Synthesis, Characterization, and Catalytic Studies of Lithium Complexes: Efficient Initiators for Ring-Opening Polymerization of l-Lactide
Abstract
The reaction of 2,2‘-ethylidenebis(4,6-di- tert -butylphenol) (EDBP-H 2 ) with n BuLi in tetrahydrofuran (THF), giving [(EDBP-H)Li(THF) 3 ] ( 1 ) in high yield. However, the reaction of EDBP-H 2 with n BuLi in the presence of benzyl alcohol (BnOH) in diethyl ether or tetrahydrofuran produces compounds [(EDBP-H)Li(BnOH)] 2 ( 2 ) and [(EDBP-H)Li(BnOH)(THF) 2 ] ( 3 ), respectively. Further reaction of 2 with excess of THF produces 3 . Alternatively, 3 can also be prepared by the reaction of benzyl alcohol with 1 in toluene. Experimental results show that 2 and 3 efficiently initiate the ring-opening polymerization (ROP) of l -lactide in a controlled fashion, yielding polymers with very narrow polydispersity indexes in a wide range of monomer-to-initiator ratios. Block copolymers, polystyrene- b -poly( l -lactide), have also been prepared from the ring-opening polymerization of l -latide catalyzed by 3 using polystyrene as a macroinitiator.
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Heterobimetallic complexes 80 and 81 exhibited higher catalytic activity than did homo-bimetallic complexes 83 and 84.
“Although the catalytic activity of complex 82 is difficult to compare with that of complex 80 and complex 81 because of different reaction conditions, heterobimetallic complexes 80 and 81 exhibited higher catalytic activity than did homo-bimetallic complexes 83 and 84.”
From Multinuclear metal catalysts in ring-opening polymerization of ε‑caprolactone and lactide: Cooperative and electronic effects between metal centers (2023) · cites this paper as [96]
Cites
Biodegradable Long-Circulating Polymeric Nanospheres
Gref, R., Minamitake, Y., Peracchia, M. T., Trubetskoy, V. S., Torchilin, V. P., & Langer, R. (1994) · Science · doi:10.1126/science.8128245 · Cited by 2,924 · see citing works
Controlled Ring-Opening Polymerization of Lactide and Glycolide
Dechy-Cabaret, O., Martin-Vaca, B., & Bourissou, D. (2004) · Chemical Reviews · doi:10.1021/cr040002s · Cited by 2,257 · see citing works
Narrow molecular weight resins by a free-radical polymerization process
Georges, M. K., Veregin, R. P. N., Kazmaier, P. M., & Hamer, G. K. (1993) · Macromolecules · doi:10.1021/ma00063a054 · Cited by 2,088 · see citing works
Biodegradable block copolymers as injectable drug-delivery systems
Jeong, B., Bae, Y. H., Lee, D. S., & Kim, S. W. (1997) · Nature · doi:10.1038/42218 · Cited by 1,999 · see citing works
Polymerization of Lactide with Zinc and Magnesium β-Diiminate Complexes: Stereocontrol and Mechanism
Chamberlain, B. M., Cheng, M., Moore, D. R., Ovitt, T. M., Lobkovsky, E. B., & Coates, G. W. (2001) · Journal of the American Chemical Society · doi:10.1021/ja003851f · Cited by 1,207 · see citing works
Sawhney, A. S., Pathak, C. P., & Hubbell, J. A. (1993) · Macromolecules · doi:10.1021/ma00056a005 · Cited by 969 · see citing works
Loss of Circadian Behavioral Rhythms and per RNA Oscillations in the Drosophila Mutant timeless
Sehgal, A., Price, J. L., Man, B., & Young, M. W. (1994) · Science · doi:10.1126/science.8128246 · Cited by 651 · see citing works
Influence of CO2 emission rates on the stability of the thermohaline circulation
Stocker, T. F., & Schmittner, A. (1997) · Nature · doi:10.1038/42224 · Cited by 575 · see citing works
Ordered Nanoporous Polymers from Polystyrene−Polylactide Block Copolymers
Zalusky, A. S., Olayo-Valles, R., Wolf, J. H., & Hillmyer, M. A. (2002) · Journal of the American Chemical Society · doi:10.1021/ja0278584 · Cited by 553 · see citing works
Chisholm, M. H., Eilerts, N. W., Huffman, J. C., Iyer, S. S., Pacold, M., & Phomphrai, K. (2000) · Journal of the American Chemical Society · doi:10.1021/ja002160g · Cited by 444 · see citing works
Group 13 Compounds Incorporating Salen Ligands
Atwood, D. A., & Harvey, M. J. (2000) · Chemical Reviews · doi:10.1021/cr990008v · Cited by 422 · see citing works
Metalloporphyrins as Initiators for Living and Immortal Polymerizations
Aida, T., & Inoue, S. (1996) · Accounts of Chemical Research · doi:10.1021/ar950029l · Cited by 370 · see citing works
Microstructure Analysis of Poly(lactic acid) Obtained by Lithium tert-Butoxide as Initiator
Kasperczyk, J. (1995) · Macromolecules · doi:10.1021/ma00115a028 · Cited by 204 · see citing works
Mesoporous Polystyrene Monoliths
Zalusky, A. S., Olayo‐Valles, R., Taylor, C. J., et al. (2001) · Journal of the American Chemical Society · doi:10.1021/ja003936g · Cited by 203 · see citing works
Directions for environmentally biodegradable polymer research
Swift, G. (1993) · Accounts of Chemical Research · doi:10.1021/ar00027a005 · Cited by 185 · see citing works
Doi, Y., Kunioka, M., Nakamura, Y., & Soga, K. (1987) · Macromolecules · doi:10.1021/ma00178a006 · Cited by 159 · see citing works
Kinetik und Mechanismus der ringöffnenden Polymerisation von L(—)‐Lactid
Dittrich, V. W., & Schulz, R. C. (1971) · Die Angewandte Makromolekulare Chemie · doi:10.1002/apmc.1971.050150109 · Cited by 149 · see citing works
Discrete Yttrium(III) Complexes as Lactide Polymerization Catalysts
Chamberlain, B. M., Yongping, S., Hagadorn, J. R., Hemmesch, E. W., Young, V. G., Pink, M., Hillmyer, M. A., & Tolman, W. B. (1999) · Macromolecules · doi:10.1021/ma990005k · Cited by 139 · see citing works
Jedliński, Z., Wałach, W., Kurcok, P., & Adamus, G. (1991) · Die Makromolekulare Chemie · doi:10.1002/macp.1991.021920914 · Cited by 116 · see citing works
Šimić, V., Spassky, N., & Hubert-Pfalzgraf, L. G. (1997) · Macromolecules · doi:10.1021/ma970615p · Cited by 114 · see citing works
Living and immortal polymerizations
Aida, T. (1994) · Progress in Polymer Science · doi:10.1016/0079-6700(94)90003-5 · Cited by 104 · see citing works
Kasperczyk, J., & Bero, M. (2000) · Polymer · doi:10.1016/s0032-3861(99)00421-8 · Cited by 77 · see citing works
Highly reactive yttrium alkoxide as new initiator for the polymerization of β‐butyrolactone
Borgne, A. L., Pluta, C., & Spassky, N. (1994) · Macromolecular Rapid Communications · doi:10.1002/marc.1994.030151208 · Cited by 72 · see citing works
Hovestadt, W., Keul, H., & Höcker, H. (1992) · Polymer · doi:10.1016/0032-3861(92)90497-k · Cited by 49 · see citing works
Hovestadt, W., Müller, A. J., Keul, H., et al. (1990) · Die Makromolekulare Chemie Rapid Communications · doi:10.1002/marc.1990.030110605 · Cited by 30 · see citing works
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Biocompatible Initiators for Lactide Polymerization
Platel, R., Hodgson, L., & Williams, C. (2008) · Polymer Reviews · doi:10.1080/15583720701834166 · Cited by 706 · see citing works
Wu, L.-J., Lee, W., Kumar Ganta, P., Chang, Y.-L., Chang, Y.-C., & Chen, H.-Y. (2023) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2022.214847 · Cited by 96 · see citing works
Chen, H.-Y., Liu, M.-Y., Sutar, A. K., & Lin, C.-C. (2010) · Inorganic Chemistry · doi:10.1021/ic901938e · Cited by 95 · see citing works
Self-citationInitiation of ring-opening polymerization of lactide: The effect of metal alkoxide catalyst
Cheshmedzhieva, D., Angelova, I., Ilieva, S., Georgiev, G. S., & Galabov, B. (2012) · Computational and Theoretical Chemistry · doi:10.1016/j.comptc.2012.06.015 · Cited by 27 · see citing works
Ge, F., Dan, Y., Al-Khafaji, Y., Prior, T. J., Jiang, L., Elsegood, M. R. J., & Redshaw, C. (2016) · RSC Advances · doi:10.1039/c5ra24816g · Cited by 22 · see citing works
- Authors
- Hsueh, M.-L., Huang, B.-H., Wu, J., & Lin, C.-C.
- Affiliations
- National Chung Hsing University (TW)
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-10-21
- Volume
- 38
- Issue
- 23
- Pages
- 9482-9487
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W1996369328
- Cited by
- 93
- References
- 25
- Citations by year
- 2026: 1 · 2024: 2 · 2023: 3 · 2022: 4 · 2020: 1 · 2019: 2 · 2017: 5 · 2016: 5 · 2015: 3 · 2014: 4 · 2013: 4 · 2012: 15
- FWCI
- 3.41
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Macromolecules (publishedVersion)
- 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
- lithium complexes, ring-opening polymerization, L-lactide, n-butyllithium, benzyl alcohol, controlled radical polymerization, block copolymers, macroinitiator, polydispersity index
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