Ring size-reactivity relationship in radical ring-opening copolymerisation of thionolactones with vinyl pivalate
Open accessAbstract
The radical ring-opening copolymerisation of unsubstituted thionolactones of different ring sizes has been investigated. DFT calculations and experimental results show the importance of the stabilization of the intermediate ring-retained radical.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Very recently, a few reports on radical polymerizations of cyclic thiocarbonyl compounds indicated that some thionolactones were incorporated into a polymer as a mixture of ring-opened and cyclic structures with and without β-scission, depending on the monomer structure and polymerization conditions.
“Very recently, a few reports on radical polymerizations of cyclic thiocarbonyl compounds indicated that some thionolactones were incorporated into a polymer as a mixture of ring-opened and cyclic structures with and without β-scission, respectively, which depended on the monomer structure and the polymerization conditions.37−39”
From Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones (2023) · cites this paper as [39]
Cites
Grimme, S., Antony, J., Ehrlich, S., & Krieg, H. (2010) · The Journal of Chemical Physics · doi:10.1063/1.3382344 · Cited by 59,686 · see citing works
Atmospheric transport and deposition of microplastics in a remote mountain catchment
Allen, S., Allen, D., Phoenix, V. R., Roux, G. L., Durantez, P., Simonneau, A., Binet, S., & Galop, D. (2019) · Nature Geoscience · doi:10.1038/s41561-019-0335-5 · Cited by 2,469 · see citing works
Calculation of Solvation Free Energies of Charged Solutes Using Mixed Cluster/Continuum Models
Bryantsev, V. S., Diallo, M. S., & Goddard, W. A. (2008) · The Journal of Physical Chemistry B · doi:10.1021/jp802665d · Cited by 699 · see citing works
Choy, C. A., Robison, B. H., Gagné, T. O., Erwin, B., Firl, E., Halden, R. U., Hamilton, J. A., Katija, K., Lisin, S. E., Rolsky, C. B., et al. (2019) · Scientific Reports · doi:10.1038/s41598-019-44117-2 · Cited by 561 · see citing works
Tardy, A., Nicolas, J., Gigmes, D., Lefay, C., & Guillaneuf, Y. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00319 · Cited by 469 · see citing works
Degradable vinyl polymers for biomedical applications
Delplace, V., & Nicolas, J. (2015) · Nature Chemistry · doi:10.1038/nchem.2343 · Cited by 400 · see citing works
Radical Approach to Thioester-Containing Polymers
Smith, R. A., Fu, G., McAteer, O., Xu, M., & Gutekunst, W. R. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.8b12154 · Cited by 248 · see citing works
Thionation with the Reagent Combination of Phosphorus Pentasulfide and Hexamethyldisiloxane
Curphey, T. J. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo0256742 · Cited by 234 · see citing works
Yuan, P., Sun, Y., Xu, X., Luo, Y., & Hong, M. (2021) · Nature Chemistry · doi:10.1038/s41557-021-00817-9 · Cited by 183 · see citing works
Degradable vinyl copolymers through thiocarbonyl addition–ring-opening (TARO) polymerization
Bingham, N. M., & Roth, P. J. (2019) · Chemical Communications · doi:10.1039/c8cc08287a · Cited by 176 · see citing works
Bailey, W. J., Ni, Z., & Wu, S. R. (1982) · Macromolecules · doi:10.1021/ma00231a006 · Cited by 171 · see citing works
Structure and properties of polyurethanes based on halogenated and nonhalogenated soy-polyols
Petrovìć, Z. S., Guo, A., & Zhang, W. (2000) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/1099-0518(20001115)38:22 · Cited by 160 · see citing works
Mechanisms of hydrolysis of thioacetals
Satchell, D. P. N., & Satchell, R. S. (1990) · Chemical Society Reviews · doi:10.1039/cs9901900055 · Cited by 95 · see citing works
Spick, M. P., Bingham, N. M., Li, Y., de Jesus, J., Costa, C., Bailey, M. J., & Roth, P. J. (2020) · Macromolecules · doi:10.1021/acs.macromol.9b02497 · Cited by 89 · see citing works
Bingham, N. M., Nisa, Q. U., Chua, S. H. L., Fontugne, L., Spick, M. P., & Roth, P. J. (2020) · ACS Applied Polymer Materials · doi:10.1021/acsapm.0c00503 · Cited by 80 · see citing works
Galanopoulo, P., Gil, N., Gigmes, D., Lefay, C., Guillaneuf, Y., Lages, M., Nicolas, J., Lansalot, M., & D'Agosto, F. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202117498 · Cited by 73 · see citing works
Controlled Organocatalytic Ring-Opening Polymerization of ε-Thionocaprolactone
Datta, P. P., & Kiesewetter, M. K. (2016) · Macromolecules · doi:10.1021/acs.macromol.6b00136 · Cited by 66 · see citing works
Polyesters by a Radical Pathway: Rationalization of the Cyclic Ketene Acetal Efficiency
Tardy, A., Gil, N., Plummer, C. M., Siri, D., Gigmès, D., Lefay, C., & Guillaneuf, Y. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.202005114 · Cited by 61 · see citing works
Ivanchenko, O., Authesserre, U., Coste, G., Mazières, S., Destarac, M., & Harrisson, S. (2021) · Polymer Chemistry · doi:10.1039/d1py00080b · Cited by 56 · see citing works
Self-citationFree Radical Ring-Opening Polymerization of 4-n-Hexyl- and 4-n-Decyl-2-methylene-1,3-dioxolanes
Bailey, W. J., Wu, S., & Ni, Z. (1982) · Journal of Macromolecular Science Part A - Chemistry · doi:10.1080/00222338208077212 · Cited by 52 · see citing works
Anionic Ring-Opening Polymerization of ε-Thionocaprolactone
Sanda, F., Jirakanjana, D., Hitomi, M., & Endo, T. (1999) · Macromolecules · doi:10.1021/ma990977s · Cited by 50 · see citing works
Plummer, C. M., Gil, N., Dufils, P.-E., Wilson, D. J., Lefay, C., Gigmes, D., & Guillaneuf, Y. (2021) · ACS Applied Polymer Materials · doi:10.1021/acsapm.1c00569 · Cited by 45 · see citing works
Kamiki, R., Kubo, T., & Satoh, K. (2023) · Macromolecular Rapid Communications · doi:10.1002/marc.202200537 · Cited by 41 · see citing works
Mothe, S. R., Tan, J. S. J., Chennamaneni, L. R., Aidil, F., Su, Y., Kang, H. C., Lim, F. C. H., & Thoniyot, P. (2020) · Journal of Polymer Science · doi:10.1002/pol.20200210 · Cited by 39 · see citing works
Radical ring-opening polymerization of sustainably-derived thionoisochromanone
Prebihalo, E. A., Luke, A. M., Reddi, Y., LaSalle, C. J., Shah, V. M., Cramer, C. J., & Reineke, T. M. (2023) · Chemical Science · doi:10.1039/d2sc06040j · Cited by 35 · see citing works
First Example of Cationic Ring-Opening Polymerization of γ-Thionobutyrolactone
Kikuchi, H., Tsubokawa, N., & Endo, T. (2005) · Chemistry Letters · doi:10.1246/cl.2005.376 · Cited by 30 · see citing works
Lactide-derived monomers for radical thiocarbonyl addition ring-opening copolymerisation
Ivanchenko, O., Mazières, S., Harrisson, S., & Destarac, M. (2022) · Polymer Chemistry · doi:10.1039/d2py00893a · Cited by 29 · see citing works
Self-citationOrganocatalytic ring-opening polymerization of thionolactones: anything O can do, S can do better
Kalana, U. L. D. I., Datta, P. P., Hewawasam, R. S., Kiesewetter, E. T., & Kiesewetter, M. K. (2020) · Polymer Chemistry · doi:10.1039/d0py01393e · Cited by 19 · see citing works
Insertion of Degradable Thioester Linkages into Styrene and Methacrylate PolymersPreprint
Rix, M. F. I., Higgs, S. J., Dodd, E. M., Coles, S. J., Bingham, N. M., & Roth, P. J. (2022) · ChemRxiv · doi:10.26434/chemrxiv-2022-cdt52 · Cited by 13 · see citing works
Zaorska, E., Gawryś-Kopczyńska, M., Ostaszewski, R., Ufnal, M., & Koszelewski, D. (2021) · Bioorganic Chemistry · doi:10.1016/j.bioorg.2021.104650 · Cited by 5 · see citing works
Fritschi, S. P., Linden, A., & Heimgartner, H. (2016) · Helvetica Chimica Acta · doi:10.1002/hlca.201600023 · Cited by 4 · see citing works
Radical ring-opening polymerization of sustainably-derived thionoisochromanonePreprint
Prebihalo, E. A., Luke, A., Reddi, Y., et al. (2022) · ChemRxiv · doi:10.26434/chemrxiv-2022-rgl2d · Cited by 2 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Watanabe, H., & Kamigaito, M. (2023) · Journal of the American Chemical Society · doi:10.1021/jacs.3c01796 · Cited by 51 · see citing works
Rix, M. F. I., Collins, K., Higgs, S. J., Dodd, E. M., Coles, S. J., Bingham, N. M., & Roth, P. J. (2023) · Macromolecules · doi:10.1021/acs.macromol.3c01811 · Cited by 34 · see citing works
Ivanchenko, O., Mazières, S., Harrisson, S., & Destarac, M. (2023) · Macromolecules · doi:10.1021/acs.macromol.3c00312 · Cited by 22 · see citing works
Self-citationKuroda, K., & Ouchi, M. (2023) · Angewandte Chemie International Edition · doi:10.1002/anie.202316875 · Cited by 18 · see citing works
pH‐Controlled Reversible Folding of Copolymers via Formation of β‐sheet Secondary Structures
Sbordone, F., Micallef, A. S., & Frisch, H. (2024) · Angewandte Chemie International Edition · doi:10.1002/anie.202319839 · Cited by 13 · see citing works
Dardé, T., Diomar, E., Schultze, X., & Taton, D. (2024) · Angewandte Chemie International Edition · doi:10.1002/anie.202411249 · Cited by 13 · see citing works
Ivanchenko, O., & Destarac, M. (2023) · ACS Macro Letters · doi:10.1021/acsmacrolett.3c00676 · Cited by 12 · see citing works
Self-citationDegradable Vinyl-Based Polymers by Radical Ring-Opening Polymerization: A User Guide
Luzel, B., Kouider, S., D’Agosto, F., Gigmès, D., Lansalot, M., Bates, C. M., Ackerman, E., Labalme, S., Johnson, J. A., Niu, J., et al. (2026) · ACS Polymers Au · doi:10.1021/acspolymersau.5c00191 · Cited by 11 · see citing works
Backbone Degradable Polymers via Chain-growth Radical Polymerization
Lai, H., & Ouchi, M. (2025) · Chinese Journal of Polymer Science · doi:10.1007/s10118-025-3278-x · Cited by 11 · see citing works
Degradable N-Vinyl Copolymers through Radical Ring-Opening Polymerization of Cyclic Thionocarbamates
Calderón‐Díaz, A., Boggiano, A. C., Xiong, W. H., Kaiser, N., & Gutekunst, W. R. (2024) · ACS Macro Letters · doi:10.1021/acsmacrolett.4c00550 · Cited by 10 · see citing works
Li, J., Luo, Q., Lin, Y.-X., Xi, Z., & Zhao, L. (2025) · Current Opinion in Chemical Engineering · doi:10.1016/j.coche.2025.101131 · Cited by 6 · see citing works
Thioester-rich degradable copolymers from a thionolactone and S-vinyl and P-vinyl monomers
Hepburn, K. S., Zulkifli, N. S., Delorme, C., Kazmi, T., Bakar, R. A., & Roth, P. J. (2024) · Polymer · doi:10.1016/j.polymer.2024.127485 · Cited by 5 · see citing works
Ivanchenko, O., Mazières, S., Mallet‐Ladeira, S., Harrisson, S., & Destarac, M. (2024) · Macromolecules · doi:10.1021/acs.macromol.4c01259 · Cited by 5 · see citing works
Self-citationpH‐Controlled Reversible Folding of Copolymers via Formation of β‐sheet Secondary Structures
Sbordone, F., Micallef, A. S., & Frisch, H. (2024) · Angewandte Chemie · doi:10.1002/ange.202319839 · Cited by 5 · see citing works
Hepburn, K. S., & Roth, P. J. (2026) · Polymer Chemistry · doi:10.1039/d5py00805k · Cited by 3 · see citing works
Dithioketal Polymers Via Radical Polymerization of γ‐Dithiobutyrolactone
Odnoroh, M., Ivanchenko, O., Kroeger, A. A., Coote, M. L., Mazières, S., & Destarac, M. (2026) · Angewandte Chemie · doi:10.1002/ange.2024128 · Cited by 2 · see citing works
Self-citationNayak, S., Biswas, S., & Das, A. (2026) · Macromolecules · doi:10.1021/acs.macromol.5c03257 · Cited by 1 · see citing works
Dithioketal Polymers Via Radical Polymerization of γ‐Dithiobutyrolactone
Odnoroh, M., Ivanchenko, O., Kroeger, A. A., Coote, M. L., Mazières, S., & Destarac, M. (2026) · Angewandte Chemie International Edition · doi:10.1002/anie.2024128 · Cited by 1 · see citing works
Self-citationKuroda, K., & Ouchi, M. (2023) · Angewandte Chemie · doi:10.1002/ange.202316875 · Cited by 1 · see citing works
Dardé, T., Diomar, E., Schultze, X., & Taton, D. (2024) · Angewandte Chemie · doi:10.1002/ange.202411249
Dardé, T., Schultze, X., & Taton, D. (2025) · Journal of the American Chemical Society · doi:10.1021/jacs.5c17893
Deng, Y., Mehner, F., & Gaitzsch, J. (2026) · Elsevier eBooks · doi:10.1016/b978-0-323-95486-0.00202-7
- Authors
- Ivanchenko, O., Mazières, S., Poli, R., Harrisson, S., & Destarac, M.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Corresponding author
- Harrisson, Simon
- Destarac, Mathias
- Venue
- Polymer Chemistry
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2022
- Volume
- 13
- Issue
- 45
- Pages
- 6284-6292
- ISSN
- 1759-9954 (ISSN-L)
- 1759-9962
- OpenAlex
- W4312697934
- Cited by
- 22
- References
- 31
- Citations by year
- 2026: 6 · 2025: 3 · 2024: 7 · 2023: 6
- FWCI
- 1.52
- Type
- journal article
- Language
- en
- Open access
- green
- hal.science
- Licence
- Locations
- Polymer Chemistry (publishedVersion)
- HAL (submittedVersion, other-oa)
- Funders
- Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Photopolymerization techniques and applications
- Keywords
- thionolactones, vinyl pivalate, ring size, reactivity ratios, radical stabilization, copolymerization kinetics
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review