The Quest for Converting Biorenewable Bifunctional α-Methylene-γ-butyrolactone into Degradable and Recyclable Polyester: Controlling Vinyl-Addition/Ring-Opening/Cross-Linking Pathways
Abstract
α-Methylene-γ-butyrolactone (MBL), a naturally occurring and biomass-sourced bifunctional monomer, contains both a highly reactive exocyclic C═C bond and a highly stable five-membered γ-butyrolactone ring. Thus, all previous work led to exclusive vinyl-addition polymerization (VAP) product P(MBL) VAP . Now, this work reverses this conventional chemoselectivity to enable the first ring-opening polymerization (ROP) of MBL, thereby producing exclusively unsaturated polyester P(MBL) ROP with M n up to 21.0 kg/mol. This elusive goal was achieved through uncovering the thermodynamic, catalytic, and processing conditions. A third reaction pathway has also been discovered, which is a crossover propagation between VAP and ROP processes, thus affording cross-linked polymer P(MBL) CLP . The formation of the three types of polymers, P(MBL) VAP, P(MBL) CLP, and P(MBL) ROP, can be readily controlled by adjusting the catalyst (La)/initiator (ROH) ratio, which is determined by the unique chemoselectivity of the La–X (X = OR, NR 2, R) group. The resulting P(MBL) ROP is degradable and can be readily postfunctionalized into cross-linked or thiolated materials but, more remarkably, can also be fully recycled back to its monomer thermochemically. Computational studies provided the theoretical basis for, and a mechanistic understanding of, the three different polymerization processes and the origin of the chemoselectivity.
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?
These monomers can undergo polymerizations at both the alkene and ester site, making them potential substitutes for petroleum-based polyacrylates and polyesters.
“These monomers can undergo polymerizations at both the alkene and ester site, making them potential substitutes for petroleum-based polyacrylates and polyesters.176,177”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [177]
Using similar conditions (-60 °C, Ln/ROH = 1/3) to that of γ-BL, they were able to achieve the selective ROP of MBL to produce poly(MBL) with Mn up to 21 kDa, which can be facilely recycled back to the monomer MBL by heating the polymer ≥ 100 °C for 1 h in the presence of catalysts.
“Using similar conditions (-60 °C, Ln/ROH = 1/3) to that of γ-BL, they were able to achieve the selective ROP of MBL to produce poly(MBL) with Mn up to 21 kDa, which can be facilely recycled back to the monomer MBL by heating the polymer ≥ 100 °C for 1 h in the presence of catalysts.”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [177]
Cites
Hoyle, C. E., & Bowman, C. N. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200903924 · Cited by 4,209 · see citing works
Recent Developments in Ring Opening Polymerization of Lactones for Biomedical Applications
Albertsson, A.-C., & Varma, I. K. (2003) · Biomacromolecules · doi:10.1021/bm034247a · Cited by 1,582 · see citing works
‘Click’ Chemistry in Polymer and Materials Science
Binder, W. H., & Sachsenhofer, R. (2007) · Macromolecular Rapid Communications · doi:10.1002/marc.200600625 · Cited by 1,560 · see citing works
Organocatalytic Ring-Opening Polymerization
Kamber, N. E., Jeong, W., Waymouth, R. M., Pratt, R. C., Lohmeijer, B. G. G., & Hedrick, J. L. (2007) · Chemical Reviews · doi:10.1021/cr068415b · Cited by 1,489 · see citing works
Plant oil renewable resources as green alternatives in polymer science
Meier, M. A. R., Metzger, J. O., & Schubert, U. S. (2007) · Chemical Society Reviews · doi:10.1039/b703294c · Cited by 1,487 · see citing works
Applications of Orthogonal “Click” Chemistries in the Synthesis of Functional Soft Materials
Iha, R. K., Wooley, K. L., Nyström, A. M., Burke, D. J., Kade, M. J., & Hawker, C. J. (2009) · Chemical Reviews · doi:10.1021/cr900138t · Cited by 1,468 · see citing works
Polymers from Renewable Resources: A Challenge for the Future of Macromolecular Materials
Gandini, A. (2008) · Macromolecules · doi:10.1021/ma801735u · Cited by 1,115 · see citing works
Polymers from Renewable Resources: A Perspective for a Special Issue of Polymer Reviews
Williams, C. K., & Hillmyer, M. A. (2008) · Journal of macromolecular science. Part C, Reviews in macromolecular chemistry and physics/Journal of macromolecular science. Reviews in macromolecular chemistry and physics · doi:10.1080/15583720701834133 · Cited by 979 · see citing works
Organocatalysis: Opportunities and Challenges for Polymer Synthesis
Kiesewetter, M. K., Shin, E. J., Hedrick, J. L., & Waymouth, R. M. (2010) · Macromolecules · doi:10.1021/ma9025948 · Cited by 907 · see citing works
Polymerization of lactide and related cyclic esters by discrete metal complexes
O'Keefe, B. J., Hillmyer, M. A., & Tolman, W. B. (2001) · Journal of the Chemical Society, Dalton Transactions · doi:10.1039/b104197p · Cited by 825 · see citing works
Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production
Delidovich, I., Hausoul, P. J. C., Deng, L., Pfützenreuter, R., Rose, M., & Palkovits, R. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00354 · Cited by 773 · see citing works
‘Click’ Chemistry in Polymer and Material Science: An Update
Binder, W. H., & Sachsenhofer, R. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800089 · Cited by 756 · see citing works
Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides
Gandini, A., Lacerda, T. M., Carvalho, A. J. F., & Trovatti, E. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00264 · Cited by 755 · see citing works
Hong, M., & Chen, E. Y.-X. (2016) · Nature Chemistry · doi:10.1038/nchem.2391 · Cited by 677 · see citing works
Self-citationSynthesis and Biological Activity of α‐Methylene‐γ‐butyrolactones
Hoffmann, H. M. R., & Rabe, J. P. (1985) · Angewandte Chemie International Edition in English · doi:10.1002/anie.198500941 · Cited by 653 · see citing works
Aliphatic Polyester Block Polymers: Renewable, Degradable, and Sustainable
Hillmyer, M. A., & Tolman, W. B. (2014) · Accounts of Chemical Research · doi:10.1021/ar500121d · Cited by 635 · see citing works
“Clicking” Polymers or Just Efficient Linking: What Is the Difference?
Barner‐Kowollik, C., Prez, F. D., Espeel, P., et al. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201003707 · Cited by 632 · see citing works
From monomers to polymers from renewable resources: Recent advances
Gandini, A., & Lacerda, T. M. (2015) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2014.11.002 · Cited by 621 · see citing works
Thermal decomposition of biodegradable polyesters—II. Poly(lactic acid)
Kopinke, F.-D., Remmler, M., Mackenzie, K., Möder, M., & Wachsen, O. (1996) · Polymer Degradation and Stability · doi:10.1016/0141-3910(96)00102-4 · Cited by 614 · see citing works
Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆
JEROME, C., & LECOMTE, P. (2008) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2008.02.008 · Cited by 590 · see citing works
Modern Polyesters: Chemistry and Technology of Polyesters and Copolyesters
(2004) · Wiley eBooks · doi:10.1002/0470090685 · Cited by 590 · see citing works
Coordination Polymerization of Polar Vinyl Monomers by Single-Site Metal Catalysts
Chen, E. Y. ‐. (2009) · Chemical Reviews · doi:10.1021/cr9000258 · Cited by 576 · see citing works
Self-citationThe quest for sustainable polyesters – insights into the future
Vilela, C., Sousa, A. F., Fonseca, A. C., Serra, A. C., Coelho, J. F. J., Freire, C. S. R., & Silvestre, A. J. D. (2014) · Polym. Chem. · doi:10.1039/c3py01213a · Cited by 527 · see citing works
Group transfer polymerization - polymerization of acrylic monomers
Sogah, D. Y., Hertler, W. R., Webster, O. W., et al. (1987) · Macromolecules · doi:10.1021/ma00173a006 · Cited by 511 · see citing works
Aliphatic Polyesters: Synthesis, Properties and Applications
Albertsson, A., & Varma, I. K. (2002) · Advances in polymer science · doi:10.1007/3-540-45734-8_1 · Cited by 507 · see citing works
The Renaissance of α‐Methylene‐γ‐butyrolactones: New Synthetic Approaches
Kitson, R. R. A., Millemaggi, A., & Taylor, R. J. K. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200903108 · Cited by 456 · see citing works
Catalytic synthesis of α-methylene-γ-valerolactone: a biomass-derived acrylic monomer
Manzer, L. E. (2004) · Applied Catalysis A General · doi:10.1016/j.apcata.2004.05.048 · Cited by 441 · see citing works
Synthesis of biodegradable polymers from renewable resources
Tschan, M. J. ‐., Brûlé, E., Haquette, P., & Thomas, C. M. (2011) · Polymer Chemistry · doi:10.1039/c2py00452f · Cited by 426 · see citing works
Amgoune, A., Thomas, C. M., Roisnel, T., & Carpentier, J. (2005) · Chemistry - A European Journal · doi:10.1002/chem.200500856 · Cited by 424 · see citing works
McNeill, I. C., & Leiper, H. A. (1985) · Polymer Degradation and Stability · doi:10.1016/0141-3910(85)90035-7 · Cited by 404 · see citing works
Synthetic Polymers from Sugar-Based Monomers
Galbis, J. A., García‐Martín, M. D. G., de‐Paz, M. ‐., & Galbis, E. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00242 · Cited by 362 · see citing works
Zhang, Y., Miyake, G. M., & Chen, E. Y. ‐. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201005534 · Cited by 298 · see citing works
Self-citationSauer, A., Kapelski, A., Fliedel, C., Dagorne, S., Kol, M., & Okuda, J. (2013) · Dalton Transactions · doi:10.1039/c3dt00010a · Cited by 294 · see citing works
Liu, X., Shang, X., Tang, T., Hu, N., Pei, F., Cui, D., Chen, X., & Jing, X. (2007) · Organometallics · doi:10.1021/om0700359 · Cited by 289 · see citing works
Mecerreyes, D., Jérôme, R., & Dubois, P. (2007) · Advances in Polymer Science · doi:10.1007/3-540-49196-1_1 · Cited by 272 · see citing works
Ma, H., & Okuda, J. (2005) · Macromolecules · doi:10.1021/ma048284l · Cited by 270 · see citing works
Hong, M., & Chen, E. Y. ‐. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201601092 · Cited by 259 · see citing works
Self-citationMechanically triggered heterolytic unzipping of a low-ceiling-temperature polymer
Diesendruck, C. E., Peterson, G. I., Kulik, H. J., Kaitz, J. A., Mar, B. D., May, P. A., White, S. R., Martı́nez, T. J., Boydston, A. J., & Moore, J. S. (2014) · Nature Chemistry · doi:10.1038/nchem.1938 · Cited by 246 · see citing works
Thermodynamic Presynthetic Considerations for Ring-Opening Polymerization
Olsén, P., Odelius, K., & Albertsson, A.-C. (2016) · Biomacromolecules · doi:10.1021/acs.biomac.5b01698 · Cited by 244 · see citing works
Zhang, Y., Miyake, G. M., John, M. G., Falivene, L., Caporaso, L., Cavallo, L., & Chen, E. Y. ‐. (2012) · Dalton Transactions · doi:10.1039/c2dt30427a · Cited by 219 · see citing works
Self-citationChemically Recyclable Biobased Polyurethanes
Schneiderman, D. K., Vanderlaan, M. E., Mannion, A. M., Panthani, T. R., Batiste, D. C., Wang, J. Z., Bates, F. S., Macosko, C. W., & Hillmyer, M. A. (2016) · ACS Macro Letters · doi:10.1021/acsmacrolett.6b00193 · Cited by 213 · see citing works
Carpentier, J. (2010) · Macromolecular Rapid Communications · doi:10.1002/marc.201000114 · Cited by 192 · see citing works
A Virtual Issue ofMacromolecules: “Polymers from Renewable Resources”
Coates, G. W., & Hillmyer, M. A. (2009) · Macromolecules · doi:10.1021/ma902107w · Cited by 185 · see citing works
Carpentier, J. (2015) · Organometallics · doi:10.1021/acs.organomet.5b00540 · Cited by 183 · see citing works
Why δ-Valerolactone Polymerizes and γ-Butyrolactone Does Not
Houk, K. N., Jabbari, A., Hall, H. K., & Alemán, C. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo702567v · Cited by 176 · see citing works
Recent Developments in Ring-Opening Polymerization of Lactones
Lecomte, P., & Jérôme, C. (2011) · Advances in Polymer Science · doi:10.1007/12_2011_144 · Cited by 163 · see citing works
Coordination polymerization of heterocyclic and heterounsaturated monomers
Kuran, W. (1998) · Progress in Polymer Science · doi:10.1016/s0079-6700(97)00031-2 · Cited by 154 · see citing works
MacDonald, J. P., & Shaver, M. P. (2016) · Polymer Chemistry · doi:10.1039/c5py01606a · Cited by 146 · see citing works
Thermoplastic Elastomers Derived from Menthide and Tulipalin A
Shin, J., Lee, Y., Tolman, W. B., & Hillmyer, M. A. (2012) · Biomacromolecules · doi:10.1021/bm3012852 · Cited by 139 · see citing works
Probing Site Cooperativity of Frustrated Phosphine/Borane Lewis Pairs by a Polymerization Study
Xu, T., & Chen, E. Y. ‐. (2014) · Journal of the American Chemical Society · doi:10.1021/ja412445n · Cited by 137 · see citing works
Self-citationZhang, Y., & Chen, E. Y. ‐. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201108019 · Cited by 134 · see citing works
Self-citationThermodynamics and Kinetics of Ring‐Opening Polymerization
Duda, A., & Kowalski, A. (2009) · doi:10.1002/9783527628407.ch1 · Cited by 128 · see citing works
Atom Transfer Radical Polymerization of Tulipalin A: A Naturally Renewable Monomer
Mosnáček, J., & Matyjaszewski, K. A. (2008) · Macromolecules · doi:10.1021/ma8010813 · Cited by 127 · see citing works
Unsaturated Polyesters. Structure and Properties.
Cass, R. A. (1965) · Journal of the American Chemical Society · doi:10.1021/ja01088a051 · Cited by 126 · see citing works
Block and random copolymers of ε-caprolactone
Duda, A., Biela, T., Libiszowski, J., Penczek, S., Dúbois, P., Mecerreyes, D., & Jérôme, R. (1998) · Polymer Degradation and Stability · doi:10.1016/s0141-3910(97)00167-5 · Cited by 111 · see citing works
Poly(α-methylene-γ-butyrolactone) Synthesis, Configurational Structure, and Properties
Akkapeddi, M. K. (1979) · Macromolecules · doi:10.1021/ma60070a002 · Cited by 109 · see citing works
Zhang, Y., Schmitt, M., Falivene, L., Caporaso, L., Cavallo, L., & Chen, E. Y. ‐. (2013) · Journal of the American Chemical Society · doi:10.1021/ja4088677 · Cited by 100 · see citing works
Self-citationRing strain and polymerizability of cyclic esters
Saiyasombat, W., Molloy, R., Nicholson, T. M., Johnson, A. F., Ward, I. M., & Poshyachinda, S. (1998) · Polymer · doi:10.1016/s0032-3861(97)10370-6 · Cited by 93 · see citing works
Thermodynamic Control of the Polymerizability of Five-, Six-, and Seven-Membered Lactones
Alemán, C., Betran, O., Casanovas, J., Houk, K. N., & Hall, H. K. (2009) · The Journal of Organic Chemistry · doi:10.1021/jo9010969 · Cited by 89 · see citing works
Miyake, G. M., Zhang, Y., & Chen, E. Y. ‐. (2010) · Macromolecules · doi:10.1021/ma100615t · Cited by 89 · see citing works
Self-citationMosnáček, J., Yoon, J. A., Juhari, A., Koynov, K., & Matyjaszewski, K. A. (2009) · Polymer · doi:10.1016/j.polymer.2009.02.037 · Cited by 84 · see citing works
Duda, A., Penczek, S., Dúbois, P., Mecerreyes, D., & Jérôme, R. (1996) · Macromolecular Chemistry and Physics · doi:10.1002/macp.1996.021970408 · Cited by 77 · see citing works
Biomass Derivatives: A Sustainable Source of Chemicals
Manzer, L. E. (2006) · ACS symposium series · doi:10.1021/bk-2006-0921.ch004 · Cited by 76 · see citing works
Hong, M., & Chen, E. Y. ‐. (2014) · Macromolecules · doi:10.1021/ma5007717 · Cited by 73 · see citing works
Self-citationPolymerization of (RS)- and (R)-α-methylene-γ-methyl-γ-butyrolactone
Suenaga, J., Sutherlin, D. M., & STILLE, J. K. (1984) · Macromolecules · doi:10.1021/ma00142a080 · Cited by 72 · see citing works
Bicomponent Transparent Polyester Networks with Shape Memory Effect
Zhou, J., Schmidt, A. M., & Ritter, H. (2009) · Macromolecules · doi:10.1021/ma901402a · Cited by 72 · see citing works
Juhari, A., Mosnáček, J., Yoon, J. A., Nese, A., Koynov, K., Kowalewski, T., & Matyjaszewski, K. A. (2010) · Polymer · doi:10.1016/j.polymer.2010.08.017 · Cited by 70 · see citing works
Zhang, Y., Gustafson, L. O., & Chen, E. Y. ‐. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2053573 · Cited by 70 · see citing works
Self-citationEvaluation of methylene lactone monomers in dental resins
Stansbury, J. W., & Antonucci, J. M. (1992) · Dental Materials · doi:10.1016/0109-5641(92)90098-w · Cited by 57 · see citing works
Chen, X., Caporaso, L., Cavallo, L., & Chen, E. Y. ‐. (2012) · Journal of the American Chemical Society · doi:10.1021/ja301811s · Cited by 57 · see citing works
Self-citationThe free radical copolymerization characteristics of α-methylene γ-butyrolactone
Akkapeddi, M. K. (1979) · Polymer · doi:10.1016/0032-3861(79)90145-9 · Cited by 56 · see citing works
Radical‐initiated homo‐ and copolymerization of α‐methylene‐γ‐butyrolactone
Ueda, M., Takahashi, M., Imai, Y., et al. (1982) · Journal of Polymer Science Polymer Chemistry Edition · doi:10.1002/pol.1982.170201008 · Cited by 56 · see citing works
Uyama, H., Kobayashi, S., Morita, M., Habaue, S., & Okamoto, Y. (2001) · Macromolecules · doi:10.1021/ma010893v · Cited by 52 · see citing works
Qi, G., Nolan, M., Schork, F. J., et al. (2008) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.22909 · Cited by 47 · see citing works
Hu, Y., Xu, X. F., Zhang, Y., et al. (2010) · Macromolecules · doi:10.1021/ma101901y · Cited by 45 · see citing works
Anionic polymerization of MMA and renewable methylene butyrolactones by resorbable potassium salts
Hu, Y., Gustafson, L. O., Zhu, H., & Chen, E. Y. ‐. (2011) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.24628 · Cited by 44 · see citing works
Self-citationChen, J., & Chen, E. (2015) · Molecules · doi:10.3390/molecules20069575 · Cited by 43 · see citing works
Self-citationSemirigid Biobased Polymer Brush: Poly(α-methylene-γ-butyrolactone) Brushes
Higaki, Y., Okazaki, R., & Takahara, A. (2012) · ACS Macro Letters · doi:10.1021/mz3002148 · Cited by 42 · see citing works
Biobased Polymers from Plant-Derived Tulipalin A
Agarwal, S., Jin, Q., & Maji, S. (2012) · ACS symposium series · doi:10.1021/bk-2012-1105.ch013 · Cited by 41 · see citing works
Synthesis of β-methyl-α-methylene-γ-butyrolactone from biorenewable itaconic acid
Gowda, R. R., & Chen, E. Y. ‐. (2014) · Organic Chemistry Frontiers · doi:10.1039/c3qo00089c · Cited by 36 · see citing works
Self-citationVobecka, Z., Wei, C., Tauer, K., et al. (2015) · Polymer · doi:10.1016/j.polymer.2015.04.074 · Cited by 36 · see citing works
Organocatalytic and Chemoselective Polymerization of Multivinyl-Functionalized γ-Butyrolactones
Gowda, R. R., & Chen, E. Y. ‐. (2016) · ACS Macro Letters · doi:10.1021/acsmacrolett.6b00370 · Cited by 36 · see citing works
Self-citationFree Radical Copolymerization Kinetics of γ-Methyl-α-methylene-γ-butyrolactone (MeMBL)
Cockburn, R. A., Siegmann, R., Payne, K. A., et al. (2011) · Biomacromolecules · doi:10.1021/bm200400s · Cited by 34 · see citing works
Radical‐initiated polymerization of β‐methyl‐α‐methylene‐γ‐butyrolactone
Pittman, C. U., & Lee, H. (2003) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.10719 · Cited by 33 · see citing works
Schmitt, M., Falivene, L., Caporaso, L., Cavallo, L., & Chen, E. Y. ‐. (2014) · Polymer Chemistry · doi:10.1039/c3py01579c · Cited by 33 · see citing works
Self-citationGowda, R. R., & Chen, E. Y. ‐. (2013) · Dalton Transactions · doi:10.1039/c3dt50430a · Cited by 28 · see citing works
Self-citationMullin, R. (2004) · Chemical & Engineering News · doi:10.1021/cen-v082n045.p029 · Cited by 28 · see citing works
Hu, Y., Wang, X., Chen, Y., et al. (2013) · Organometallics · doi:10.1021/om301128g · Cited by 27 · see citing works
Sustainable Polymers from Biomass‐Derived α‐Methylene‐γ‐Butyrolactones
Gowda, R. R., & Chen, E. Y. ‐. (2013) · Encyclopedia of Polymer Science and Technology · doi:10.1002/0471440264.pst606 · Cited by 22 · see citing works
Self-citationGowda, R. R., Caporaso, L., Cavallo, L., et al. (2014) · Organometallics · doi:10.1021/om500661y · Cited by 11 · see citing works
Self-citationSynthesis and Characterization of Tulipalin-Based Polymers
Lee, C., & Song, K. E. (2014) · Asian Journal of Chemistry · doi:10.14233/ajchem.2014.17098 · Cited by 6 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Catalysis as an Enabling Science for Sustainable Polymers
Zhang, X., Fevre, M., Jones, G. O., & Waymouth, R. M. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00329 · Cited by 936 · see citing works
Chemically recyclable polymers: a circular economy approach to sustainability
Hong, M., & Chen, E. Y.-X. (2017) · Green Chemistry · doi:10.1039/c7gc01496a · Cited by 876 · see citing works
Self-citationA synthetic polymer system with repeatable chemical recyclability
Zhu, J.-B., Watson, E. M., Tang, J., & Chen, E. Y.-X. (2018) · Science · doi:10.1126/science.aar5498 · Cited by 709 · see citing works
Self-citationClosed-loop recycling of plastics enabled by dynamic covalent diketoenamine bonds
Christensen, P. R., Scheuermann, A. M., Loeffler, K. E., & Helms, B. A. (2019) · Nature Chemistry · doi:10.1038/s41557-019-0249-2 · Cited by 676 · see citing works
Bio-based polyesters: Recent progress and future prospects
Zhang, Q., Song, M., Xu, Y., Wang, W., Wang, Z., & Zhang, L. (2021) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2021.101430 · Cited by 433 · see citing works
Design principles for intrinsically circular polymers with tunable properties
Shi, C., Reilly, L. T., Phani Kumar, V. S., Coile, M. W., Nicholson, S. R., Broadbelt, L. J., Beckham, G. T., & Chen, E. Y.-X. (2021) · Chem · doi:10.1016/j.chempr.2021.10.004 · Cited by 219 · see citing works
Self-citationSynthetic biodegradable polyhydroxyalkanoates (PHAs): Recent advances and future challenges
Westlie, A. H., Quinn, E. C., Parker, C. R., & Chen, E. Y.-X. (2022) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2022.101608 · Cited by 166 · see citing works
Self-citationProgress in Catalytic Ring-Opening Polymerization of Biobased Lactones
Al-Shok, L., Haddleton, D. M., & Adams, F. (2022) · Advances in Polymer Science · doi:10.1007/12_2021_111 · Cited by 10 · see citing works
- Authors
- Tang, X., Hong, M., Falivene, L., Caporaso, L., Cavallo, L., & Chen, E. Y.-X.
- Affiliations
- Colorado State University (US)
- King Abdullah University of Science and Technology (SA)
- University of Salerno (IT)
- Corresponding author
- Cavallo, Luigi
- Chen, Eugene Y.-X.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-10-19
- Volume
- 138
- Issue
- 43
- Pages
- 14326-14337
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2529856920
- Semantic Scholar
- 34cbd0ec51cd436b9fa7ff598a57d1d7ce076c5f
- Cited by
- 179
- References
- 91
- Citations by year
- 2026: 10 · 2025: 16 · 2024: 28 · 2023: 25 · 2022: 25 · 2021: 16 · 2020: 13 · 2019: 13 · 2018: 19 · 2017: 13
- FWCI
- 6.14
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- King Abdullah University of Science and Technology Repository (King Abdullah University of Science and Technology) (submittedVersion)
- Funders
- Division of Chemistry (1300267)
- King Abdullah University of Science and Technology
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- α-methylene-γ-butyrolactones, ring-opening polymerization, vinyl addition polymerization, polymer networks, chemoselectivity, lanthanum catalyst, bio-based monomers, degradable polyesters, thiolation, polymerization mechanism, biomass-derived polymers
- MeSH terms
- Alkenes, Models, Molecular, Molecular Conformation, Polyesters, Thermodynamics, 4-Butyrolactone, Polymerization
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
