Fluorine Chemistry and High-Performance Materials

Image
Fluorine Chemistry and High-Performance Materials
Group leader
prof_roeschenthaler.jpg
Fluorine, a small atom with a great impact
Specific themes and goals

We synthesize and develop:

  • Fluorinating and polyfluoroalkylating as well as fluorinated building blocks to modify biological and pharmacological active compounds
  • Modern fluorinated liquid crystal molecules for LCD-displays
  • High-performance lithium-ion battery electrolyte components
  • Novel bisphosphonates, active agents against osteoporosis and bone cancer
  • New perfluorinated monomers for copolymerization
Highlights and impact
  • We synthesized and investigated fluorine- and phosphorus-containing compounds for their application in material science and medicinal chemistry.
  • We design and developed lithium battery electrolytes.
  • We synthesized and used fluorinated monomers in high-performance polymers.
  • We used new small molecules containing phosphorus and fluorine as bioactive compounds.
  • The group contributed to two books, and filed five patents.
Group composition & projects/funding

Between 2019 and 2022, the group consisted of six postdoctoral research associates and two PhD candidates working on basic research projects concerning organofluorine chemistry. They were supported by the German Research Foundation (DFG) jointly with the National Natural Science Foundation of China (NSFC) and the Czech Science Foundation (GACR). Further projects deal with lithium battery component development supported by the Federal Ministry of Economy and Energy (BMWi), together with the Münster Electrochemical Energy Technology (MEET) research center and companies like Bosch and BASF. In industrially oriented projects, we designed and developed fluorinated high-performance materials.

Scientific Partners

Prof. Veit Wagner, Jacobs University Bremen gGmbH, Bremen (Germany).

Profs Yi Pan, Yi Wang, Youxuan Zheng, School of Chemistry and Chemical Engineering, Nanjing University, and Prof. Jianlin Han, Dr. Haibo Mei, College of Chemical Engineering, Nanjing Forestry University, Nanjing (China).

Dr. Petr Beier, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague (Czech Republic).

Prof. Henryk Koroniak, Department of Chemistry, Adam Mickiewicz University, Poznań (Poland).

Prof. Martin Winter, Institute of Physical Chemistry and MEET (Münster Electrochemical Energy Technology), University of Münster, and Dr. Isidora Čekić-Lasković, Helmholtz Institute Münster (HI MS), Münster (Germany).

Profs Yair Ein-Eli and Moris Eisen, Technion - Israel Institute of Technology, Haifa (Israel).

Prof. Dr. Vadim Soloshonok, Faculty of Chemistry, University of the Basque Country, San Sebastian (Spain).

Prof. Dr. Simon Grabowsky, Department of Chemistry and Biochemistry, University of Bern, Bern (Switzerland).

Prof. Hiroyuki Konno, Yamagata University, Yamagata (Japan).

Prof. David O’Hagan, University of St. Andrews, St. Andrews, Scotland (UK).

Prof. Jun Wang, Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology (SUSTech), Shenzhen (China).

Reviewer: Science, Angewandte Chemie, Journal of Fluorine Chemistry, Journal Organic Chemistry, Tetrahedron Letters, Tetrahedron, Inorganic Chemistry, Organic Letters, Chemistry A European Journal, Dalton Transactions, Synthesis. Evaluator for ETH Zürich. Reviewer for the DFG (including DIP), ERC, DAAD, EurasiaNet, Emmy Noether-Stipendium, Alexander von Humboldt Foundation, Research Awards etc., US-Israel Binational Science Foundation, ACS Petroleum Research Fund, Russian, Polish and Czech Research Foundation, Singapure Agency for Science, Technology and Research, Böhringer Foundation, Carl Zeiß Foundation, Israel Ministry of Innovation, Science and Technology.

Conferences: Member of the International Advisory Board of the 14th European Symposium on Fluorine Chemistry, Poznan (Poland). Chair of the 18th Int. Symposium on Fluorine Chemistry, July 30 – August 4, 2006, in Bremen with approx. 450 participants. Chair of the Bremen Fluorine Days 2016 (www.bremenfluorinedays.com), July 3-7, 2016, with 140 participants. Member of the National Advisory Board, 20th European Symposium on Fluorine Chemistry August 14 – 19, 2022, Berlin. 

240+ contributions to international conferences and active participation also as session chair at numerous international conferences on phosphorus, fluorine, inorganic ring and heteroatom chemistry.

140+ lectures at research institutions and chemical companies in Canada, USA, Israel, China, Japan, Denmark, former GDR, Italy, France, Spain, Estonia, Poland, Russia, Czech Republic, Ukraine, Netherlands, Kazakhstan, Australia.

Selected publications

Publications and Patents/Patent applications: total approx. 397 publications in peer reviewed journals, 32 book chapters, 45 patents and patent-applications; h-factor 39. 

Guided 1 Habilitation, supervised 38 PhD students, 26 Dipl.-Chem., 2 Master students, 44 international postdoctoral scientists, hosted 20 visiting professors. 

ORCID iD 0000-0002-4809-6510.

Publications

  1. Synthesis and characterization of oxazaborinin phosphonate for blue OLED emitter applications, J. Köhling, V. Kozel, V. Jovanov, R. Pajkert, S. N. Tverdomed, O. Gridenco, M. Fugel, S. Grabowsky, G.-V. Röschenthaler, V. Wagner, ChemPhysChem., 2019, 20, 665–671.

  2. Fluorinated Cyclic Phosphorus(III)-based Additives for High Voltage Application: Structure-Reactivity Influence on the CEI Formation and Overall Cell Performance, N. von Aspern, D. Diddens, M. Börner, T. Kobayashi, O. Stubbmann-Kazakova, V. Kozel, G.-V. Röschenthaler, M. Fyta, J. Smiatek, M. Winter, I. Cekic-Laskovic, Appl. Mat. & Interfaces, 2019, 11, 16605-16618. 

  3. Mediator and Additive Free Trifluoromethyl-Fluorination of Terminal Alkenes by Persistent Perfluoroalkyl Radical, A. Sato, M. V. Ponomarenko, T. Ono, G.-V. Röschenthaler, V. A. Soloshonok, Eur. J. Org. Chem., 2019, 4417-4421. 

  4. Fluorine and Lithium: Ideal Partners for High Performance Rechargeable Battery Electrolytes, N. von Aspern, G.-V. Röschenthaler, M. Winter, I. Cekic-Laskovic, Angew. Chem. Int. Ed., 2019, 58, 15978–16000, doi.org/10.1002/anie.201901381; Fluor und Lithium: Ideale Partner für Elektrolyte in wiederaufladbaren Hochleistungsbatterien, N. von Aspern, G.-V. Röschenthaler, M. Winter, I. Cekic-Laskovic, Angew. Chem. 2019, 131, 16124–16147, https://doi.org/10.1002/ange.201901381.

  5. The self-disproportionation of enantiomers (SDE) via column chromatography of β-amino-α,α-difluorophosphonic acid derivatives, M. Kwiatkowska; M. Marcinkowska; A. Wzorek, R. Pajkert, J. Han, K. D. Klika, V. A Soloshonok, G.-V. Röschenthaler, Amino Acids, 2019, 51, 1377-1385. 

  6. Complementary bonding analysis of the N–Si peri-interaction in pentacoordinated silicon compounds using quantum crystallography, M. Fugel, M. V. Ponomarenko, M. F. Hesse, L. A. Malaspina, F. Kleemiss, K. Sugimoto, A. Genoni, G.-V. Röschenthaler, S. Grabowsky, J. Chem. Soc. Dalton Trans., 2019, 16330-16339. 

  7. Convenient synthesis of racemic 4,4-difluoro glutamic acid derivative via Michael addition of Ni(II)-complex of dehydroalanine Schiff base, Y. Tokairin, V. A. Soloshonok, H. Konno, H. Moriwaki, G.-V. Röschenthaler, J. Fluorine Chem., 2019, 227, 109376.

  8. Uncommon fluorination of enones with xenon difluoride, I. I. Gerus, Y. I. Zhuk, L. N. Kacharova, G.-V. Röschenthaler, E. N. Shaitanova, A. E. Sorochinskii, S. I. Vdovenko, J. Wojcik, J. Fluorine Chem., 2020, 229, 109413.

  9. Non-flammable Fluorinated Phosphorus(III)-based Electrolytes for Advanced Lithium Ion Battery Performance, N. von Aspern, M. Leissing, C. Wölke, D. Diddens, T. Kobayashi, M. Börner, O. Stubbmann-Kazakova, V. Kozel, G.-V. Röschenthaler, J. Smiatek, S. Nowak, M. Winter, I. Cekic-Laskovic, ChemElectroChem, 2020, 7, 1499–1508.

  10. Thermolysis of β-Fluorosulfonyl perfluoropropanoic acid derivatives: New synthetic routes for perfluorinated cyclic sulfones, S. N. Tverdomed, M. E. Hirschberg, R. Pajkert, K. Hintzer, G.-V. Röschenthaler, J. Fluorine Chem., 2020, 233, 109500.

  11. Asymmetric Synthesis of 4,4-(Difluoro)glutamic Acid via Chiral Ni(II)-Complexes of Dehydroalanine Schiff Bases. Effect of the Chiral Ligands Structure on the Stereochemical Outcome, Y. Tokairin, Y. Shigeno, J. Han, G.-V. Röschenthaler, H. Konno, H. Moriwaki, V. A. Soloshonok, ChemistryOpen, 2020, 9, 93–96. DOI: 10.1002/open.201900343

  12. Application of perfluoro(2-propoxypropyl vinyl ether) (PPVE-2) in the synthesis of perfluoro(propyl vinyl ether) (PPVE-1), S. N. Tverdomed, M. E. Hirschberg, R. Pajkert, K. Hintzer, S. M. Smith, G.-V. Röschenthaler, J. Fluorine Chem., 2020, 233,109508. 

  13. Selectfluor-promoted oxidative reaction of disulfides and amines: access to sulfinamides, H. Mei, J. Liu, R. Pajkert, G.-V. Röschenthaler, J. Han, Organic & Biomolecular Chem., 2020, 18, 3761-3766. DOI: 10.1039/d0ob00720j.

  14. Chemistry of electrochemical oxidative reactions of sulfinate salts, H. Mei, R. Pajkert, L. Wang, G.-V. Röschenthaler, J. Han, Green Chemistry, 2020, 22, 3028-3059. DOI: 10.1039/d0gc01025a 

  15. Tailored ß-diketones as effective surface passivation for solution processed zinc oxide thin film transistors, J. Köhling, V. Jovanov, N. Kalinovich, G.-V. Röschenthaler, V. Wagner, Organic Electronics, 2020, 86, 105906; https://doi.org/10.1016/j.orgel.2020.105906.

  16. Janus face all-cis 1,2,4,5-tetrakis(trifluoromethyl)- and all-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)-cyclohexanes, C. Yu, A. Kütt, G.-V. Röschenthaler, T. Lebl, D. B. Cordes, A. M. Z. Slawin, M. Bűhl, D. O’Hagan, Angew. Chem. Int. Ed. 2020, 59(45), 19905-19909. doi.org/10.1002/anie.202008662; Angew. Chem. 2020, 132, 20077–20081. doi.org/10.1002/ange.202008662. 

  17. Selectfluor 作用下二芳基二硫醚和醇的双亚磺酰化反应制备亚磺酸酯Selectfluor-promoted twofold sulfination of alcohols for synthesis of sulfinic ester from diaryldisulfides, Aiyao Liu, Jiang Liu, Haibo Mei, G.-V. Röschenthaler, Jianlin Han, Youji Huaxue (Chinese J. Org. Chem.), 2020, 40, 1926-1933.

  18. Design of (β-diazo-α,α-difluoroethyl) phosphonates and their application as masked carbenes in visible light-promoted coupling reactions with sulfonic acids, H. Mei, J. Liu, R. Pajkert, L. Wang, G.-V. Röschenthaler, J. Han, Org. Chem. Frontiers 2021, 8(4), 767-772; DOI: 10.1039/d0qo01394c.

  19. Front Cover Picture: Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications, Adv. Synth. Catal. 12/2021, 2911.

  20. VIP: Recent Advances in Synthesis of Difluoromethylene Phosphonates for Biological Applications, M. Shevchuk, Q. Wang, R. Pajkert, J. Xu, H. Mei, G.-V. Röschenthaler, J. Han, Adv. Synth. & Cat., 2021, 363, 2912– 2968; DOI: 10.1002/adsc.202001464. 

  21. Oxamates as 1,2-Diketone Equivalents: The Effect of Fluorine, J. Köhling, N. Kalinovich, R. Pajkert, S. Tverdomed, E. Lork, V. Wagner, G.-V. Röschenthaler, ChemSelect, 2021, 6, 1882-1886; 

  22. In Situ Generation of Unstable Difluoromethylphosphonate-Containing Di-azoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones, H. Mei, L. Wang, R. Pajkert, Q. Wang, J. Xu, J. Liu, G.-V. Röschenthaler, J. Han, Org. Lett., 2021, 23, 1130−1134.

  23. Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety, R. Pajkert, H. Koroniak, P. Kafarski, G.-V. Röschenthaler, OrgBioChem., 2021, 19(22), 4871-4876.

  24. Esterification of carboxylic acids with (β-diazo-α,α-difluoroethyl)phosphonates under photochemical conditions, 光化学条件下(β-重氮-α,α-二氟乙基)膦酸酯与羧酸的酯化反应, J. Liu, J. Xu, R. Pajkert, H. Mei, G.-V. Röschenthaler, J. Han, Acta Chim. Sinica 2021, 79, 747-750; DOI: 10.6023/A21030096.

  25. Base-mediated reactions of malonic acid derivatives with perfluorinated olefins: Novel synthetic routes to perfluorinated carboxylic acid (PFCA) ionomers, S. N. Tverdomed, M. E. Hirschberg, R. Pajkert, K. Hintzer, G.-V. Röschenthaler, J. Fluorine Chem., 2021, 250, 109864.

  26. Silver(I) pentafluorooxosulphate – A Versatile Reagent for the Synthesis of OSF5-Compounds, A. Haupt, D. Duvinage, E. Lork, M. Ponomarenko, G.-V. Röschenthaler, Angew. Chem. Int. Ed., 2021, 60(33), 17866-17870, DOI: 10.1002/anie.202107587, 

  27. Difluorobis(pentafluoroethyl)phosphoranide – A promising building block for phosphoranidometal complexes, M. Keßler, H.-G. Stammler, B. Neumann, G.-V. Röschenthaler, B. Hoge, Inorg. Chem., 2021, 60(21), 16466-16473; DOI.ORG/10.1021/acs.inorgchem.1c02307.

  28. [3+2] Cycloaddition Reactions of β-Diazo-α,α-difluoromethylphosphonates with α,β-Unsaturated Esters, Q. Wang, L. Wang, R. Pajkert, I. Hajdin, J. Liu, H. Mei, G.-V. Röschenthaler, J. Han, J. Fluorine Chem. 2021, 251, 109899; doi.org/10.1016/j.jfluchem.2021.109899. 

  29. Multigram Synthesis of Difluoromethylene Phosphonic and Phosphinic Amides and Phosphine Oxides via Formal [2,3]-Sigmatropic Allyl Phosphite – Allylphosphonate Rearrangement, M. Shevchuk, G.-V. Röschenthaler, Synthesis, 2022; 54, 171-183, DOI: 10.1055/a-1578-2848.

  30. Facile synthesis of (β-chlorodifluoroethyl)phosphonates via chlorination reaction of difluoroalkyl diazo derivatives with HCl, J. Liu, R. Pajkert, L. Wang, H. Mei, G.-V. Röschenthaler, J. Han, Chinese Chem. Lett., 2022, 33, 2429–2432, https://doi.org/10.1016/j.cclet.2021.10.066.

  31. Synthesis, Reactivity and Structural Properties of Trifluoromethylphosphoranides, O. O. Shyshkov, A. A. Kolomeitsev, B. Hoge, E. Lork, A. Haupt, M. Keßler, G.-V. Röschenthaler, Chemistry Eur. J., 2022, 28, e20210430; DOI: 10.1002/chem.202104308. 

  32. OnePot Reaction of (βAminoα,αdifluoroethyl)phosphonates with Trifluoromethylated Ketones via AzaWittig Reagents, Haibo Mei, Qian Wang, R. Pajkert, Jiang Liu, G.-V. Röschenthaler, Jianlin Han, Adv. Synth. & Cat., 2022, 364(12), 1969-1974; DOI: 10.1002/adsc.202200330.

  33. The free Difluorobis(pentafluoroethyl)phosphoranide Ion and its Ligand Properties, M. Keßler, L. Hartmann, H.-G. Stammler, B. Neumann, G.-V. Röschenthaler, B. Hoge, Inorg. Chem., 2022, 61, 10833-10843.

  34. Chemistry of Difluoromethylene Phosphonates: History, State of the Art, and Prospects, M. Shevchuk,, G.-V. Röschenthaler, Ukr. Bioorg. Acta, 2022. 17, 40-55.

  35. Ru-Catalyzed Hydrogen Atom Transfer/C–F Bond Cleavage of Difluoroalkyl Diazos with Hantzsch Ester via a Photocatalytic Radical Process, Qian Wang, Nana Wang, Jiang Liu, Haibo Mei, R. Pajkert, M. Kessler, G.-V. Röschenthaler, Jianlin Han, Organic Letters 2022, 24(43), 8036-8040.

  36. Triorganylphosphoranides – Realization of an Unusual Structural Motif Utilizing Electron Withdrawing Pentafluoroethyl Groups, M. Keßler, M. Kapiza, H.-G. Stammler, B. Neumann, G.-V. Röschenthaler, B. Hoge, ChemPlusChem., 2023, e202200436. 

  37. Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups, I. Hajdin, R. Pajkert, M. Keßler, Jianlin Han, Haibo Mei, G.-V. Röschenthaler, Beilstein J. Org. Chem. 2023, 19, 541–549.

  38. Interaction of O- and P-nucleophiles with perfluorinated olefins: Novel synthetic route to fluorinated phosphorus-containing monomers, S. N. Tverdomed, M. E. Hirschberg, R. Pajkert, K. Vlasov, G.-V. Röschenthaler, J. Fluorine Chem., 2023, 269, 110152.

  39. Rh-catalyzed H2O coupling/C–F bond cleavage of fluorinated diazoalkanes enabling synthesis of α-fluoro-β-ketophosphonates, Qian Wang, Jiang Liu, Haibo Mei, R. Pajkert, G.-V. Röschenthaler, Jianlin Han, Adv.Synth. & Cat., 2023, 365, 2883– 2887. DOI 10.1002/adsc.202300595.

  40. Blended salt electrolyte design for enhancement of NMC811||graphite cell performance, Peng Yan, M. Shevchuk, C. Wölke, M. Baghernejad, F. Pfeiffer, D. Berghus, G.-V. Röschenthaler, M. Winter, I. Cekic-Laskovic, Small Struct. 2024, 2300425 (1-18). DOI: 10.1002/sstr.202300425.

  41. Aza-Wittig reaction of (β-diazo-α,α-difluoroethyl)phosphonates with aldehydes for the synthesis of difluoromethylphosphonate-containing hydrazones, Qian Wang, R. Pajkert, Haibo Mei, G.-V. Röschenthaler, Jianlin Han, J. Fluorine Chem., 2024, 273, 110226.

  42. Regioselective Synthesis of 3H-Pyrazoles bearing the Difluoromethyl Phosphonate Group, I. Hajdin, R. Pajkert; Haibo Mei; Jianlin Han; G.-V. Röschenthaler, J. Fluorine Chem., 2024, 273, 110218.

  43. Rhodium-catalyzed O-H insertion reactions to (2-diazo-1,1,3,3,3-pentafluoropropyl)phosphonate: A convenient access to fluorinated β-alkoxy vinyl phosphonates, I. Hajdin, R. Pajkert, Haibo Mei, Jianlin Han, D. Duvinage, J. Beckmann, G.-V. Röschenthaler, Org. Lett., submitted.

  44. Synthesis of N-Sulfenylimines via an Electrochemical Radical Coupling of Amines and Thiols Mediated by Bromide Ions, Qian Wang, Jiang Liu, Haibo Mei, R. Pajkert, G.-V. Röschenthaler, Jianlin Han, Org. Lett. submitted.

  45. Synthetic Route to Hydroxy-Bisphosphonate Derivatives of Aspartic, Malic and Thiomalic Acids, R. Pajkert; G.-V. Röschenthaler; Jianlin Han; Haibo Mei; E. Lork; I. Lüddecke; D. Chizhov, Eur. J. Org. Chem., submitted.
     

Book Chapters
 

  1. The Formation of Bonds between Halogens and Group VB (N, P, As, Sb, Bi) Elements in “Inorganic Reactions and Methods” (Ed. J. J. Zuckermann) (G.-V. Röschenthaler), Vol. 3, p. 194-220 (1989);

  2. Functional Compounds Based on Hypervalent Sulfur Fluorides, (P. Kirsch, G.-V. Röschenthaler), ACS Symp. Ser. 949, 2007, 221-244.

  3. Pentacoordinate and hexacoordinate phosphorus compounds in A Specialist Periodical Research: Organophosphorus Chemistry G.-V. Röschenthaler, 37, 247-261 (2008).

  4. Fluor, ein Element für (fast) alle Fälle in „Persistente Perfluorverbindungen – eine Gefahr für Mensch und Umwelt?“ (Hrsg. Bayerisches Landesamt für Umwelt), G.-V. Röschenthaler, Münchner Beiträge zur Abwasser-, Fischerei- und Flussbiologie, Bd. 59 (2008) 11-33.

  5. Pentacoordinate and hexacoordinate phosphorus compounds in A Specialist Periodical Research: Organophosphorus Chemistry G.-V. Röschenthaler, 2009, 38, 318-331.

  6. Pentacoordinate and hexacoordinate phosphorus compounds G.-V. Röschenthaler, R. Pajkert, Specialist Periodical Research: Organophosphorus Chemistry 39, 290-307 (2010).

  7. Pentacoordinate and hexacoordinate phosphorus compounds G.-V. Röschenthaler, R. Pajkert, A Specialist Periodical Research: Organophosphorus Chemistry, 2011, 40, 297-315.

  8. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2012, 41, 322-348.

  9. Pentafluoroethyl Lithium: Reactions with Carbonyl Compounds and Epoxides, O. Kazakova, G.-V. Röschenthaler in Efficient Preparation of Fluorine Compounds (Ed. H. W. Roesky, Wiley, 2013, chap.28, p. 203-207.

  10. Synthesis of -Hydroxy-α,α-difluoromethylenephosphonates, O. Kazakova, G.-V. Röschenthaler in Efficient Preparation of Fluorine Compounds (Ed. H. W. Roesky, Wiley, 2013, chap. 29, p. 203-207.

  11. Synthesis of Pentafluoro-λ6-sulfanyl-Substituted Acetylenes for Liquid Crystals, O. Kazakova, M. Ponomarenko, G.-V. Röschenthaler in Efficient Preparation of Fluorine Compounds (Ed. H. W. Roesky, Wiley, 2013, 30, 208-2011. 

  12. Delocalized Lipophilic Cations as a Source of Naked Fluoride and Phase-Transfer Catalysts, O. Kazakova, N. Kalinovich, G.-V. Röschenthaler in Efficient Preparation of Fluorine Compounds (Ed. H. W. Roesky, Wiley, 2013, 31, 212-2017. 

  13. Methyltrifluoropyruvate Imines Possessing N-oxalyl and N-Phosphonoformyl Groups: Precursors to a Variety of α-CF3-α-Amino Acid Derivatives, O. Kazakova, G.-V. Röschenthaler in Efficient Preparation of Fluorine Compounds (Ed. H. W. Roesky, Wiley, 2013, chapter 32, p. 218-224.

  14. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry 2013, 42, 197-215. 

  15. CF3O- and CF3S-Containing Heterocycles: Synthesis and Biological Activity in Nenajdenko (ed.) Fluorine in Heterocyclic Chemistry Volume 1: 5-Membered Heterocycles and Macrocycles, Springer Heidelberg, 2014, O. Kazakova, G.-V. Röschenthaler, 555-587.

  16. Novel fluorinated solvents and additives for lithium ion batteries in Nakajima/Groult (eds.) Advanced Fluorine-Based Materials for Energy Conversion, Elsevier, T. Böttcher, N. Kalinovich, O. Kazakova, M. Ponomarenko, K. Vlasov, M. Winter, G.-V. Röschenthaler, 2015, 125-145; http://dx.doi.org/10.1016/B978-0-12-800679-5.00006-3.

  17. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry 2014, 43, 348-365.

  18. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2015, 44, 378-396.

  19. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2016, 45, 354-374.

  20. Carbene Adducts of Silicon(IV) Chlorides: Versatile Reagents for Carbene Transfer and Sources for Cationic Silicon(IV) Complexes, T. Böttcher, G.-V. Röschenthaler in H. W. Roesky (Ed.) „Efficient Methods for Preparing Silicon Compounds“, Elsevier, 2016, 339-354 (chapter 25).

  21. M. Shevchuk, G.-V. Röschenthaler, Synthesis by Substitution of Metals Science of Synthesis - Vol. 34 (update) - Section 34.1.2.6, Thieme, Stuttgart, 2016, 363-373.

  22. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2017, 46, 323–341; DOI: 10.1039/9781788010689.

  23. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2018, 47, 340–362.

  24. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2019, 48, 380-399.

  25. M. Ponomarenko, G.-V. Röschenthaler, Recent Progress in Chemistry of SF5-Olefins and Aliphatic Organic Compounds in Frontiers of Organofluorine Chemistry (World Scientific), Ed. Iwao Ojima, 2020, 251-279. DOI: org/10.1142/9781786347336_0005.

  26. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2020, 49, 332–348.

  27. G.-V. Röschenthaler, 2,2-Difluoro-1,3-dimethylimidazolidine, a multifaceted molecule in The Curious World of Fluorinated Molecules, Chapter 10, 295-301, 2021; Elsevier Amsterdam, Oxford, Cambridge, B978-0-12-819874-2.00006-0.

  28. R. Pajkert, G.-V. Röschenthaler, Science of Synthesis, Vol. 42 (update 2020), 42.18. Product Class 18: Pentacoordinated Phosphoranes, Science of Synthesis Knowledge Updates, 2022, 1, 365-393; DOI: 10.1055/sos-SD-142-00235. 

  29. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler, Organophosphorus Chemistry, 2021, 50, 409-428.

  30. R. Pajkert, G.-V. Röschenthaler, Science of Synthesis, Vol. 42 (update 2020), 42.19. Product Class 19: Hexacoordinated Phosphates, Science of Synthesis Knowledge Updates, 2022, 1, 395-412; DOI: 10.1055/sos-SD-142-00248.

  31. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler,Organophosphorus Chemistry, 2023, 51, 328-354.

  32. Pentacoordinated and hexacoordinated compounds, R. Pajkert, G.-V. Röschenthaler,Organophosphorus Chemistry, 2024, 52, 232-253.
     

Patents and Patent applications

  1. Electrolytes for double-layer capacitors, Yu. A. Maletin, N. G. Strizhakova, V. Yu. Isotov, A. A. Mironova, C. G. Kosatchkov, A. A. Kolomeitsev, G. N. Kojdan, A. A. Kolomeitsev, A. P. Marchenko, G.-V. Röschenthaler, Pat. Ukraine UA 21528A (priority from 20.3.95). 

  2. New 4-phenyl- and 4-(4-substituted-phenyl)-n-butane-1-hydroxy-1,1-diphosphonic acids and per(trimethylsilyl) esters and known analogs are useful as targeted cytostatic drugs, Yu. Pustovit, W. Greb, H. Blum, G.-V. Röschenthaler, DE 10114352 C1 (EUCRO European Contract Research GmbH & Co. KG), WO 02076515, EP 1370565, US 2004087554, AT 279422, ES 2230493, JP 2004531497. 

  3. Method of Producing 1-Hydroxy-1,1-diphosphonic Acid Compounds, Yu. Pustovit, W. Greb, H. Blum, G.-V. Röschenthaler, (EUCRO European Contract Research GmbH & Co. KG), DE 50201297. 

  4. Borate salts for use in electrochemical cells, M. Schmidt, U. Heider, G. Bissky, A. Kadyrov, A. Kolomeitsev, G.-V. Röschenthaler, DE 10103189 (Merck KGaA), priority 24.1.2001, EP 1229038, US 2002/0160261, BR 0200169, JP 2002305024, CA 2368990.

  5. Bis(alkylthio)carbenium Salts, D. Sevenard, P. Kirsch, G.-V. Röschenthaler (Merck KGaA) DE 10106577, JP 2004525894 (A), US 2004063985 (A1) , US 6875894 (B2), WO 02064583 (A2), WO 02064583 (A3).

  6. Improved Method for Producing Nuclear Fluorinated Aromatic Compounds, A. Marhold, M. Henrich, A. Kolomeitsev, G.-V. Röschenthaler, DE 10129057 (BAYER AG) priority 15.6.2001, EP 1266904, US 7091362 (B2).

  7. Process for preparing polyfluoroalkyllithium compounds, A. Marhold, M. Henrich, A. Kolomeitsev, J. Barten, A. Kadyrov, G.-V. Röschenthaler, (BAYER AG)., DE 10128703, EP 1266902, US 2003065135, JP 2003055385, JP 4309096 B2, US 6872861 B2. 

  8. Preparation of perfluoroalkylthiolates, useful as intermediates for e.g. plant agents and pharmaceuticals, comprises reaction of (aryl)perfluoro-alkylsilanes with elemental sulfur, in the presence of a fluoride ion donor, G. Bissky, A. Kolomeitsev, P. Kirsch, G.-V. Röschenthaler, DE 10254597 (Merck KGaA), priority 21.12.2001. 

  9. Production of pentafluoro sulfuranide compounds, useful as organic fluorinating agents, involves reduction of sulfur hexafluoride with a divalent cation-forming reducing agent e.g. tetrakis dimethylamino-ethylene, D. Sevenard, P. Kirsch, A. A. Kolomeitsev, G.-V. Röschenthaler, DE 10220901 (Merck KGaA). 

  10. New onium pentafluorosulfuranide salts useful as fluorinating agents and agents for introducing pentafluorosulfuranide groups into organic compounds, D. Sevenard, P. Kirsch, A. A. Kolomeitsev, G.-V. Röschenthaler, DE 10321114 (Merck KGaA). 

  11. Production of pentafluoro sulfuranide compounds, useful as organic fluorinating agents, involves reduction of sulfur hexafluoride with a divalent cation-forming reducing agent e.g. tetrakis dimethylamino-ethylene, D. Sevenard, P. Kirsch, A. A. Kolomeitsev, G.-V. Röschenthaler, DE 10321112 (Merck KGaA).

  12. α,α-Difluoroamine, Mixture of the same, Method for Producing the same and the Method for Producing Fluorinated Compound, J. Barten, A. Kolomeitsev, A. Marhold, P. Hilgers, W. Ebenbeck, G.-V. Röschenthaler, DE 10300112 (BAYER AG), EP 1437342, US 2005085474.

  13. ,-Difluoramine und Difluormethylen-,-diazoverbindungen, A. Kolomeitsev, A. Marhold, W. Ebenbeck, G.-V. Röschenthaler, DE 10300113 (BAYER AG), JP 2004210792, EP 1439170, US2004198975.

  14. Bisphosphonsäure-Derivate, V. Hengst, J. Diederichs, H. Schreier, W. Greb, O. Shyshkov, G.-V. Röschenthaler (MSC Micro Carrier Systems GmbH, Neuss) DE 102004032781.

  15. Lipid-Derivatized Bisphosphonic Acid, W. Greb, O. Shyshkov, G.-V. Röschenthaler, V. Hengst (MSC Micro Carrier Systems GmbH, Neuss) WO 2005070952, US 2007154537, US 7455856, JP 2007518746, EP 1706415, AT 527277. JP 4851946 (B2). 

  16. Stickstoff-haltige Phosphoniumsalze, H.-P. Krimmer, T. Riermeier, M. Gómez, J. Almena, A. A. Kolomeitsev, J. Barten, G.-V. Röschenthaler, (Degussa AG), DE 102006010034 (eingereicht 4.3.2006, veröffentlicht 6.9.2007).

  17. Verwendung von Guanidin-Derivaten als Beschleuniger bei der Härtung von Epoxidharzsystemen, A. A. Kolomeitsev, J. Barten, G.-V. Röschenthaler, H.-P. Krimmer, M. Gómez Andreu, (Degussa AG), DE 102006056311 (eingereicht am 29.11.2006, offengelegt 5.6.2008). 

  18. Process for the preparation of fluorinated carboxylic acids by oxidation of fluorinated alcohols, K. Hintzer, D. E. Vogel, M. A. Guerra, J. Ignatowska, G.-V. Röschenthaler, O. Shyshkov, K. M. Vogel, T. Zipplies (Dyneon 3M) WO 2011050131 A3, US 2012184770 A1, US 8809580 B2, RU 2012111106 A, RU 2545172 C2, JP 2015096545 A, JP 2013508394 A, JP 5731518 B2, EP 2490995 A2, EP 2490995 A4, CN 102574765 A. 

  19. Surface active substances with terminal pentafluorsulfoxy group. P. Kirsch, W. Hierse, E. Claus, M. Kleineidam, G.-V. Röschenthaler, N. Kalinovich, (Merck KgaA, Darmstadt), 2012, DE 102011114650 A1.

  20. Surface active substances with terminal pentafluorsulfoxy group. P. Kirsch, W. Hierse, E. Claus, M. Kleineidam, G.-V. Röschenthaler, N. Kalinovich, (Merck KgaA, Darmstadt), 2012, DE 102011114651 A1. 

  21. Organische Verbindungen mit der –SF4OSF5-Endgruppe, N. Kalinovich, R. Mews, G.-V. Röschenthaler, M. Bremer, D. Pauluth, (Merck KgaA, Darmstadt), (2012), DE 102011011858 A1.

  22. Electrolytes comprising propylene carbonate for batteries and accumulators, M. Winter, G.-V. Röschenthaler, R. Schmitz, S. Passerini, A. Lex-Balducci, R. Müller, S. Nowak, M. Kunze, E. Krämer, O. Kazakova, (Universität Münster, Jacobs University Bremen) (2012), WO 2012084066 A1.

  23. Lithium-2-methoxy-1,1,2,2-tetrafluoro-ethanesulfonate and use thereof as conductive salt in lithium-based energy accumulators, M. Winter, C. Schreiner, A. Lex-Balducci, R. Müller, R. Schmitz, R. Schmitz, N. Kalinovich, K. Vlasov, G.-V. Röschenthaler (Universität Münster, Jacobs University Bremen) (2013), DE 102011052156 A1, WO 2013014180 A1, EP 2737568, US 2014377667. 

  24. Electrolyte additive for a lithium-based energy storage device, G.-V. Röschenthaler, T. Böttcher, N. Kalinovich, M. Winter, S. Passerini, M. Kunze, A. Lex-Balducci, C. Dippel, R. Schmidt, R. Müller (Universität Münster, Jacobs University Bremen), DE 102011055028 A1, WO 2013064530 A1, US 9466437

  25. 6,6-Difluoro-1,2,4-thiadiazinane-3,5-dione-1,1-dioxide derivatives, production and use thereof, N. Kalinovich, G.-V. Röschenthaler, T. Schedlbauer, J. Kasnatscheew, K. Vlasov, R. Schmitz, R. W. Schmitz, R. A. Mueller, M. Winter, S. Passerini (Jacobs University Bremen, Universität Münster), DE 102012105 377 A1, WO 2013189481 A1, US 20150188191; US 9905885. 

  26. Electrolyte salt for lithium-based energy stores, G.-V. Röschenthaler, M. Winter, S. Passerini, K. Vlasov, N. Kalinovich, C. Schreiner, R. W. Schmitz, R. A. Müller, R. Schmitz, T. Schedlbauer, A. Lex-Balducci, M. Kunze, (Universität Münster, Jacobs University Bremen), DE 102012101670 A1; WO 2013127866 A1, US 20150044573.

  27. Solvent for electrolytes for lithium-based energy storage, Lösungsmittel für Elektrolyte, S. Passerini, R. W. Schmitz, R. Schmitz, R. A. Müller, C. Schreiner, T. Schedlbauer, M. Winter, G.-V. Röschenthaler, N. Kalinovich, M. Ponomarenko, (Universität Münster, Jacobs University Bremen), DE 102012104567 A1.

  28. Tetrachlorosilane complexes with diaminocarbene and imidazolylidene ligands as carbene transfer reagents, T. Böttcher, B. S. Bassil, G.-V. Röschenthaler (Jacobs University Bremen) DE 112013001653 A5, EP 2828272 A1, EP 2828272 B1, WO 2013139332 A1.

  29. Polysubstituted aminocyanoaryl phosphonates as prospective antiinflammatory and antihyperglycemic agents and process for their synthesis, S. Tverdomed, B. Duda, G.-V. Röschenthaler (Jacobs University Bremen), 2013, DE 102012104007 A1, WO 2013167117 A1, US 2015322100 A1.

  30. Semiconductor component with protected function film, V. Wagner, M. Ortel, N. Kalinovich, G.-V. Röschenthaler (Jacobs University Bremen), DE 102012107959 A1.

  31. Semiconductor component with protected functional layer for oxides and device fabrication, V. Wagner, M. Ortel, N. Kalinovich, O. Kazakova, G.-V. Röschenthaler (Jacobs University Bremen), DE 102012110019, WO 2014032655 A2.

  32. Verfahren zur Herstellung von Arylschwefelpentafluoriden, P. Beier, M. Ponomarenko, K. Lummer, G.-V. Röschenthaler, (Czech Academy of Sciences, Jacobs University Bremen), DE 102013104346 A1. 

  33. Method for the manufacture of fluorinated cyclic carbonates and their use for lithium batteries, J.-H. Lee, J.-A. Chol, H.-K. Hwang, M. Bomkamp, S. Tverdomed, M. Shevchuk, N. Kalinovich, G.-V. Röschenthaler (Solvay SA) WO 2017017210 A1, CN 107849004 (A), EP 3124479 (A1), KR 20180035791 (A), US 2018219256 (A1), JP 2018529638 (A).

  34. Methods for converting fluorinated compounds to fluorinated acycl fluorides, K. Hintzer, M. Hirschberg, S.Tverdomed, R. Pajkert, G.-V. Röschenthaler (3M Dyneon, Burgkirchen), WO 2017112445 (A3). EP 3394023 (A2), JP 2018538345 (A), US 10737998 (B2).

  35. Conversion of a perfluorinated vinyl ether into a partially fluorinated saturated ether derivative, M. E. Hirschberg,K. Hintzer, Zai-Ming Qiu, G.-V. Röschenthaler, R: Pajkert, S. N. Tverdomed, WO 2017112629 A1, JP 6691220 B2, EP 3394021 B1, US 10723683 B2.

  36. methods of Making a polyfluorinated allyl ether and compounds relating to the methods, K. Hintzer, M. Hirschberg, S. Tverdomed, R. Pajkert, G.-V. Röschenthaler (3M Dyneon, Burgkirchen), WO 2018211457 A2, EP 3394021 (A1) JP 2019500373 (A), US11292763, CN 110770200 B, EP 3625201. 

  37. Process for Preparing Methyl Phosphinic Acid Butyl Ester, A. Yacovan, A. Shterenberg, L. Erchov, S. Fronton, M. Shevchuk, N. Kalinovich, O. Stubbmann-Kazakova, G.-V. Röschenthaler (Adama AGAN, Ashdod, Israel), US 2019375771 (A1), WO 2018154385 A1, TW 201840578 (A), AR 110993 (A1), CA 3052108 (A1), CN 110494438 (A), KR 20190122722 (A), BR 112019017391 (A2), JP 7104480 B2, US 11466041. 

  38. Methods of making polyfunctional polyfluorinated compounds M. E. Hirschberg, K. Hintzer, W. M. Lamanna, S. M. Smith, G.-V. Röschenthaler, R. Pajkert, S. N Tverdomed, (3M Dyneon, Burgkirchen), WO 2019123342 A1, CN 111511711 A, EP 3728177 A1, US 20210070686 A1.

  39. Method for producing an electronic component which includes a self-assembled monolayer, P. Kirsch, S. Resch, H. Seim, M. Tornow, T. Kamiyama, G.-V. Röschenthaler R. Pajkert (Merck KgaA, Darmstadt), DE 102018004733 A1, WO 2019238649 A1, TW 202005975 A. , KR 20210019071 A, CN 112262434, US 20210257569.

  40. Electrolyte comprising a phosphite as an additive or co-solvent, lithium rechargeable battery comprising said electrolyte, and method for producing the phosphite, N. von Aspern, V. Kozel, O. Stubbmann-Kazakova, I. Cekic-Laskovic, M. Winter, G.-V. Röschenthaler (Jacobs University Bremen gGmbH, Forschungszentrum Jülich GmbH), DE 102018116475 A1, WO 2020007425 A1, CN 112470311, US 20210273263, JP 2021528806, EP 3818579. 

  41. Multifunctional fluorinated compound, fluorinated polymers made from the compound, and related methods, M. E. Hirschberg, K. Hintzer, G.-V. Röschenthaler, S. N. Tverdomed, R. Pajkert (3M Dyneon, Burgkirchen) WO 2020245724 A1, CN 113906038, US 20220227696, JP 2022535815, EP 3818579.

  42. Process to the production of a chemical compound with several steps, G.-V. Röschenthaler (Jacobs University Bremen gGmbH), DE 102019117590 A1.

  43. Imidazolinylid-Verbindung zur Verwendung als Shut-Down-Additiv für Lithium-Ionen-Batterien sowie Elektrolyt und Batterie, Imidazolinylide compound for use as shutdown additive in electrolytes of lithium-ion batteries, G.-V. Röschenthaler, I. Cekic-Laskovic, N. von Aspern, M. Winter, M. Shevchuk, (Jacobs University Bremen gGmbH, Forschungszentrum Jülich GmbH) DE 102020103326, WO 2021160226, KR 2022139316, CN 115280570, US 20230099524, JP 2023513253.

  44. Multifunctional Fluorinated Phosphorus Compounds. Methods of Making and Articles and Uses thereof, M. E. Hirschberg, M. W. Muggli, R. Pajkert G.-V. Röschenthaler, S. N. Tverdomed, (3M Dyneon, Burgkirchen) WO 2023079414 A1.

  45. Hydroxyaminophosphinic acid derivatives, P. Kirsch, H. Seim, F. Voges, G.-V. Röschenthaler, R. Pajkert, WO2024074413, EP4349842.