Paper of the month: Dual stimuli responsive self-healing and malleable materials based on dynamic thiol-Michael chemistry

Chakma et al. exploit dynamic thiol-Michael chemistry to prepare dual responsive self-healing and malleable materials.

Dynamically crosslinked polymeric materials have received significant attention owing to their unique characteristics including the introduction of mechanical properties and the possibility to extend a material’s lifetime. These materials can typically find use in a wide range of applications such as coatings and elastomers. Konkolewicz and co-workers significantly contributed towards this direction by developing a facile synthesis of dynamic materials with thiol-maleimide based adducts. Maleimides are of particular importance as they consist of a highly reactive vinyl group for thiol-Michael addition reactions and typically demonstrate very high yields under mild conditions. To synthesize such materials, a thiol-maleimide cross linker (2-((1-(2-(acryloyloxy)ethyl)-2,5-dioxopyrrolidin-3-yl)thio)ethylacrylate) was initially synthesized and subsequently incorporated into a polymer matrix of hydroxyethyl acrylate. The properties of the elastomeric materials were then carefully evaluated by tensile testing, creep recovery, swelling studies, differential scanning calorimetry and rheological experiments. It was found that these polymeric materials showed dynamic behaviours like self-healing and malleability at elevated pH values and temperatures. In addition, these materials possess significant healing properties and are mechanically stable towards creep deformation at room temperature and pressure. Their stimuli responsive self-healing, elastic, malleable and mechanically stable nature in combination with the facile nature of the synthesis paves the way for potential utilization in different applications that require enhanced properties and functions.

Dual stimuli responsive self-healing and malleable materials based on dynamic thiol-Michael chemistry

Tips/comments directly from the authors:

1. The synthetic techniques used to make the thiol-Michael based crosslinker (TMMDA) are very simple, but extra care should be given to store the crosslinker in the refrigerator or freezer. Storing the crosslinker at room temperature may result in background polymerization and eventually lead to loss of the crosslinker.

2. Although conventional free radical polymerization was used as a tool for polymerization, other polymerization techniques can be used as well. Although, reactivity of the thiol moiety has to be considered in that case.

3. Self-healing polymers are commonly responsive to single stimulus (e.g. temperature responsive Diels-Alder based polymer or light responsive disulfide polymer). TMMDA crosslinked materials developed in this paper have self-healing properties with both temperature and pH stimulus, giving them enhanced functionality and responsive character.

4. Dynamic materials synthesized in this article, based on the thiol-Michael reaction, showed malleability or reshape ability in response to both elevated temperature and pH. As a result, materials can be re-shaped into new configurations upon application of stimuli.

5. The thiol-Michael adducts are essentially static in the absence of thermal and pH stimulus, making the materials mechanically stable and creep resistant under ambient conditions.

 

Dual stimuli responsive self-healing and malleable materials based on dynamic thiol-Michael chemistry, Polym. Chem., 2017, 8, 6534-6543, DOI: 10.1039/C7PY01356F

 

About the webwriter

Dr. Athina Anastasaki is a Web Writer for Polymer Chemistry. She is currently a Global Marie Curie Fellow working alongside Professor Craig Hawker at the University of California, Santa Barbara (UCSB). Please, visit this link for more information.
Athina

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2018 Polymer Chemistry Lectureship is now open for nominations!

Do you know an early-career researcher who deserves recognition for their contribution to the polymer chemistry field?

Now is your chance to put them forward for the accolade they deserve.

Polymer Chemistry is pleased to announce that nominations are now being accepted for its 2018 Lectureship award. This annual award was established in 2015 to honour an early-stage career scientist who has made a significant contribution to the polymer chemistry field.

Previous winners

2017 – Julien Nicolas, Université Paris Sud, France

2016 – Feihe HuangZhejiang University, China

2015 – Richard HoogenboomGhent University, Belgium

Qualification

To be eligible for the Polymer Chemistry Lectureship, the candidate should be in the earlier stages of their scientific career, typically within 15 years of attaining their doctorate or equivalent degree, and will have made a significant contribution to the field.

Description

The recipient of the award will be asked to present a lecture at the Macro18 World Polymer Congress in Cairns, Australia, where they will also be presented with the award. The Polymer Chemistry Editorial Office will provide financial support to the recipient for travel and accommodation costs.

The recipient will also be asked to contribute a lead article to the journal and will have their work showcased free of charge on the front cover of the issue in which their article is published.

Selection

The recipient of the award will be selected and endorsed by the Polymer Chemistry Editorial Board.

Nominations

Those wishing to make a nomination should send details of the nominee, including a brief C.V. and a letter supporting the nomination, to the Polymer Chemistry Editorial Office by 15thJanuary 2018. Self-nomination is not permitted.

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Paper of the month: Polymer synthesis by mimicking nature’s strategy: the combination of ultra-fast RAFT and the Biginelli reaction

Wu et al. report the combination of ultra-fast RAFT and Biginelli reaction to prepare a large polymer library.

Nature is capable of synthesizing an unlimited number of biomacromolecules (e.g. proteins) with remarkable structures and functions by simply starting from only 20 amino acids. This process lies in the precise sequence-controlled polymerization of amino acids to control the primary structures of polypeptide precursors, followed by a highly efficient post-translation modification in order to define these structures.

Polymer synthesis by mimicking nature’s strategy

Inspired by nature’s strategy to synthesize proteins, Tao and co-workers developed a two-stage method to synthesize a large number of polymers with precisely controlled structures, different functionalities and various molecular diversities. Key to their strategy is the combination of controlled radical polymerization and post-polymerization modification. Specifically, reversible addition-fragmentation chain transfer (RAFT) polymerization was utilized to synthesize the polymer precursors starting from only 3 acrylamide monomers. By repeating the polymerization with different monomer sequences, 6 triblock copolymers with controlled chain ends, molecular weights and molar mass distributions were obtained. The different polarity of all synthesized precursors was then confirmed by reverse-phase high performance liquid chromatography (HPLC). The triblock copolymers were subsequently modified via the Biginelli reaction to rapidly generate 60 derivatives in a high-throughput (HPT) manner. HTP analyses was also conducted as an efficient and quick way to verify specific functionalities (e.g. radical scavengers, metal chelating agents, etc.).

In summary, the authors presented an efficient strategy to prepare and characterize large libraries of polymers with diverse structures and functions.

Tips/comments directly from the authors:

1. For the Biginelli reaction, acetic acid/MgCl2 is an efficient solvent/catalyst system to smoothly get the targeted compounds. However, this system is not as efficient for aliphatic aldehydes. Fortunately, the Biginelli reaction has been studied for more than 100 years and as such, many other solvent/catalyst systems have been established in this time. Thus, people can choose different conditions to perform the Biginelli reaction for the post-polymerization modification depending on the specific requirements and applications.

2. For the high throughput analysis of radical scavengers, the oxygen in the air might also quench the radical, and the radical colour was found to fade faster in summer than in winter. Thus, the use of fresh reagents and careful recording of the temperature is recommended.

3. The ultra-fast RAFT was used in the present work as a model polymerization to prepare copolymers. The authors believe other advanced controlled radical polymerization techniques (SET-ATRP, photo-induced CRPs, sulfur-free RAFT, etc.) can also be used to prepare multiblock copolymers, especially when thermo-sensitive monomers are used.

Polymer synthesis by mimicking nature’s strategy: the combination of ultra-fast RAFT and the Biginelli reaction, Polym. Chem., 2017, 8, 5679-5687, DOI: 10.1039/c7py01313b

 

About the webwriter
Athina

Dr. Athina Anastasaki is a Web Writer for Polymer Chemistry. She is currently a Global Marie Curie Fellow working alongside Professor Craig Hawker at the University of California, Santa Barbara (UCSB). Please visit this link for more information.

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Paper of the month: Sequence-coded ATRP macroinitiators

Telitel et al. report the synthesis of sequence-coded ATRP macroinitiators followed by a controlled polymerization

The development of strategies that allow the translation of the precise monomer sequence control achieved in nature over macromolecular structure (e.g. DNA) to whole synthetic systems is an exciting field in current polymer science. In particular, the fabrication of sequence-defined polymers paves the way for a diverse range of applications. For example, these macromolecules can be used to store monomer-coded information. Lutz and his team has pioneered this field and recently described the synthesis of digitally-encoded polyurethanes using an orthogonal solid-phase iterative approach. This class of materials is particularly interesting thanks to their unique physicochemical properties and straightforward sequencing by tandem mass spectrometry.

Sequence-coded ATRP macroinitiators

In the current contribution, Lutz and co-workers expand the application pool of these materials by covalently linking sequence-coded oligomers to other synthetic polymers. Sequence-coded oligourethanes were initially synthesized by orthogonal solid phase iterative chemistry on a modified Wang resin. While still attached to the solid support, the ω-OH-termini of the oligourethanes were transformed into atom transfer radical polymerization (ATRP) initiators by esterification with α-bromoisobutyryl bromide. Then, the oligomers were detached from the solid support and their cleaved α -COOH-termini were esterified with ethanol yielding monodisperse ATRP macro initiators. Upon polymerization of styrene from these precise oligomers, well-defined blocky architectures were obtained containing sequence-coded oligourethane segments. The polymerization was well-controlled, yielding materials with narrow molecular mass distributions and good agreement between theoretical and experimental molecular weights. Importantly, for a given macroinitiator length, the coded sequence of oligourethane had no influence on the ATRP process. Overall, these exciting results open up interesting perspectives for the development of plastic materials containing sequence-coded traceability barcodes.

Tips/comments directly from the authors:

  1. Sequence-coded oligourethanes have an interesting tendency to crystallize, which is currently under investigation. Consequently, these oligomers are usually relatively easy to characterize in solution directly after their synthesis but may become less soluble in standard solvents with time and storage.
  2. As mentioned in the communication, the tendency toward self-organization of the oligourethanes might influence their macroinitiator behavior. The preliminary results shown in this communication indicate that a controlled radical polymerization behavior is attainable with these macroinitiators. However, a deeper understanding of the initiation step is probably mandatory.
  3. The atom transfer radical polymerization of styrene was chosen as a simple polymerization model in the present work. Nevertheless, other controlled radical polymerization techniques might, of course, be considered for preparing such materials.

Sequence-coded ATRP macroinitiators Polym. Chem., 2017, 8, 4988-4991, DOI: 10.1039/C7PY00496F

 

About the webwriter

Athina Anastasaki

Dr. Athina Anastasaki is a Web Writer for Polymer Chemistry. She is currently a Global Marie Curie Fellow working alongside Professor Craig Hawker at the University of California, Santa Barbara (UCSB). Please, visit this link for more information.

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Photopolymerization Fundamentals 2017 Poster Prize Winner

Congratulations to Abishek Shete, who was awarded the Polymer Chemistry Best Poster Award at Photopolymerization Fundamentals 2017, in Boulder, Colorado, USA. Abishek is currently carrying out research in the CJK Polymer Research group at the University of Delaware.

In addition, due to the high number of exellent poster presentations, three candidates were given honourable mentions;

  • Dillon Love, University of Colorado,
  • Hanns Houck, Karlsruhe Institute of Technology, Ghent University, Queensland University of Technology,
  • Camila Uzcategui, University of Colorado.

Congratulations to all winners!

 

Polymer Chemistry Poster Prize Winners Photopolymerization Fundamentals 2017

Left to right: Christopher Barner-Kowollik (Editor in Chief of Polymer Chemistry), Abishek Shete, (Main Poster Prize Winner) Dillon Love, (Honorable Mention) Hanns Houck, (Honorable Mention) Camila Uzcategui, (Honorable Mention) Christopher Bowman (Chair of the 2017 Photopolymerization Fundamentals Conference)

 

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Paper of the month: Block co-polyMOFs: assembly of polymer-polyMOF hybrids via iterative exponential growth and “click” chemistry

MacLeod and Johnson report the synthesis of block co-polyMOFs via a combination of iterative exponential growth and copper “click” chemistry

Block copolymer (BCP) assemblies are derived from covalently linked polymer chains and can undergo phase separation and thus find use in a wide range of applications including micropatterning, battery and electronic technologies. Metal-organic frameworks (MOFs) are another class of self-assembled matter consisting of crystalline networks with angstrom-scale order and permanent porosity. Owing to these advantageous properties, they can enable functions such as gas, energy storage, catalysis and selective-separation.

 

In the Johnson group, impressive efforts have been made to merge amorphous polymer networks with multi-component supramolecular assembly to generate soft materials with novel properties. In their current contribution, the group expands these types of hybrid materials by reporting a novel BCP where one block is a uniform benzene dicarboxylate (BDC)-based oligomer synthesized by iterative exponential growth (IEG), and the other is polystyrene (PS) prepared by atom transfer radical polymerization (ATRP). In order to achieve this, the authors initially synthesized the BDC-based oligomer with a defined end-functionality bearing an alkyne group that would allow for further diversification. This alkyne group was subsequently used to couple to azide-terminated polystyrene. In the presence of Zn ions, this BCP forms a “block co-polyMOF” (BCPMOF) material comprised of polyMOF domains embedded in a PS matrix.

The presented work is the first demonstration that it is possible to generate a crystalline polyMOF-amorphous polymer hybrid material from a single diblock copolymer. As such, BCPMOFs represent a new composite material that possesses the processability of the polymers while exhibiting enhanced stability towards ambient conditions when compared to the isolated MOFs. The ultimate goal of the group is to obtain BCPMOFs with robust mechanical properties, high surface areas, and tunable, well-defined domain sizes.

 

Tips/comments directly from the authors:

  1. In the synthesis of the mono benzylated diethyl 2,5-dihydroxyterephthalate, A, UV absorbance can readily distinguish the starting material from the product. The starting material elutes before the product and can be isolated for reuse.
  2. As noted in the supporting information, side products can occur during the coupling reaction to form L1. It is critical that ethanol is used to maintain the ethyl ester.
  3. The coupling reactions tend to require longer reaction times as the molecular weight of the reactants grows. Upon scaling up of the reactions, do not be temped to increase the concentration too much as it can lead to side product formation.
  4. The same synthetic protocols were used to form polyMOFs and block co-polyMOFs: 2.5 eq Zn(II) per BDC unit in Ln, was combined with Ln(PS) in DMF, heated at 100°C for 24h, followed by DMF washings to remove excess Zn(II) and unreacted ligand. Unlike the purification and isolation of L2 and L4, special care was taken for L4PS-Zn to use minimal organic solvent due to the solubility imparted by polystyrene.

 

Block co-polyMOFs: assembly of polymer-polyMOF hybrids via iterative exponential growth and “click” chemistry
Polym. Chem., 2017, 8, 4488-4493, DOI: 10.1039/c7py00922d

 

About the web writer


Dr. Athina Anastasaki is a web writer for Polymer Chemistry. She is currently a Global Marie Curie Fellow working alongside Professor Craig Hawker at the University of California, Santa Barbara (UCSB). Please visit this website for more information.

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Focus on: Antimicrobial polymers

Antimicrobial agents kill or inhibit the growth of microorganisms, and can be sub-divided into several classes depending on the type of microorganism they target. Sub-divisions include, antibacterial, antifungal, antiviral and antiparasitic agents. In particular, antibacterial agents are incredibly important worldwide, with the emergence of multi-drug resistant bacteria. Antibiotic-resistant infections are becoming an increased health and economic burden on society. As such the development of new antibacterials continues to be paramount to limiting the spread of multi-drug resistant bacteria.

This month we focus on three articles published in Polymer Chemistry which have reported the use of antimicrobial polymers. In each case the polymers reported have antibacterial properties, and in one article polymers were also investigated for their antifungal properties.

 

 

1. Cationic peptidopolysaccharides synthesized by ‘click’ chemistry with enhanced broad-spectrum antimicrobial activities
Yajuan Su, Liang Tian, Meng Yu, Qiang Gao, Dehui Wang, Yuewei Xi, Peng Yang, Bo Lei, Peter X. Ma, Peng Li
Polym. Chem., 2017, 8, 3788-3800; DOI: 10.1039/C7PY00528H

Cationic peptidopolysaccharides were prepared through the grafting of ε-poly-L-lysine (EPL) to a chitosan (CS) backbone by thiol-ene “click” chemistry. The resulting CS-g-EPL polymers were assessed for their antimicrobial activity against Gram negative bacteria, Gram positive bacteria and fungi, which showed broad-spectrum antimicrobial activity. In addition the hemolytic activity of the polymers was determined, and the lead candidate was further investigated for it’s biocompatability.

2. Astaxanthin-based polymers as new antimicrobial compounds
S. Weintraub, T. Shpigel, L. G. Harris, R. Schuster, E. C. Lewis, D. Y. Lewitus
Polym. Chem., 2017, 8, 4182-4189; DOI: 10.1039/C7PY00663B

Astaxanthin (ATX) is an organic pigment produced by fungi and algae, possessing various therapeutic properties. Polyesters were prepared using carbodiimide-mediated coupling of ATX, which is a diol, with alkyl- and PEG-diacids. The diacid used influenced the resulting physico–chemical–mechanical properties of the polymers. Antibacterial activity was observed against three strains of bacteria, including MRSA, and the materials were found to be non-toxic in an in vivo wound healing model.

3. Bio-inspired peptide decorated dendrimers for a robust antibacterial coating on hydroxyapatite
Yaping Gou, Xiao Yang, Libang He, Xinyuan Xu, Yanpeng Liu, Yuebo Liu, Yuan Gao, Qin Huang, Kunneng Liang, Chunmei Ding, Jiyao Li, Changsheng Zhao, Jianshu Li
Polym. Chem., 2017, 8, 4264-4279; DOI: 10.1039/C7PY00811B

The authors report the use of a salivary statherin protein inspired dendrimer, for use as an antibacterial coating for implanted biomaterials. A peptide sequence was coupled to the surface of a G4 PAMAM dendrimer, by Michael addition. The materials showed adsorption to hydroxyapatite surfaces with sufficient binding strength to survive washing. The adsorbed dendrimers endowed antimicrobial properties observed by an inhibition of biofilm formation and through in vivo experiments.

 

Read these articles for free until September 10th


About the webwriterFiona Hatton

Dr. Fiona Hatton is a web writer for Polymer Chemistry. She is currently a postdoctoral researcher in the Armes group at the University of Sheffield, UK. Find her on Twitter: @fi_hat

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Paper of the month: Acceleration and improved control of aqueous RAFT/MADIX polymerization of vinylphosphonic acid in the presence of alkali hydroxides

Seiler et al. report the acceleration and improved control of vinylphosphonic acid in the presence of alkali hydroxides during both conventional and RAFT/MADIX polymerization.

Phosphonic acid functionalized polymers find use in a wide range of applications such as metal protection, polymer electrolyte membranes flame retardancy and dentistry. This is thanks to their unique characteristics including their acidic nature, stability, proton conductivity and metal binding ability. Vinyl phosphonic acid (VPA) in particular is a structurally simple example of such monomers which is not only affordable but also provides with a polymer (PVPA) with phosphonic acid groups that are directly attached to the backbone.

 

 

Despite the popularity and applicability of this polymer, the polymerization of VPA is typically slow yielding incomplete conversions which necessitates the need for additional costly and time-consuming purification steps. Destarac, Harrisson and co-workers were capable to circumvent this by investigating the effect of adding various alkali hydroxides to the conventional (free radical) and reversible addition-fragmentation transfer polymerization/macromolecular design by interchange of xanthates (RAFT/MADIX) radical polymerizations. Both types of polymerizations were strongly affected by the addition of NaOH. The authors found that by adding 1 equivalent of NaOH they could significantly increase the rate of the polymerization and the final conversion for both conventional and RAFT/MADIX polymerizations while larger quantities led to retardation of the reaction. A wide range of alkali hydroxides were also studied including H+, Li+, K+ and NH4+. It was shown that the dispersity of the final polymer decreases as the ionic radius of the counterion increases (H+ > Li+> Na+ > K+ > NH4+) while the acceleration of the polymerization follows the order Na+ > K+ > NH4+> Li+ > H+). Overall, the fastest rates of polymerizations were obtained in the presence of 0.5 equivalent of NaOH, while the same concentration of KOH or NH4OH allowed for a moderate acceleration on the polymerization rate combined with an improved control over the molar masses. Thus, this simple and cost-effective strategy can significantly improve the efficiency of the polymerization of VPA by simultaneously enhancing the reaction rate and the control over the molar masses.

 

 

Tips/comments directly from the authors:

  1. Take care to control the temperature when neutralizing the VPA – the reaction is very exothermic!
  2. Use NaOH for the most significant acceleration of polymerization and NH4OH for the strongest reduction in dispersity of the polymer.
  3. PVPA homopolymer can be precipitated in MeOH, but many PVPA-containing DHBCs must be purified by dialysis due to the small difference in solubility between PVPA and VPA and the low volatility of VPA.

 

Read this exciting research for free until 10/09/2017 through a registered RSC account.

Acceleration and improved control of aqueous RAFT/MADIX polymerization of vinylphosphonic acid in the presence of alkali hydroxides
Polym. Chem., 2017, 8, 3825-3832, DOI: 10.1039/c7py00747g

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About the webwriterAthina Anastasaki

Dr. Athina Anastasaki is a web writer for Polymer Chemistry. She is currently a Global Marie Curie Fellow working alongside Professor Craig Hawker at the University of California, Santa Barbara (UCSB). Please visit this website for more

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8th Symposium on Controlled Radical Polymerization

American Chemical Society, Chemistry for Life ®

 

Polymer Chemistry is pleased to be sponsoring the 8th Symposium on Controlled Radical Polymerization, held during this year’s ACS Fall Meeting in Washington, DC and organised by Brent SumerlinHaifeng Gao, Krzysztof Matyjaszewski and Nicolay Tsarevsky.

The symposium, which will take place on Sunday 20 August, will also feature a talk from Polymer Chemistry 2017 Lectureship winner Dr Julien Nicolas, as well as sessions on:

  • New macromolecular architectures and new ATRP initiating systems
  • Kinetics of radical polymerizations deduced via SP-PLP-EPR
  • RAFT 20 years later: Elements of RAFT navigation
  • Ionic auxiliaries for stereocontrolled radical polymerization
  • Mechanistic studies of transition metal catalyzed radical termination
  • Living radical polymerization using organic catalysts: Synthesis and applications
  • Electrochemistry for ATRP
  • Iron mediated controlled radical polymerisation
  • Designer polymers from palladium-catalyzed cross-coupling reactions

Registration for this event is now open – please visit the ACS website to register.

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Welcoming our new Polymer Chemistry Editor-in-Chief

We are excited to welcome new Editor-in-Chief Christopher Barner-Kowollik (Queensland University of Technology) to the Polymer Chemistry Editorial Board

 

 

Prof. Barner-Kowollik

Christopher Barner-Kowollik is Professor of Materials Science and head of the Soft Matter Materials Laboratory at the Queensland University of Technology. He has published over 510 peer-reviewed studies and won several awards for his research, most recently the coveted Erwin-Schrödinger Award of the Helmholtz association (2016) and a Laureate Fellowship from the Australian Research Council (2017).

His main research interests are situated at the interface of organic, polymer and biochemistry and focus on a wide range of polymer-related research fields, such as the (photochemical) synthesis of complex macromolecular architectures with highly-defined functionality and composition, advanced synthesis via polymer ligation techniques and macromolecular transformations at ambient temperature in solution and on surfaces, with a strong focus on light-induced methodologies, advanced photolithographic processes, fundamental investigations into polymerization mechanisms and kinetics, as well as high resolution imaging and characterization of macromolecular chain structures via mass spectrometric methods in solution and on surfaces.

 

Christopher has been an Associate Editor for Polymer Chemistry since 2009, and we are delighted that he has agreed to become our new Editor-in-Chief! Welcome to the new position!

Christopher takes over from Professor David Haddleton, who has led the journal since its launch in 2009. We would like to thank Professor Haddleton for his excellent work as Editor-in-Chief and will be delighted to continue working with him as an Advisory Board member.

As Polymer Chemistry Editor-in-Chief, Christopher will be handling submissions to the journal. Why not submit your next paper to his Editorial Office?

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