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11 pages, 1295 KiB

Open AccessArticle

A Convenient and Highly Efficient Strategy for Esterification of Poly (γ-Glutamic Acid) with Alkyl Halides at Room Temperature

by Youhong Ai, Yangyang Zhan, Dongbo Cai and Shouwen Chen

Polymers 2025, 17(1), 10; https://doi.org/10.3390/polym17010010 - 25 Dec 2024

Cited by 1 | Viewed by 936

Abstract

The presented work discusses the highly efficient esterification of poly (γ-glutamic acid) (γ-PGA) with alkyl halides at room temperature. The esterification reaction was completed within 3 h, and the prepared γ-PGA esters were obtained with excellent yields (98.6%) when 1,1,3,3-tetramethylguanidine (TMG) was used [...] Read more.

The presented work discusses the highly efficient esterification of poly (γ-glutamic acid) (γ-PGA) with alkyl halides at room temperature. The esterification reaction was completed within 3 h, and the prepared γ-PGA esters were obtained with excellent yields (98.6%) when 1,1,3,3-tetramethylguanidine (TMG) was used as a promoter. The influence of the amount of TMG, solvent, reaction conditions, and alkyl halides on the esterification reaction was examined. It was found that polar aprotic solvents, such as N-Methylpyrrolidone (NMP) and 1,3-Dimethyl-2-imidazolidinone (DMI), were favorable for the esterification. Non-polar or weakly polar solvents (i.e., dichloroethane, acetonitrile) were not favorable for the esterification. Water as a solvent had a negative effect on esterification. The reactivity of bromine halogenated compounds was higher than that of chlorine halogenated compounds but lower than that of iodine halogenated compounds. The structures of the prepared γ-PGA ester were confirmed by ¹H NMR and FT-IR spectroscopy. Thermal stability and hydrophobic properties of the resulting product were tested. The results showed that the prepared γ-PGA propyl ester had high thermal stability (up to 267 °C) and showed good hydrophobicity (contact angle 118.7°). Full article

(This article belongs to the Section Polymer Chemistry)

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12 pages, 2923 KiB

Open AccessEditor’s ChoiceCommunication

CO₂ Absorption by Solvents Consisting of TMG Protic Ionic Liquids and Ethylene Glycol: The Influence of Hydrogen Bonds

by Bohao Lu, Yixing Zeng, Mingzhe Chen, Shaoze Zhang and Dezhong Yang

Atmosphere 2024, 15(2), 229; https://doi.org/10.3390/atmos15020229 - 14 Feb 2024

Cited by 2 | Viewed by 2012

Abstract

Herein, the absorption of CO₂ by the TMG-based (TMG: 1,1,3,3-tetramethylguanidine) ionic liquids (ILs) and the absorbents formed by TMG ILs and ethylene glycol (EG) is studied. The TMG-based ILs used are formed by TMG and 4-fluorophenol (4-F-PhOH) or carvacrol (Car), and their [...] Read more.

Herein, the absorption of CO₂ by the TMG-based (TMG: 1,1,3,3-tetramethylguanidine) ionic liquids (ILs) and the absorbents formed by TMG ILs and ethylene glycol (EG) is studied. The TMG-based ILs used are formed by TMG and 4-fluorophenol (4-F-PhOH) or carvacrol (Car), and their viscosities are low at 25 °C. The CO₂ uptake capacities of [TMGH][4-F-PhO] and [TMGH][Car] are low (~0.09 mol CO₂/mol IL) at 25 °C and 1.0 atm. However, the mixtures [TMGH][4-F-PhO]-EG and [TMGH][Car]-EG show much higher capacities (~1.0 mol CO₂/mol IL) than those of parent ILs, which is unexpected because of the low CO₂ capacity of EG (0.01 mol CO₂/mol EG) in the same conditions. NMR spectra and theoretical calculations are used to determine the reason for these unexpected absorption behaviors. The spectra and theoretical results show that the strong hydrogen bonds between the [TMGH]⁺ cation and the phenolate anions make the used TMG-based ILs unreactive to CO₂, resulting in the low CO₂ capacity. In the Ils-EG mixtures, the hydrogen bonds formed between EG and phenolate anions can weaken the [TMGH]⁺–anion hydrogen bond strength, so ILs-EG mixtures can react with CO₂ and present high CO₂ capacities. Full article

(This article belongs to the Special Issue Advances in CO₂ Capture and Absorption)

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19 pages, 3618 KiB

Open AccessArticle

Rapeseed Oil as Feedstock for Bio-Based Thermoset Foams Obtained via Michael Addition Reaction

by Mikelis Kirpluks, Arnis Abolins, Darta Eihe, Ralfs Pomilovskis and Anda Fridrihsone

Polymers 2024, 16(1), 117; https://doi.org/10.3390/polym16010117 - 29 Dec 2023

Cited by 5 | Viewed by 1738

Abstract

Rapeseed oil was used to develop thermoset foams via Michael addition reaction by mixing two liquid components, Michael donor and Michael acceptor. The foaming of the curing thermoset was achieved by the physical blowing agent which expanded from the reacting foam mass due [...] Read more.

Rapeseed oil was used to develop thermoset foams via Michael addition reaction by mixing two liquid components, Michael donor and Michael acceptor. The foaming of the curing thermoset was achieved by the physical blowing agent which expanded from the reacting foam mass due to an exothermic curing reaction. The influence of the rapeseed oil-based Michael donor functionality on the foaming process and the characteristics of the obtained thermoset foams was studied. The 1,1,3,3-tetramethylguanidine catalyst’s influence on the foaming process kinetics was studied using FOAMAT equipment. The curing of the bio-based thermoset was analysed using a dielectric polarisation sensor. The morphology of the developed thermoset foam was analysed using a scanning electron microscope and the obtained foams were characterized using TGA, DSC, DMA and mechanical analysis tests. A direct correlation between the thermoset foam polymer crosslinking density and foaming reactivity, mechanical properties and glass transition temperature were determined. Obtained rapeseed oil based thermoset foams had a relatively low thermal conductivity of 33.9–35.4 mW/(m·K) which allows their use as thermal insulation material in civil engineering applications. Full article

(This article belongs to the Special Issue Recent Advances in Polyurethane Materials)

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9 pages, 901 KiB

Open AccessArticle

Synthesis of Mixed Chitin Esters via Acylation of Chitin in Deep Eutectic Solvents

by Yusuke Egi and Jun-ichi Kadokawa

Molecules 2023, 28(24), 8132; https://doi.org/10.3390/molecules28248132 - 16 Dec 2023

Cited by 3 | Viewed by 1749

Abstract

The development of efficient derivatization methods of chitin, such as acylation, has been identified to confer new properties and functions to chitin. In this study, we investigate the synthesis of mixed chitin esters via the acylation of chitin in deep eutectic solvents (DESs) [...] Read more.

The development of efficient derivatization methods of chitin, such as acylation, has been identified to confer new properties and functions to chitin. In this study, we investigate the synthesis of mixed chitin esters via the acylation of chitin in deep eutectic solvents (DESs) comprising 1-allyl-3-methylimidazolum chloride and 1,1,3,3-tetramethylguanidine based on a previous study that reported the development of efficient acylation of chitin in the DES to obtain single chitin esters. A stearoyl group was selected as the first substituent, which was combined with several bulky acyl and long oleoyl groups as the second substituents. After dissolution of chitin in the DES (2 wt%), the acylation reactions were conducted using stearoyl and the desired acyl chlorides for 1 h + 24 h at 100 °C in the resulting solutions. The IR and ¹H NMR spectra of the isolated products confirmed the structures of mixed chitin esters with two different substituents. The substituent ratios in the derivatives, which were estimated via the ¹H NMR analysis, were changed according to the feed ratios of two acyl chlorides. Full article

(This article belongs to the Special Issue Organic Reactions in Deep Eutectic Solvents)

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14 pages, 4668 KiB

Open AccessArticle

Synthesis and Hydrogelation of Star-Shaped Graft Copolypetides with Asymmetric Topology

by Thi Ha My Phan, Yu-Hsun Yang, Yi-Jen Tsai, Fang-Yu Chung, Tooru Ooya, Shiho Kawasaki and Jeng-Shiung Jan

Gels 2022, 8(6), 366; https://doi.org/10.3390/gels8060366 - 9 Jun 2022

Cited by 3 | Viewed by 2830

Abstract

To study the self-assembly and hydrogel formation of the star-shaped graft copolypeptides with asymmetric topology, star-shaped poly(_L-lysine) with various arm numbers were synthesized by using asymmetric polyglycerol dendrimers (PGDs) as the initiators and 1,1,3,3-tetramethylguanidine (TMG) as an activator for OH groups, [...] Read more.

To study the self-assembly and hydrogel formation of the star-shaped graft copolypeptides with asymmetric topology, star-shaped poly(_L-lysine) with various arm numbers were synthesized by using asymmetric polyglycerol dendrimers (PGDs) as the initiators and 1,1,3,3-tetramethylguanidine (TMG) as an activator for OH groups, followed by deprotection and grafting with indole or phenyl group on the side chain. The packing of the grafting moiety via non-covalent interactions not only facilitated the polypeptide segments to adopt more ordered conformations but also triggered the spontaneous hydrogelation. The hydrogelation ability was found to be correlated with polypeptide composition and topology. The star-shaped polypeptides with asymmetric topology exhibited poorer hydrogelation ability than those with symmetric topology due to the less efficient packing of the grafted moiety. The star-shaped polypeptides grafted with indole group on the side chain exhibited better hydrogelation ability than those grafted with phenyl group with the same arm number. This report demonstrated that the grafted moiety and polypeptide topology possessed the potential ability to modulate the polypeptide hydrogelation and hydrogel characteristics. Full article

(This article belongs to the Special Issue Hydrogels with Appropriate/Tunable Properties for Biomedical Applications)

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16 pages, 5645 KiB

Open AccessArticle

Effects of Ionic Liquids on Laccase from Trametes versicolor

by Aashka Y. Patel, Austin K. Clark, Nicholas J. Paradis, Meeraj Amin, Timothy D. Vaden, Chun Wu and Gregory A. Caputo

Biophysica 2021, 1(4), 429-444; https://doi.org/10.3390/biophysica1040031 - 20 Oct 2021

Cited by 5 | Viewed by 3665

Abstract

Interactions between ionic liquids and biomolecules are of great interest due to the intrinsic properties of ionic liquids and the flexibility allowed by mixing and matching cations and anions to create unique ionic liquids. A number of ionic liquid–biomolecule studies have focused on [...] Read more.

Interactions between ionic liquids and biomolecules are of great interest due to the intrinsic properties of ionic liquids and the flexibility allowed by mixing and matching cations and anions to create unique ionic liquids. A number of ionic liquid–biomolecule studies have focused on interactions with proteins, including industrially relevant enzymes. One of these, laccase from Trametes versicolor, is a naturally derived enzyme used in the breakdown of phenolic compounds in a wide variety of industries, especially useful in breakdown of lignocellulosic materials. Here, a combination of experiments and molecular dynamics (MD) simulations was used to investigate the interactions of ionic liquids with laccase. Enzyme kinetics assays indicated that ionic liquids composed of tetramethylguanidine (TMG) and either serine or threonine caused significant reduction in enzymatic activity, while kinetics was not impacted by TMG-Asp or TMG-Glu ionic liquids. Similarly, intrinsic fluorescence of laccase in the presence of TMG-Ser and TMG-Thr exhibited a shift in spectral properties consistent with structural destabilization, but again TMG-Asp and TMG-Glu had no impact. MD simulations of laccase and ABTS with/without TMG-Ser ionic liquid provided insight into the deactivation mechanism of laccase. The simulations indicated that TMG-Ser disrupts laccase’s electron transfer mechanism. Full article

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15 pages, 3290 KiB

Open AccessArticle

Process Development for Flexible Films of Industrial Cellulose Pulp Using Superbase Ionic Liquids

by Diana C. M. Ribeiro, Rafael C. Rebelo, Francesco De Bon, Jorge F. J. Coelho and Arménio C. Serra

Polymers 2021, 13(11), 1767; https://doi.org/10.3390/polym13111767 - 28 May 2021

Cited by 19 | Viewed by 4160

Abstract

Due to environmental concerns, more attention has been given to the development of bio-based materials for substitution of fossil-based ones. Moreover, paper use is essential in daily routine and several applications of industrial pulp can be developed. In this study, transparent films were [...] Read more.

Due to environmental concerns, more attention has been given to the development of bio-based materials for substitution of fossil-based ones. Moreover, paper use is essential in daily routine and several applications of industrial pulp can be developed. In this study, transparent films were produced by industrial cellulose pulp solubilization in tetramethylguanidine based ionic liquids followed by its regeneration. Films were characterized by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), UV/Vis spectroscopy, proton nuclear magnetic resonance (¹H-NMR), dynamic scanning calorimetry (DSC), thermal analysis (TG), and X-ray diffraction (XRD). Mechanical tests showed that films have a good elongation property, up to 50%, depending on ionic liquid incorporation. The influence of the conjugated acid and dissolution temperature on mechanical properties were evaluated. These results revealed the potential of this methodology for the preparation of new biobased films. Full article

(This article belongs to the Special Issue State-of-the-Art Polymer Science and Technology in Portugal (2020,2021))

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18 pages, 5806 KiB

Open AccessArticle

Tuned Bis-Layered Supported Ionic Liquid Catalyst (SILCA) for Competitive Activity in the Heck Reaction of Iodobenzene and Butyl Acrylate

by Nemanja Vucetic, Pasi Virtanen, Ayat Nuri, Andrey Shchukarev, Jyri-Pekka Mikkola and Tapio Salmi

Catalysts 2020, 10(9), 963; https://doi.org/10.3390/catal10090963 - 22 Aug 2020

Cited by 5 | Viewed by 3460

Abstract

A thorough experimental optimization of supported ionic liquid catalyst (SILCA) was performed in order to obtain a stable and efficient catalyst for the Heck reaction. Out of fifteen proposed structures, propyl imidazolium bromide-tetramethylguanidinium pentanoate modified SiO₂ loaded with PdCl₂ appeared to [...] Read more.

A thorough experimental optimization of supported ionic liquid catalyst (SILCA) was performed in order to obtain a stable and efficient catalyst for the Heck reaction. Out of fifteen proposed structures, propyl imidazolium bromide-tetramethylguanidinium pentanoate modified SiO₂ loaded with PdCl₂ appeared to be the most stable and to have a good activity in the reaction between butylacrylate and iodobezene, resulting in a complete conversion in 40 min at 100 °C, in four consecutive experiments. This study elucidated on the stability of the catalytic system with an ionic liquid layer during the catalyst synthesis but also under reaction conditions. In the bis-layered catalyst, the imidazolium moiety as a part of internal layer, brought rigidity to the structure, while in external layer pentanoic acid gave sufficiently acidic carboxylic group capable to coordinate 1,1,3,3-tetramethylguanidine (TMG) and thus, allow good dispersion of Pd nanoparticles. The catalyst was characterized by means of XPS, FT-IR, TEM, ICP-OES, ζ-potential, EDX, TGA, and ¹³C NMR. The release and catch mechanism was observed, whereas Pd re-deposition can be hindered by catalyst poisoning and eventual loss of palladium. Full article

(This article belongs to the Special Issue Ionic Liquids in Catalysis)

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7 pages, 1880 KiB

Open AccessArticle

Temperature-Dependent Enhancement Effects for TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene) with 2-Methylimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Glycidyl Phenyl Ether

by Osamu Shimomura, Suguru Sasaki, Kaori Kume, Atsushi Ohtaka and Ryôki Nomura

Inorganics 2019, 7(7), 83; https://doi.org/10.3390/inorganics7070083 - 30 Jun 2019

Cited by 3 | Viewed by 3749

Abstract

The catalytic effects of 1,1,3,3-Tetramethylguanidine (TMG), 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) in the reaction with glycidyl phenyl ether (GPE) at 40 °C were investigated. For the reaction, the %conversion of GPE was only 11%, carried out at 40 °C [...] Read more.

The catalytic effects of 1,1,3,3-Tetramethylguanidine (TMG), 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) in the reaction with glycidyl phenyl ether (GPE) at 40 °C were investigated. For the reaction, the %conversion of GPE was only 11%, carried out at 40 °C over 14 days in the presence of TBD.Additionally, there was little catalytic activity for the same reaction performed under typical storage conditions at 25 °C. The effect of TBD with 2-methylimidazole-intercalated α-zirconium phosphate (α-ZrP∙2MIm), as a latent thermal initiating system in the reaction with GPE, was then examined. The reaction did not proceed within 1 h at 80 °C. On increasing the temperature to 120 °C, the %conversion reached 75% for reaction at 1 h. Under typical storage conditions (7 days at 25 °C), the %conversion of GPE was only 7%. With addition of TBD to α-ZrP∙2MIm, reagent stability was maintained, and the polymerization reaction proceeded rapidly with the application of heat. Full article

(This article belongs to the Special Issue Inorganic Layered Compounds)

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4 pages, 233 KiB

Open AccessProceeding Paper

New Active Pharmaceutical Ingredient-Ionic Liquids (API-ILs) Derived from Indomethacin and Mebendazole

by Verónica Fernandez-Stefanuto and Emilia Tojo

Proceedings 2019, 9(1), 48; https://doi.org/10.3390/ecsoc-22-05781 - 14 Nov 2018

Cited by 14 | Viewed by 2130

Abstract

The transformation of two solid Active Pharmaceutical Ingredients (APIs) into new ionic liquids (IL)s that incorporate APIs (API-ILs) is reported. The structures of the APIs (indomethacin and mebendazole) were selected by their susceptibility to being transformed into API-ILs (either to form the cation [...] Read more.

The transformation of two solid Active Pharmaceutical Ingredients (APIs) into new ionic liquids (IL)s that incorporate APIs (API-ILs) is reported. The structures of the APIs (indomethacin and mebendazole) were selected by their susceptibility to being transformed into API-ILs (either to form the cation or the anion) and their limited bioavailability due to their low solubility in water. The counterions, such as those derived from 2-dimethylaminoethanol (DMEA), tetramethylguanidine (TMG), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2] (TED), <i>p</i>-toluensulfonic acid, glycolic acid, methanesulfonic acid, and saccharin, were carefully chosen, aiming for high biocompatibility, low toxicity, and high water solubility. The synthesis was carried out by direct treatment of the API with the corresponding selected acid or base. Finally, the solubility in water of all the synthesized salts was determined. Full article

(This article belongs to the Proceedings of 22nd International Electronic Conference on Synthetic Organic Chemistry)

11 pages, 1350 KiB

Open AccessArticle

Conversion of Carbohydrates into Platform Chemicals Catalyzed by Alkaline Ionic Liquids

by Xiaojia Du, Jie Zhang, Yuehai Wang and Yongshui Qu

Catalysts 2017, 7(9), 245; https://doi.org/10.3390/catal7090245 - 23 Aug 2017

Cited by 9 | Viewed by 4850

Abstract

A series of alkaline ionic liquids (ILs) including 1-butyl-3-methylimidazolium benzoate ([BMIM]PHCOO), 1-butyl-3-methylimidazolium carbonate ([BMIM]₂CO₃), 1-butyl-3-methylimidazolium acetate ([BMIM]OAc), 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), ethanolamine tetrafluoroborate ([MEA]BF₄), and 1,1,3,3-tetramethylguanidine (TMG)-based ILs, etc., were synthesized and utilized as catalysts for the conversion [...] Read more.

A series of alkaline ionic liquids (ILs) including 1-butyl-3-methylimidazolium benzoate ([BMIM]PHCOO), 1-butyl-3-methylimidazolium carbonate ([BMIM]₂CO₃), 1-butyl-3-methylimidazolium acetate ([BMIM]OAc), 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), ethanolamine tetrafluoroborate ([MEA]BF₄), and 1,1,3,3-tetramethylguanidine (TMG)-based ILs, etc., were synthesized and utilized as catalysts for the conversion of carbohydrates into 5-HMF. 1,1,3,3-tetramethylguanidine tetrafluoroborate ([TMG]BF₄) was confirmed to exhibit excellent catalytic activity, and was much cheaper than other ILs such as 1-butyl-3-methylimidazolium chloride ([BMIM]Cl) for use as a solvent in the conversion of C₆ carbohydrates into 5-HMF. The 5-HMF yields from fructose, glucose, cellobiose, and microcrystalline cellulose (MCC) were 74.19%, 27.33%, 20.20%, and 17.73%, respectively. In addition, the possible pathway of carbohydrates (MCC, cellobiose, glucose, etc.) conversion into 5-HMF with [TMG]BF₄ as a catalyst was speculated, and the conversion of glucose into 5-HMF was determined to likely be the committed step in the transformation of MCC catalyzed by [TMG]BF₄. Full article

(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)

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11 pages, 13968 KiB

Open AccessArticle

Crystal Structures of New Ammonium 5-Aminotetrazolates

by Martin Lampl, Robert Salchner, Gerhard Laus, Doris E. Braun, Volker Kahlenberg, Klaus Wurst, Gerda Fuhrmann, Herwig Schottenberger and Hubert Huppertz

Crystals 2014, 4(4), 439-449; https://doi.org/10.3390/cryst4040439 - 19 Nov 2014

Viewed by 7090

Abstract

The crystal structures of three salts of anionic 5-aminotetrazole are described. The tetramethylammonium salt (P ) forms hydrogen-bonded ribbons of anions which accept weak C–H···N contacts from the cations. The cystamine salt (C2/c) shows wave-shaped ribbons of anions [...] Read more.

The crystal structures of three salts of anionic 5-aminotetrazole are described. The tetramethylammonium salt (P ) forms hydrogen-bonded ribbons of anions which accept weak C–H···N contacts from the cations. The cystamine salt (C2/c) shows wave-shaped ribbons of anions linked by hydrogen bonds to screw-shaped dications. The tetramethylguanidine salt (P2₁/c) exhibits layers of anions hydrogen-bonded to the cations. Full article

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13 pages, 820 KiB

Open AccessArticle

New Guanidine-Pyridine Copper Complexes and Their Application in ATRP

by Alexander Hoffmann, Olga Bienemann, Ines Dos Santos Vieira and Sonja Herres-Pawlis

Polymers 2014, 6(4), 995-1007; https://doi.org/10.3390/polym6040995 - 1 Apr 2014

Cited by 32 | Viewed by 10697

Abstract

The guanidine hybrid ligands, (tetramethylguanidine)methylenepyridine (TMGpy) and (dimethylethyleneguanidine)methylenepyridine (DMEGpy), were proven to be able to stabilize copper complexes active in the solvent-free polymerization of styrene at 110 °C using 1-phenylethylbromide as the initiator. The polymerization proceeded after first-order kinetics, and polystyrenes with polydispersities [...] Read more.

The guanidine hybrid ligands, (tetramethylguanidine)methylenepyridine (TMGpy) and (dimethylethyleneguanidine)methylenepyridine (DMEGpy), were proven to be able to stabilize copper complexes active in the solvent-free polymerization of styrene at 110 °C using 1-phenylethylbromide as the initiator. The polymerization proceeded after first-order kinetics, and polystyrenes with polydispersities around 1.2 could be obtained. Using the ligand, DMEGpy, three new copper guanidine-pyridine complexes could be synthesized and structurally characterized. Their structural characteristics are discussed. Full article

(This article belongs to the Special Issue Controlled/Living Radical Polymerization)

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