Controlled Ring-Opening Polymerization of ε-Caprolactone Promoted by “in Situ” Formed Yttrium Alkoxides

Martin, Eric; Dubois, Philippe; Jérôme, Robert

doi:10.1021/ma991045r

Cited by 144biodegradable polymer synthesis and propertiesAdvanced Polymer Synthesis and CharacterizationCarbon dioxide utilization in catalysis

Controlled Ring-Opening Polymerization of ε-Caprolactone Promoted by “in Situ” Formed Yttrium Alkoxides

Martin, Eric, Dubois, Philippe, Jérôme, Robert·2000·Macromolecules

DOI 10.1021/ma991045r

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Abstract

The ring-opening polymerization of ε-caprolactone has been initiated by [tris(hexamethyldisilyl)amide]yttrium in the presence of an excess of 2-propanol. This initiating system is very active even at high alcohol-to-Y molar ratio. Polymers with controlled molecular parameters ( M n, end groups) and low dispersity are formed as result of fast alkoxide/alcohol exchange. At molar excess of 2-propanol higher than 100, this exchange is no longer quantitative. The in situ formed active species involved in this new initiating system are different from those ones present in the commercial yttrium oxo-isopropoxide Y 5 (μ-O)(O i Pr) 13 cluster. Evidence is provided by 1 H NMR spectroscopy.

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Y[N(SiMe3)2]3 added with alcohol is able to initiate ROP by converting in situ the inactive yttrium precursor into active Y alkoxide.
“Commercially available tris(bis(trimethylsilyl)amido) yttrium (Y[N(SiMe 3 ) 2 ] 3 ) added with alcohol is able to initiate ROP by converting in situ the inactive yttrium precursor into active Y alkoxide [18].”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [18]
In the Y[N(SiMe3)2]3/alcohol system, Mn can be predicted from the monomer/alcohol molar ratio and the molecular weight distribution is narrow even at high monomer conversion.
“In addition to Mn, which can be predicted from the monomer/alcohol molar ratio, the molecular weight distribution is narrow even at high monomer conversion.”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [18]
At a molar excess of 50, all the alcohol molecules participate in the exchange and thus in the initiation of ε-CL polymerization at 20 °C.
“At a molar excess of 50, all the alcohol molecules participate to the exchange and thus to the initiation of ε-CL polymerization at 20 °C.”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [18]
The rapid exchange between the in situ-formed yttrium alkoxide and the alcohol allows the average number of initiated chains to be controlled by the excess of alcohol with respect to Y.
“The rapid exchange between the in situ-formed yttrium alkoxide and the alcohol allows the average number of the initiated chains to be controlled by the excess of alcohol with respect to Y.”
From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [18]

Macromolecular engineering of polylactones and polylactides. 4. Mechanism and kinetics of lactide homopolymerization by aluminum isopropoxide
Dúbois, P., Jacobs, C., Jérôme, R., & Teyssié, P. (1991) · Macromolecules · doi:10.1021/ma00009a022 · Cited by 477 · see citing works
Self-citation
Organolanthanide-Initiated Living Polymerizations of ε-Caprolactone, δ-Valerolactone, and β-Propiolactone
Yamashita, M., Takemoto, Y., Ihara, E., & Yasuda, H. (1996) · Macromolecules · doi:10.1021/ma951400n · Cited by 247 · see citing works
Macromolecular engineering of polylactones and polylactides. 5. Synthesis and characterization of diblock copolymers based on poly-iε-caprolactone and poly(L,L or D,L)lactide by aluminum alkoxides
Jacobs, C., Dúbois, P., Jérôme, R., & Teyssié, P. (1991) · Macromolecules · doi:10.1021/ma00011a001 · Cited by 218 · see citing works
Self-citation
Recent advances in alkoxo and aryloxo chemistry of scandium, yttrium and lanthanoids
Mehrotra, R. C., Singh, A., & Tripathi, U. M. (1991) · Chemical Reviews · doi:10.1021/cr00006a007 · Cited by 209 · see citing works
Chemistry of yttrium triisopropoxide revisited. Characterization and crystal structure of Y5(.mu.5-O)(.mu.3-OPr-iso)4(.mu.2-OPr-iso)4(OPr-iso)5
Poncelet, O. J. C., Sartain, W. J., Hubert-Pfalzgraf, L. G., Folting, K., & Caulton, K. G. (1989) · Inorganic Chemistry · doi:10.1021/ic00301a021 · Cited by 195 · see citing works
Synthesis, characterization, and miscibility of caprolactone random copolymers
Vion, J. M., Jérôme, R., Teyssié, P., Aubin, M., & Prud'homme, R. E. (1986) · Macromolecules · doi:10.1021/ma00161a009 · Cited by 162 · see citing works
Self-citation
Kinetics and Mechanism of l -Lactide Polymerization Using Two Different Yttrium Alkoxides as Initiators
Stevels, W. M., Ankoné, M. J. K., Dijkstra, P. J., & Feijén, J. (1996) · Macromolecules · doi:10.1021/ma9605311 · Cited by 158 · see citing works
Polymerization of .epsilon.-Caprolactone Initiated by Aluminum Isopropoxide Trimer and/or Tetramer
Duda, A., & Penczek, S. (1995) · Macromolecules · doi:10.1021/ma00122a001 · Cited by 155 · see citing works
Novel Rare Earth Catalysts for the Living Polymerization and Block Copolymerization of ε-Caprolactone
Shen, Y., Shen, Z., Zhang, Y., & Yao, K. (1996) · Macromolecules · doi:10.1021/ma9518060 · Cited by 152 · see citing works
Polylactones, 19. Anionic polymerization of <scp>L</scp>‐lactide in solution
Kricheldorf, H. R., & Kreiser‐Saunders, I. (1990) · Die Makromolekulare Chemie · doi:10.1002/macp.1990.021910508 · Cited by 149 · see citing works
Kinetics and Mechanism of ε-Caprolactone Polymerization Using Yttrium Alkoxides as Initiators
Stevels, W. M., Ankoné, M. J. K., Dijkstra, P. J., & Feijén, J. (1996) · Macromolecules · doi:10.1021/ma960701+ · Cited by 124 · see citing works
Pentanuclear oxoalkoxide clusters of scandium, yttrium, indium and ytterbium, X-ray crystal structures of [M5(μ5-O)(μ3-OPri)4(μ2-OPri)4(OPri)5] (M = In, Yb)
Bradley, D. C., Chudzynska, H., Frigo, D. M., Hammond, M. E., Hursthouse, M. B., & Mazid, M. A. (1990) · Polyhedron · doi:10.1016/s0277-5387(00)80281-8 · Cited by 119 · see citing works
Polymerization of lactones, 12. Polymerization of <scp>L</scp>‐dilactide and <scp>L,D</scp>‐dilactide in the presence of potassium methoxide
Jedliński, Z., Wałach, W., Kurcok, P., & Adamus, G. (1991) · Die Makromolekulare Chemie · doi:10.1002/macp.1991.021920914 · Cited by 116 · see citing works
Ring-Opening Polymerization of d , l -Lactide Using Rare-Earth μ-Oxo Isopropoxides as Initiator Systems
Šimić, V., Spassky, N., & Hubert-Pfalzgraf, L. G. (1997) · Macromolecules · doi:10.1021/ma970615p · Cited by 114 · see citing works
Well defined block copolymers of ε‐caprolactone and L ‐lactide using Y5(μ‐O)(OiPr)13 as an initiator
Stevels, W. M., Ankoné, M. J. K., Dijkstra, P. J., & Feijén, J. (1995) · Macromolecular Chemistry and Physics · doi:10.1002/macp.1995.021960415 · Cited by 96 · see citing works
Polymerization of ε-Caprolactone Initiated by Aluminum Isopropoxide Carried Out in the Presence of Alcohols and Diols. Kinetics and Mechanism
Duda, A. (1996) · Macromolecules · doi:10.1021/ma951442b · Cited by 91 · see citing works
Macromolecular engineering of polylactones and polylactides. 14. A carbon-13 and aluminum-27 NMR study of the effect of .gamma.-butyrolactone on the structure of aluminum isopropoxide in toluene
Ropson, N., Dúbois, P., Jérôme, R., & Teyssié, P. (1993) · Macromolecules · doi:10.1021/ma00076a012 · Cited by 54 · see citing works
Self-citation
Ring Opening Polymerization of ε-Caprolactone by Rare Earth Alkoxide–CCl4 Systems
Shen, Y., Shen, Z., Zhang, F., & Zhang, Y. (1995) · Polymer Journal · doi:10.1295/polymj.27.59 · Cited by 45 · see citing works
Telechelic poly(ε‐caprolactone) terminated at both ends with OH groups and its derivatization
Sosnowski, S., Słomkowski, S., Penczek, S., & Florjańczyk, Z. (1991) · Die Makromolekulare Chemie · doi:10.1002/macp.1991.021920701 · Cited by 29 · see citing works
Reaction of (Cp2*LnH)2 (LnY, La) and Cp2* Y(2‐C6H4CH2NME2) with esters and amides and molecular structure of [Cp2* Y (μ‐OCMeCHC(OEt)O)]2
Deelman, B., Wierda, F., Meetsma, A., & Teuben, J. H. (1995) · Applied Organometallic Chemistry · doi:10.1002/aoc.590090518 · Cited by 13 · see citing works
Polymerization of ethylene oxide using yttrium isopropoxide
Choi, Y. K., Stevels, W. M., Ankoné, M. J. K., Dijkstra, P. J., Kim, S. W., & Feijén, J. (1996) · Macromolecular Chemistry and Physics · doi:10.1002/macp.1996.021971111 · Cited by 5 · see citing works

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Synthesis of polycaprolactone: A review
Labet, M., & Thielemans, W. (2009) · Chemical Society Reviews · doi:10.1039/b820162p · Cited by 1,673 · 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
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
Metal-catalyzed immortal ring-opening polymerization of lactones, lactides and cyclic carbonates
Ajellal, N., Carpentier, J.-F., Guillaume, C., Guillaume, S. M., Helou, M., Poirier, V., Sarazin, Y., & Trifonov, A. (2010) · Dalton Transactions · doi:10.1039/c001226b · Cited by 494 · see citing works
Recent developments in organolanthanide polymerization catalysts
Hou, Z., & Wakatsuki, Y. (2002) · Coordination Chemistry Reviews · doi:10.1016/s0010-8545(02)00111-x · Cited by 444 · see citing works
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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
Kinetics and Mechanism of l -Lactide Polymerization by Rare Earth Metal Silylamido Complexes: Effect of Alcohol Addition
Ma, H., & Okuda, J. (2005) · Macromolecules · doi:10.1021/ma048284l · Cited by 270 · see citing works
A Novel and Versatile Calcium-Based Initiator System for the Ring-Opening Polymerization of Cyclic Esters
Zhong, Z., Dijkstra, P. J., Birg, C., Westerhausen, M., & Feijén, J. (2001) · Macromolecules · doi:10.1021/ma0019510 · Cited by 236 · see citing works
Ring-opening polymerization by lithium catalysts: an overview
Sutar, A. K., Maharana, T., Dutta, S., Chen, C., & Lin, C. (2009) · Chemical Society Reviews · doi:10.1039/b912806a · Cited by 221 · see citing works
Versatile catalytic systems based on complexes of zinc, magnesium and calcium supported by a bulky bis(morpholinomethyl)phenoxy ligand for the large-scale immortal ring-opening polymerisation of cyclic esters
Poirier, V., Roisnel, T., Carpentier, J., & Sarazin, Y. (2009) · Dalton Transactions · doi:10.1039/b917799j · Cited by 219 · see citing works
Discrete, Solvent-Free Alkaline-Earth Metal Cations: Metal···Fluorine Interactions and ROP Catalytic Activity
Sarazin, Y., Liu, B., Roisnel, T., Maron, L., & Carpentier, J. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2024977 · Cited by 217 · see citing works
Titanium, zinc and alkaline-earth metal complexes supported by bulky O,N,N,O-multidentate ligands: syntheses, characterisation and activity in cyclic esterpolymerisation
Sarazin, Y., Howard, R. H., Hughes, D. L., Humphrey, S. M., & Bochmann, M. (2006) · Dalton Trans. · doi:10.1039/b511851d · Cited by 204 · see citing works
Rare-earth metal complexes as catalysts for ring-opening polymerization of cyclic esters
Lyubov, D. M., Tolpygin, A. O., & Trifonov, A. A. (2019) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2019.04.013 · Cited by 195 · see citing works
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Amgoune, A., Thomas, C. M., & Carpentier, J. (2007) · Macromolecular Rapid Communications · doi:10.1002/marc.200600862 · Cited by 195 · see citing works
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Nakano, A., Osuka, A., Yamazaki, T., Nishimura, Y., Akimoto, S., Yamazaki, I., Itaya, A., Murakami, M., & Miyasaka, H. (2001) · Chemistry - A European Journal · doi:10.1002/1521-3765(20010716)7:14 · Cited by 90 · 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
Controlled ring-opening polymerization of lactide by group 3 metal complexes
Amgoune, A., Thomas, C. M., & Carpentier, J. (2007) · Pure and Applied Chemistry · doi:10.1351/pac200779112013 · Cited by 155 · see citing works
Heterobimetallic Lanthanide/Sodium Phenoxides: Efficient Catalysts for Amidation of Aldehydes with Amines
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Zhou, S., Wang, S.-W., Yang, G.-S., Liu, X.-Y., Sheng, E.-H., Zhang, K.-H., Cheng, L., & Huang, Z.-X. (2003) · Polyhedron · doi:10.1016/s0277-5387(03)00042-1 · Cited by 130 · see citing works
Novel Single Rare Earth Aryloxide Initiators for Ring-Opening Polymerization of 2,2-Dimethyltrimethylene Carbonate
Ling, J., Shen, Z., & Huang, Q. (2001) · Macromolecules · doi:10.1021/ma0107657 · Cited by 128 · see citing works
Aluminum Complexes Supported by Tridentate Aminophenoxide Ligand as Efficient Catalysts for Ring-Opening Polymerization of ε-Caprolactone
Chen, C., Huang, C., & Huang, B. (2004) · Macromolecules · doi:10.1021/ma0492014 · Cited by 113 · see citing works
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Yao, W., Mu, Y., Gao, A., Gao, W., & Ye, L. (2008) · Dalton Transactions · doi:10.1039/b719017d · Cited by 107 · see citing works
Dinuclear and polynuclear lanthanide coordination complexes containing polyazine ligands: Synthesis and luminescent properties
Swavey, S., & Swavey, R. (2009) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2009.05.015 · Cited by 105 · see citing works
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Sheng, E., Wang, S., Yang, G., Zhou, S., Cheng, L., Zhang, K., & Huang, Z.-X. (2003) · Organometallics · doi:10.1021/om020562m · Cited by 101 · see citing works
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Tridentate anilido‐aldimine magnesium and zinc complexes as efficient catalysts for ring‐opening polymerization of ε‐caprolactone and L ‐lactide
Tsai, Y., Lin, C., Lin, C., & Ko, B. (2009) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.23544 · Cited by 85 · see citing works
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Ma, H., Melillo, G., Oliva, L., Spaniol, T. P., Englert, U., & Okuda, J. (2005) · Dalton Transactions · doi:10.1039/b416875e · Cited by 77 · see citing works
Controlled Ring‐Opening Polymerization of Lactones and Lactide Initiated by Lanthanum Isopropoxide, 2. Mechanistic Studies
Save, M., & Soum, A. H. (2002) · Macromolecular Chemistry and Physics · doi:10.1002/macp.200290043 · Cited by 72 · see citing works
Cannizzaro-Type Disproportionation of Aromatic Aldehydes to Amides and Alcohols by Using Either a Stoichiometric Amount or a Catalytic Amount of Lanthanide Compounds
Zhang, L., Wang, S., Zhou, S., Yang, G., & Sheng, E. (2006) · The Journal of Organic Chemistry · doi:10.1021/jo060063l · Cited by 72 · see citing works
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Ikpo, N., Barbon, S. M., Drover, M. W., Dawe, L. N., & Kerton, F. M. (2012) · Organometallics · doi:10.1021/om300757u · Cited by 64 · see citing works
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Grunova, E. V., Kirillov, E., Roisnel, T., & Carpentier, J. (2008) · Organometallics · doi:10.1021/om800611c · Cited by 63 · see citing works
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Yao, W., Mu, Y., Gao, A., Su, Q., Liu, Y., & Zhang, Y. (2008) · Polymer · doi:10.1016/j.polymer.2008.03.035 · Cited by 60 · see citing works
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Self-citation
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Roesky, P. W. (2003) · Zeitschrift für anorganische und allgemeine Chemie · doi:10.1002/zaac.200300240 · Cited by 54 · see citing works
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Xie, W., Zhu, W., & Shen, Z. (2007) · Polymer · doi:10.1016/j.polymer.2007.09.021 · Cited by 53 · see citing works
Lanthanide chalcogenolate complexes: Syntheses, structures and applications in organic chemistry
Li, H., Zhu, Y., Cheng, M.-L., Ren, Z., Lang, J., & Shen, Q. (2006) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2006.02.005 · Cited by 52 · see citing works
Monomer insertion mechanism of ring-opening polymerization of ɛ-caprolactone with yttrium alkoxide intermediate: A DFT study
Liu, J., Ling, J., Li, X., & Shen, Z. (2008) · Journal of Molecular Catalysis A Chemical · doi:10.1016/j.molcata.2008.10.038 · Cited by 50 · see citing works
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Zhang, L., Wang, S., Sheng, E., & Zhou, S. (2005) · Green Chemistry · doi:10.1039/b504890g · Cited by 49 · see citing works
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Kostakis, K., Mourmouris, S., Karanikolopoulos, G., Pitsikalis, M., & Hadjichristidis, N. (2007) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.22099 · Cited by 44 · see citing works
Ring-opening polymerization of six-membered cyclic esters catalyzed by tetrahydroborate complexes of rare earth metals
Nakayama, Y., Sasaki, K., Watanabe, N., Cai, Z., & Shiono, T. (2009) · Polymer · doi:10.1016/j.polymer.2009.08.024 · Cited by 43 · see citing works
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Enolic Schiff-base aluminum complexes and their application in lactide polymerization
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Self-citation
Anionic lanthanide phenoxide complexes as novel single‐component initiators for the polymerization of ε‐caprolactone and trimethylene carbonate
Sheng, H., Zhou, L., Zhang, Y., Yao, Y., & Shen, Q. (2007) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21888 · Cited by 39 · see citing works
Homolysis of the Eu−N Bond. Synthesis, Structural Characterization, and Catalytic Activity of Novel Europium(II) Complexes
Wang, S., Zhou, S., Sheng, E., Xie, M., Zhang, K., Cheng, L., Yan, F., Mao, L., & Huang, Z.-X. (2003) · Organometallics · doi:10.1021/om030306p · Cited by 39 · see citing works
Chloroyttrium 2-(1-(Arylimino)alkyl)quinolin-8-olate Complexes: Synthesis, Characterization, and Catalysis of the Ring-Opening Polymerization of ε-Caprolactone
Zhang, W., Liu, S., Yang, W., Hao, X., Glaser, R., & Sun, W. (2012) · Organometallics · doi:10.1021/om300778g · Cited by 38 · see citing works
Organic acids catalyzed polymerization of ε‐caprolactone: Synthesis and characterization
Olędzka, E., & Narine, S. S. (2010) · Journal of Applied Polymer Science · doi:10.1002/app.32897 · Cited by 37 · see citing works
Homolysis of the Ln–N (Ln = Yb, Eu) bond. Synthesis, structural characterization and catalytic activity of ytterbium( ii ) and europium( ii ) complexes with methoxyethyl functionalized indenyl ligands
Zhang, K., Zhang, W., Wang, S., Sheng, E., Yang, G., Xie, M., Zhou, S., Yan, F., Mao, L., & Huang, Z.-X. (2004) · Dalton Transactions · doi:10.1039/b314115b · Cited by 37 · see citing works
Synthesis and molecular structure of new heterometal alkoxide clusters Ln2Na8(OCH2CF3)14(THF)6 (Ln=Sm,Y,Yb): Highly active catalysts for polymerization of ε-caprolactone and trimethylene carbonate
Sheng, H., Li, J., Zhang, Y., Yao, Y., & Shen, Q. (2008) · Polyhedron · doi:10.1016/j.poly.2008.01.031 · Cited by 34 · see citing works
Synthesis, characterization, and mechanism studies on novel rare‐earth calixarene complexes initiating ring‐opening polymerization of 2,2‐dimethyltrimethylene carbonate
Ling, J., Shen, Z., & Zhu, W. (2003) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.10678 · Cited by 34 · see citing works
Efficient catalysts for ring‐opening polymerization of ε‐caprolactone and β‐butyrolactone: Synthesis and characterization of zinc complexes based on benzotriazole phenoxide ligands
Tai, Y., Li, C., Lin, C., Liu, Y., Ko, B., & Sun, Y. (2011) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.24845 · Cited by 32 · see citing works
Controlled synthesis of biodegradable lactide polymers and copolymers using novel in situ generated or single-site stereoselective polymerization initiators
Zhong, Z., Dijkstra, P. J., & Feijén, J. (2004) · Journal of Biomaterials Science Polymer Edition · doi:10.1163/1568562041271066 · Cited by 32 · see citing works
Synthesis and characterization of poly(DTC‐b‐PEG‐b‐DTC) triblock and poly(TMC‐b‐DTC‐b‐PEG‐b‐DTC‐b‐TMC) pentablock copolymers and kinetics of the polymerization
Ling, J., Chen, W., & Shen, Z. (2005) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.20648 · Cited by 32 · see citing works
Synthesis, Characterization, and Activity of Yttrium(III) Nitrate Complexes Bearing Tripodal Phosphine Oxide and Mixed Phosphine–Phosphine Oxide Ligands
Sues, P. E., Lough, A. J., & Morris, R. H. (2012) · Inorganic Chemistry · doi:10.1021/ic3010147 · Cited by 31 · see citing works
Syndioselective ring-opening polymerization and copolymerization of trans-1,4-cyclohexadiene carbonate mediated by achiral metal- and organo-catalysts
Diallo, A. K., Kirillov, E., Slawinski, M., Brusson, J., Guillaume, S. M., & Carpentier, J. (2015) · Polymer Chemistry · doi:10.1039/c4py01713g · Cited by 30 · see citing works
Synthesis, Characterization, and Catalytic Activity of Some Neodymium(III), Ytterbium(II), and Europium(II) Complexes with Pyrrolidinyl‐ and Piperidinyl‐Functionalized Indenyl Ligands
Zhou, S., Wang, S., Sheng, E., Zhang, L., Yu, Z., Xi, X., Chen, G., Luo, W. J., & Li, Y. (2007) · European Journal of Inorganic Chemistry · doi:10.1002/ejic.200601102 · Cited by 30 · see citing works
Synthesis and molecular structure of the cationic samarium phenoxide complex [(ArO)2Sm(DME)2][BPh4] · THF and its catalytic activity for the polymerization of ε-caprolactone
Sheng, H., Zhou, H., Guo, H., Sun, H., Yao, Y., Wang, J., Zhang, Y., & Shen, Q. (2006) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2006.11.013 · Cited by 30 · see citing works
Immortal ring-opening polymerization of ε-caprolactone by a neat magnesium catalyst system: an approach to obtain block and amphiphilic star polymers in situ
Wang, Y., Liu, B., Wang, X., Zhao, W. M., Liu, D., Liu, X., & Cui, D. (2014) · Polymer Chemistry · doi:10.1039/c4py00384e · Cited by 29 · see citing works
Homolysis of the Ln−N (Ln = Yb, Eu) Bond − Synthesis, Structure, and Catalytic Activity of Ytterbium( II ) and Europium( II ) Complexes Having (Dimethylamino)propyl‐ and (Dimethylamino)ethyl‐Functionalized Indenyl Ligands
Sheng, E., Zhou, S., Wang, S., Yang, G., Wu, Y., Yan, F., Mao, L., & Huang, Z.-X. (2004) · European Journal of Inorganic Chemistry · doi:10.1002/ejic.200400077 · Cited by 29 · see citing works
Group 13 and Lanthanide Complexes Supported by Tridentate Tripodal Triamine Ligands: Structural Diversity and Polymerization Catalysis
Zhu, H., & Chen, E. Y. ‐. (2007) · Organometallics · doi:10.1021/om700587w · Cited by 28 · see citing works
Miktoarm star copolymers of poly(ϵ‐caprolactone) from a novel heterofunctional initiator
Priftis, D., Pitsikalis, M., & Hadjichristidis, N. (2007) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.22261 · Cited by 26 · see citing works
Synthesis of poly(ε-caprolactone) diols and EO–CL block copolymers and their characterization by liquid chromatography and MALDI-TOF-MS
Ahmed, H., Trathnigg, B., Kappe, C. O., & Saf, R. (2009) · European Polymer Journal · doi:10.1016/j.eurpolymj.2009.12.006 · Cited by 24 · see citing works
A computational insight into a metal mediated pathway for the ring-opening polymerization (ROP) of lactides by an ionic {(NHC)2Ag}+X− (X = halide) type N-heterocyclic carbene (NHC) complex
Stephen, R., Sunoj, R. B., & Ghosh, P. (2011) · Dalton Transactions · doi:10.1039/c1dt10345h · Cited by 23 · see citing works
Synthesis, characterization, and catalytic activity of divalent organolanthanide complexes with new tetrahydro-2H-pyranyl-functionlized indenyl ligands
Wang, S., Wang, S., Zhou, S., Yang, G., Luo, W., Hu, N., Zhou, Z., & Song, H. (2007) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2007.01.029 · Cited by 23 · see citing works
Syntheses, crystal structures and catalytic properties of a series of lanthanide(III) bis(trimethylsilyl)amide chloride complexes: [{((Me3Si)2N)2Nd(μ′-Cl)Li(THF)3}(μ-Cl)]2, [{((Me3Si)2N)2Ln(μ′-Cl)Li(THF)2}(μ3-Cl)]2 (Ln = Eu, Ho), and [{(Me3Si)2NLn(μ′-Cl)2Li(THF)2}(μ-Cl)]2 (Ln = Nd, Sm, Eu, Ho, Yb)
Li, H., Xu, Q., Chen, J.-X., Cheng, M.-L., Zhang, Y., Zhang, W., Lang, J., & Shen, Q. (2004) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2004.07.044 · Cited by 23 · see citing works
A novel approach to RE–OR bond from in situ reaction of rare earth triflates and sodium alkoxides: A versatile catalyst for living ring-opening polymerization of ε-caprolactone
You, L., Shen, Z., Kong, J., & Ling, J. (2014) · Polymer · doi:10.1016/j.polymer.2014.03.032 · Cited by 22 · see citing works
Ring‐opening polymerization of ε‐caprolactone catalyzed by Yttrium trisphenolate in the presence of 1,2‐propanediol. Do both primary and secondary hydroxyl groups initiate polymerization?
Ling, J., Liu, J., Shen, Z., & Hogen‐Esch, T. E. (2011) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.24637 · Cited by 22 · see citing works
Cyclic versus linear polylactide: Straightforward access using a single catalyst
Hu, C., Louisy, E., Fontaine, G., & Bonnet, F. (2017) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.28699 · Cited by 22 · see citing works
Cubane‐Type Polynuclear Zinc Complexes Containing Tridentate Schiff Base Ligands: Synthesis, Characterization, and Ring‐Opening Polymerization Studies of rac‐Lactide and ε‐Caprolactone
Ghosh, S., Spannenberg, A., & Mejía, E. (2017) · Helvetica Chimica Acta · doi:10.1002/hlca.201700176 · Cited by 22 · see citing works
One‐Pot Synthesis of Lactide–Styrene Diblock Copolymers via Catalytic Immortal Ring‐Opening Polymerization of Lactide and Nitroxide‐Mediated Polymerization of Styrene
Poirier, V., Duc, M., Carpentier, J., & Sarazin, Y. (2010) · ChemSusChem · doi:10.1002/cssc.201000021 · Cited by 21 · see citing works
Rapid ring‐opening polymerization of 1,4‐dioxan‐2‐one initiated by titanium alkoxides
Zeng, J., Srinivansan, M., Li, Y., Narayan, R., & Wang, Y. (2010) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.24399 · Cited by 21 · see citing works
Polymerization of Poly(ε-caprolactone) Using Yttrium Triflate
Kunioka, M., Wang, Y., & Onozawa, S. (2003) · Polymer Journal · doi:10.1295/polymj.35.422 · Cited by 21 · see citing works
Di‐nuclear zinc complexes containing tridentate imino‐benzotriazole phenolate derivatives as efficient catalysts for ring‐opening polymerization of cyclic esters and copolymerization of phthalic anhydride with cyclohexene oxide
Chang, C., Chuang, H., Chen, T.-Y., Li, C.-Y., Lin, C., Lee, T., Ko, B., & Huang, H. (2015) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.27902 · Cited by 20 · see citing works
Synthesis and Characterization of Europium(III) and Terbium(III) Complexes: An Advanced Undergraduate Inorganic Chemistry Experiment
Swavey, S. (2010) · Journal of Chemical Education · doi:10.1021/ed100188m · Cited by 19 · see citing works
The crucial roles of guest water in a biocompatible coordination network in the catalytic ring-opening polymerization of cyclic esters: a new mechanistic perspective
Chen, S., Zhang, F.-H., Huang, K., Tian, F., Zhang, Z., Zhou, R., Feng, X., Zhou, X., He, M., Gu, J., et al. (2020) · Chemical Science · doi:10.1039/c9sc06024c · Cited by 18 · see citing works
Novel direct synthetic approach to thiol‐functionalized poly(ε‐caprolactone) by highly chemselective and low costly rare earth phenolate catalysts
Zhu, N., Ling, J., Zhu, Y., Sun, W., & Shen, Z. (2010) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.24233 · Cited by 18 · see citing works
Homo‐ and Copolymerization of ε‐Caprolactone and 2,2‐Dimethyltrimethylene Carbonate by Rare Earth Initiators
Shen, Z., Zhu, G., & Ling, J. (2002) · Chinese Journal of Chemistry · doi:10.1002/cjoc.20020201136 · Cited by 18 · see citing works
Ring Opening Polymerization
Lecomte, P., & Jérôme, R. (2004) · Wiley eBooks · doi:10.1002/0471440264.pst497 · Cited by 18 · see citing works
Self-citation
Heterogeneous Double Metal Cyanide Catalyzed Synthesis of Poly(ε-caprolactone) Polyols for the Preparation of Thermoplastic Elastomers
Tran, C. H., Lee, M.-W., Park, S., Jeong, J. E., Lee, S.-J., Song, W., Huh, P., & Kim, I. (2021) · Catalysts · doi:10.3390/catal11091033 · Cited by 17 · see citing works
Site-Isolated Main-Group Tris (2-pyridyl)borate Complexes by Pyridine Substitution and Their Ring-Opening Polymerization Catalysis
Qian, J., & Comito, R. J. (2022) · Inorganic Chemistry · doi:10.1021/acs.inorgchem.2c01289 · Cited by 17 · see citing works
Polymers of ε-Caprolactone Using New Copper(II) and Zinc(II) Complexes as Initiators: Synthesis, Characterization and X-Ray Crystal Structures
Posada, A. F., Macias, M. A., Movilla, S., Miscione, G. P., Pérez, L. D., & Hurtado, J. (2018) · Polymers · doi:10.3390/polym10111239 · Cited by 17 · see citing works
Dimeric samarium(III) alkoxides bearing N2O2 tetradentate Schiff bases and their utility for the catalytic epoxidation of trans-chalcone
Schuetz, S. A., Bowman, E. A., Silvernail, C. M., Day, V. W., & Belot, J. A. (2004) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2004.11.011 · Cited by 17 · see citing works
Lanthanide Amide‐catalyzed Aza‐Henry Reaction of N‐Tosyl Imines with Nitroalkanes
Zhang, L., Wu, H., Su, S., & Wang, S. (2009) · Chinese Journal of Chemistry · doi:10.1002/cjoc.200990346 · Cited by 16 · see citing works
Zinc‐based catalyst for the ring‐opening polymerization of cyclic esters
Yuan, Y., Jing, X., Xiao, H., Chen, X., & Huang, Y. (2011) · Journal of Applied Polymer Science · doi:10.1002/app.33956 · Cited by 16 · see citing works
LnNa8[OC(CH3)3]10(OH) alkoxide clusters: Highly active single‐component catalysts for the homopolymerization and copolymerization of ε‐caprolactone and trimethylene carbonate
Sheng, H., Li, J., Yao, Y. Z. Y., & Shen, Q. (2009) · Journal of Applied Polymer Science · doi:10.1002/app.29428 · Cited by 16 · see citing works
Thiol-functionalized branched and linear poly(ε-caprolactone): Direct synthesis, characterization and application in stabilizing silver nanoparticles
Zhu, N., Feng, W., Zhang, Z., Fang, Z. D., Li, Z., & Guo, K. (2015) · Polymer · doi:10.1016/j.polymer.2015.10.053 · Cited by 16 · see citing works

“In Situ” Formation of Yttrium Alkoxides: A Versatile and Efficient Catalyst for the ROP of ε-Caprolactone
Martin, É., Dúbois, P., & Jérôme, R. (2003) · Macromolecules · doi:10.1021/ma034236+ · Cited by 60 · see citing works
Self-citation
Controlled Ring-opening Polymerization of ε-Caprolactone Initiated by in situ Formed Yttrium Tribenzyloxide Complex
Zhen, L. (2011)
Ring‐opening polymerization of ε‐caprolactone catalyzed by Yttrium trisphenolate in the presence of 1,2‐propanediol. Do both primary and secondary hydroxyl groups initiate polymerization?
Ling, J., Liu, J., Shen, Z., & Hogen‐Esch, T. E. (2011) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.24637 · Cited by 22 · see citing works
Ring-opening polymerization of ?-caprolactone initiated by rare earth complex catalysts
Deng, X., Zhu, Z., Xiong, C., & Zhang, L. (1997) · Journal of Applied Polymer Science · doi:10.1002/(sici)1097-4628(19970516)64:7 · Cited by 19 · see citing works
Kinetics and Mechanism of ε-Caprolactone Polymerization Using Yttrium Alkoxides as Initiators
Stevels, W. M., Ankoné, M. J. K., Dijkstra, P. J., & Feijén, J. (1996) · Macromolecules · doi:10.1021/ma960701+ · Cited by 124 · see citing works

Authors: Martin, E., Dubois, P., & Jérôme, R.
Affiliations: Center for Education and Research on Macromolecules (CERM), University of Liège, Sart-Tilman, B6, 4000 Liège, Belgium, and Laboratory of Polymeric and Composite Materials, University of Mons-Hainaut, Place du Parc 20, 7000 Mons, Belgium
University of Mons (BE)
Venue: Macromolecules
Publisher: American Chemical Society (ACS)
Published: 2000-02-18
Volume: 33
Issue: 5
Pages: 1530-1535
ISSN: 0024-9297 (ISSN-L)
1520-5835
DOI: 10.1021/ma991045r
OpenAlex: W1987289038
Cited by: 144
References: 21
Citations by year: 2025: 5 · 2023: 3 · 2022: 4 · 2021: 2 · 2020: 3 · 2019: 1 · 2018: 1 · 2017: 2 · 2016: 2 · 2015: 5 · 2014: 3 · 2013: 2 · 2012: 5
FWCI: 6.90
Type: journal article
Language: en
Open access: closed
Locations: Macromolecules (publishedVersion)
ORBi (University of Liège) (submittedVersion)
Topics: Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
Keywords: ε-caprolactone, ring-opening polymerization, isopropanol, molecular weight control, polymer end groups

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Controlled Ring-Opening Polymerization of ε-Caprolactone Promoted by “in Situ” Formed Yttrium Alkoxides

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