Bimetallic anilido-aldimine Al or Zn complexes for efficient ring-opening polymerization of ε-caprolactone
Abstract
Four bimetallic Al or Zn complexes supported by anilido-aldimine ligands (o-C6H4(NHAr)-CH=N)2CH2CH2 (Ar = 2,6-Me2C6H3,L1H2; Ar = 2,6-iPr2C6H3, L2H2) have been synthesized and characterized. Treatment of L1H2 or L2H2 with two equiv. of AlMe3 gives bimetallic complex L1(AlMe2)2 1 or L2 (AlMe2)2 2, respectively. Reaction of L1H2 or L2H2 with two equiv. of ZnEt2 leads to bimetallic complex L1(ZnEt)2 3 or L2(ZnEt)2 4, respectively. All of the complexes 1-4 are efficient catalysts for ring-opening polymerization of epsilon-caprolactone (CL) in the presence of benzyl alcohol and catalyze the polymerization of CL in living fashion yielding polymers with a narrow polydispersity index. The activity of bimetallic Zn complexes 3 and 4 is higher than bimetallic Al complexes 1 and 2.
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Complex 46 exhibited higher catalytic activity in CL polymerization than did complex 47 because of intermetallic cooperation.
“Compared with the CL polymerization by mononuclear Zn complex 47 reported by Ko's group, [84] complex 46 exhibited higher catalytic activity in CL polymerization than did complex 47 because of intermetallic cooperation.”
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 [84]
Cites
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
Chemical syntheses of biodegradable polymers
Okada, M. (2002) · Progress in Polymer Science · doi:10.1016/s0079-6700(01)00039-9 · Cited by 1,202 · 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
WU, J., YU, T., CHEN, C., & LIN, C. (2006) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2005.07.010 · Cited by 779 · see citing works
Biodegradable Polymeric Materials
Chiellini, E., & Solaro, R. (1996) · Advanced Materials · doi:10.1002/adma.19960080406 · Cited by 567 · see citing works
Moore, D. R., Cheng, M., Lobkovsky, E. B., & Coates, G. W. (2003) · Journal of the American Chemical Society · doi:10.1021/ja030085e · Cited by 515 · see citing works
Kowalski, A. K., Duda, A., & Penczek, S. (2000) · Macromolecules · doi:10.1021/ma9906940 · Cited by 409 · see citing works
Biodegradable polymers for biomedical uses
Hayashi, T. (1994) · Progress in Polymer Science · doi:10.1016/0079-6700(94)90030-2 · Cited by 341 · see citing works
O'Keefe, B. J., Breyfogle, L. E., Hillmyer, M. A., & Tolman, W. B. (2002) · Journal of the American Chemical Society · doi:10.1021/ja012689t · Cited by 297 · see citing works
Bimetallic Anilido-Aldimine Zinc Complexes for Epoxide/CO2 Copolymerization
Lee, B. Y., Kwon, H. Y., Lee, S. Y., Na, S. J., Han, S., Yun, H., Lee, H., & Park, Y.-W. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0435135 · Cited by 295 · see citing works
Chmura, A. J., Davidson, M. G., Jones, M. D., Lunn, M. D., Mahon, M. F., Johnson, A. F., Khunkamchoo, P., Roberts, S. L., & Wong, S. S. F. (2006) · Macromolecules · doi:10.1021/ma061028j · Cited by 277 · see citing works
Polymerization of l , l -Dilactide Initiated by Tin(II) Butoxide
Kowalski, A., Libiszowski, J., Duda, A., & Penczek, S. (2000) · Macromolecules · doi:10.1021/ma991751s · Cited by 271 · see citing works
Chisholm, M. H., Huffman, J. C., & Phomphrai, K. (2001) · Journal of the Chemical Society Dalton Transactions · doi:10.1039/b008158m · Cited by 241 · see citing works
Zhong, Z., Dijkstra, P. J., Birg, C., Westerhausen, M., & Feijén, J. (2001) · Macromolecules · doi:10.1021/ma0019510 · Cited by 236 · see citing works
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
Chen, H.-Y., Huang, B.-H., & Lin, C.-C. (2005) · Macromolecules · doi:10.1021/ma050672f · Cited by 166 · see citing works
Alcazar‐Roman, L. M., O'Keefe, B. J., Hillmyer, M. A., & Tolman, W. B. (2003) · Dalton Transactions · doi:10.1039/b303760f · Cited by 163 · see citing works
Yu, R., Hung, C., Huang, J., Lee, H.-Y., & Chen, J. (2002) · Inorganic Chemistry · doi:10.1021/ic025785j · Cited by 161 · see citing works
Sánchez‐Barba, L. F., Hughes, D. L., Humphrey, S. M., & Bochmann, M. (2006) · Organometallics · doi:10.1021/om050892h · Cited by 158 · see citing works
Zhou, S., Wang, S., Yang, G., et al. (2007) · Organometallics · doi:10.1021/om070234s · Cited by 148 · see citing works
Martin, E., Dubois, P., & Jérôme, R. (2000) · Macromolecules · doi:10.1021/ma991045r · Cited by 144 · see citing works
Nomura, N., Aoyama, T., Ishii, R., & Kondo, T. (2005) · Macromolecules · doi:10.1021/ma050606d · Cited by 140 · see citing works
Breyfogle, L. E., Williams, C. K., Young, V. G., Hillmyer, M. A., & Tolman, W. B. (2005) · Dalton Transactions · doi:10.1039/b507014g · Cited by 130 · see citing works
Novel Zinc and Magnesium Alkyl and Amido Cations for Ring-Opening Polymerization Reactions
Sarazin, Y., Schormann, M., & Bochmann, M. (2004) · Organometallics · doi:10.1021/om0497691 · Cited by 128 · see citing works
Shueh, M.-L., Wang, Y.-S., Huang, B.-H., Kuo, C.-Y., & Lin, C.-C. (2004) · Macromolecules · doi:10.1021/ma049778l · Cited by 127 · see citing works
Chen, C., Huang, C., & Huang, B. (2003) · Dalton Transactions · doi:10.1039/b307365c · Cited by 115 · see citing works
Chen, C., Huang, C., & Huang, B. (2004) · Macromolecules · doi:10.1021/ma0492014 · Cited by 113 · see citing works
Silvernail, C. M., Yao, L. J., Hill, L. M. R., Hillmyer, M. A., & Tolman, W. B. (2007) · Inorganic Chemistry · doi:10.1021/ic700581s · Cited by 113 · see citing works
Dagorne, S., Bideau, F. L., Welter, R., Bellemin‐Laponnaz, S., & Maisse-Francois, A. (2007) · Chemistry - A European Journal · doi:10.1002/chem.200601112 · Cited by 112 · see citing works
Ring-Opening Polymerization of ε-Caprolactone and l -Lactide Using Aluminum Thiolates as Initiator
Huang, C., Wang, F.-C., Ko, B., Yu, T., & Lin, C. (2001) · Macromolecules · doi:10.1021/ma0014719 · Cited by 111 · see citing works
Cayuela, J., Bounor-Legaré, V., Cassagnau, P., & Michel, A. (2006) · Macromolecules · doi:10.1021/ma051272v · Cited by 110 · see citing works
Chmura, A. J., Davidson, M. G., Jones, M. D., Lunn, M. D., & Mahon, M. F. (2006) · Dalton Trans. · doi:10.1039/b513345a · Cited by 108 · see citing works
Yu, T., Wu, C., Chen, C.-C., Huang, B., Wu, J., & Lin, C. (2005) · Polymer · doi:10.1016/j.polymer.2005.04.079 · Cited by 105 · see citing works
Bok, T., Yun, H., & Lee, B. Y. (2006) · Inorganic Chemistry · doi:10.1021/ic060060r · Cited by 103 · see citing works
Lewiński, J., Horeglad, P., Dranka, M., & Justyniak, I. (2004) · Inorganic Chemistry · doi:10.1021/ic049337i · Cited by 102 · see citing works
Chen, M.-Z., Sun, H., Li, W., Wang, Z.-G., Shen, Q., & Zhang, Y. (2006) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2006.01.031 · Cited by 101 · see citing works
Milione, S., Grisi, F., Centore, R., & Tuzi, A. (2005) · Organometallics · doi:10.1021/om050902e · Cited by 100 · see citing works
Hsueh, M., Huang, B., & Lin, C. (2002) · Macromolecules · doi:10.1021/ma020574j · Cited by 99 · see citing works
Chakraborty, D., & Chen, E. Y. ‐. (2002) · Organometallics · doi:10.1021/om011051n · Cited by 93 · see citing works
Lewiński, J., Horeglad, P., Wójcik, K., & Justyniak, I. (2005) · Organometallics · doi:10.1021/om050295v · Cited by 93 · see citing works
Calcium methoxide initiated ring-opening polymerization of ϵ-caprolactone and L-lactide
Zhong, Z., Ankoné, M. J. K., Dijkstra, P. J., Birg, C., Westerhausen, M., & Feijen, J. (2001) · Polymer Bulletin · doi:10.1007/s002890170088 · Cited by 90 · see citing works
A Comparative Study in the Ring-Opening Polymerization of Lactides and Propylene Oxide
Chisholm, M. H., Navarro-Llobet, D., & Simonsick, W. J. (2001) · Macromolecules · doi:10.1021/ma011328v · Cited by 78 · see citing works
Chen, H.-L., Ko, B., Huang, B., & Lin, C. (2001) · Organometallics · doi:10.1021/om010425+ · Cited by 78 · see citing works
Titanium and Zirconium Complexes for Polymerization of Propylene and Cyclic Esters
Gornshtein, F., Kapon, M., Botoshansky, M., & Eisen, M. S. (2007) · Organometallics · doi:10.1021/om060723c · Cited by 77 · see citing works
Chiral Amido Aluminum and Zinc Alkyls: A Synthetic, Structural, and Polymerization Study
Chakraborty, D., & Chen, E. Y. ‐. (2003) · Organometallics · doi:10.1021/om020889n · Cited by 76 · see citing works
Amgoune, A., Lavanant, L., Thomas, C. M., Chi, Y., Welter, R., Dagorne, S., & Carpentier, J. (2005) · Organometallics · doi:10.1021/om050512s · Cited by 75 · see citing works
Takashima, Y., Nakayama, Y., Hirao, T., Yasuda, H., & Harada, A. (2004) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2003.10.042 · Cited by 74 · see citing works
Zhong, Z., Schneiderbauer, S., Dijkstra, P. J., Westerhausen, M., & Feijén, J. (2003) · Polymer Bulletin · doi:10.1007/s00289-003-0211-7 · Cited by 74 · see citing works
Antelmann, B., Chisholm, M. H., Iyer, S. S., Huffman, J. C., Navarro-Llobet, D., Pagel, M. D., Simonsick, W. J., & Zhong, W. (2001) · Macromolecules · doi:10.1021/ma0102316 · Cited by 72 · see citing works
Walker, D. A., Woodman, T. J., Schormann, M., et al. (2003) · Organometallics · doi:10.1021/om020690a · Cited by 71 · see citing works
Liu, X., Gao, W., Mu, Y., Li, G., Ye, L., Xia, H., Ren, Y., & Feng, S. (2005) · Organometallics · doi:10.1021/om049143a · Cited by 70 · see citing works
Self-citationDavidson, M. G., Jones, M. D., Lunn, M. D., & Mahon, M. F. (2006) · Inorganic Chemistry · doi:10.1021/ic051708n · Cited by 68 · see citing works
Dagorne, S., Lavanant, L., Welter, R., Chassenieux, C., Haquette, P., & Jaouen, G. (2003) · Organometallics · doi:10.1021/om0302185 · Cited by 67 · see citing works
Zhou, H., Guo, H., Yao, Y., Zhou, L., Sun, H., Sheng, H., Zhang, Y., & Shen, Q. (2007) · Inorganic Chemistry · doi:10.1021/ic061805w · Cited by 65 · see citing works
Zheng, G., & Stöver, H. D. H. (2003) · Macromolecules · doi:10.1021/ma0212902 · Cited by 64 · see citing works
Delbridge, E. E., Dugah, D. T., Nelson, C. R., Skelton, B. W., & WHITE, A. H. (2006) · Dalton Transactions · doi:10.1039/b613409b · Cited by 64 · see citing works
Wang, H., Chan, H., Okuda, J., & Xie, Z. (2005) · Organometallics · doi:10.1021/om050079m · Cited by 63 · see citing works
Sheng, H., Xu, F., Yao, Y., Zhang, Y., & Shen, Q. (2007) · Inorganic Chemistry · doi:10.1021/ic701238w · Cited by 61 · see citing works
Huang, B.-H., Lin, C.-N., Hsueh, M.-L., Athar, T., & Lin, C.-C. (2006) · Polymer · doi:10.1016/j.polymer.2006.07.015 · Cited by 61 · see citing works
Martin, É., Dúbois, P., & Jérôme, R. (2003) · Macromolecules · doi:10.1021/ma034236+ · Cited by 60 · see citing works
Xu, X., Zhang, Z., Yao, Y., Zhang, Y., & Shen, Q. (2007) · Inorganic Chemistry · doi:10.1021/ic701148z · Cited by 59 · see citing works
Lewiński, J., Horeglad, P., Tratkiewicz, E., Grzenda, W., Lipkowski, J. S., & Kołodziejczyk, E. (2004) · Macromolecular Rapid Communications · doi:10.1002/marc.200400412 · Cited by 51 · see citing works
Lee, W., Hsieh, H., Hsieh, C.-C., et al. (2006) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2006.11.015 · Cited by 50 · see citing works
Ring‐opening polymerization of substituted ε‐caprolactones with a chiral (salen) AlOiPr complex
ten Breteler, M. R., Zhong, Z., Dijkstra, P. J., et al. (2006) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21841 · Cited by 47 · see citing works
Deshayes, G., Mercier, F. A. G., Degée, P., Verbruggen, I., Biesemans, M., Willem, R., & Dúbois, P. (2003) · Chemistry - A European Journal · doi:10.1002/chem.200304769 · Cited by 46 · see citing works
Wang, Z., & Qi, C. (2007) · Organometallics · doi:10.1021/om0610400 · Cited by 46 · see citing works
Doyle, D. J., Gibson, V. C., & White, A. J. P. (2006) · Dalton Transactions · doi:10.1039/b615080b · Cited by 40 · see citing works
Wang, S., Tang, X., Vega, A. I., et al. (2007) · Organometallics · doi:10.1021/om060979i · Cited by 40 · see citing works
Binda, P. I., & Delbridge, E. E. (2007) · Dalton Transactions · doi:10.1039/b710070a · Cited by 39 · see citing works
Chakraborty, D., & Chen, E. Y. ‐. (2001) · Macromolecules · doi:10.1021/ma011813q · Cited by 36 · see citing works
Kuo, P., Chang, J.-C., Lee, W., et al. (2005) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2005.06.024 · Cited by 32 · see citing works
Xu, X., Yao, Y., Hu, M., Zhang, Y., & Shen, Q. (2006) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21550 · Cited by 31 · see citing works
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
Qi, C., & Wang, Z. (2006) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21561 · Cited by 29 · see citing works
Lecomte, P., Stassin, F., & Jérôme, R. (2004) · Macromolecular Symposia · doi:10.1002/masy.200451125 · Cited by 26 · see citing works
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
Strunkina, L. I., Minacheva, M. K., Lyssenko, K. A., et al. (2005) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2005.09.027 · Cited by 21 · see citing works
Wu, Y., Wang, S., Qian, C., et al. (2005) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2005.06.017 · Cited by 19 · see citing works
Bimetallic and cationic aluminum with N3O2 chelate ligands
Liu, S., Muñoz‐Hernández, M., & Atwood, D. A. (2000) · Journal of Organometallic Chemistry · doi:10.1016/s0022-328x(99)00575-6 · Cited by 18 · see citing works
Champouret, Y., Nodes, W. J., Scrimshire, J. A., et al. (2007) · Dalton Transactions · doi:10.1039/b709385c · Cited by 11 · see citing works
Aluminum(III) complexes containing O,O chelating ligand
Dostál, L., Jambor, R., Cı́sařová, I., et al. (2007) · Applied Organometallic Chemistry · doi:10.1002/aoc.1226 · Cited by 5 · see citing works
Cationic Ring-Opening Polymerization(CROP) major mechanistic phenomena
Penczek, S. (2000) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/(sici)1099-0518(20000601)38:11
Flagged first, then by citations
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Arbaoui, A., & Redshaw, C. (2010) · Polymer Chemistry · doi:10.1039/b9py00334g · Cited by 383 · 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, L., Li, W., Yuan, D., Zhang, Y., Shen, Q., & Yao, Y. (2015) · Inorganic Chemistry · doi:10.1021/acs.inorgchem.5b00022 · Cited by 83 · see citing works
Yu, X.-F., & Wang, Z.-X. (2013) · Dalton Transactions · doi:10.1039/c2dt32520a · Cited by 58 · see citing works
Gruszka, W., Walker, L. C., Shaver, M. P., & Garden, J. A. (2020) · Macromolecules · doi:10.1021/acs.macromol.0c00277 · Cited by 49 · see citing works
Han, H.-L., Liu, Y., Liu, J.-Y., Nomura, K., & Li, Y.-S. (2013) · Dalton Transactions · doi:10.1039/c3dt50264c · Cited by 41 · see citing works
Shi, T., Zheng, Q.-D., Zuo, W.-W., Liu, S.-F., & Li, Z.-B. (2018) · Chinese Journal of Polymer Science · doi:10.1007/s10118-018-2039-5 · Cited by 39 · see citing works
Osorio Meléndez, D., Castro‐Osma, J. A., Lara‐Sánchez, A., Rojas, R. S., & Otero, A. (2017) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/pola.28629 · Cited by 38 · see citing works
Nakonkhet, C., Nanok, T., Wattanathana, W., Chuawong, P., & Hormnirun, P. (2017) · Dalton Transactions · doi:10.1039/c7dt02435e · Cited by 31 · see citing works
Wang, P., Chao, J., & Chen, X. (2018) · Dalton Transactions · doi:10.1039/c7dt04522k · Cited by 26 · see citing works
Wang, C.-H., Li, C.-Y., Lin, C.-H., Liu, Y.-C., & Ko, B.-T. (2011) · Inorganic Chemistry Communications · doi:10.1016/j.inoche.2011.05.046 · Cited by 25 · see citing works
Gruszka, W., Sha, H., Buchard, A., & Garden, J. A. (2022) · Catalysis Science & Technology · doi:10.1039/d1cy01914g · Cited by 24 · see citing works
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Allan, L. E. N., Bélanger, J. A., Callaghan, L. M., Cameron, D. J. A., Decken, A., & Shaver, M. P. (2012) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2012.02.003 · Cited by 22 · see citing works
Hsu, C.-Y., Tseng, H.-C., Vandavasi, J. K., Lu, W.-Y., Wang, L.-F., Chiang, M. Y., Lai, Y.-C., Chen, H.-Y., & Chen, H.-Y. (2017) · RSC Advances · doi:10.1039/c7ra02136d · Cited by 20 · see citing works
Lai, F.-J., Chiu, L.-L., Lee, C.-L., Lu, W.-Y., Lai, Y.-C., Ding, S., Chen, H.-Y., & Wu, K.-H. (2019) · Polymer · doi:10.1016/j.polymer.2019.121812 · Cited by 17 · see citing works
- Authors
- Yao, W., Mu, Y., Gao, A., Gao, W., & Ye, L.
- Affiliations
- Jilin University (CN)
- Corresponding author
- Mu, Ying
- Venue
- Dalton Transactions
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2008
- Issue
- 24
- Pages
- 3199
- ISSN
- 1477-9226 (ISSN-L)
- 1477-9234
- OpenAlex
- W1999632283
- Cited by
- 107
- References
- 82
- Citations by year
- 2026: 3 · 2024: 3 · 2023: 1 · 2022: 4 · 2021: 3 · 2020: 2 · 2019: 4 · 2018: 1 · 2017: 11 · 2016: 10 · 2015: 6 · 2014: 9 · 2013: 10 · 2012: 17
- FWCI
- 3.28
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Dalton Transactions (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Organometallic Complex Synthesis and Catalysis
- Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
- Keywords
- bimetallic complexes, aluminum complexes, zinc complexes, ε-caprolactone, ring-opening polymerization, living polymerization, benzyl alcohol, polydispersity index
- MeSH terms
- Anilides, Caproates, Imines, Lactones, Models, Molecular, Organometallic Compounds, Polymers, Molecular Structure, Aluminum Compounds, Zinc Compounds
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