4345, pp 688-694.
Cockburn, R. A.; Siegmann, R.; Payne, K. A.; Beuermann, S.; Mckenna, T. F. L.; Hutchinson, R. A. Free Radical Copolymerization Kinetics of γ-Methyl-α-methylene-γ-butyrolactone (MeMBL). Biomacromolecules 2011, 12, 2319-2326, 10.1021/bm200400s
Miyake, G. M.; Zhang, Y.; Chen, E. Y.-X. Polymerizability of Exo-methylene-lactide toward vinyl addition and ring opening. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1523-1532, 10.1002/pola.27629
Brandenburg, C. J. Graft Copolymers of Methylene Lactones and Process for Emulsion Polymerization of Methylene Lactones. U.S. Patent 6,841,627 (B2), 2005.
Kollár, J.; Mrlík, M.; Moravčíková, D.; Kroneková, Z.; Liptaj, T.; Lacík, I.; Mosnáček, J. Tulips: A Renewable Source of Monomer for Superabsorbent Hydrogels. Macromolecules 2016, 49, 4047-4056, 10.1021/acs.macromol.6b00467
Ramram, M. B.; Chen, D.; Ma, Y.; Wang, L.; Yang, W. Stabilizer-free precipitation copolymerization of renewable bio-based α-methylene-γ-butyrolactone and styrene. J. Macromol. Sci., Part A: Pure Appl.Chem. 2016, 53, 484-491, 10.1080/10601325.2016.1189281
Moreno, M.; Goikoetxea, M.; de la Cal, J. C.; Barandiara, M. J. From Fatty Acid and Lactone Biobased Monomers Toward Fully Renewable Polymer Latexes. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 3543-3549, 10.1002/pola.27422
Mosnáček, J.; Matyjaszewski, K. Atom Transfer Radical Polymerization of Tulipalin A: A Naturally Renewable Monomer. Macromolecules 2008, 41, 5509-5511, 10.1021/ma8010813
Mosnáček, J.; Yoon, J. A.; Juhari, A.; Koynov, K.; Matyjaszewski, K. Synthesis, Morphology and Mechanical Properties of Linear Triblock Copolymers Based on Poly(α-Methylene-γ-Butyrolactone). Polymer 2009, 50, 2087-2094, 10.1016/j.polymer.2009.02.037
Juhari, A.; Mosnáček, J.; Yoon, J. A.; Nese, A.; Koynov, K.; Kowalewski, T.; Matyjaszewski, K. Star-like poly (n-butyl acrylate)-b-poly (α-methylene-γ-butyrolactone) block copolymers for high temperature thermoplastic elastomers applications. Polymer 2010, 51, 4806-4813, 10.1016/j.polymer.2010.08.017
Ding, K.; John, A.; Shin, J.; Lee, Y.; Quinn, T.; Tolman, W. B.; Hillmyer, M. A. High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers. Biomacromolecules 2015, 16, 2537-2539, 10.1021/acs.biomac.5b00754
Higaki, Y.; Okazaki, R.; Takahara, A. Semirigid Biobased Polymer Brush: Poly(α-methylene-γ-butyrolactone) Brushes. ACS Macro Lett. 2012, 1, 1124-1127, 10.1021/mz3002148
Trotta, J. T.; Jin, M.; Stawiasz, K. J.; Michaudel, Q.; Chen, W.-L.; Fors, B. P. Synthesis of Methylene Butyrolactone Polymers from Itaconic Acid. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2730-2737, 10.1002/pola.28654
Qi, G.; Nolan, M.; Schork, F. J.; Jones, C. W. Emulsion and controlled miniemulsion polymerization of the renewable monomer γ-methyl-α-methylene-γ-butyrolactone. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 5929-5944, 10.1002/pola.22909
Xu, S.; Huang, J.; Xu, S.; Luo, Y. RAFT ab initio emulsion copolymerization of γ-methyl-α-methylene-γ-butyrolactone and styrene. Polymer 2013, 54, 1779-1785, 10.1016/j.polymer.2013.02.007
Debuigne, A.; Jérôme, C.; Detrembleur, C. Organometallic-mediated radical polymerization of "less activated monomers": Fundamentals, challenges and opportunities. Polymer 2017, 115, 285-307, 10.1016/j.polymer.2017.01.008
Poli, R. New phenomena in organometallic-mediated radical polymerization (OMRP) and perspectives for control of less active monomers. Chem.-Eur. J. 2015, 21, 6988-7001, 10.1002/chem.201500015
Hurtgen, M.; Detrembleur, C.; Jerome, C.; Debuigne, A. Insight into Organometallic-Mediated Radical Polymerization. Polym. Rev. 2011, 51, 188-213, 10.1080/15583724.2011.566401
Demarteau, J.; Debuigne, A.; Detrembleur, C. Organocobalt Complexes as Sources of Carbon-Centered Radicals for Organic and Polymer Chemistries. Chem. Rev. 2019, 119, 6906-6955, 10.1021/acs.chemrev.8b00715
Debuigne, A.; Caille, J.-R.; Jérôme, R. Highly efficient cobalt-mediated radical polymerization of vinyl acetate. Angew. Chem., Int. Ed. 2005, 44, 1101-1104, 10.1002/anie.200461333
Debuigne, A.; Champouret, Y.; Jérôme, R.; Poli, R.; Detrembleur, C. Mechanistic insights into the cobalt-mediated radical polymerization (CMRP) of vinyl acetate with cobalt(III) adducts as initiators. Chem.-Eur. J. 2008, 14, 4046-4059, 10.1002/chem.200701867
Morin, A. N.; Detrembleur, C.; Jérôme, C.; De Tullio, P.; Poli, R.; Debuigne, A. Effect of head-to-head addition in vinyl acetate controlled radical polymerization: why is Co(acac)2-mediated polymerization so much better?. Macromolecules 2013, 46, 4303-4312, 10.1021/ma400651a
Dréan, M.; Guégan, P.; Detrembleur, C.; Jérôme, C.; Rieger, J.; Debuigne, A. Controlled synthesis of poly(vinylamine)-based copolymers by organometallic-mediated radical polymerization. Macromolecules 2016, 49, 4817-4827, 10.1021/acs.macromol.6b00992
Stiernet, P.; Dréan, M.; Jérôme, C.; Midoux, P.; Guégan, P.; Rieger, J.; Debuigne, A. Tailor-Made Poly(vinylamine)s via Thermal or Photochemical Organometallic Mediated Radical Polymerization. ACS Symposium Series, 2018; Vol. 1284, pp 17-349.
Dréan, M.; Debuigne, A.; Goncalves, C.; Jérôme, C.; Midoux, P.; Rieger, J.; Guégan, P. Use of Primary and Secondary Polyvinylamines for Efficient Gene Transfection. Biomacromolecules 2017, 18, 440-451, 10.1021/acs.biomac.6b01526
Debuigne, A.; Morin, A. N.; Kermagoret, A.; Piette, Y.; Detrembleur, C.; Jérôme, C.; Poli, R. Key Role of Intramolecular Metal Chelation and Hydrogen Bonding in the Cobalt-Mediated Radical Polymerization ofN-Vinyl Amides. Chem.-Eur. J. 2012, 18, 12834-12844, 10.1002/chem.201201456
Scholten, P. B. V.; Demarteau, J.; Gennen, S.; De Winter, J.; Grignard, B.; Debuigne, A.; Meier, M. A. R.; Detrembleur, C. Merging CO2-based building blocks with cobalt-mediated radical polymerization for the synthesis of functional poly(vinyl alcohol)s. Macromolecules 2018, 51, 3379-3393, 10.1021/acs.macromol.8b00492
Scholten, P. B. V.; Detrembleur, C.; Meier, M. A. R. Plant-Based Nonactivated Olefins: A New Class of Renewable Monomers for Controlled Radical Polymerization. ACS Sustainable Chem. Eng. 2019, 7, 2751-2762, 10.1021/acssuschemeng.8b05926
Piette, Y.; Debuigne, A.; Jérôme, C.; Bodart, V.; Poli, R.; Detrembleur, C. Cobalt-mediated radical (co)polymerization of vinyl chloride and vinyl acetate. Polym. Chem. 2012, 3, 2880-2891, 10.1039/c2py20413d
Banerjee, S.; Ladmiral, V.; Debuigne, A.; Detrembleur, C.; Poli, R.; Améduri, B. Organometallic-Mediated Radical Polymerization of Vinylidene Fluoride. Angew. Chem., Int. Ed. 2018, 57, 2934-2937, 10.1002/anie.201712347
Kermagoret, A.; Debuigne, A.; Jérôme, C.; Detrembleur, C. Precision design of ethylene-and polar-monomer-based copolymers by organometallic-mediated radical polymerization. Nat. Chem. 2014, 6, 179-187, 10.1038/nchem.1850
Demarteau, J.; Kermagoret, A.; Jérôme, C.; Detrembleur, C.; Debuigne, A. Controlled synthesis of ethylene-vinyl acetate based copolymers by organometallic mediated radical polymerization. ACS Symposium Series, 2015; Vol. 1188 (Controlled Radical Polymerization), pp 47-61.
Demarteau, J.; De Winter, J.; Detrembleur, C.; Debuigne, A. Ethylene/vinyl acetate-based macrocycles via organometallic-mediated radical polymerization and CuAAC "click" reaction. Polym. Chem. 2018, 9, 273-278, 10.1039/c7py01891f
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenb, D. J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
Reiher, M. Theoretical Study of the Fe(phen)2(NCS)2 Spin-Crossover Complex with Reparametrized Density Functionals. Inorg. Chem. 2002, 41, 6928-6935, 10.1021/ic025891l
Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. A set of f-polarization functions for pseudo-potential basis sets of the transition metals Sc-Cu, Y-Ag and La-Au. Chem. Phys. Lett. 1993, 208, 111-114, 10.1016/0009-2614(93)80086-5
Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J. Chem. Phys. 2010, 132, 154104, 10.1063/1.3382344
Bryantsev, V. S.; Diallo, M. S.; Goddard III, W. A., III Calculation of Solvation Free Energies of Charged Solutes Using Mixed Cluster/Continuum Models. J. Phys. Chem. B 2008, 112, 9709-9719, 10.1021/jp802665d
Fineman, M.; Ross, S. D. Linear method for determining monomer reactivity ratios in copolymerization. J. Polym. Sci. 1950, 5, 259-262, 10.1002/pol.1950.120050210
Kelen, T.; Tüdös, F. Analysis of the Linear Methods for Determining Copolymerization Reactivity Ratios. I. A New Improved Linear Graphic Method. J. Macromol. Sci., Part A: Pure Appl.Chem. 1975, 9, 1-27, 10.1080/00222337508068644
Wamsley, A.; Jasti, B.; Phiasivongsa, P.; Li, X. Synthesis of random terpolymers and determination of reactivity ratios ofN-carboxyanhydrides of leucine, β-benzyl aspartate, and valine. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 317-325, 10.1002/pola.11020
Ting, J. M.; Navale, T. S.; Bates, F. S.; Reineke, T. M. Precise compositional control and systematic preparation of multimonomeric statistical copolymers. ACS Macro Lett. 2013, 2, 770-774, 10.1021/mz4003112
Skeist, I. Copolymerization: the Composition Distribution Curve. J. Appl. Chem. Sci. 1946, 68, 1781-1784, 10.1021/ja01213a031
García-álvarez, J.; Díez, J.; Vidal, C. Pd(ii)-catalyzed cycloisomerisation of γ-alkynoic acids and one-pot tandem cycloisomerisation/CuAAC reactions in water. Green Chem. 2012, 14, 3190-3196, 10.1039/c2gc36176k
Saavedra, B.; Pérez, J. M.; Rodríguez-álvarez, M. J.; García-álvarez, J.; Ramón, D. J. Impregnated palladium on magnetite as a water compatible catalyst for the cycloisomerization of alkynoic acid derivatives. Green Chem. 2018, 20, 2151-2157, 10.1039/c8gc00229k
Rodríguez-álvarez, M. J.; Vidal, C.; Díez, J.; García-álvarez, J. Introducing Deep Eutectic Solvents as Biorenewable Media for Au(I)-Catalysed Cycloisomerisation of γ-Alkynoic Acids: An Unprecedented Catalytic System. Chem. Commun. 2014, 50, 12927-12929, 10.1039/c4cc05904b
Ramsay, W. J.; Bell, N. A. W.; Qing, Y.; Bayley, H. Single-Molecule Observation of the Intermediates in a Catalytic Cycle. J. Am. Chem. Soc. 2018, 140, 17538-17546, 10.1021/jacs.8b09282
Fernandes, T. A.; Galvão, A. M.; do Rego, A. M. B.; Carvalho, M. F. N. N. Cu(I) Camphor Coordination Polymers: Synthesis and Study of the Catalytic Activity for Cyclization of 4-Pentyn-1-oic Acid. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 3316-3323, 10.1002/pola.27393
Naidu, S.; Rajasekhara Reddy, S. A Green and Recyclable Copper and Ionic Liquid Catalytic System for the Construction of Poly-heterocyclic Compounds via One-pot Tandem Coupling Reaction. ChemistrySelect 2017, 2, 1196-1201, 10.1002/slct.201601872
Leconte, N.; du Moulinet d'Hardemare, A.; Philouze, C.; Thomas, F. A Highly Active Diradical Cobalt(III) Catalyst for the Cycloisomerization of Alkynoic Acids. Chem. Commun. 2018, 54, 8241-8244, 10.1039/c8cc04459g
Maria, S.; Kaneyoshi, H.; Matyjaszewski, K.; Poli, R. Effect of Electron Donors on the Radical Polymerization of Vinyl Acetate Mediated by [Co(acac)2]: Degenerative Transfer versus Reversible Homolytic Cleavage of an Organocobalt(III) Complex. Chem.-Eur. J. 2007, 13, 2480-2492, 10.1002/chem.200601457
Debuigne, A.; Poli, R.; Jérôme, R.; Jérôme, C.; Detrembleur, C. Key role of metal-coordination in cobalt-mediated radical polymerization of vinyl acetate. ACS Symposium Series, 2009, Vol. 1024, pp 131-147.
Debuigne, A.; Caille, J.-R.; Willet, N.; Jérôme, R. Synthesis of poly(vinyl acetate) and poly(vinyl alcohol) containing block copolymers by combination of cobalt-mediated radical polymerization and ATRP. Macromolecules 2005, 38, 9488-9496, 10.1021/ma051246x
Detrembleur, C.; Stoilova, O.; Bryaskova, R.; Debuigne, A.; Mouithys-Mickalad, A.; Jérôme, R. Preparation of well-defined PVOH/C60 nanohybrids by cobalt-mediated radical polymerization of vinyl acetate. Macromol. Rapid Commun. 2006, 27, 498-504, 10.1002/marc.200500871
Bryaskova, R.; Willet, N.; Debuigne, A.; Jérôme, R.; Detrembleur, C. Synthesis of Poly(vinyl acetate)-b-Polystyrene and Poly(vinyl alcohol)-b-Polystyrene copolymers by Cobalt-Mediated Radical Polymerization. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 81-89, 10.1002/pola.21806
Park, S.-S.; Yoon, H.-S. Acid-Catalyzed Hydrolysis Reaction of Poly(vinyl acetate). Polymer (Korea) 2005, 29, 304-307
Hassan, C. M.; Peppas, N. A.. Structure and Applications of Poly(vinyl alcohol) Hydrogels Produced by Conventional Crosslinking or by Freezing/Thawing Methods. Biopolymers: PVA Hydrogels, Anionic Polymerisation Nanocomposites; Advances in Polymer Science; Springer, 2000, Vol. 153, pp 37-65.
Debuigne, A.; Willet, N.; Jérôme, R.; Detrembleur, C. Amphiphilic poly(vinyl acetate)-b-poly(N-vinylpyrrolidone) and novel double hydrophilic poly(vinyl alcohol)-b-poly(N-vinylpyrrolidone) block copolymers prepared by cobalt-mediated radical polymerization. Macromolecules 2007, 40, 7111-7118, 10.1021/ma0712908
Bernard, J.; Favier, A.; Zhang, L.; Nilasaroya, A.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Poly(vinyl ester) Star Polymers via Xanthate-Mediated Living Radical Polymerization: From Poly(vinyl alcohol) to Glycopolymer Stars. Macromolecules 2005, 38, 5475-5484, 10.1021/ma050050u
Harrisson, S.; Liu, X.; Ollagnier, J.-N.; Coutelier, O.; Marty, J.-D.; Destarac, M. RAFT Polymerization of Vinyl Esters: Synthesis and Applications. Polymers 2014, 6, 1437-1488, 10.3390/polym6051437
Arai, K.; Okuzono, M.; Shikata, T. Reason for the High Solubility of Chemically Modified Poly(vinyl alcohol)s in Aqueous Solution. Macromolecules 2015, 48, 1573-1578, 10.1021/ma502602r