Non-toxic catalysts for ring-opening polymerizations of biodegradable polymers at room temperature for biohybrid materials

Hege, Cordula S.; Schiller, Stefan M.

doi:10.1039/c3gc42044b

Cited by 77biodegradable polymer synthesis and propertiesCarbon dioxide utilization in catalysisSynthetic Organic Chemistry Methods

Non-toxic catalysts for ring-opening polymerizations of biodegradable polymers at room temperature for biohybrid materials

Hege, Cordula S., Schiller, Stefan M.·2014·Green Chem.

DOI 10.1039/c3gc42044b

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Abstract

Biodegradable biopolymers are versatile materials with a wide range of applications including suture, scaffolds, growth chambers and matrix materials for tissue-engineering and regenerative medicine. Their synthesis is usually based on tin-salts at high temperatures. Strategies to replace tin are interesting due to the toxicity of tin for aquatic organisms and potentially problematic effects in higher organisms. In the framework of this study we investigate nontoxic iron catalysts (iron chloride, bromide and perchlorate) and their potential to facilitate ring-opening polymerizations (ROP) at room temperature. To find the best combination of a catalyst and an initiator for the ROP of ε-caprolactone, three iron-catalysts were analysed with four different initiators (water, isopropyl alcohol, benzyl alcohol and 2-allyl phenol). Functional entities such as the allyl group are interesting for bioconjugation and may allow functional access to functional biohybrid materials. The polymerizations were carried out solvent free in bulk and yielded polymers in the range 10–20 kDa for large monomer to catalyst/initiator ratios analysed by GPC, NMR and MALDI-TOF. We find that commercial iron salts can replace tin salts in many cases and allow for the ROP of ε-caprolactone at room temperature while tin(II) 2-ethylhexanoate Sn(Oct)2 does not facilitate ROP at room temperature. The use of iron based ROP catalysts opens interesting access to biopolymers utilizing a nontoxic metal ion at low temperatures in a solvent free reaction scheme saving energy and the environment.

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Use of simple iron(iii) catalysts were reported for CL and LA, but in most cases, relatively high dispersities were obtained.
“The use of simple iron(iii) catalysts were reported for CL58 and LA,59,60 but in most cases, relatively high dispersities were obtained.61,62”
From Iron( <scp>ii</scp> ) carboxylates and simple carboxamides: an inexpensive and modular catalyst system for the synthesis of PLLA and PLLA-PCL block copolymers (2023) · cites this paper as [61]

Synthesis of polycaprolactone: A review
Labet, M., & Thielemans, W. (2009) · Chemical Society Reviews · doi:10.1039/b820162p · Cited by 1,673 · see citing works
The in vivo degradation, absorption and excretion of PCL-based implant
Sun, H., Mei, L., Song, C. X., Cui, X., & Wang, P. (2005) · Biomaterials · doi:10.1016/j.biomaterials.2005.09.019 · Cited by 977 · 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
Organic Catalysis for Ring-Opening Polymerization
Dove, A. P. (2012) · ACS Macro Letters · doi:10.1021/mz3005956 · Cited by 545 · see citing works
A “Tag-and-Modify” Approach to Site-Selective Protein Modification
Chalker, J. M., Bernardes, G. J. L., & Davis, B. G. (2011) · Accounts of Chemical Research · doi:10.1021/ar200056q · Cited by 354 · see citing works
Mechanistic comparison of cyclic ester polymerizations by novel iron(III)-alkoxide complexes: Single vs. multiple site catalysis
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
Tyrosine-Selective Protein Alkylation Using π-Allylpalladium Complexes
Tilley, S. D., & Francis, M. B. (2006) · Journal of the American Chemical Society · doi:10.1021/ja057106k · Cited by 287 · see citing works
Polypeptide–polymer bioconjugates
Canalle, L. A., Löwik, D. W. P. M., & van Hest, J. C. M. (2009) · Chemical Society Reviews · doi:10.1039/b807871h · Cited by 265 · see citing works
Cytotoxicity of some catalysts commonly used in the synthesis of copolymers for biomedical use
Tanzi, M. C., Verderio, P., Lampugnani, M. G., Resnati, M., Dejana, E., & Sturani, E. (1994) · Journal of Materials Science Materials in Medicine · doi:10.1007/bf00058971 · Cited by 218 · 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
Rapid and Controlled Polymerization of Lactide by Structurally Characterized Ferric Alkoxides
O'Keefe, B. J., Monnier, S. M., Hillmyer, M. A., & Tolman, W. B. (2000) · Journal of the American Chemical Society · doi:10.1021/ja003537l · Cited by 207 · see citing works
Emerging synthetic approaches for protein–polymer conjugations
Broyer, R. M., Grover, G. N., & Maynard, H. D. (2011) · Chemical Communications · doi:10.1039/c0cc04062b · Cited by 200 · see citing works
Controlled Polymerization of dl -Lactide and ε-Caprolactone by Structurally Well-Defined Alkoxo-Bridged Di- and Triyttrium(III) Complexes
Chamberlain, B. M., Jazdzewski, B. A., Pink, M., Hillmyer, M. A., & Tolman, W. B. (2000) · Macromolecules · doi:10.1021/ma0000834 · Cited by 131 · see citing works
Polymerization of .epsilon.-Caprolactone by Divalent Samarium Complexes
Evans, W. J., & Katsumata, H. (1994) · Macromolecules · doi:10.1021/ma00086a056 · Cited by 113 · see citing works
A well-defined iron(ii) alkoxide initiator for the controlled polymerisation of lactide
Gibson, V. C., Marshall, E. L., Navarro-Llobet, D., White, A. J. P., & Williams, D. J. (2002) · Journal of the Chemical Society Dalton Transactions · doi:10.1039/b209703f · Cited by 111 · see citing works
Absorption, distribution and excretion of inorganic tin in rats
Hiles, R. A. (1974) · Toxicology and Applied Pharmacology · doi:10.1016/0041-008x(74)90208-7 · Cited by 96 · see citing works
Lipase/esterase-catalyzed ring-opening polymerization: A green polyester synthesis technique
Yang, Y., Yu, Y., Zhang, Y., Liu, C., Shi, W., & Li, Q. (2011) · Process Biochemistry · doi:10.1016/j.procbio.2011.07.016 · Cited by 94 · see citing works
Short-term toxicity studies on some salts and oxides of tin in rats
Groot, A. P., FERON, V. J., & Til, H. P. (1973) · Food and Cosmetics Toxicology · doi:10.1016/0015-6264(73)90058-8 · Cited by 92 · see citing works
The toxicity of tin in canned fruit juices and solid foods
Benoy, C. J., Hooper, P. A., & Schneider, R. (1971) · Food and Cosmetics Toxicology · doi:10.1016/0015-6264(71)90152-0 · Cited by 79 · see citing works
Environmentally benign process for bulk ring opening polymerization of lactones using iron and ruthenium chloride catalysts
Gowda, R. R., & Chakraborty, D. (2009) · Journal of Molecular Catalysis A: Chemical · doi:10.1016/j.molcata.2008.11.010 · Cited by 59 · see citing works
Tin and inorganic tin compounds
Howe, P. D., & Watts, P. (2005) · World Health Organization eBooks · Cited by 57 · see citing works
SnCl2-induced DNA damage and repair inhibition of MMS-caused lesions in V79 Chinese hamster fibroblasts
Viau, C. M., Guecheva, T. N., Sousa, F. G., Pungartnik, C., Brendel, M., Saffi, J., & Henriques, J. A. P. (2009) · Archives of Toxicology · doi:10.1007/s00204-009-0409-z · Cited by 49 · see citing works
Organotin compounds and aquatic bacteria: A review
Cooney, J. J. (1995) · Helgoland Marine Research · doi:10.1007/bf02368390 · Cited by 46 · see citing works
Aluminium complexes bearing functionalized trisamido ligands and their reactivity in the polymerization of ε-caprolactone and rac-lactide
Thibault, M., & Fontaine, F. (2010) · Dalton Transactions · doi:10.1039/c0dt00005a · Cited by 44 · see citing works
Genotoxic effects of stannous chloride (SnCl2) in K562 cell line
Dantas, F. J. D. S., de Mattos, J. C. P., Moraes, M. O., Viana, M. E., Lage, C. A. S., Cabral-Neto, J. B., Leitão, Á. C., Bernardo-Filho, M., Bezerra, R. J. A. C., de Carvalho, J. J., et al. (2002) · Food and Chemical Toxicology · doi:10.1016/s0278-6915(02)00087-x · Cited by 32 · see citing works
Effect of various dietary components on absorption and tissue distribution of orally administered inorganic tin in rats
Fritsch, P., Blanquat, G. D. S., & Derache, R. (1977) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(77)80322-2 · Cited by 28 · see citing works
Effects of oral administration of two tin compounds to rats over prolonged periods
Roe, F. J. C., Boyland, E. J., & Millican, K. (1965) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(65)80085-2 · Cited by 28 · see citing works
Comparative in vitro Cytotoxicity Toward Human Osteoprogenitor Cells of Polycaprolactones Synthesized from Various Metallic Initiators
Schappacher, M., Hellaye, M. L., Bareille, R., Durrieu, M., & Guillaume, S. M. (2009) · Macromolecular Bioscience · doi:10.1002/mabi.200900184 · Cited by 27 · see citing works
An Electrospun Degradable Scaffold Based on a Novel Hydrophilic Polyester for Tissue‐Engineering Applications
Seyednejad, H., Ji, W., Schuurman, W., Dhert, W. J. A., Malda, J., Yang, F., Jansen, J. A., van Nostrum, C. F., Vermonden, T., & Hennink, W. E. (2011) · Macromolecular Bioscience · doi:10.1002/mabi.201100229 · Cited by 19 · see citing works
Intracerebral microinjection of stannous 2‐ethylhexanoate affects dopamine turnover in cerebral cortex and locomotor activity in rats
Yamada, T., Jung, D., Sawada, R., & Tsuchiya, T. (2008) · Journal of Biomedical Materials Research Part B Applied Biomaterials · doi:10.1002/jbm.b.31115 · Cited by 15 · see citing works
Kinetic Study of the Al‐Schiff's Base Initiated Polymerization of ε‐caprolactone and Synthesis of Graft Poly(methylmethacrylate‐g‐caprolactone)
Motala‐Timol, S., Bhaw‐Luximon, A., & Jhurry, D. (2005) · Macromolecular Symposia · doi:10.1002/masy.200590026 · Cited by 14 · see citing works
De-novo Generierung von vaskularisiertem Gewebe mittels unterschiedlicher Gefässstielkonfigurationen in perforierten und geschlossenen Wachstumskammern
Dolderer, J. H., Kehrer, A., Schiller, S. M., Schröder, U. H., Köhler, K., Schaller, H., & Siegel-Axel, D. I. (2010) · Wiener Medizinische Wochenschrift · doi:10.1007/s10354-009-0734-0 · Cited by 5 · see citing works
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Reactive compatibilization of plant polysaccharides and biobased polymers: Review on current strategies, expectations and reality
Imre, B., García, L., Puglia, D., & Vilaplana, F. (2018) · Carbohydrate Polymers · doi:10.1016/j.carbpol.2018.12.082 · Cited by 156 · see citing works
Recent progress in the application of group 1, 2 & 13 metal complexes as catalysts for the ring opening polymerization of cyclic esters
Gao, J., Zhu, D., Zhang, W., Solan, G. A., Ma, Y., & Sun, W. (2019) · Inorganic Chemistry Frontiers · doi:10.1039/c9qi00855a · Cited by 116 · see citing works
Synthesis of biodegradable polymers: A review on the use of schiff-base metal complexes as catalysts for the ring opening polymerization (ROP) of cyclic esters
Santoro, O., Zhang, X., & Redshaw, C. (2020) · Catalysts · doi:10.3390/catal10070800 · Cited by 111 · see citing works
Meglumine catalyzed expeditious four-component domino protocol for synthesis of pyrazolopyranopyrimidines in aqueous medium
Li, X.-T., Zhao, A., Mo, L., & Zhang, Z. (2014) · RSC Advances · doi:10.1039/c4ra08689a · Cited by 86 · see citing works
Salen, salan and salalen iron( <scp>iii</scp> ) complexes as catalysts for CO <sub>2</sub> /epoxide reactions and ROP of cyclic esters
Cozzolino, M., Leo, V., Tedesco, C., Mazzeo, M., & Lamberti, M. (2018) · Dalton Transactions · doi:10.1039/c8dt03169j · Cited by 83 · see citing works
One‐Step In Situ Polymerization: A Facile Design Strategy for Block Copolymer Electrolytes
Guo, K., Wang, J., Shi, Z., Wang, Y., Xie, X., & Xue, Z. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202213606 · Cited by 83 · see citing works
Discrete iron-based complexes: Applications in homogeneous coordination-insertion polymerization catalysis
Champouret, Y., Hashmi, O. H., & Visseaux, M. (2019) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2019.03.015 · Cited by 80 · see citing works
New biomaterials from renewable resources – amphiphilic block copolymers from δ-decalactone
Bansal, K. K., Kakde, D. D., Purdie, L., Irvine, D. J., Howdle, S. M., Mantovani, G., & Alexander, C. (2015) · Polymer Chemistry · doi:10.1039/c5py01203a · Cited by 60 · see citing works
Effect of surface-grafted cellulose nanocrystals on the thermal and mechanical properties of PLLA based nanocomposites
de Paula, E. L., Roig, F., Mas, A., Habas, J., Mano, V., Pereira, F. V., & Robin, J. (2016) · European Polymer Journal · doi:10.1016/j.eurpolymj.2016.09.019 · Cited by 54 · see citing works
Electrochemical preparation and characterization of PNIPAM-HAp scaffolds for bone tissue engineering
Ribeiro, C. A., Martins, M. V. S., Bressiani, A. H. D. A., Bressiani, J. C., Leyva, M. E., & de Queiroz, A. A. A. (2017) · Materials Science and Engineering C · doi:10.1016/j.msec.2017.07.048 · Cited by 54 · see citing works
The role of ligand redox non-innocence in ring-opening polymerization reactions catalysed by bis(imino)pyridine iron alkoxide complexes
Delle Chiaie, K. R., Biernesser, A. B., Ortuño, M. A., Dereli, B., Iovan, D. A., Wilding, M. J. T., Li, B., Cramer, C. J., & Byers, J. A. (2017) · Dalton Transactions · doi:10.1039/c7dt03067c · Cited by 48 · see citing works
Molecular bionics – engineering biomaterials at the molecular level using biological principles
Rodríguez‐Arco, L., Poma, A., Ruiz‐Pérez, L., Scarpa, E., Ngamkham, K., & Battaglia, G. (2018) · Biomaterials · doi:10.1016/j.biomaterials.2018.10.044 · Cited by 48 · see citing works
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Wang, Y., Wang, X., Zhang, W., & Sun, W. (2023) · Organometallics · doi:10.1021/acs.organomet.3c00028 · Cited by 46 · see citing works
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Laboratory-Scale Life-Cycle Assessment: A Comparison of Existing and Emerging Methods of Poly(ε-caprolactone) Synthesis
Ang, P., Mothe, S. R., Chennamaneni, L. R., Aidil, F., Hsien Hui, K. H. O. O., & Thoniyot, P. (2020) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.0c06247 · Cited by 43 · see citing works
The Role of Alkoxide Initiator, Spin State, and Oxidation State in Ring-Opening Polymerization of ε-Caprolactone Catalyzed by Iron Bis(imino)pyridine Complexes
Ortuño, M. A., Dereli, B., Chiaie, K. R. D., Biernesser, A. B., Qi, M., Byers, J. A., & Cramer, C. J. (2018) · Inorganic Chemistry · doi:10.1021/acs.inorgchem.7b02964 · Cited by 35 · see citing works
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Folate-Targeted Cholesterol-Grafted Lipo-Polymeric Nanoparticles for Chemotherapeutic Agent Delivery
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Vidal, J. L., Yavitt, B. M., Wheeler, M. D., Kolwich, J., Donovan, L. N., Sit, C. S., Hatzikiriakos, S. G., Jalsa, N. K., MacQuarrie, S., & Kerton, F. M. (2021) · Sustainable Chemistry and Pharmacy · doi:10.1016/j.scp.2021.100586 · Cited by 28 · see citing works
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Lu, Y., Schmidt, C., & Beuermann, S. (2014) · Macromolecular Chemistry and Physics · doi:10.1002/macp.201400474 · Cited by 28 · see citing works
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Dzienia, A., Maksym, P., Hachuła, B., Tarnacka, M., Biela, T., Golba, S., Zięba, A., Chorążewski, M., Kamiński, K., & Paluch, M. (2019) · Polymer Chemistry · doi:10.1039/c9py01134j · Cited by 27 · see citing works
Biodegradable poly(3-hydroxybutyrate-co-4-hydroxybutyrate) films coated with tannic acid as an active food packaging material
Park, J. J., Choi, Y. H., Sim, E. J., Lee, E., Yoon, K. C., & Park, W. H. (2022) · Food Packaging and Shelf Life · doi:10.1016/j.fpsl.2022.101009 · Cited by 27 · see citing works
Zinc/magnesium–sodium/lithium heterobimetallic triphenolates: Synthesis, characterization, and application as catalysts in the ring-opening polymerization of l-lactide and CO2/epoxide coupling
Sun, Y., Wang, L., Yu, D., Tang, N., & Wu, J. (2014) · Journal of Molecular Catalysis A Chemical · doi:10.1016/j.molcata.2014.06.017 · Cited by 27 · see citing works
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Nakayama, Y., Kosaka, S., Yamaguchi, K., Gentaro, Y., Tanaka, R., & Shiono, T. (2016) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.28383 · Cited by 23 · see citing works
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Rana, S., Maddila, S., Yalagala, K., Maddila, S., & Jonnalagadda, S. B. (2015) · ChemistryOpen · doi:10.1002/open.201500121 · Cited by 20 · see citing works
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Highly efficient iron(II) catalysts toward ring opening polymerization of ε-caprolactone through in situ initiation
Dou, J., Zhu, D., Zhang, W., Wang, R., Wang, S., Zhang, Q., Zhang, X., & Sun, W.-H. (2019) · Inorganica Chimica Acta · doi:10.1016/j.ica.2019.01.040 · Cited by 19 · see citing works
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Geng, C., Peng, Y., Wang, L., Roesky, H. W., & Liu, K. (2016) · Dalton Transactions · doi:10.1039/c6dt00078a · Cited by 15 · see citing works
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Zhang, K., Bai, T., & Ling, J. (2023) · Macromolecules · doi:10.1021/acs.macromol.3c01359 · Cited by 11 · see citing works
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Ma, X., Wang, H., Wang, Z., Lv, Y., & Wei, Z. (2024) · European Polymer Journal · doi:10.1016/j.eurpolymj.2024.112972 · Cited by 11 · see citing works
Homoleptic, bis‐ligated magnesium complexes for ring‐opening polymerization of lactide and lactones: Synthesis, structure, polymerization behavior and mechanism studies
Chen, X., Wang, B., Pan, L., & Li, Y. (2019) · Applied Organometallic Chemistry · doi:10.1002/aoc.4770 · Cited by 11 · see citing works
Ring-opening polymerization of ε-caprolactone from cellulose acetate by reactive processing
Imre, B., Kiss, E. Z., Domján, A., Cui, L., & Pukánszky, B. (2021) · Cellulose · doi:10.1007/s10570-021-04038-8 · Cited by 9 · see citing works
Homoleptic and Heteroleptic Substituted Amidomethylpyridine Iron Complexes: Synthesis, Structure and Polymerization of rac‐Lactide
Hashmi, O. H., Capet, F., Visseaux, M., & Champouret, Y. (2022) · European Journal of Inorganic Chemistry · doi:10.1002/ejic.202200073 · Cited by 9 · see citing works
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Shang, X., Zhang, W., & Lang, J. (2016) · RSC Advances · doi:10.1039/c5ra22279f · Cited by 9 · see citing works
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Synthesis and characterization of star-shaped carboxyl group functionalized poly(lactic acid) through polycondensation reaction
Kucharczyk, P., Zednı́k, J., & Sedlařík, V. (2016) · Macromolecular Research · doi:10.1007/s13233-017-5014-z · Cited by 8 · see citing works
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Hartanto, D. T., Tung, J.-Y., Aziz, G. D. A., Kusumastuti, Y., Shirosaki, Y., & Wang, M. (2025) · Analytica Chimica Acta · doi:10.1016/j.aca.2025.343668 · Cited by 7 · see citing works
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Wang, Y., Zhang, W., Wang, X., Zuo, W., Xue, X., Ma, Y., & Sun, W. (2023) · RSC Advances · doi:10.1039/d3ra05867k · Cited by 7 · see citing works
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Kirchhecker, S., Nguyen, N., Reichert, S., Lützow, K., Eselem Bungu, P. S., Jacobi von Wangelin, A., Sandl, S., & Neffe, A. T. (2023) · RSC Advances · doi:10.1039/d3ra03112h · Cited by 6 · see citing works
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One‐Step In Situ Polymerization: A Facile Design Strategy for Block Copolymer Electrolytes
Guo, K., Wang, J., Shi, Z., Wang, Y., Xie, X., & Xue, Z. (2022) · Angewandte Chemie · doi:10.1002/ange.202213606 · Cited by 6 · see citing works
Amphiphilic Pentablock Copolymers Prepared from Pluronic and ε-Caprolactone by Enzymatic Ring Opening Polymerization
El‐Fattah, A. A., Fernandes, E. G., Chiellini, E., & Chiellini, E. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms23031390 · Cited by 6 · see citing works
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Injectable and photocurable macromonomers synthesized using a novel heterometallic magnesium-titanium metal-organic catalystPreprint
Niedźwiedź, M., Ignaczak, W., Sobolewski, P., Demirci, G., & Fray, M. E. (2022) · ChemRxiv · doi:10.26434/chemrxiv-2022-jn0mj · Cited by 4 · see citing works
High pressure phase behavior and thermodynamic modeling of the carbon dioxide + chloroform + globalide system
Girardi, D. G. L., Letsch, A. L., Rebelatto, E. A., Mayer, D. A., & de Oliveira, J. V. (2023) · Fluid Phase Equilibria · doi:10.1016/j.fluid.2023.113831 · Cited by 3 · see citing works
Iron–Aryloxide Complex Bearing Bis(dipyrromethene) Ligands for the Ring-Opening Polymerization of ε-Caprolactone
Yu, B., Xu, X., Huang, Z.-N., Tao, K., Sun, H., Yang, Q., & Wang, W. (2023) · Organometallics · doi:10.1021/acs.organomet.2c00618 · Cited by 3 · see citing works
Ring-Opening Polymerization of Lactones Catalyzed by Silicon-Based Lewis Acid
Nakayama, Y., Katagi, K., Tanaka, R., & Shiono, T. (2023) · International Journal of Polymer Science · doi:10.1155/2023/4391372 · Cited by 2 · see citing works
Injectable and photocurable macromonomers synthesized using a heterometallic magnesium–titanium metal–organic catalyst for elastomeric polymer networks
Niedźwiedź, M., Ignaczak, W., Sobolewski, P., Goszczyńska, A., Demirci, G., & Fray, M. E. (2023) · RSC Advances · doi:10.1039/d3ra02157b · Cited by 2 · see citing works
Biobased Polymers from Food Waste Feedstock and Their Synthesis
Cecchi, T. (2021) · Springer eBooks · doi:10.1007/978-3-030-63436-0_6 · Cited by 2 · see citing works
Flexible nanoscale co‐continuous structures prepared by controlled crazing of ethylene‐octene elastomers and in‐situ polymerization of conductive networks
Kornberg, A. B., Thompson, M. R., & Zhu, S. (2022) · The Canadian Journal of Chemical Engineering · doi:10.1002/cjce.24796 · Cited by 1 · see citing works
Ooptical limiting properties of polymer-dye nanohybrids: a comparison between polylactide and PMMA hosts
Müller, O., Hege, C. S., Guerchoux, M., Dandois, M., Trendel, P., & Merlat, L. (2019) · doi:10.1117/12.2531814
Self-citation
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Ochkhikidze, N., Titvinidze, G., Gverdtsiteli, M. G., Otinashvili, G., Tugushi, D., & Katsarava, R. D. (2020) · Journal of Macromolecular Science Part A · doi:10.1080/10601325.2020.1800411
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Jain, I., & Malik, P. (2022) · Lecture notes in bioengineering · doi:10.1007/978-981-19-1084-5_8
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Ahmadova, I., Tapdiqov, S. Z., Eroğlu, M. S., & Bostan, M. S. (2023) · Journal of Polymer Research · doi:10.1007/s10965-023-03678-7
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Santos, C. C. D. O. (2022) · doi:10.47749/t/unicamp.2022.1257009
Ring-Opening Homo- and Copolymerization of Cyclic Esters Catalyzed by Iron(III) Triflate
Nakayama, Y., Omori, T., Tanaka, R., & Shiono, T. (2024) · Catalysts · doi:10.3390/catal14120945
Gram-scale synthesis of a multi-stimuli-responsive fluorescent polycaprolactone dye via indolo[2,3-b]quinoxaline derivative capping: Aggregation-induced emission, acidochromism, and latent fingerprint development
Hu, H., Zhang, B., Duan, H., & Deng, P. (2026) · Dyes and Pigments · doi:10.1016/j.dyepig.2026.114104
Iron(III) N-Hydroxyformamidine Complexes: Structural Features, Solvatochromic Behavior and Preliminary Catalytic ActivitiesPreprint
Juma, D. O., Njogu, E. M., Munzeiwa, W. A., Zamisa, S. J., & Ouma, O. B. (2026) · SSRN Electronic Journal · doi:10.2139/ssrn.7435202

Progress of Ring-Opening Polymerization of Cyclic Esters Catalyzed by Iron Compounds
Wang, Y., Wang, X., Zhang, W., & Sun, W. (2023) · Organometallics · doi:10.1021/acs.organomet.3c00028 · Cited by 46 · see citing works
Metal catalysts for ε-caprolactone polymerisation
Arbaoui, A., & Redshaw, C. (2010) · Polymer Chemistry · doi:10.1039/b9py00334g · Cited by 383 · see citing works
Recent Advances in the Titanium-Based Catalysts for Ring-Opening Polymerization
Wang, W. (2024) · ACS Omega · doi:10.1021/acsomega.4c00048 · Cited by 26 · see citing works
Efficient, Non-Toxic Polylactide Synthesis
Swager, T. M., & Sletten, E. M. (2012) · Synfacts · doi:10.1055/s-0032-1317435
Catalytic ring-opening polymerization of cyclic esters to biodegradable polyesters using N,N'- and N,O-ligand supported Cu(II), Mg(II) and Zn(II) complexes.
Munzeiwa, W. (2018) · ResearchSpace (University of KwaZulu-Natal)

Authors: Hege, C. S., & Schiller, S. M.
Affiliations: University of Freiburg (DE)
Corresponding author: Schiller, Stefan M.
ORCID: Hege, Cordula S.
Schiller, Stefan M.
Venue: Green Chem.
Publisher: Royal Society of Chemistry (RSC)
Published: 2014
Volume: 16
Issue: 3
Pages: 1410-1416
ISSN: 1463-9262 (ISSN-L)
1463-9270
DOI: 10.1039/c3gc42044b
OpenAlex: W2105691442
Cited by: 77
References: 32
Citations by year: 2026: 3 · 2025: 3 · 2024: 4 · 2023: 11 · 2022: 12 · 2021: 5 · 2020: 8 · 2019: 9 · 2018: 5 · 2017: 4 · 2016: 8 · 2015: 2 · 2014: 3
FWCI: 1.65
Type: journal article
Language: en
Open access: closed
Locations: Green Chemistry (publishedVersion)
Topics: Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
Physical Sciences › Chemistry › Organic Chemistry › Synthetic Organic Chemistry Methods
Keywords: ring-opening polymerization, iron catalysts, ε-caprolactone, biodegradable polymers, room-temperature polymerization, solvent-free polymerization, initiators, biohybrid materials, tissue engineering, regenerative medicine, bioconjugation, iron chloride, iron perchlorate, iron bromide

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Non-toxic catalysts for ring-opening polymerizations of biodegradable polymers at room temperature for biohybrid materials

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