Radical Polymerization of Methylene Heterocyclic Compounds: Functional Polymer Synthesis and Applications

[en] Synthetic polymers sustain a wide range of applications but the quest for further sophistication and functionalization of polymers remains topical to improve their scope and performance. In this respect, the radical polymerization of exo-methylene heterocyclic compounds (MHCs) is attractive. Compared to the classical acyclic vinyl monomers constrained to the vinyl-type polymerization pro- cess, MHCs can undergo different polymerization modes, namely the radical ring-retaining polymerization (rRRP) and the radical ring- opening polymerization (rROP). In rRRP, the cyclic group is preserved and inserted as side group of the polymer backbone offering a myr- iad of post-polymerization modifications whereas functional groups are incorporated within the backbone of linear polymers and confer them some degradability in rROP. Herein, recent advances in the radical polymerization of MHCs as well as the variety of macromol- ecular structures and applications it offers are highlighted. The reversible deactivation radical polymerization of MHCs leading to well-defined MHC-based macromolecular architectures, including multifunctional, stimuli-responsive and degradable polymers, is also discussed. The review emphasizes the current limitations of the rad- ical polymerization of MHCs as well as future prospects including the development of innovative bio-based MHCs. Overall, the radical poly- merization of MCHs represents a powerful macromolecular engineer- ing tool and a broad field of exploration for polymer chemists.

Research Center/Unit :

CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège
CERM - Center for Education and Research on Macromolecules - ULiège

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

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 :

Radical Polymerization of Methylene Heterocyclic Compounds: Functional Polymer Synthesis and Applications

Publication date :

21 February 2023

Journal title :

Polymer Reviews

ISSN :

1558-3724

eISSN :

1558-3716

Publisher :

Informa UK Limited

Volume :

Issue :

Pages :

805-851

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://www.tandfonline.com/doi/pdf/10.1080/15583724.2023.2181819

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique
FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen
EOS - The Excellence Of Science Program

Funding text :

The authors thank the "Fonds National pour la Recherche Scientifique” (F.R.S.-FNRS) and the Fonds Wetenschappelijk Onderzoek – Vlaanderen (FWO) for financial support in the frame of the EOS project n?O019618F (ID EOS: 30902231). A.D. is FNRS Senior Research Associate and thanks FNRS for financial support. The authors thanks C. Detrembleur for fruitful discussion.

Available on ORBi :

since 28 February 2023

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Bibliography

Nesvadba, P. Radical Polymerization in Industry. Encycl. Radicals Chem. Biol. Mater. 2012, 4, 1701–1736. DOI: 10.1002/9781119953678.rad080.
Corrigan, N.; Jung, K.; Moad, G.; Hawker, C. J.; Matyjaszewski, K.; Boyer, C. Reversible-Deactivation Radical Polymerization (Controlled/Living Radical Polymerization): From Discovery to Materials Design and Applications. Prog. Polym. Sci. 2020, 111, 101311. DOI: 10.1016/j.progpolymsci.2020.101311.
Goto, A.; Fukuda, T. Kinetics of Living Radical Polymerization. Prog. Polym. Sci. 2004, 29, 329–385. DOI: 10.1016/j.progpolymsci.2004.01.002.
Moad, G.; Rizzardo, E. The History of Nitroxide- Mediated Polymerization. Nitroxide Mediat. Polym. Fundam. Appl. Mater. Sci. 2015, 1–44. DOI: 10.1039/9781782622635-00001.
Nicolas, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B. Nitroxide-Mediated Polymerization. Prog. Polym. Sci. 2013, 38, 63–235. DOI: 10.1016/j.progpolymsci.2012.06.002.
Grubbs, R. B. Nitroxide-Mediated Radical Polymerization: Limitations and Versatility. Polym. Rev. 2011, 51, 104–137. DOI: 10.1080/15583724.2011.566405.
Tebben, L.; Studer, A. Nitroxides: Applications in Synthesis and in Polymer Chemistry. Angew. Chem. Int. Ed. 2011, 50, 5034–5068. DOI: 10.1002/anie.201002547.
Hurtgen, M.; Detrembleur, C.; Jerome, C.; Debuigne, A. Insight into Organometallic-Mediated Radical Polymerization. Polym. Rev. 2011, 51, 188–213. DOI: 10.1080/15583724.2011.566401.
Allan, L. E. N.; Perry, M. R.; Shaver, M. P. Organometallic Mediated Radical Polymerization. Prog. Polym. Sci. 2012, 37, 127–156. DOI: 10.1016/j.progpolymsci.2011.07.004.
Debuigne, A.; Jérôme, C.; Detrembleur, C. Organometallic-Mediated Radical Polymerization of ‘Less Activated Monomers’: Fundamentals, Challenges and Opportunities. Polymer 2017, 115, 285–307. DOI: 10.1016/j.polymer.2017.01.008.
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. DOI: 10.1021/acs.chemrev.8b00715.
Matyjaszewski, K. Advanced Materials by Atom Transfer Radical Polymerization. Adv. Mater. 2018, 30, 1706441–1706422. DOI: 10.1002/adma.201706441.
Matyjaszewski, K.; Tsarevsky, N. V. Macromolecular Engineering by Atom Transfer Radical Polymerization. J. Am. Chem. Soc. 2014, 136, 6513–6533. DOI: 10.1021/ja408069v.
Ouchi, M.; Terashima, T.; Sawamoto, M. Transition Metal-Catalyzed Living Radical Polymerization: Toward Perfection in Catalysis and Precision Polymer Synthesis. Chem. Rev. 2009, 109, 4963–5050. DOI: 10.1021/cr900234b.
Szczepaniak, G.; Fu, L.; Jafari, H.; Kapil, K.; Matyjaszewski, K. Making ATRP More Practical: Oxygen Tolerance. Acc. Chem. Res. 2021, 54, 1779–1790. DOI: 10.1021/acs.accounts.1c00032.
Zard, S. Z. Discovery of the RAFT/MADIX Process: Mechanistic Insights and Polymer Chemistry Implications. Macromolecules 2020, 53, 8144–8159. DOI: 10.1021/acs.macromol.0c01441.
Moad, G.; Rizzardo, E. A 20th Anniversary Perspective on the Life of RAFT (RAFT Coming of Age). Polym. Int. 2020, 69, 658–661. DOI: 10.1002/pi.5944.
Perrier, S. 50th Anniversary Perspective: RAFT Polymerization - A User Guide. Macromolecules 2017, 50, 7433–7447. DOI: 10.1021/acs.macromol.7b00767.
Hill, M. R.; Carmean, R. N.; Sumerlin, B. S. Expanding the Scope of RAFT Polymerization: Recent Advances and New Horizons. Macromolecules 2015, 48, 5459–5469. DOI: 10.1021/acs.macromol.5b00342.
Phommalysack-Lovan, J.; Chu, Y.; Boyer, C.; Xu, J. PET-RAFT Polymerisation: Towards Green and Precision Polymer Manufacturing. Chem. Commun. 2018, 54, 6591–6606. DOI: 10.1039/C8CC02783H.
Nothling, M. D.; Fu, Q.; Reyhani, A.; Allison-Logan, S.; Jung, K.; Zhu, J.; Kamigaito, M.; Boyer, C.; Qiao, G. G. Progress and Perspectives beyond Traditional RAFT Polymerization. Adv. Sci. (Weinh) 2020, 7, 2001656–2001612. DOI: 10.1002/advs.202001656.
Yamago, S. Precision Polymer Synthesis by Degenerative Transfer Controlled/Living Radical Polymerization Using Organotellurium, Organostibine, and Organobismuthine Chain-Transfer Agents. Chem. Rev. 2009, 109, 5051–5068. DOI: 10.1021/cr9001269.
Fan, W.; Yamago, S. Synthesis of Poly(N-Vinylamide)s and Poly(Vinylamine)s and Their Block Copolymers by Organotellurium-Mediated Radical Polymerization. Angew. Chem. Int. Ed. 2019, 58, 7113–7116. Ed. DOI: 10.1002/anie.201902940.
Kleinm, E.; Schulze, T. Ring-Opening Polymerization of Heterocycles Bearing Substituted and Unsubstituted Exo-Methylene Groups - A Review. Acta Polym. 1999, 50, 1–19. DOI: 10.1002/(sici)1521-4044(19990101)50:1 < 1::aid-apol1 > 3.0.co;2-o.
Tardy, A.; Nicolas, J.; Gigmes, D.; Lefay, C.; Guillaneuf, Y. Radical Ring-Opening Polymerization: Scope, Limitations, and Application to (Bio)Degradable Materials. Chem. Rev. 2017, 117, 1319–1406. DOI: 10.1021/acs.chemrev.6b00319.
Sardon, H.; Mecerreyes, D.; Basterretxea, A.; Avérous, L.; Jehanno, C. From Lab to Market: Current Strategies for the Production of Biobased Polyols. ACS Sustainable Chem. Eng. 2021, 9, 10664–10677. DOI: 10.1021/acssuschemeng.1c02361.
Fagnani, D. E.; Tami, J. L.; Copley, G.; Clemons, M. N.; Getzler, Y. D. Y. L.; McNeil, A. J. 100th Anniversary of Macromolecular Science Viewpoint: Redefining Sustainable Polymers. ACS Macro Lett. 2021, 10, 41–53. DOI: 10.1021/acsmacrolett.0c00789.
Zhang, Z.; Jiang, P. P.; Liu, D.; Feng, S.; Zhang, P.; Wang, Y.; Fu, J.; Agus, H. Research Progress of Novel Bio-Based Plasticizers and Their Applications in Poly(Vinyl Chloride). J. Mater. Sci. 2021, 56, 10155–10182. DOI: 10.1007/s10853-021-05934-x.
Kato, Y.; Yoshida, H.; Shoji, K.; Sato, Y.; Nakajima, N.; Ogita, S. A Facile Method for the Preparation of α-Methylene-γ-Butyrolactones from Tulip Tissues by Enzyme-Mediated Conversion. Tetrahedron Lett. 2009, 50, 4751–4753. DOI: 10.1016/j.tetlet.2009.06.018.
Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. The Renaissance of α-Methylene-γ-Butyrolactones: New Synthetic Approaches. Angew. Chem. Int. Ed. 2009, 48, 9426–9451. DOI: 10.1002/anie.200903108.
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. DOI: 10.1021/acs.macromol.6b00467.
Liu, J.; Flegel, J.; Otte, F.; Pahl, A.; Sievers, S.; Strohmann, C.; Waldmann, H. Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids. Angew. Chem. Int. Ed. Engl. 2021, 60, 21384–21395. DOI: 10.1002/anie.202106654.
David, M. C.; Rial, C.; Varela, R. M.; Molinillo, J. M. G.; Mac, F. A. Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C17-Sesquiterpenoids and a Study of Their Phytotoxic Activity. J. Nat. Prod. 2021, 84, 2295–2302. DOI: 10.1021/acs.jnatprod.1c00396.
Manzer, L. E. Biomass Derivatives: A Sustainable Source of Chemicals. ACS Symp. Ser. 2006, 921, 40–51. DOI: 10.1021/bk-2006-0921.ch004.
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. DOI: 10.1002/pola.28654.
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. DOI: 10.1039/c3qo00089c.
Olsén, P.; Odelius, K.; Albertsson, A. C. Thermodynamic Presynthetic Considerations for Ring-Opening Polymerization. Biomacromolecules 2016, 17, 699–709. DOI: 10.1021/acs.biomac.5b01698.
Alemán, C.; Betran, O.; Casanovas, J.; Houk, K. N.; Hall, H. K. Thermodynamic Control of the Polymerizability of Five-, Six-, and Seven-Membered Lactones. J. Org. Chem. 2009, 74, 6237–6244. DOI: 10.1021/jo9010969.
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. DOI: 10.1021/jacs.6b07974.
Akkapeddi, M. K. Poly(α-Methylene-γ-Butyrolactone) Synthesis, Configurational Structure, and Properties. Macromolecules 1979, 12, 546–551. DOI: 10.1021/ma60070a002.
Suenaga, J.; Sutherlin, D. M.; Stille, J. K. Polymerization of (RS)- and (R)-α-Methylene-γ-Methyl- γ- Butyrolactone. Macromolecules 1984, 17, 2913–2916. DOI: 10.1021/ma00142a080.
Ueda, M.; Takahashi, M.; Imai, Y.; Pittman, C. U. Radical-Initiated Homo- and Copolymerization of α-Methylene-γ-Butyrolactone. J. Polym. Sci. Polym. Chem. Ed. 1982, 20, 2819–2828. DOI: 10.1002/pol.1982.170201008.
Katsikas, L.; Avramović, M.; Cortés, R. D. B.; Milovanović, M.; Kalagasidis-Krušić, M. T.; Popović, I. G. The Thermal Stability of Poly(Methyl Methacrylate) Prepared by RAFT Polymerisation. J. Serb. Chem. Soc. 2008, 73, 915–921. DOI: 10.2298/JSC0809915K.
Agarwal, S.; Jin, Q.; Maji, S. Biobased Polymers from Plant-Derived Tulipalin A. ACS Symp. Ser. 2012, 1105, 197–212. DOI: 10.1021/bk-2012-1105.ch013.
Brandenburg, C. J. Graft Copolymers of Methylene Lactones and Process for Emulsion Polymerization of Methylene Lactones. US 6841627 B2, 2005.
Akkapeddi, M. K. The Free Radical Copolymerization Characteristics of α-Methylene-γ-Butyrolactone. Polymer 1979, 20, 1215–1216. DOI: 10.1016/0032-3861(79)90145-9.
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. DOI: 10.1016/j.polymer.2009.02.037.
Ramram, M. B.; Chen, D.; Ma, Y.; Wang, L.; Yang, W. 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. DOI: 10.1080/10601325.2016.1189281.
Trumbo, D. L. The Copolymerization of 2- and 3-Vinyl Thiophene with α-Methylene-γ- Butyrolactone. Polym. Bull. 1991, 26, 271–275. DOI: 10.1007/BF00587969.
Pickett, J. E.; Ye, Q.; Steiger, D. Tulipalin Copolymers.US 7932336 B2, 2011.
Mullen, B.; Rodwogin, M.; Stollmaier, F.; Yontz, D.; Leibig, C. New Bio-Derived Superabsorbents from Nature. Green Mater. 2013, 1, 186–190. DOI: 10.1680/gmat.12.00018.
Satoh, K. Controlled/Living Polymerization of Renewable Vinyl Monomers into Bio-Based Polymers. Polym. J. 2015, 47, 527–536. DOI: 10.1038/pj.2015.31.
Mosnáček, J.; Matyjaszewski, K. Atom Transfer Radical Polymerization of Tulipalin A: A Naturally Renewable Monomer. Macromolecules 2008, 41, 5509–5511. DOI: 10.1021/ma8010813.
Higaki, Y.; Okazaki, R.; Takahara, A. Semirigid Biobased Polymer Brush: Poly(α-Methylene-γ- Butyrolactone) Brushes. ACS Macro Lett. 2012, 1, 1124–1127. DOI: 10.1021/mz3002148.
Pittman, C. U.; Lee, H. Radical-Initiated Polymerization of β-Methyl- α-Methylene-γ-Butyrolactone. J. Polym. Sci. A Polym. Chem. 2003, 41, 1759–1777. DOI: 10.1002/pola.10719.
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. A Polym. Chem. 2008, 46, 5929–5944. DOI: 10.1002/pola.22909.
Ueda, M.; Takahashi, M.; Imai, Y.; Pittman, C. U. Synthesis and Homopolymerization Kinetics of α-Methylene-δ-Valerolactone, an Exo-Methylene Cyclic Monomer with a Nonplanar Ring System Spanning the Radical Center. Macromolecules 1983, 16, 1300–1305. DOI: 10.1021/ma00242a009.
Ueda, M.; Suzuki, T.; Takahashi, M.; Li, Z. B.; Koyama, K.; Pittman, C. U. Radical Copolymerization of Styrene with α-Methylene-δ-Valerolactone: Role of Depropagation in the Mechanism. Macromolecules 1986, 19, 558–565. DOI: 10.1021/ma00157a010.
Sinnwell, S.; Ritter, H. Ring-Opening Homo- and Copolymerization of α-Methylene-ε-Caprolactone. Macromolecules 2006, 39, 2804–2807. DOI: 10.1021/ma0527146.
Oral, I.; Abetz, V. A Highly Selective Polymer Material Using Benzo-9-Crown-3 for the Extraction of Lithium in Presence of Other Interfering Alkali Metal Ions. Macromol. Rapid Commun. 2021, 42, 2000746. DOI: 10.1002/marc.202000746.
Casadellà, A.; Galama, A. H.; Schaetzle, O.; Loos, K. Effect of Diffusion and Migration on the Selectivity of a Polymer Inclusion Membrane Containing Dicyclohexano-18-Crown-6. Macromol. Chem. Phys. 2016, 217, 1600–1606. DOI: 10.1002/macp.201600037.
Habaue, S.; Morita, M.; Okamoto, Y. Stereospecific Anionic Polymerization of a-(Alkoxymethyl)Acrylate Derivatives Affording Novel Vinyl Polymers with Macrocyclic Side Chains. Polymer 2002, 43, 3469–3474. DOI: 10.1016/S0032-3861(02)00045-9.
Smith, Q.; Huang, J.; Matyjaszewski, K.; Loo, Y. Controlled Radical Polymerization and Copolymerization of 5-Methylene-2-Phenyl-1,3-Dioxolan-4-One by ATRP Has Generated Significant Interest Because This Route. Macromolecules 2005, 38, 5581–5586. DOI: 10.1021/ma050393s.
Kumar, B.; Negi, Y. S. Synthesis and Characterization of Poly(Potassium 1-Hydroxy Acrylate) and Its Derivatives by Using Different Efficient Catalysts. Polymer 2015, 80, 159–170. DOI: 10.1016/j.polymer.2015.10.060.
Kohsaka, Y.; Matsumoto, Y.; Zhang, T.; Matsuhashi, Y.; Kitayama, T. Kitayama, T. α-Exomethylene Lactone Possessing Acetal-Ester Linkage: Polymerization and Postpolymerization Modification for Water-Soluble Polymer. J. Polym. Sci. Part A: Polym. Chem. 2016, 54, 955–961. DOI: 10.1002/pola.27931.
Kumar, B.; Negi, Y. S. Properties and Thermal Stability of Water-Soluble Poly(Potassium 1-Hydroxyacrylate-Co-Styrene) Copolymer. Polym. Int. 2018, 67, 111–120. DOI: 10.1002/pi.5484.
Kumar, B.; Negi, Y. S. Synthesis and Thermal Properties of Novel Poly(Potassium 1-Hydroxy Acrylate-Co-Potassium Acrylate) Based Copolymer. Mater. Lett. 2018, 232, 196–201. DOI: 10.1016/j.matlet.2018.08.123.
Tanaka, H.; Kibayashi, T.; Okuda, K.; Kashihara, S. Stereospecific Reversible Deactivation Radical Polymerization of Biomass-Based Acrylates for Precise Control of Tacticity and Molecular Weight. J. Polym. Sci. Part A: Polym. Chem. 2017, 55, 445–456. DOI: 10.1002/pola.28412.
Fuoco, T.; Finne-Wistrand, A.; Pappalardo, D. A Route to Aliphatic Poly(Ester)s with Thiol Pendant Groups: From Monomer Design to Editable Porous Scaffolds. Biomacromolecules 2016, 17, 1383–1394. DOI: 10.1021/acs.biomac.6b00005.
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. DOI: 10.1002/pola.27629.
Rizzardo, E.; Chong, Y. K.; Evans, R. A.; Moad, G.; Thang, S. H. Control of Polymer Structure by Chain Transfer Processes. Macromol. Symp. 1996, 111, 1–11. DOI: 10.1002/masy.19961110103.
Phelan, M.; Aldabbagh, F.; Zetterlund, P. B.; Yamada, B. Mechanism and Kinetics of the Free Radical Ring-Opening Polymerization of Cyclic Allylic Sulfide Lactones. Polymer. 2005, 46, 12046–12056. DOI: 10.1016/j.polymer.2005.11.006.
Ratcliffe, L. P. D.; Couchon, C.; Armes, S. P.; Paulusse, J. M. J. Inducing an Order-Order Morphological Transition via Chemical Degradation of Amphiphilic Diblock Copolymer Nano-Objects. Biomacromolecules 2016, 17, 2277–2283. DOI: 10.1021/acs.biomac.6b00540.
Du, J.; Choi, B.; Liu, Y.; Feng, A.; Thang, S. H. Degradable PH and Redox Dual Responsive Nanoparticles for Efficient Covalent Drug Delivery. Polym. Chem. 2019, 10, 1291–1298. DOI: 10.1039/C8PY01583J.
Barner-Kowollik, C.; Buback, M.; Egorov, M.; Fukuda, T.; Goto, A.; Olaj, O. F.; Russell, G. T.; Vana, P.; Yamada, B.; Zetterlund, P. B. Critically Evaluated Termination Rate Coefficients for Free-Radical Polymerization: Experimental Methods. Macromol. Chem. Phys. 2002, 203, 2570–2582. DOI: 10.1016/j.progpolymsci.2005.02.001.
Evans, R. A.; Moad, G.; Rizzardo, E.; Thang, S. H. New Free-Radical Ring-Opening Acrylate Monomers. Macromolecules 1994, 27, 7935–7937. DOI: 10.1021/ma00104a062.
Delplace, V.; Nicolas, J. Degradable Vinyl Polymers for Biomedical Applications. Nature Chem. 2015, 7, 771–784. DOI: 10.1038/nchem.2343.
Pesenti, T.; Nicolas, J. 100th Anniversary of Macromolecular Science Viewpoint: Degradable Polymers from Radical Ring-Opening Polymerization: Latest Advances, New Directions, and Ongoing Challenges. ACS Macro Lett. 2020, 9, 1812–1835. DOI: 10.1021/acsmacrolett.0c00676.
Paulusse, J. M. J.; Amir, R. J.; Evans, R. A.; Hawker, C. J. Free Radical Polymers with Tunable and Selective Bio- and Chemical Degradability. J. Am. Chem. Soc. 2009, 131, 9805–9812. DOI: 10.1021/ja903245p.
Chaumont, P.; Asgarzadeh, F.; Colombani, D.; Arotcarena, M.; Baudouin, A.; Synthesis, Characterization and Hydrolysis of Poly[Styrene-Co-(6-Methylene-l,4-Oxathiepane-7-One)] and Poly[Styrene-Co-(6-Methylene-5-Methyl-1,4-Oxathiepane-7-One)]. Macromol. Chem. Phys. 1998, 199, 2577–2582. DOI: 10.1002/(SICI)1521-3935(19981101)199:11 < 2577::AID-MACP2577 > 3.0.CO;2-2.
Maiti, S. N.; Spevak, P.; Singh, M. P.; Micetich, R. G.; Reddy, A. V. N. Reductive Cleavage of Symmetrical Disulfides with Hydrazines. Synth. Commun. 1988, 18, 575–581. DOI: 10.1080/00397919308020392.
Warren, N. J.; Rosselgong, J.; Madsen, J.; Armes, S. P. Disulfide-Functionalized Diblock Copolymer Worm Gels. Biomacromolecules 2015, 16, 2514–2521. DOI: 10.1021/acs.biomac.5b00767.
Huang, H.; Sun, B.; Huang, Y.; Niu, J. Radical Cascade-Triggered Controlled Ring-Opening Polymerization of Macrocyclic Monomers. J. Am. Chem. Soc. 2018, 140, 10402–10406. DOI: 10.1021/jacs.8b05365.
Wang, W.; Zhou, Z.; Sathe, D.; Tang, X.; Moran, S.; Jin, J.; Haeffner, F.; Wang, J.; Niu, J. Degradable Vinyl Random Copolymers via Photocontrolled Radical Ring‐Opening Cascade Copolymerization. Angew. Chemie Int. Ed. 2021, 44325, 1–10. DOI: 10.1002/anie.202113302.
Kohsaka, Y.; Tanimoto, Y. Synthesis of Thermo-Responsive Polymer via Radical (Co)Polymerization of N, N-Dimethyl-α-(Hydroxymethyl)Acrylamide with N, N-Diethylacrylamide. Polymers (Basel). 2016, 8, 374. DOI: 10.3390/polym8100374.
Xie, X.; Hogen-Esch, T. E. Anionic Synthesis of Narrow Molecular Weight Distribution Water-Soluble Poly(N,N-Dimethylacrylamide) and Poly(N-Acryloyl-N′-Methylpiperazine). Macromolecules 1996, 29, 1746–1752. DOI: 10.1021/ma950688d.
Heyns, I. M.; Pfukwa, R.; Klumperman, B. Synthesis, Characterization, and Evaluation of Cytotoxicity of Poly(3-Methylene-2-Pyrrolidone). Biomacromolecules 2016, 17, 1795–1800. DOI: 10.1021/acs.biomac.6b00210.
Ueda, M.; Takahashi, M.; Suzuki, T. Polymerization of α-Methylene-N-Methylpyrrolidone. J. Polym. Sci. Polym. Phys. Ed. 1983, 20, 1139–1149. DOI: 10.1002/pol.1983.170210420.
Iskander, G. M.; Ovenell, T. R.; Davis, T. P. Synthesis and Properties of Poly(1-Alkyl-3-Methylene-2-Pyrrolidone)S. Macromol. Chem. Phys. 1996, 197, 3123–3133. DOI: 10.1002/macp.1996.021971006.
Neuhaus, K.; Ritter, H. Forgotten Monomers: Isotactic Polymers from N-Benzyl-3-Methylenepyrrolidin-2-One via Free Radical Polymerization. Polym. Int. 2015, 64, 1690–1694. DOI: 10.1002/pi.4963.
Ueda, M.; Mori, H.; Ito, H. Radical Polymerization of N-Phenyl-α-Methylene-β-Lactam. J. Polym. Sci. A Polym. Chem. 1990, 28, 2597–2607. DOI: 10.1002/pola.1990.080281002.
Watanabe, H.; Matsumoto, A.; Otsu, T. Polymerization of N-Alkyl-Substituted Itaconimides and N-(Alkyl-Substituted Phenyl) Itaconimides and Characterization of the Resulting Polymers. J. Polym. Sci. A Polym. Chem. 1994, 32, 2073–2083. DOI: 10.1002/pola.1994.080321109.
Satoh, K.; Lee, D. H.; Nagai, K.; Kamigaito, M. Precision Synthesis of Bio-Based Acrylic Thermoplastic Elastomer by RAFT Polymerization of Itaconic Acid Derivatives. Macromol. Rapid Commun. 2014, 35, 161–167. DOI: 10.1002/marc.201300638.
Anand, V.; Agarwal, S.; Greiner, A.; Choudhary, V. Synthesis of Methyl Methacrylate and N-Aryl Itaconimide Block Copolymers via Atom-Transfer Radical Polymerization. Polym. Int. 2005, 54, 823–828. DOI: 10.1002/pi.1776.
Miyaji, H.; Satoh, K.; Kamigaito, M. Bio-Based Polyketones by Selective Ring-Opening Radical Polymerization of α-Pinene-Derived Pinocarvone. Angew. Chem. Int. Ed. 2016, 55, 1372–1376. DOI: 10.1002/anie.201509379.
Nakano, R.; Ito, S.; Nozaki, K. Copolymerization of Carbon Dioxide and Butadiene via a Lactone Intermediate. Nature Chem. 2014, 6, 325–331. DOI: 10.1038/nchem.1882.
Moon, S.; Masada, K.; Nozaki, K. R. Polymer-Chain Modification: Ring-Opening and Closing of Polylactone. J. Am. Chem. Soc. 2019, 141, 10938–10942. DOI: 10.1021/jacs.9b03205.
Balley, William J Free Radical Ring-Opening Polymerization. Polym. J. 1985, 17, 85–95. DOI: 10.1295/polymj.17.85.
Wang, Z.; Poli, R.; Detrembleur, C.; Debuigne, A. Organometallic-Mediated Radical (Co)Polymerization of γ-Methylene-γ-Butyrolactone: Access to PH-Responsive Poly(Vinyl Alcohol) Derivatives. Macromolecules 2019, 52, 8976–8988. DOI: 10.1021/acs.macromol.9b01838.
Wang, Z.; Debuigne, A. Multi-Responsive γ-Methylene-γ-Butyrolactone/N-Vinyl Caprolactam Copolymers Involving PH-Dependent Reversible Lactonization. Polym. Chem. 2022, 13, 5212–5225.DOI: 10.1039/d2py00713d.
Dabral, S.; Bayarmagnai, B.; Hermsen, M.; Schieβl, J.; Mormul, V.; Hashmi, A. S. K.; Schaub, T. Silver-Catalyzed Carboxylative Cyclization of Primary Propargyl Alcohols with CO2. Org. Lett. 2019, 21, 1422–1425. 21. DOI: 10.1021/acs.orglett.9b00156.
Gennen, S.; Grignard, B.; Tassaing, T.; Jérôme, C.; Detrembleur, C. CO2-Sourced α-Alkylidene Cyclic Carbonates: A Step Forward in the Quest for Functional Regioregular Poly(Urethane)s and Poly(Carbonate)S. Angew. Chem. Int. Ed. Engl. 2017, 56, 10394–10398. DOI: 10.1002/anie.201704467.
Siragusa, F.; Broeck, E.; Van Den; Ocando, C.; Mu, A. J.; Smet, G.; De; Maes, B. U. W.; Winter, J.; De; Speybroeck, V.; Van; Grignard, B.; Detrembleur, C. Access to Biorenewable and CO2‑Based Polycarbonates from Exovinylene Cyclic Carbonates. ACS Sustain. Chem. Eng. 2021, 5, 1714–1728. DOI: 10.1021/acssuschemeng.0c07683.
Lee, T.; Cho, I. Radical Polymerization of 4-Methylene-l,3-Dioxolan-2-One and Its Hydrolyzed Water-Soluble Polymer. Makromol. Chem., Rapid Commun. 1989, 10, 453–456. DOI: 10.1002/marc.1989.030100904.
Ochiai, B.; Sano, Y.; Endo, T. Synthesis and Crosslinking of Oligo (Carbonate-Ketone) Obtained by Radical Polymerization of 4-Methylene-5,5-Dimethyl-1,3-Dioxolan-2-One. J. Netw. Polym. 2005, 26, 132–137. DOI: 10.11364/networkpolymer1996.26.132.
Cho, I. New Ring-Opening Polymerizations for Copolymers Having Controlled Microstructures. Prog. Polym. Sci. 2000, 25, 1043–1087. DOI: 10.1016/S0079-6700(00)00022-8.
Scholten, P. B. V.; Demarteau, J.; Gennen, S.; De Winter, J.; Grignard, B.; Debuigne, A. A. R.; Meier, M.; 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. DOI: 10.1021/acs.macromol.8b00492.
B. V. Scholten, P.; Cartigny, G.; Grignard, B.; Debuigne, A.; Cramail, H. A. R.; Meier, M.; Detrembleur, C. Functional Polyethylenes by Organometallic-Mediated Radical Polymerization of Biobased Carbonates. ACS Macro Lett. 2021, 10, 313–320. 10. DOI: 10.1021/acsmacrolett.1c00037.
Tallmadge, H.; Collum, E. B.; Enolates, D. E. Solution Structures of Lithiated Oxazolidinone-Derived Enolates. J. Am. Chem. Soc. 2015, 137, 13087–13095. DOI: 10.1021/jacs.5b08207.
Zhang, Z. B.; Collum, D. Structures and Reactivities of Sodiated Evans Enolates: Role of Solvation and Mixed Aggregation on the Stereochemistry and Mechanism of Alkylations. J. Am. Chem. Soc. 2019, 141, 388–401. DOI: 10.1021/jacs.8b10364.
Baruah, S.; Aier, M.; Puzari, A. (S)-4-(4-Aminobenzyl)-2-Oxazolidinone Based 2-Azetidinones for Antimicrobial Application and Luminescent Sensing of Divalent Metal Cations. J. Heterocycl. Chem. 2020, 57, 2498–2511. DOI: 10.1002/jhet.3965.
Zhang, D.; Zhang, Y.; Fan, Y.; Rager, M. N.; Guérineau, V.; Bouteiller, L.; Li, M. H.; Thomas, C. M. Polymerization of Cyclic Carbamates: A Practical Route to Aliphatic Polyurethanes. Macromolecules 2019, 52, 2719–2724. DOI: 10.1021/acs.macromol.9b00436.
Kim, K.; Hwang, D.; Kim, S.; Park, S. O.; Cha, H.; Lee, Y.-S.; Cho, J.; Kwak, S. K.; Choi, N.-S. Cyclic Aminosilane-Based Additive Ensuring Stable Electrode-Electrolyte Interfaces in Li-Ion Batteries. Adv. Energy Mater. 2020, 10, 2000012. DOI: 10.1002/aenm.202000012.
Yeganeh, H.; Jamshidi, S.; Talemi, P. H. Characterization and Properties of Novel Thermally Stable Poly(Urethane-Oxazolidone) Elastomers. Eur. Polym. J. 2006, 42, 1743–1754. DOI: 10.1016/j.eurpolymj.2006.02.011.
Pelzer, T.; Eling, B.; Thomas, H. J.; Luinstra, G. A. Toward Polymers with Oxazolidin-2-One Building Blocks through Tetra-n-Butyl-Ammonium Halides (Cl, Br, I) Catalyzed Coupling of Epoxides with Isocyanates. Eur. Polym. J. 2018, 107, 1–8. DOI: 10.1016/j.eurpolymj.2018.07.039.
Wang, Z.; Detrembleur, C.; Debuigne, A. Reversible Deactivation Radical (Co)Polymerization of Dimethyl Methylene Oxazolidinone towards Responsive Vicinal Aminoalcohol-Containing Copolymers. Polym. Chem. 2020, 11, 7207–7220. DOI: 10.1039/D0PY01255F.
Wang, Z.; Vertruyen, B.; Taghipour, H.; Detrembleur, C.; Debuigne, A. CO2 -Derived Methylene Oxazolidinone: A Platform Building Block for Functionalizing Ethylene–Vinyl Alcohol Copolymers. Macromolecules 2021, 54, 10415–10427. DOI: 10.1021/acs.macromol.1c01895.
Balley, W. J.; Zheng, Z.-F. Synthesis and Double Ring-Opening Polymerization of Cyclic Ketals of γ-Methylenelactones. J. Polym. Sci. Part A Polym. Chem. 1991, 29, 437–446. DOI: 10.1002/pola.1991.080290317.
Hiraguri, Y.; Endo, T. Preparation and Radical Ring-Opening Polymerization of 2-Substituted-4-Methylene-1,3-Dioxolanes. J. Polym. Sci. A Polym. Chem. 1989, 27, 4403–4411. DOI: 10.1002/pola.1989.080271317.
Pan, C.-Y.; Wu, Z.; Bailey, W. J. Preparation and Polymerization of 2-Phenyl-4-Methylene-1,3-Dioxolan. J. Polym. Sci. C Polym. Lett. 1987, 25, 243–248. DOI: 10.1002/pol.1987.140250602.
Bulletin, P.; Morariu, S.; Simionescu, B. C.; Chemistry, M. Free-Radical Ring-Opening Polymerization of 2-(o-Chlorophenyl)-4-Methylene-1,3-Dioxolane. Polym. Bull. 1993, 30, 7–12. DOI: 10.1007/BF00296227.
Hiraguri, Y.; Endo, T. Novel Synthesis of a Polyketone via Radical Ring-Opening Polymerization of 2,2-Diphenyl-4-Methylene-1,3-Dioxolane. J. Am. Chem. Soc. 1987, 109, 3779–3780. DOI: 10.1021/ja00246a044.
Hiraguri, Y.; Endo, T. Effect of Temperature on Radical Ring-Opening Polymerization of 2,2-Diphenyl-4-Methylene-1,3-Dioxolane. J. Polym. Sci. A Polym. Chem. 1989, 27, 2135–2138. DOI: 10.1002/pola.1989.080270630.
Hiraguri, Y.; Endo, T. Synthesis and Radical Ring-Opening Polymerization of 2,2-Diphenyl-4-Methylene-5-Methyl-1,3-Dioxolane, Alternating Copolymer of Propylene, and Carbon Monoxide. J. Polym. Sci. A Polym. Chem. 1992, 30, 689–690. DOI: 10.1002/pola.1992.080300422.
Hiraguri, Y.; Endo, T. Synthesis and Radical Polymerization of 2-Methylene-1,4-Dioxaspiro-6,7-8,9-Dibenzo[4.4]Nona-6,8-Diene. J. Polym. Sci. A Polym. Chem. 1990, 28, 2881–2883. DOI: 10.1002/pola.1990.080281025.
Hiraguri, Y.; Sugizaki, T.; Endo, T. Substituent Effects on Radical Polymerization Behavior of 2,2-(4,4’-Disubstituted-Diphenyl)-4-Methylene-1,3-Dioxolanes. Macromolecules 1990, 23, 1–5. DOI: 10.1021/ma00203a001.
Sugiyama, J.; Yokozawa, T.; Endo, T. Production of Polymers from Polymers. Novel Template Polymerization via Radical Ring-Opening Isomerization. J. Am. Chem. Soc. 1993, 115, 2041–2042. DOI: 10.1021/ja00058a063.
Sugiyama, J.; Yokozawa, T.; Endo, T. Radical Polymerization of 4-Methylene-2-Phenyl-2-(4-Vinylphenyl)-l,3-Dioxolane as a Bifunctional Monomer Containing Differential Reactivity. Macromolecules 1993, 26, 2842–2846. DOI: 10.1021/ma00063a032.
Hiraguri, Y.; Endo, T. Incorporation of Ketone Group into Vinyl Polymers by Radical Copolymerization of 2,2-Diphenyl-Kmethylene-l,3-Dioxolane with Vinyl Monomers. J. Polym. Sci. C Polym. Lett. 1989, 27, 1–4. DOI: 10.1002/pol.1989.140270101.
Koizumi, T.; Hasegawa, Y.; Takata, T.; Endo, T. Synthesis and Photodegradation of Polyacrylonitrile Having Ketone Group Obtained from Radical Copolymerization of 2,2-Diphenyl-4-Methylene-1,3-Dioxolane with Acrylonitrile. J. Polym. Sci. A Polym. Chem. 1994, 32, 3193–3195. DOI: 10.1002/pola.1994.080321621.
Kashima, R.; Kajita, A.; Kubo, T.; Kamigaito, M.; Satoh, K. Hydrophilic Bio-Based Polymers by Radical Copolymerization of Cyclic Vinyl Ethers Derived from Glycerol. Chem. Commun. (Camb) 2022, 58, 8766–8769. DOI: 10.1039/d2cc02651a.
Jia, X.; Li, M.; Han, S.; Wang, C.; Wei, Y. Controlled Free Radical Double Ring-Opening Polymerization of 8,9-Benzo-2-Methylene-1,4,6-Trioxaspiro [4,4] Nonane. Mater. Lett. 1997, 31, 137–139. DOI: 10.1016/S0167-577X(96)00260-1.
Tardy, A.; Honoré, J.; Siri, D.; Nicolas, J.; Gigmes, D.; Lefay, C.; Guillaneuf, Y. A Comprehensive Kinetic Study of the Conventional Free-Radical Polymerization of Seven-Membered Cyclic Ketene Acetals. Polym. Chem. 2017, 8, 5139–5147. DOI: 10.1039/C7PY00337D.
Jackson, A. W. Reversible-Deactivation Radical Polymerization of Cyclic Ketene Acetals. Polym. Chem. 2020, 11, 3525–3545. DOI: 10.1039/D0PY00446D.
Folini, J.; Murad, W.; Mehner, F.; Meier, W.; Gaitzsch, J. Updating Radical Ring-Opening Polymerisation of Cyclic Ketene Acetals from Synthesis to Degradation. Eur. Polym. J. 2020, 134, 109851. DOI: 10.1016/j.eurpolymj.2020.109851.
Tardy, A.; Gil, N.; Plummer, C. M.; Siri, D.; Gigmes, D.; Lefay, C.; Guillaneuf, Y. Polyesters by a Radical Pathway: Rationalization of the Cyclic Ketene Acetal Efficiency. Angew. Chem. Int. Ed. Engl. 2020, 59, 14517–14526. DOI: 10.1002/anie.202005114.
Reddy Mothe, S.; Tan, J. S. J.; Chennamaneni, L. R.; Aidil, F.; Su, Y.; Kang, H. C.; Lim, F. C. H.; Thoniyot, P. A Systematic Investigation of the Ring Size Effects on the Free Radical Ring-Opening Polymerization (RROP) of Cyclic Ketene Acetal (CKA) Using Both Experimental and Theoretical Approach. J. Polym. Sci. 2020, 58, 1728–1738. DOI: 10.1002/pol.20200210.
Bailey, W. J.; Ni, Z.; Wu, S. R. Synthesis of Poly-ε-Caprolactone via a Free Radical Mechanism. Free Radical Ring-Opening Polymerization of 2-Methylene- 1,3-Dioxepane. J. Polym. Sci. Polym. Chem. Ed. 1982, 20, 3021–3030. DOI: 10.1002/pol.1982.170201101.
Jin, S.; Gonsalves, K. E. A Study of the Mechanism of the Free-Radical Ring-Opening Polymerization of 2-Methylene-1,3-Dioxepane. Macromolecules 1997, 30, 3104–3106. DOI: 10.1021/ma961590h.
Hiracuri, Y.; Tokiwa, Y. Synthesis of Copolymers Composed of 2-Methylene-1,3,6-Trioxocane and Vinyl Monomers and Their Enzymic Degradation. J. Polym. Sci. A Polym. Chem. 1993, 31, 3159–3163. DOI: 10.1002/pola.1993.080311233.
Hiraguri, Y.; Tokiwa, Y. Syntheses of Biodegradable Functional Polymers by Radical Ring-Opening Polymerization of 2-Methylene-1,3,6-Trioxocane. J. Polym. Environ. 2010, 18, 116–121. DOI: 10.1007/s10924-010-0175-2.
Bailey, W. J.; Wu, S.-R.; Ni, Z. Synthesis and Free Radical Ring-Opening Polymerization of 2-Methylene-4-Phenyl-1,3-Dioxolane. Makromol. Chem. 1982, 183, 1913–1920. DOI: 10.1002/macp.1982.021830811.
He, T.; Zou, Y. F.; Pan, C. Y. Controlled/"Living" Radical Ring-Opening Polymerization of 5,6-Benzo-2-Methylene-1,3-Dioxepane Based on Reversible Addition-Fragmentation Chain Transfer Mechanism. Polym. J. 2002, 34, 138–143. DOI: 10.1295/polymj.34.138.
Yuan, J. Y.; Pan, C. Y.; Tang, B. Z. “Living” Free Radical Ring-Opening Polymerization of 5,6-Benzo-2-Methylene-1,3-Dioxepane Using the Atom Transfer Radical Polymerization Method. Macromolecules 2001, 34, 211–214. DOI: 10.1021/ma0004099.
Tardy, A.; Delplace, V.; Siri, D.; Lefay, C.; Harrisson, S. D.; Fatima Albergaria Pereira, B.; Charles, L.; Gigmes, D.; Nicolas, J.; Guillaneuf, Y. Scope and Limitations of the Nitroxide-Mediated Radical Ring-Opening Polymerization of Cyclic Ketene Acetals. Polym. Chem. 2013, 4, 4776–4787. DOI: 10.1039/c3py00719g.
Delplace, V.; Guégain, E.; Harrisson, S.; Gigmes, D.; Guillaneuf, Y.; Nicolas, J. A Ring to Rule Them All: A Cyclic Ketene Acetal Comonomer Controls the Nitroxide-Mediated Polymerization of Methacrylates and Confers Tunable Degradability. Chem. Commun. 2015, 51, 12847–12850. DOI: 10.1039/C5CC04610F.
Delplace, V.; Harrisson, S.; Tardy, A.; Gigmes, D.; Guillaneuf, Y.; Nicolas, J. Nitroxide-Mediated Radical Ring-Opening Copolymerization: Chain-End Investigation and Block Copolymer Synthesis. Macromol. Rapid Commun. 2014, 35, 484–491. DOI: 10.1002/marc.201300809.
Delplace, V.; Tardy, A.; Harrisson, S.; Mura, S.; Gigmes, D.; Guillaneuf, Y.; Nicolas, J. Degradable and Comb-like PEG-Based Copolymers by Nitroxide-Mediated Radical Ring-Opening Polymerization. Biomacromolecules 2013, 14, 3769–3779. DOI: 10.1021/bm401157g.
Bell, C. A.; Hedir, G. G.; O'Reilly, R. K.; Dove, A. P. Controlling the Synthesis of Degradable Vinyl Polymers by Xanthate-Mediated Polymerization. Polym. Chem. 2015, 6, 7447–7454. DOI: 10.1039/C5PY01156F.
Ding, D.; Pan, X.; Zhang, Z.; Li, N.; Zhu, J.; Zhu, X. A Degradable Copolymer of 2-Methylene- 1,3-Dioxepane and Vinyl Acetate by Photo-Induced Cobalt-Mediated Radical Polymerization. Polym. Chem. 2016, 7, 5258–5264. DOI: 10.1039/C6PY01061J.
Zeng, T.; You, Y.; Zeng, T.; You, W.; Chen, G.; Nie, X.; Zhang, Z.; Xia, L.; Hong, C.; Chen, C. Degradable PE-Based Copolymer with Controlled Ester Structure Incorporation by Cobalt-Mediated Radical Copolymerization under Mild Condition. Iscience 2020, 23, 100904. DOI: 10.1016/j.isci.2020.100904.
Hedir, G. G.; Bell, C. A.; O'Reilly, R. K.; Dove, A. P. Functional Degradable Polymers by Radical Ring-Opening Copolymerization of MDO and Vinyl Bromobutanoate: Synthesis, Degradability and Post-Polymerization Modification. Biomacromolecules 2015, 16, 2049–2058. DOI: 10.1021/acs.biomac.5b00476.
Tardy, A.; Honoré, J.-C.; Tran, J.; Siri, D.; Delplace, V.; Bataille, I.; Letourneur, D.; Perrier, J.; Nicoletti, C.; Maresca, M.; et al. Radical Copolymerization of Vinyl Ethers and Cyclic Ketene Acetals as a Versatile Platform to Design Functional Polyesters. Angew. Chem. 2017, 129, 16742–16747. DOI: 10.1002/ange.201707043.
Wais, U.; Chennamaneni, L. R.; Thoniyot, P.; Zhang, H.; Jackson, A. W. Main-Chain Degradable Star Polymers Comprised of PH-Responsive Hyperbranched Cores and Thermoresponsive Polyethylene Glycol-Based Coronas. Polym. Chem. 2018, 9, 4824–4839. DOI: 10.1039/C8PY01113C.
Kertsomboon, T.; Agarwal, S.; Chirachanchai, S. UCST-Type Copolymer through the Combination of Water- Soluble Polyacrylamide and Polycaprolactone-Like Polyester. Macromol. Rapid Commun. 2020, 41, 2000243. 2020, DOI: 10.1002/marc.202000243.
Folini, J.; Huang, C.-H.; Anderson, J. C.; Meier, W. P.; Gaitzsch, J. Novel Monomers in Radical Ring-Opening Polymerisation for Biodegradable and PH Responsive Nanoparticles. Polym. Chem. 2019, 10, 5285–5288. DOI: 10.1039/C9PY01103J.
Hedir, G.; Stubbs, C.; Aston, P.; Dove, A. P.; Gibson, M. I. Synthesis of Degradable Poly(Vinyl Alcohol) by Radical Ring-Opening Copolymerization and Ice Recrystallization Inhibition Activity. ACS Macro Lett. 2017, 6, 1404–1408. DOI: 10.1021/acsmacrolett.7b00905.
Undin, J.; Finne-Wistrand, A.; Albertsson, A. C. Adjustable Degradation Properties and Biocompatibility of Amorphous and Functional Poly(Ester-Acrylate)-Based Materials. Biomacromolecules 2014, 15, 2800–2807. DOI: 10.1021/bm500689g.
Undin, J.; Illanes, T.; Finne-Wistrand, A.; Albertsson, A. C. Random Introduction of Degradable Linkages into Functional Vinyl Polymers by Radical Ring-Opening Polymerization, Tailored for Soft Tissue Engineering. Polym. Chem. 2012, 3, 1260–1266. DOI: 10.1039/c2py20034a.
Yang, Y.; Yu, K.; Liu, S.; Yan, J.; Lai, H.; Xing, F.; Xiao, P. Radical Ring-Opening Single Unit Monomer Insertion：an Approach to Degradable and Biocompatible Sequence-Defined Oligomers. Macromolecules 2021, 54, 10923–10930. DOI: 10.1021/acs.macromol.1c01991.
Bailey, W. J.; Endo, T.; Gapud, B.; Lin, Y.-N.; Ni, Z.; Pan, C.-Y.; Shaffer, S. E.; Wu, S.-R.; Yamazaki, N.; Yonezawa, K. Synthesis of Functionally-Terminated Oligomers by Free Radical Ring-Opening Polymerization. J. Macromol. Sci. Part A - Chem. Pure Appl. Chem. 1984, 21, 979–995. DOI: 10.1080/00222338408056586.
Wickel, H.; Agarwal, S.; Greiner, A. Homopolymers and Random Copolymers of 5,6-Benzo-2-Methylene-1,3-Dioxepane and Methyl Methacrylate: Structural Characterization Using 1D and 2D NMR. Macromolecules 2003, 36, 2397–2403. DOI: 10.1021/ma025983u.
Agarwal, S. Microstructural Characterization and Properties Evaluation of Poly (Methyl Methacrylate-Co-Ester)S. Polym. J. 2007, 39, 163–174. DOI: 10.1295/polymj.PJ2006137.
Yuan, J. Y.; Pan, C. Y. “Living” Free Radical Ring-Opening Copolymerization of 4,7-Dimethyl-2-Methylene-1,3-Dioxepane and Conventional Vinyl Monomers. Eur. Polym. J. 2002, 38, 2069–2076. DOI: 10.1016/S0014-3057(02)00085-X.
Ren, L.; Agarwal, S. S. Synthesis, Characterization, and Properties Evaluation of Poly[(N-Isopropylacrylamide)-Co-Ester]S. Macromol. Chem. Phys. 2007, 208, 245–253. DOI: 10.1002/macp.200600484.
Agarwal, S.; Kumar, R.; Kissel, T.; Reul, R. Synthesis of Degradable Materials Based on Caprolactone and Vinyl Acetate Units Using Radical Chemistry. Polym. J. 2009, 41, 650–660. DOI: 10.1295/polymj.PJ2009091.
Hill, M. R.; Kubo, T.; Goodrich, S. L.; Figg, C. A.; Sumerlin, B. S. Alternating Radical Ring-Opening Polymerization of Cyclic Ketene Acetals: Access to Tunable and Functional Polyester Copolymers. Macromolecules 2018, 51, 5079–5084. DOI: 10.1021/acs.macromol.8b00889.
Tardy, A.; Gil, N.; Plummer, C. M.; Zhu, C.; Harrisson, S.; Siri, D.; Nicolas, J.; Gigmes, D.; Guillaneuf, Y.; Lefay, C. DFT-Calculation-Assisted Prediction of the Copolymerization between Cyclic Ketene Acetals and Traditional Vinyl Monomers. Polym. Chem. 2020, 11, 7159–7169. DOI: 10.1039/D0PY01179G.
Lai, H.; Ouchi, M. M. Backbone-Degradable Polymers via Radical Copolymerizations of Pentafluorophenyl Methacrylate with Cyclic Ketene Acetal：Pendant Modification and Efficient Degradation by Alternating-Rich Sequence. ACS Macro Lett. 2021, 10, 1223–1228. DOI: 10.1021/acsmacrolett.1c00513.
Cui, H.; Liu, Y.; Cheng, Y.; Zhang, Z.; Zhang, P.; Chen, X.; Wei, Y. In Vitro Study of Electroactive Tetraaniline-Containing Thermosensitive Hydrogels for Cardiac Tissue Engineering. Biomacromolecules 2014, 15, 1115–1123. DOI: 10.1021/bm4018963.
Jin, Q.; Maji, S.; Agarwal, S. Novel Amphiphilic, Biodegradable, Biocompatible, Cross-Linkable Copolymers: Synthesis, Characterization and Drug Delivery Applications. Polym. Chem. 2012, 3, 2785–2793. DOI: 10.1039/c2py20364b.
Zhang, Y.; Zheng, M.; Kissel, T.; Agarwal, S. Design and Biophysical Characterization of Bioresponsive Degradable Poly(Dimethylaminoethyl Methacrylate) Based Polymers for in Vitro DNA Transfection. Biomacromolecules 2012, 13, 313–322. DOI: 10.1021/bm2015174.
Yang, Y.; Shi, K.; Yu, K.; Xing, F.; Lai, H.; Zhou, Y.; Xiao, P. Degradable Hydrogel Adhesives with Enhanced Tissue Adhesion, Superior Self-Healing, Cytocompatibility, and Antibacterial Property. Adv. Healthcare Mater. 2022, 11, 2, 2101504. DOI: 10.1002/adhm.202101504.
Dai, G.; Xie, Q.; Ma, C.; Zhang, G. G. Biodegradable Poly(Ester-Co-Acrylate) with Antifoulant Pendant Groups for Marine anti-Biofouling. ACS Appl. Mater. Interfaces 2019, 11, 11947–11953. DOI: 10.1021/acsami.9b01247.
Oh, X. Y.; Ge, Y.; Goto, A. Synthesis of Degradable and Chemically Recyclable Polymers Using 4,4-Disubstituted Five-Membered Cyclic Ketene Hemiacetal Ester (CKHE) Monomers. Chem. Sci. 2021, 12, 13546–13556. DOI: 10.1039/d1sc03560f.
Kazama, A.; Kohsaka, Y. Radical Polymerization of “Dehydroaspirin” with the Formation of a Hemiacetal Ester Skeleton: A Hint for Recyclable Vinyl Polymers. Polym. Chem. 2019, 10, 2764–2768. DOI: 10.1039/C9PY00474B.
Kobayashi, S.; Kadokawa, J.; Matsumura, Y.; Yen, I. F.; Uyama, H. Radical Copolymerization of 2-MEm-1,3-Dithiane with Styrene and Methyl Methacrylate. J. Macromol. Sci. Part A 1992, 29, 243–250. S3 DOI: 10.1080/10101329208054589.
Kobayashi, S.; Kadokawa, J.; Shoda, S.; Uyama, H. Radical Polymerization of 2-Methylene-1,3-Dithiane. J. Macromol. Sci. Part A–Chem. 1991, 28, 1–5. DOI: 10.1080/00222339108054376.