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2. Optimizing the Ion Conductivity and Mechanical Stability of Polymer Electrolyte Membranes Designed for Use in Lithium Ion Batteries: Combining Imidazolium-Containing Poly(ionic liquids) and Poly(propylene carbonate).

Author

Kiriy, Nataliya, Özenler, Sezer, Voigt, Pauline, Kobsch, Oliver, Meier-Haack, Jochen, Arnhold, Kerstin, Janke, Andreas, Muza, Upenyu L., Geisler, Martin, Lederer, Albena, Pospiech, Doris, Kiriy, Anton, and Voit, Brigitte

Subjects
POLYELECTROLYTES, PROPYLENE carbonate, LITHIUM-ion batteries, POLYMERIC membranes, FLUOROETHYLENE, SOLID electrolytes, IONIC conductivity, MECHANICAL behavior of materials
Abstract

State-of-the-art Li batteries suffer from serious safety hazards caused by the reactivity of lithium and the flammable nature of liquid electrolytes. This work develops highly efficient solid-state electrolytes consisting of imidazolium-containing polyionic liquids (PILs) and lithium bis(trifluoromethane sulfonyl)imide (LiTFSI). By employing PIL/LiTFSI electrolyte membranes blended with poly(propylene carbonate) (PPC), we addressed the problem of combining ionic conductivity and mechanical properties in one material. It was found that PPC acts as a mechanically reinforcing component that does not reduce but even enhances the ionic conductivity. While pure PILs are liquids, the tricomponent PPC/PIL/LiTFSI blends are rubber-like materials with a Young's modulus in the range of 100 MPa. The high mechanical strength of the material enables fabrication of mechanically robust free-standing membranes. The tricomponent PPC/PIL/LiTFSI membranes have an ionic conductivity of 10−6 S·cm−1 at room temperature, exhibiting conductivity that is two orders of magnitude greater than bicomponent PPC/LiTFSI membranes. At 60 °C, the conductivity of PPC/PIL/LiTFSI membranes increases to 10−5 S·cm−1 and further increases to 10−3 S·cm−1 in the presence of plasticizers. Cyclic voltammetry measurements reveal good electrochemical stability of the tricomponent PIL/PPC/LiTFSI membrane that potentially ranges from 0 to 4.5 V vs. Li/Li+. The mechanically reinforced membranes developed in this work are promising electrolytes for potential applications in solid-state batteries. [ABSTRACT FROM AUTHOR]

Published
2024
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4. Synthesis of Conjugated Polymers with Complex Architecture for Photovoltaic Applications

Author

Kiriy, Anton, Krebs, Frederik C., Abe, Akihiro, Series editor, Albertsson, Ann-Christine, Series editor, Coates, Geoffrey W, Series editor, Genzer, Jan, Series editor, Kobayashi, Shiro, Series editor, Lee, Kwang-Sup, Series editor, Leibler, Ludwik, Series editor, Long, Timothy E., Series editor, Möller, Martin, Series editor, Okay, Oguz, Series editor, Percec, Virgil, Series editor, Tang, Ben Zhong, Series editor, Terentjev, Eugene M., Series editor, Theato, Patrick, Series editor, Vicent, Maria J., Series editor, Voit, Brigitte, Series editor, Wiesner, Ulrich, Series editor, Zhang, Xi, Series editor, and Leo, Karl, editor

Published
2017
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6. Sequentially processed P3HT/CN6-CP•−NBu4+ films: interfacial or bulk doping?

Author

Karpov, Yevhen, Kiriy, Nataliya, Formanek, Petr, Hoffmann, Cedric, Beryozkina, Tetyana, Hambsch, Mike, Al-Hussein, Mahmoud, Mannsfeld, Stefan, Büchner, Bernd, Debnath, Bipasha, Bretschneider, Michael, Krupskaya, Yulia, Lissel, Franziska, Kiriy, Anton, Karpov, Yevhen, Kiriy, Nataliya, Formanek, Petr, Hoffmann, Cedric, Beryozkina, Tetyana, Hambsch, Mike, Al-Hussein, Mahmoud, Mannsfeld, Stefan, Büchner, Bernd, Debnath, Bipasha, Bretschneider, Michael, Krupskaya, Yulia, Lissel, Franziska, and Kiriy, Anton

Abstract

Derivatives of the hexacyano-[3]-radialene anion radical (CN6-CP•−) emerge as a promising new family of p-dopants having a doping strength comparable to that of archetypical dopant 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane (F4TCNQ). Here, mixed solution (MxS) and sequential processing (SqP) doping methods are compared by using a model semiconductor poly(3-hexylthiophene) (P3HT) and the dopant CN6-CP•−NBu4+ (NBu4+ = tetrabutylammonium). MxS films show a moderate yet thickness-independent conductivity of ≈0.1 S cm−1. For the SqP case, the highest conductivity value of ≈6 S cm−1 is achieved for the thinnest (1.5–3 nm) films whereas conductivity drops two orders of magnitudes for 100 times thicker films. These results are explained in terms of an interfacial doping mechanism realized in the SqP films, where only layers close to the P3HT/dopant interface are doped efficiently, whereas internal P3HT layers remain essentially undoped. This structure is in agreement with transmission electron microscopy, atomic force microscopy, and Kelvin probe force microscopy results. The temperature-dependent conductivity measurements reveal a lower activation energy for charge carriers in SqP samples than in MxS films (79 meV vs 110 meV), which could be a reason for their superior conductivity.

Published
2023

9. Charge‐Compensated N‐Doped π ‐Conjugated Polymers: Toward both Thermodynamic Stability of N‐Doped States in Water and High Electron Conductivity

Author

Borrmann, Fabian, primary, Tsuda, Takuya, additional, Guskova, Olga, additional, Kiriy, Nataliya, additional, Hoffmann, Cedric, additional, Neusser, David, additional, Ludwigs, Sabine, additional, Lappan, Uwe, additional, Simon, Frank, additional, Geisler, Martin, additional, Debnath, Bipasha, additional, Krupskaya, Yulia, additional, Al‐Hussein, Mahmoud, additional, and Kiriy, Anton, additional

Published
2022
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13. Short Excited‐State Lifetimes Mediate Charge‐Recombination Losses in Organic Solar Cell Blends with Low Charge‐Transfer Driving Force

Author

Shivhare, Rishi, primary, Moore, Gareth John, additional, Hofacker, Andreas, additional, Hutsch, Sebastian, additional, Zhong, Yufei, additional, Hambsch, Mike, additional, Erdmann, Tim, additional, Kiriy, Anton, additional, Mannsfeld, Stefan C. B., additional, Ortmann, Frank, additional, and Banerji, Natalie, additional

Published
2021
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18. Ultrasoft and High-Mobility Block Copolymers for Skin-Compatible Electronics

Author

Ditte, Kristina, Perez, Jonathan, Chae, Soosang, Hambsch, Mike, Al-Hussein, Mahmoud, Komber, Hartmut, Formanek, Peter, Mannsfeld, Stefan C.B., Fery, Andreas, Kiriy, Anton, and Lissel, Franziska

Subjects
block copolymers, stretchable organic electronics, skin-compatible electronics, organic field-effect transistors
Abstract

Polymer semiconductors (PSCs) are an essential component of organic field-effect transistors (OFETs), but their potential for stretchable electronics is limited by their brittleness and failure susceptibility upon strain. Herein, a covalent connection of two state-of-the-art polymers���semiconducting poly-diketo-pyrrolopyrrole-thienothiophene (PDPP-TT) and elastomeric poly(dimethylsiloxane) (PDMS)���in a single triblock copolymer (TBC) chain is reported, which enables high charge carrier mobility and low modulus in one system. Three TBCs containing up to 65 wt% PDMS were obtained, and the TBC with 65 wt% PDMS content exhibits mobilities up to 0.1 cm2 V���1 s���1, in the range of the fully conjugated reference polymer PDPP-TT (0.7 cm2 V���1 s���1). The TBC is ultrasoft with a low elastic modulus (5 MPa) in the range of mammalian tissue. The TBC exhibits an excellent stretchability and extraordinary durability, fully maintaining the initial electric conductivity in a doped state after 1500 cycles to 50% strain. �� 2020 The Authors. Advanced Materials published by Wiley-VCH GmbH

Published
2020
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19. AB-Versus AA+BB-Suzuki polycondensation: A palladium/Tris(tert‐butyl)phosphine catalyst can outperform conventional catalysts

Author

Zhang, Kenan, Tkachov, Roman, Ditte, Kristina, Kiriy, Nataliya, Kiriy, Anton, Vot, Brigitte, and Publica

Subjects
Suzuki polycondensation, conjugated polymer, palladium catalyst
Abstract

A Pd/Pt‐Bu3 catalyst having bulky, electron‐rich ligands significantly outperforms conventional ""step‐growth catalysts"" Pd(PPh3)4 and Pd(Po‐Tol3)3 in the Suzuki polycondensation of the AB‐type arylene‐based monomers, such as some of the substituted fluorenes, carbazoles, and phenylenes. In the AA+BB polycondensation, Pd/Pt‐Bu3 also performs better under homogeneous reaction conditions, in combination with the organic base Et4NOH. The superior performance of Pd/Pt‐Bu3 is discussed in terms of its higher reactivity in the oxidative addition step and inherent advantages of the intramolecular catalyst transfer, which is a key step joining catalytic cycles of the AB‐polycondensation. These findings are applied to the synthesis of a carbazole‐based copolymer designed for the use as a hole conductor in solution‐processed organic light‐emitting diodes.

Published
2020

20. Conductive polymer brushes of regioregular head-to-tail poly(3-alkylthiophenes) via catalyst-transfer surface-initiated polycondensation

Author

Senkovskyy, Volodymyr, Kuckling, Dirk, Khanduyeva, Natalya, Kiriy, Anton, Komber, Hartmut, Oertel, Ulrich, and Stamm, Manfred

Subjects
Surface chemistry -- Research, Conducting polymers -- Chemical properties, Monomolecular films -- Chemical properties, Chemistry
Abstract

The surface-initiated polycondensation of 2-bromo-5-chloromagnesio-3-alkylthiophene is used to grow conductive polymer (CP) brushes of regioregular head-to-tail poly(3-alkylthiophenes) (P3AT). The selective chain growth polycondensation of the monomer when exposed to Ni(II) macroinitiator layers is found to be economical.

Published
2007

23. Cascade of coil-globule conformational transitions of single flexible polyelectrolyte molecules in poor solvent

Author

Kiriy, Anton, Gorodyska, Ganna, Minko, Sergly, Jaeger, Werner, Stepanek, Petr, and Stamm, Manfred

Subjects
Mica -- Analysis, Ammonium chloride -- Research, Ammonium paratungstate -- Research, Ammonium compounds -- Research, Polyelectrolytes -- Research, Chemistry
Abstract

Hydrophobic flexible polyelectrolyte molecules of ply(2-Vinylpyridine) and poly(methacryloyloxyethyl dimethylbenzylammonium chloride) are trapped and frozen due to adsorption on the mica surface is shown. An increase in the ionic strength of the solution induces the cascade of abrupt conformational transitions due to the intrachain segregation from elongated coil to compact globule conformations through intermediate pearl necklace globule conformations with different amounts of beads per chain.

Published
2002

24. Mineralization of single flexible polyelectrolyte molecules

Author

Minko, Sergiy, Kiriy, Anton, Gorodyska, Ganna, Stamm, Manfred, and Enemark, John H.

Subjects
Miniaturization (Electronics) -- Research, Polyelectrolytes -- Research, Metallizing, Nanotechnology, Mineralogical research, Chemistry
Abstract

Nanoparticles of different shapes and sizes are studied by researchers because of its utility in miniaturization of electronic devices, and different methods are devised for the synthesis of metallic nanowires, which includes template synthesis. It was found that molecular details of adsorbed linear flexible polyelectrolyte molecules determine the dimensions of nanostructures after metallization.

Published
2002

26. Sequentially Processed P3HT/CN6‐CP •− NBu 4+ Films: Interfacial or Bulk Doping?

Author

Karpov, Yevhen, primary, Kiriy, Nataliya, additional, Formanek, Petr, additional, Hoffmann, Cedric, additional, Beryozkina, Tetyana, additional, Hambsch, Mike, additional, Al‐Hussein, Mahmoud, additional, Mannsfeld, Stefan C. B., additional, Büchner, Bernd, additional, Debnath, Bipasha, additional, Bretschneider, Michael, additional, Krupskaya, Yulia, additional, Lissel, Franziska, additional, and Kiriy, Anton, additional

Published
2020
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32. Tuning Orientational Order of Highly Aggregating P(NDI2OD-T 2 ) by Solvent Vapor Annealing and Blade Coating

Author

Trefz, Daniel, Gross, Yannic, Dingler, Carsten, Tkachov, Roman, Hamidi-Sakr, Amer, Kiriy, Anton, McNeill, Christopher, Brinkmann, Martin, Ludwigs, Sabine, Institut Charles Sadron (ICS), Matériaux et nanosciences d'Alsace, Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Leibniz-Institut für Polymerforschung Dresden e.V. (IPF), Leibniz Association, Max Planck Institute for Dynamics and Self-Organization (MPIDS), Max-Planck-Gesellschaft, Univ Stuttgart, Inst Polymerchem, Universität Stuttgart [Stuttgart], Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), and Brinkmann, Martin

Subjects
[CHIM.POLY] Chemical Sciences/Polymers, [CHIM.POLY]Chemical Sciences/Polymers, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

33. Alkyl Branching Position in Diketopyrrolopyrrole Polymers

Author

Shivhare, Rishi, Erdmann, Tim, Hoermann, Ulrich, Collado-Fregoso, Elisa, Zeiske, Stefan, Benduhn, Johannes, Ullbrich, Sascha, Huebner, Rene, Hambsch, Mike, Kiriy, Anton, Voit, Brigitte, Neher, Dieter (Prof. Dr.), Vandewal, Koen, and Mannsfeld, Stefan C. B.

Subjects
Institut für Physik und Astronomie, ddc:530
Abstract

Diketopyrrolopyrrole (DPP)-based donor acceptor copolymers have gained a significant amount of research interest in the organic electronics community because of their high charge carrier mobilities in organic field-effect transistors (OFETs) and their ability to harvest near-infrared (NIR) photons in solar cells. In this study, we have synthesized four DPP based donor-acceptor copolymers with variations in the donor unit and the branching point of the solubilizing alkyl chains (at the second or sixth carbon position). Grazing incidence wide-angle X-ray scattering (GIWAXS) results suggest that moving the branching point further away from the polymer backbone increases the tendency for aggregation and yields polymer phases with a higher degree of crystallinity (DoC). The polymers were blended with PC70BM and used as active layers in solar cells. A careful analysis of the energetics of the neat polymer and blend films reveals that the charge-transfer state energy (E-CT) of the blend films lies exceptionally close to the singlet energy of the donor (E-D*), indicating near zero electron transfer losses. The difference between the optical gap and open-circuit voltage (V-OC) is therefore determined to be due to rather high nonradiative 418 +/- 13 mV) and unavoidable radiative voltage losses (approximate to 255 +/- 8 mV). Even though the four materials have similar optical gaps, the short-circuit current density (J(SC)) covers a vast span from 7 to 18 mA cm(-2) for the best performing system. Using photoluminescence (PL) quenching and transient charge extraction techniques, we quantify geminate and nongeminate losses and find that fewer excitons reach the donor-acceptor interface in polymers with further away branching points due to larger aggregate sizes. In these material systems, the photogeneration is therefore mainly limited by exciton harvesting efficiency.

Published
2018

41. Layer-by-Layer Assembly Enabled by the Anionic p-Dopant CN6-CP•–K+: a Route to Achieve Interfacial Doping of Organic Semiconductors

Author

Karpov, Yevhen, primary, Kiriy, Nataliya, additional, Formanek, Petr, additional, Zessin, Jakob, additional, Hambsch, Mike, additional, Mannsfeld, Stefan C. B., additional, Lissel, Franziska, additional, Beryozkina, Tetyana, additional, Bakulev, Vasiliy, additional, Voit, Brigitte, additional, and Kiriy, Anton, additional

Published
2019
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45. A Chemically Doped Naphthalenediimide-Bithiazole Polymer for n-Type Organic Thermoelectrics

Author

Wang, Suhao, Sun, Hengda, Erdmann, Tim, Wang, Gang, Fazzi, Daniele, Lappan, Uwe, Puttisong, Yuttapoom, Chen, Zhihua, Berggren, Magnus, Crispin, Xavier, Kiriy, Anton, Voit, Brigitte, Marks, Tobin J., Fabiano, Simone, Facchetti, Antonio, Wang, Suhao, Sun, Hengda, Erdmann, Tim, Wang, Gang, Fazzi, Daniele, Lappan, Uwe, Puttisong, Yuttapoom, Chen, Zhihua, Berggren, Magnus, Crispin, Xavier, Kiriy, Anton, Voit, Brigitte, Marks, Tobin J., Fabiano, Simone, and Facchetti, Antonio

Abstract

The synthesis of a novel naphthalenediimide (NDI)-bithiazole (Tz2)-based polymer [P(NDI2OD-Tz2)] is reported, and structural, thin-film morphological, as well as charge transport and thermoelectric properties are compared to the parent and widely investigated NDI-bithiophene (T2) polymer [P(NDI2OD-T2)]. Since the steric repulsions in Tz2 are far lower than in T2, P(NDI2OD-Tz2) exhibits a more planar and rigid backbone, enhancing p-p chain stacking and intermolecular interactions. In addition, the electron-deficient nature of Tz2 enhances the polymer electron affinity, thus reducing the polymer donor-acceptor character. When n-doped with amines, P(NDI2OD-Tz2) achieves electrical conductivity (approximate to 0.1 S cm(-1)) and a power factor (1.5 mu W m(-1) K-2) far greater than those of P(NDI2OD-T2) (0.003 S cm(-1) and 0.012 mu W m(-1) K-2, respectively). These results demonstrate that planarized NDI-based polymers with reduced donor-acceptor character can achieve substantial electrical conductivity and thermoelectric response., Funding Agencies|Knut and Alice Wallenberg Foundation; Swedish Foundation for Strategic Research; VINNOVA [2015-04859]; Swedish Research Council [2016-03979]; Advanced Functional Materials Center at Linkoping University [2009-00971]; U.S. Department of Commerce, National Institute of Standards and Technology, Center for Hierarchical Materials Design (CHiMaD) [70NANB14H012]; DOE Office of Science [DE-AC02-06CH11357]; DFG within the CoEcfaed [KI-1094/9, FA 1502/1-1]; Humboldt Foundation

Published
2018
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47. Sequentially Processed P3HT/CN6‐CP•−NBu4+ Films: Interfacial or Bulk Doping?

Author

Karpov, Yevhen, Kiriy, Nataliya, Formanek, Petr, Hoffmann, Cedric, Beryozkina, Tetyana, Hambsch, Mike, Al‐Hussein, Mahmoud, Mannsfeld, Stefan C. B., Büchner, Bernd, Debnath, Bipasha, Bretschneider, Michael, Krupskaya, Yulia, Lissel, Franziska, and Kiriy, Anton

Subjects
KELVIN probe force microscopy, ATOMIC force microscopy, TRANSMISSION electron microscopy, RADICAL anions, THICK films, MAGNETIC semiconductors
Abstract

Derivatives of the hexacyano‐[3]‐radialene anion radical (CN6‐CP•−) emerge as a promising new family of p‐dopants having a doping strength comparable to that of archetypical dopant 2,3,5,6‐tetrafluoro‐7,7,8,8‐tetracyano‐quinodimethane (F4TCNQ). Here, mixed solution (MxS) and sequential processing (SqP) doping methods are compared by using a model semiconductor poly(3‐hexylthiophene) (P3HT) and the dopant CN6‐CP•−NBu4+ (NBu4+ = tetrabutylammonium). MxS films show a moderate yet thickness‐independent conductivity of ≈0.1 S cm−1. For the SqP case, the highest conductivity value of ≈6 S cm−1 is achieved for the thinnest (1.5–3 nm) films whereas conductivity drops two orders of magnitudes for 100 times thicker films. These results are explained in terms of an interfacial doping mechanism realized in the SqP films, where only layers close to the P3HT/dopant interface are doped efficiently, whereas internal P3HT layers remain essentially undoped. This structure is in agreement with transmission electron microscopy, atomic force microscopy, and Kelvin probe force microscopy results. The temperature‐dependent conductivity measurements reveal a lower activation energy for charge carriers in SqP samples than in MxS films (79 meV vs 110 meV), which could be a reason for their superior conductivity. [ABSTRACT FROM AUTHOR]

Published
2020
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48. Alkyl Branching Position in Diketopyrrolopyrrole Polymers: Interplay between Fibrillar Morphology and Crystallinity and Their Effect on Photogeneration and Recombination in Bulk-Heterojunction Solar Cells

Author

Shivhare, Rishi, primary, Erdmann, Tim, additional, Hörmann, Ulrich, additional, Collado-Fregoso, Elisa, additional, Zeiske, Stefan, additional, Benduhn, Johannes, additional, Ullbrich, Sascha, additional, Hübner, René, additional, Hambsch, Mike, additional, Kiriy, Anton, additional, Voit, Brigitte, additional, Neher, Dieter, additional, Vandewal, Koen, additional, and Mannsfeld, Stefan C. B., additional

Published
2018
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50. A Chemically Doped Naphthalenediimide‐Bithiazole Polymer for n‐Type Organic Thermoelectrics

Author

Wang, Suhao, primary, Sun, Hengda, additional, Erdmann, Tim, additional, Wang, Gang, additional, Fazzi, Daniele, additional, Lappan, Uwe, additional, Puttisong, Yuttapoom, additional, Chen, Zhihua, additional, Berggren, Magnus, additional, Crispin, Xavier, additional, Kiriy, Anton, additional, Voit, Brigitte, additional, Marks, Tobin J., additional, Fabiano, Simone, additional, and Facchetti, Antonio, additional

Published
2018
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