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Polymers
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Metal-Mediated Polymer Synthesis
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Metal-Mediated Polymer Synthesis

A special issue of Polymers (ISSN 2073-4360).

Deadline for manuscript submissions: closed (31 December 2015) | Viewed by 93469

Special Issue Editor

Prof. Dr. Changle Chen

E-Mail Website
Guest Editor
Chinese Academy of Sciences Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China
Interests: metal-based polymerization catalysts; olefin polymerization; polar monomers; ring-opening polymerization; carbon-based nano-materials; industrial engineering polymers
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Metal complexes are being widely used in the controlled synthesis of various polymers. As a matter of fact, metal complexes are indispensable in numerous polymerization reactions, including controlled living radial polymerization, metal-catalyzed olefin polymerization, metathesis type polymerization, ring-opening polymerization of lactide type monomers, etc. The design and development of new metal catalysts are crucial for the discovery of new polymerization techniques and new polymeric materials.

This Special Issue focuses on the latest achievements in the field of metal mediated polymer synthesis. This Special Issue invites original papers and reviews concerning the development of new metal catalysts, new metal mediated polymerization techniques, new insights into the mechanism of metal mediated polymerization, and the application of existing metal complexes for the synthesis of new polymeric materials.

Prof. Dr. Changle Chen
Guest Editor

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Polymers is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Polymer
  • Polymerization
  • Polymer synthesis
  • Metal catalyst
  • Catalysis
  • Mechanism

Published Papers (12 papers)

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Research

1415 KiB  
Article
Synthesis and Characterization of Polystyrene-Supported Piperazine-Substituted Triazoles by CuAAC and First Evaluation for Metal Ion Extraction
by Riadh Slimi, Raja Ben Othman, Noomene Sleimi, Abid Ouerghui and Christian Girard
Polymers 2016, 8(5), 187; https://doi.org/10.3390/polym8050187 - 10 May 2016
Cited by 4 | Viewed by 5949
Abstract
The goal of this work was to synthesize substituted polystyrene for metal extraction and/or depollution by introduction of substituted piperazines as chelatants starting from Merrifield polymer. After transformation of Merrifield’s resin in azidomethyl polystyrene, click-chemistry using copper (I)-catalyzed Huisgen’s reaction (CuAAC) was performed [...] Read more.
The goal of this work was to synthesize substituted polystyrene for metal extraction and/or depollution by introduction of substituted piperazines as chelatants starting from Merrifield polymer. After transformation of Merrifield’s resin in azidomethyl polystyrene, click-chemistry using copper (I)-catalyzed Huisgen’s reaction (CuAAC) was performed to prepare different polymers grafted with 1,4-triazoles bearing the piperazines, containing an alkyne as the other counterpart in the CuAAC. The polymers were then first tested for their efficiency to remove various metal ions from neutral aqueous solutions (Fe3+, Ni2+, Cu2+, Zn2+ and Pb2+). The polymers were found to extract Ni2+ and Zn2+ with low efficiencies ≤40%. For Fe3+ and Cu2+, the average extraction was around 80%, and for Pb2+ around 50%. The global selectivity for these polymers was found to be in the order of Fe3+ ≥ Cu2+ > Pb2+ >> Ni2+ > Zn2+. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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2627 KiB  
Article
Highly Active Copolymerization of Ethylene and N-Acetyl-O-(ω-Alkenyl)-l-Tyrosine Ethyl Esters Catalyzed by Titanium Complex
by Jing Wang, Hongming Li, Runcong Zhang, Xianghui Shi, Jianjun Yi, Jian Wang, Qigu Huang and Wantai Yang
Polymers 2016, 8(3), 64; https://doi.org/10.3390/polym8030064 - 10 Mar 2016
Cited by 3 | Viewed by 7485
Abstract
A series of N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters were synthesized by the reaction of vinyl bromides (4-bromo-1-butene, 6-bromo-1-hexene, 8-bromo-1-octene and 10-bromo-1-decene) with N-acetyl-l-tyrosine ethyl ester. 1H NMR, elemental analysis, FT-IR, and mass spectra were performed for [...] Read more.
A series of N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters were synthesized by the reaction of vinyl bromides (4-bromo-1-butene, 6-bromo-1-hexene, 8-bromo-1-octene and 10-bromo-1-decene) with N-acetyl-l-tyrosine ethyl ester. 1H NMR, elemental analysis, FT-IR, and mass spectra were performed for these N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters. The novel titanium complex can catalyze the copolymerization of ethylene and N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters efficiently and the highest catalytic activity was up to 6.86 × 104 gP·(molTi)−1·h−1. The structures and properties of the obtained copolymers were characterized by FT-IR, (1H)13C NMR, GPC, DSC, and water contact angle. The results indicated that the obtained copolymers had a uniformly high average molecular weight of 2.85 × 105 g·mol−1 and a high incorporation ratio of N-acetyl-O-(but-3-enyl)-l-tyrosine ethyl ester of 2.65 mol % within the copolymer chain. The units of the comonomer were isolated within the copolymer chains. The insertion of the polar comonomer into a copolymer chain can effectively improve the hydrophilicity of a copolymer. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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1660 KiB  
Article
Homo- and Copolymerization of Ethylene and Norbornene with Anilido–Imine Chromium Catalysts
by Lixia Pei, Yong Tang and Haiyang Gao
Polymers 2016, 8(3), 69; https://doi.org/10.3390/polym8030069 - 01 Mar 2016
Cited by 14 | Viewed by 6751
Abstract
A series of anilido–imine chromium complexes have been used as precursors to catalyze homo- and copolymerization of ethylene and norbornene. The chromium complexes activated with methylalumoxane (MAO) exhibit good activities for homopolymerization of ethylene (E) to produce linear polyethylene and moderate activities for [...] Read more.
A series of anilido–imine chromium complexes have been used as precursors to catalyze homo- and copolymerization of ethylene and norbornene. The chromium complexes activated with methylalumoxane (MAO) exhibit good activities for homopolymerization of ethylene (E) to produce linear polyethylene and moderate activities for norbornene (N) polymerization to afford vinyl-type polynorbornene. Ethylene–norbornene copolymers with high incorporation of norbornene can be also produced by these catalysts. 13C NMR and differential scanning calorimetry (DSC) analyses show that the copolymers are random products, and –NNN– and –EEE– units can be observed in the microstructure of the copolymers. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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5890 KiB  
Article
Terpolymerization of Substituted Cycloolefin with Ethylene and Norbornene by Transition Metal Catalyst
by Laura Boggioni, Nella Galotto Galotto, Fabio Bertini and Incoronata Tritto
Polymers 2016, 8(3), 60; https://doi.org/10.3390/polym8030060 - 26 Feb 2016
Cited by 8 | Viewed by 9335
Abstract
Ethylene-norbornene terpolymerization experiments using 5-alkyl-substituted norbornenes (5-pentyl-2-norbornene (C5N) and 5-octyl-2-norbornene (C8N)) or dicyclopentadiene (DCPD) were conducted with two ansa-metallocenes, [Zr{(η5-C9H6)2C2H4}Cl2] (1) and [Zr{(η5-2,5-Me2 [...] Read more.
Ethylene-norbornene terpolymerization experiments using 5-alkyl-substituted norbornenes (5-pentyl-2-norbornene (C5N) and 5-octyl-2-norbornene (C8N)) or dicyclopentadiene (DCPD) were conducted with two ansa-metallocenes, [Zr{(η5-C9H6)2C2H4}Cl2] (1) and [Zr{(η5-2,5-Me2C5H2)2CHEt}Cl2] (2), activated by methylaluminoxane (MAO). The terpolymers obtained were investigated in detail by determining the microstructure and termonomer contents by 13C NMR, molar masses and thermal properties. Results were compared to those of ethylene (E)-norbornene (N) terpolymerizations with 1-octene. 2, with lower steric hindrance and a shorter bridge, gave the best activities, termonomer incorporation and molar masses. The size of the substituent in 5-alkyl substituted norbornene also plays a role. C8N gives the highest activities and molar masses, while DCPD terpolymers have the highest cycloolefin content. Terpolymers are random; their molar masses, much higher than those in 1-octene terpolymers, are in a range useful for industrial applications. Finally, Tg values up to 152 °C were obtained. For similar N content, poly(E-ter-N-ter-C8N)s and poly(E-ter-N-ter-DCPD)s have the lowest and the highest Tg values, respectively. Thus, the presence of an eight-carbon atom pendant chain in C8N increases the flexibility of the polymer chain more than a five-carbon atom pendant chain in C5N. The higher rigidity of C5N may lead to lower activities and to increasing probability of σ-bond metathesis and chain termination, as evidenced by chain-end group analysis. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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1037 KiB  
Article
Investigations of the Ligand Electronic Effects on α-Diimine Nickel(II) Catalyzed Ethylene Polymerization
by Lihua Guo, Shengyu Dai and Changle Chen
Polymers 2016, 8(2), 37; https://doi.org/10.3390/polym8020037 - 29 Jan 2016
Cited by 120 | Viewed by 8756
Abstract
The synthesis and characterization of a series of dibenzhydryl-based α-diimine Ni(II) complexes bearing a range of electron-donating or -withdrawing groups are described. Polymerization with ethylene is investigated in detail, involving the activator effect, influence of polymerization conditions on catalyst activity, thermal stability, polymer [...] Read more.
The synthesis and characterization of a series of dibenzhydryl-based α-diimine Ni(II) complexes bearing a range of electron-donating or -withdrawing groups are described. Polymerization with ethylene is investigated in detail, involving the activator effect, influence of polymerization conditions on catalyst activity, thermal stability, polymer molecular weight and melting point. All of these Ni(II) complexes show great activity (up to 6 × 106 g of PE (mol of Ni)−1·h−1), exceptional thermal stability (stable at up to 100 °C) and generate polyethylene with very high molecular weight (Mn up to 1.6 × 106) and very narrow molecular weight distribution. In the dibromo Ni(II) system, the electronic perturbations exhibit little variation on the ethylene polymerization. In the Ni(acac) system, dramatic ligand electronic effects are observed in terms of catalytic activity and polyethylene molecular weight. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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690 KiB  
Article
Highly Active and Isospecific Styrene Polymerization Catalyzed by Zirconium Complexes Bearing Aryl-substituted [OSSO]-Type Bis(phenolate) Ligands
by Norio Nakata, Tomoyuki Toda, Yusuke Saito, Takanori Watanabe and Akihiko Ishii
Polymers 2016, 8(2), 31; https://doi.org/10.3390/polym8020031 - 26 Jan 2016
Cited by 20 | Viewed by 6286
Abstract
[OSSO]-type dibenzyl zirconium(IV) complexes 9 and 10 possessing aryl substituents ortho to the phenoxide moieties (ortho substituents, phenyl and 2,6-dimethylphenyl (Dmp)) were synthesized and characterized. Upon activation with dMAO (dried methylaluminoxane), complex 9 was found to promote highly isospecific styrene polymerizations ([mm [...] Read more.
[OSSO]-type dibenzyl zirconium(IV) complexes 9 and 10 possessing aryl substituents ortho to the phenoxide moieties (ortho substituents, phenyl and 2,6-dimethylphenyl (Dmp)) were synthesized and characterized. Upon activation with dMAO (dried methylaluminoxane), complex 9 was found to promote highly isospecific styrene polymerizations ([mm] = 97.5%–99%) with high molecular weights Mw up to 181,000 g·mmol−1. When the Dmp-substituted pre-catalyst 10/dMAO system was used, the highest activity, over 7700 g·mmol(10)−1·h−1, was recorded involving the formation of precisely isospecific polystyrenes of [mm] more than 99%. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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1906 KiB  
Article
Immortal Ring-Opening Polymerization of rac-Lactide Using Polymeric Alcohol as Initiator to Prepare Graft Copolymer
by Na Liu, Bo Liu, Changguang Yao and Dongmei Cui
Polymers 2016, 8(1), 17; https://doi.org/10.3390/polym8010017 - 15 Jan 2016
Cited by 7 | Viewed by 8298
Abstract
In the presence of a small molecular protic initiator, immortal ring-opening polymerization (ROP) of lactide (LA) is a highly efficient strategy to synthesize polylactide in a controllable manner, while using polymeric alcohol as an initiator has been less investigated. A series of polymeric [...] Read more.
In the presence of a small molecular protic initiator, immortal ring-opening polymerization (ROP) of lactide (LA) is a highly efficient strategy to synthesize polylactide in a controllable manner, while using polymeric alcohol as an initiator has been less investigated. A series of polymeric alcohols (PS–OH) composed of styrene and 4.3%–18% hydroxyl functional styrene (diethyl(hydroxy(4-vinylphenyl)methyl)phosphonate, St–OH) were synthesized through reversible addition-fragmentation transfer (RAFT) polymerization. Using PS–OH as an initiator, the immortal ROP of rac-LA was catalyzed by dibutylmagnesium (MgnBu2) under various ratios of monomer to hydroxyl group within PS–OH to generate polystyrene-g-polylactide (PS–g–PLA) copolymers with different graft lengths. After thermal annealing at 115 °C, the PLA domain aggregated to nanospheres among the PS continuum. The size of the nanospheres, varying from 130.1 to 224.2 nm, was related to the graft density and length of PS–g–PLA. Nanoporous films were afforded through chemical etching of the PLA component. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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1249 KiB  
Article
Iminopyridine-Based Cobalt(II) and Nickel(II) Complexes: Synthesis, Characterization, and Their Catalytic Behaviors for 1,3-Butadiene Polymerization
by Quanquan Dai, Xiangyu Jia, Feng Yang, Chenxi Bai, Yanming Hu and Xuequan Zhang
Polymers 2016, 8(1), 12; https://doi.org/10.3390/polym8010012 - 12 Jan 2016
Cited by 20 | Viewed by 7036
Abstract
A series of iminopyridine ligated Co(II) (1a–7a) and Ni(II) (1b–7b) complexes were synthesized. The structures of complexes 3a, 4a, 5a, 7a, 5b, and 6b were determined by X-ray crystallographic analyses. [...] Read more.
A series of iminopyridine ligated Co(II) (1a–7a) and Ni(II) (1b–7b) complexes were synthesized. The structures of complexes 3a, 4a, 5a, 7a, 5b, and 6b were determined by X-ray crystallographic analyses. Complex 3a formed a chloro-bridged dimer, whereas 4a, 5a, and 7a, having a substituent (4a, 5a: CH3; 7a: Br) at the 6-position of pyridine, producing the solid structures with a single ligand coordinated to the central metal. The nickel atom in complex 5b features distorted trigonal-bipyramidal geometry with one THF molecule ligating to the metal center. All the complexes activated by ethylaluminum sesquichloride (EASC) were evaluated in 1,3-butadiene polymerization. The catalytic activity and selectivity were significantly influenced by the ligand structure and central metal. Comparing with the nickel complexes, the cobalt complexes exhibited higher catalytic activity and cis-1,4-selectivity. For both the cobalt and nickel complexes, the aldimine-based complexes showed higher catalyst activity than their ketimine counterparts. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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1916 KiB  
Article
Metathesis Polymerization Reactions Induced by the Bimetallic Complex (Ph4P)2[W2(μ-Br)3Br6]
by Despoina Chriti, Alexios Grigoropoulos, Grigorios Raptopoulos, Georgios Charalambidis, Vasilis Nikolaou, Athanassios G. Coutsolelos, Marinos Pitsikalis, Konstantinos Mertis and Patrina Paraskevopoulou
Polymers 2015, 7(12), 2611-2624; https://doi.org/10.3390/polym7121536 - 09 Dec 2015
Cited by 6 | Viewed by 6631
Abstract
The reactivity of the bimetallic complex (Ph4P)2[W2(μ-Br)3Br6] ({W 2.5 W}7+, a′2e3) towards ring opening metathesis polymerization (ROMP) of norbornene (NBE) and some of its derivatives, as well [...] Read more.
The reactivity of the bimetallic complex (Ph4P)2[W2(μ-Br)3Br6] ({W 2.5 W}7+, a′2e3) towards ring opening metathesis polymerization (ROMP) of norbornene (NBE) and some of its derivatives, as well as the mechanistically related metathesis polymerization of phenylacetylene (PA), is presented. Our results show that addition of a silver salt (AgBF4) is necessary for the activation of the ditungsten complex. Polymerization of PA proceeds smoothly in tetrahydrofuran (THF) producing polyphenylacetylene (PPA) in high yields. On the other hand, the ROMP of NBE and its derivatives is more efficient in CH2Cl2, providing high yields of polymers. 13C Cross Polarization Magic Angle Spinning (CPMAS) spectra of insoluble polynorbornadiene (PNBD) and polydicyclopentadiene (PDCPD) revealed the operation of two mechanisms (metathetic and radical) for cross-linking, with the metathesis pathway prevailing. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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1095 KiB  
Article
Reactivity Comparison of ω-Alkenols and Higher 1-Alkenes in Copolymerization with Propylene Using An Isospecific Zirconocene-MMAO Catalyst
by Benard Oloo Nyangoye, Tianyou Li, Long Chen  and Zhengguo Cai
Polymers 2015, 7(10), 2009-2016; https://doi.org/10.3390/polym7101496 - 16 Oct 2015
Cited by 3 | Viewed by 5852
Abstract
Copolymerizations of propylene with ω-alkenols (aluminum-protected 5-hexene-1-ol (AH) and 10-undecene-1-ol (AU)) and non-polar analogues (1-hexene and 1-dodecene) were conducted with a rac-[Me2Si(2-Me-4-Ph-Ind)2]ZrCl2 activated by modified methylaluminoxane. The catalytic system showed high activity for each copolymerization, of which [...] Read more.
Copolymerizations of propylene with ω-alkenols (aluminum-protected 5-hexene-1-ol (AH) and 10-undecene-1-ol (AU)) and non-polar analogues (1-hexene and 1-dodecene) were conducted with a rac-[Me2Si(2-Me-4-Ph-Ind)2]ZrCl2 activated by modified methylaluminoxane. The catalytic system showed high activity for each copolymerization, of which value was independent on the comonomer used and decreased with the increase of the comonomer concentration. The comonomer content of the copolymers obtained also decreased with the increase of the comonomer concentration in each copolymer. The evaluation of the monomer reactivity ratios indicates a preference for the propylene insertion regardless of the last inserted monomer unit in growing polymer chain in all the copolymerizations. The relative reactivity of ω-alkenols was however significantly lower than that of non-polar analogues. These results suggested that the aluminum protection of polar monomer do not affect the activity of copolymerization but significantly decrease the comonomer reactivity. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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988 KiB  
Article
Magnesium Pyrazolyl-Indolyl Complexes as Catalysts for Ring-Opening Polymerization of L-Lactide
by Chi-Tien Chen, Deng-Hao Lin and Kuo-Fu Peng
Polymers 2015, 7(10), 1954-1964; https://doi.org/10.3390/polym7101492 - 05 Oct 2015
Cited by 6 | Viewed by 8195
Abstract
A series indole-based ligand precursors, PzRIndH (R = H, PzHIndH; R = Me, PzMeIndH;R = t-Bu, PztBuIndH; and R = Ph, PzPhIndH), have been synthesized via copper-catalyzed N-arylation (for PzHIndH) [...] Read more.
A series indole-based ligand precursors, PzRIndH (R = H, PzHIndH; R = Me, PzMeIndH;R = t-Bu, PztBuIndH; and R = Ph, PzPhIndH), have been synthesized via copper-catalyzed N-arylation (for PzHIndH) or the Bartoli indole synthesis (for PzMeIndH, PztBuIndH and PzPhIndH) reactions with moderate to high yield. Reactions of these ligand precursors with 0.7 equivalentof MgnBu2 in THF (for 1) or hexane (for 2–4) afforded the bis-indolyl magnesium complexes 1–4,respectively. All the ligand precursors and related magnesium complexes have been characterizedby NMR spectroscopy and elemental analyses. The molecular structure is reported for compound 1.These novel magnesium complexes demonstrate efficient catalytic activities for the ring-opening polymerization of L-lactide in the presence of alcohol. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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2877 KiB  
Article
Synthesis of High Performance Cyclic Olefin Polymers (COPs) with Ester Group via Ring-Opening Metathesis Polymerization
by Jing Cui, Ji-Xing Yang, Yan-Guo Li and Yue-Sheng Li
Polymers 2015, 7(8), 1389-1409; https://doi.org/10.3390/polym7081389 - 04 Aug 2015
Cited by 24 | Viewed by 12099
Abstract
Novel ester group functionalized cyclic olefin polymers (COPs) with high glass transition temperature, high transparency, good mechanical performance and excellent film forming ability have been achieved in this work via efficient ring-opening metathesis copolymerization of exo-1,4,4a,9,9a,10-hexahydro-9,10(1′,2′)-benzeno-l,4-methanoanthracene (HBM) and comonomers (5-norbornene-2-yl methylacetate (NMA), [...] Read more.
Novel ester group functionalized cyclic olefin polymers (COPs) with high glass transition temperature, high transparency, good mechanical performance and excellent film forming ability have been achieved in this work via efficient ring-opening metathesis copolymerization of exo-1,4,4a,9,9a,10-hexahydro-9,10(1′,2′)-benzeno-l,4-methanoanthracene (HBM) and comonomers (5-norbornene-2-yl methylacetate (NMA), 5-norbornene-2-yl methyl 2-ethylhexanoate (NME) or 5-norbornene-2-yl methyldodecanoate (NMD)) utilizing the Grubbs first generation catalyst, Ru(CHPh)(Cl)2(PCy3)2 (Cy = cyclohexyl, G1), followed by hydrogenation of double bonds in the main chain. The fully hydrogenated copolymers were characterized by nuclear magnetic resonance, FT-IR spectroscopy analysis, gel permeation chromatography, and thermo gravimetric analysis. Differential scanning calorimetry curves showed that the glass transition temperatures (Tg) linearly decreased with the increasing of comonomers content, which was easily controlled by changing feed ratios of HBM and comonomers. Static water contact angles tests indicate that hydrophilicity of copolymers can also be modulated by changing the comonomers incorporation. Additionally, the mechanical performances of copolymers were also investigated. Full article
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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