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10. List of contributors

Author

Barrett, Colby, primary, Berger, Allison A., additional, Boltalina, Olga V., additional, DesMarteau, Darryl D., additional, Grochala, Wojciech, additional, Honda, Tadashi, additional, Hughes, Russell P., additional, Ispizua-Rodriguez, Xanath, additional, Kemnitz, Erhard, additional, Koksch, Beate, additional, Krafft, Marie Pierre, additional, Krahl, Thoralf, additional, Kraus, Florian, additional, Krishamurti, Vinayak, additional, Kvíčala, Jaroslav, additional, Mahn, Stefan, additional, Malischewski, Moritz, additional, Moschner, Johann, additional, Ojima, Iwao, additional, Roesky, Herbert W., additional, Röschenthaler, Gerd-Volker, additional, Seppelt, Konrad, additional, and Surya Prakash, G.K., additional

Published
2021
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12. Substitution Lability of the Perfluorinated Cp* Ligand in [Rh(COD)(C5(CF3)5)] Towards Triphenylpnictogens EPh3 (E=N, P, As, Sb, Bi).

Author

Kub, Nico G., Sievers, Robin, Parche, Joshua, and Malischewski, Moritz

Subjects
MOIETIES (Chemistry), ANIONS, RHODIUM, LIGANDS (Chemistry), CATIONS
Abstract

Triphenylpnictogens EPh3 (E=N, P, As, Sb, Bi) are able to displace the perfluorinated Cp* ligand in [Rh(COD)(C5(CF3)5)] (COD=1,5‐cyclooctadiene) in up to quantitative yield. The resulting ionic products contain [C5(CF3)5]− as uncoordinated counter anion. The cations feature [Rh(COD)]+ fragments, coordinated by one (N, Bi), two (P, As) or three (Sb) triphenylpnictogen moieties. Whereas coordination via the pnictogen is observed for P, As and Sb, π‐coordination of the aryl rings is observed for N and Bi. [ABSTRACT FROM AUTHOR]

Published
2024
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13. Coordination of Tetracyanoquinodimethane-Derivatives with Tris(pentafluorophenyl)borane Provides Stronger p-Dopants with Enhanced Stability

Author

Mansour, Ahmed E., Warren, Ross, Lungwitz, Dominique, Forster, Michael, Scherf, Ullrich, Opitz, Andreas, Malischewski, Moritz, Koch, Norbert, Mansour, Ahmed E., Warren, Ross, Lungwitz, Dominique, Forster, Michael, Scherf, Ullrich, Opitz, Andreas, Malischewski, Moritz, and Koch, Norbert

Abstract

Strong molecular dopants for organic semiconductors that are stable against diffusion are in demand, enhancing the performance of organic optoelectronic devices. The conventionally used p-dopants based on 7,7,8,8-tetracyanoquinodimethane (TCNQ) and its derivatives “FxTCN(N)Q”, such as 2,3,4,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ) and 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane (F6TCNNQ), feature limited oxidation strength, especially for modern polymer semiconductors with high ionization energy (IE). These small molecular dopants also exhibit pronounced diffusion in the polymer hosts. Here, we demonstrate a facile approach to increase the oxidation strength of FxTCN(N)Q by coordination with four tris(pentafluorophenyl)borane (BCF) molecules using a single-step solution mixing process, resulting in bulky dopant complexes “FxTCN(N)Q-4(BCF)”. Using a series of polymer semiconductors with IE up to 5.9 eV, we show by optical absorption spectroscopy of solutions and thin films that the efficiency of doping using FxTCN(N)Q-4(BCF) is significantly higher compared to that using FxTCN(N)Q or BCF alone. Electrical transport measurements with the prototypical poly(3-hexylthiophene-2,5-diyl) (P3HT) confirm the higher doping efficiency of F4TCNQ-4(BCF) compared to F4TCNQ. Additionally, the bulkier structure of F4TCNQ-4(BCF) is shown to result in higher stability against drift in P3HT under an applied electric field as compared to F4TCNQ. The simple approach of solution-mixing of readily accessible molecules thus offers access to enhanced molecular p-dopants for the community., Peer Reviewed

Published
2023

17. Substitution lability of the perfluorinated Cp* ligand in Rh(i) complexes

Author

Parche, Joshua, Rupf, Susanne M., Sievers, Robin, and Malischewski, Moritz

Subjects
Rh(i) complexes, Substitution lability, perfluorinated Cp* ligand, 500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
Abstract

Several cationic rhodium(I) complexes [Rh(COD)L2][C5(CF3)5] have been synthesized through substitution of the weakly bound [C5(CF3)5]− ligand from [Rh(COD)(C5(CF3)5)], further emphasizing its unique reactivity. Besides acetonitrile, pyridine derivatives with varying degrees of fluorination have been employed as ligands in order to investigate the influence of fluorination upon the binding affinity towards the resulting [Rh(COD)]+ fragment and the limit as to which the [C5(CF3)5]− ligand can be displaced. Furthermore, the newly synthesized compounds represent rare examples of rhodium complexes containing fluorinated pyridines as ligands.

Published
2023

27. Synthesis and Coordination Chemistry of Fluorinated Cyclopentadienyl Ligands.

Author

Sievers, Robin, Parche, Joshua, Kub, Nico G., and Malischewski, Moritz

Subjects
COORDINATE covalent bond, LIGANDS (Chemistry), METAL complexes, TRANSITION metals
Abstract

The incorporation of fluorinated substituents in cyclopentadienyl anions leads to distinct changes in the properties of the corresponding metal complexes, e.g., with regards to electrochemical properties or metal–ligand bonding energies. This review summarizes the synthetic challenges of the preparation and coordination of fluorinated cyclopentadienyl anions. 1 Introduction 2 Fluorinated Cyclopentadienyls 3 Cyclopentadienyls with One CF3 Group 4 Cyclopentadienyls with Four CF3 Groups 5 Cyclopentadienyls with Five CF3 Groups 6 Cyclopentadienyls with 'Fluorous Ponytails' 7 Cyclopentadienyls with C6 F5 Groups 8 Trends in Interaction Energies 9 Conclusion [ABSTRACT FROM AUTHOR]

Published
2023
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31. Increasing the oxidation power of TCNQ by coordination of B(C6F5)3

Author

Albrecht, Paul Anton, Rupf, Susanne Margot, Sellin, Malte, Schlögl, Johanna, Riedel, Sebastian, and Malischewski, Moritz

Subjects
tetracyano-quinodimethane, cyanocarbon TCNQ, oxidation power, 500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
Abstract

The oxidation power of the cyanocarbon TCNQ (tetracyano-quinodimethane) can be significantly increased to approximately E = +0.9 V vs. Cp2Fe by coordination of up to four equivalents of the strong fluorinated Lewis acid B(C6F5)3, resulting in a highly reactive but easy-to-use oxidation system. Thianthrene and tris(4-bromophenyl)amine were oxidized to the corresponding radical cations. Dianionic [TCNQ·4 B(C6F5)3]2− was formed upon reduction with two equivalents of ferrocene or decamethylcobaltocene. [TCNQ·4 B(C6F5)3]− and [TCNQ·4 B(C6F5)3]2− are rare cases of redox-active weakly-coordinating anions.

Published
2022
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34. Sequence-sorted redox-switchable hetero[3]rotaxanes

Author

Gaedke, Marius, primary, Hupatz, Henrik, additional, Witte, Felix, additional, Rupf, Susanne M., additional, Douglas, Clara, additional, Schröder, Hendrik V., additional, Fischer, Lukas, additional, Malischewski, Moritz, additional, Paulus, Beate, additional, and Schalley, Christoph A., additional

Published
2022
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35. Structural Characterization and Bonding Analysis of [Hg{Fe(CO)5}2]2+[SbF6]−2

Author

Rupf, Susanne M., Pan, Sudip, Moshtaha, Amina L., Frenking, Gernot, and Malischewski, Moritz

Abstract

The non-classical carbonyl complex [Hg{Fe(CO)5}2]2+[SbF6]−2is prepared by reaction of Hg(SbF6)2and excess Fe(CO)5in anhydrous HF. The single-crystal X-ray structure reveals a linear Fe–Hg–Fe moiety as well as an eclipsed conformation of the eight basal CO ligands. Interestingly, the Hg–Fe bond length of 2.5745(7) Å is relatively similar to the corresponding Hg–Fe bonds in literature-known [Hg{Fe(CO)4}2]2–dianions (2.52–2.55 Å), which intrigued us to analyze the bonding situation in both the dications and dianions with the energy decomposition analysis with natural orbitals for chemical valence (EDA-NOCV) method. Both species are best described as Hg(0) compounds, which are also confirmed by the shape of the HOMO-4 and HOMO-5 of the dication and dianion, respectively, in which the electron pair is located mainly at the Hg. Furthermore, for the dication and the dianion, the σ back-donation from Hg into the [Fe(CO)5]22+or the [Fe(CO)4]22–fragment is the most dominant orbital interaction and surprisingly these interaction energies are also very similar even in absolute values. The fact that both iron-based fragments are missing two electrons explains their prominent σ-acceptor properties.

Published
2023
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38. Blickpunkt Nachwuchs: Supersäuren und starke Oxidationsmittel.

Author

Malischewski, Moritz

Subjects
COORDINATE covalent bond, FLUORINE compounds, STAINLESS steel, FLUORINE, COINS
Abstract

Copyright of Nachrichten aus der Chemie is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Published
2024
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39. Sequence-sorted redox-switchable hetero[3]rotaxanes

Author

Gaedke, Marius, primary, Hupatz, Henrik, additional, Witte, Felix, additional, Rupf, Susanne Margot, additional, Douglas, Clara, additional, Schröder, Hendrik V., additional, Fischer, Lukas, additional, Malischewski, Moritz, additional, Paulus, Beate, additional, and Schalley, Christoph A., additional

Published
2021
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40. Solvent-Dependent Reactivity of Fe(CO)5under Superacidic and Oxidative Conditions

Author

Berg, Willi R., Reimann, Marc, Sievers, Robin, Rupf, Susanne M., Schlögl, Johanna, Weisser, Kilian, Krause, Konstantin B., Limberg, Christian, Kaupp, Martin, and Malischewski, Moritz

Abstract

Herein, we report the solvent-dependent reactivity of Fe(CO)5toward AsF5in either anhydrous HF or liquid SO2. The reaction of Fe(CO)5with the superacid HF/AsF5leads to the protonation of the iron center and allows for the first-time structural characterization of [FeH(CO)5]+in the solid state, representing one of the most acidic transition metal hydride complexes to ever be isolated and structurally characterized. In the aprotic but oxidation-stable solvent SO2, Fe(CO)5is oxidized and dimerized to [Fe2(CO)10]2+, which is isoelectronic with well-known Mn2(CO)10. [Fe2(CO)10]2+is the first structurally characterized example of a homoleptic dinuclear transition metal carbonyl cation. Together with Fe(CO)5and [Fe(CO)5]+•, it is a rare example of an iron-centered triad from which the neutral, the radical cationic, and the dimerized dicationic species have been structurally and spectroscopically characterized. All characterizations are well supported by quantum chemical calculations. We also make the argument that the dimerization of [Fe(CO)5]+•is largely dependent on the employed solvent.

Published
2025
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41. Isolation and Structural Characterization of Eightfold Protonated Octacyanometalates [M(CNH) 8 ] 4+ (M = Mo IV , W IV ) from Superacids

Author

Sellin, Malte, Marvaud, Valerie, Malischewski, Moritz, Freie Universität Berlin, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS Paris), and Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM]Chemical Sciences
Abstract

International audience; Octacyanometalates K 4 [Mo(CN) 8 ] and K 4 [W(CN) 8 ] are completely protonated in superacidic mixtures of anhy-drous hydrogen fluoride and antimony pentafluoride. The resulting hydrogen isocyanide complexes [Mo(CNH) 8 ] 4+ [SbF 6 ] À 4 and [W(CNH) 8 ] 4+ [SbF 6 ] À 4 are the first examples of eight-coordinate homoleptic metal complexes containing hydrogen isocyanide (CNH) ligands. The complexes were crystallographically characterized, revealing hydrogen-bonded networks with short N···H···F contacts. Low-temperature NMR measurements in HF confirmed rapid proton exchange even at À40 8C. Upon protonation, n(C N) increases of about 50 cm À1 which is in agreement with DFT calculations.

Published
2020
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49. Increasing the oxidation power of TCNQ by coordination of B(C6F5)3.

Author

Albrecht, Paul Anton, Rupf, Susanne Margot, Sellin, Malte, Schlögl, Johanna, Riedel, Sebastian, and Malischewski, Moritz

Subjects
RADICAL cations, OXIDATION, LEWIS acids
Abstract

The oxidation power of the cyanocarbon TCNQ (tetracyano-quinodimethane) can be significantly increased to approximately E = +0.9 V vs. Cp2Fe by coordination of up to four equivalents of the strong fluorinated Lewis acid B(C6F5)3, resulting in a highly reactive but easy-to-use oxidation system. Thianthrene and tris(4-bromophenyl)amine were oxidized to the corresponding radical cations. Dianionic [TCNQ·4 B(C6F5)3]2− was formed upon reduction with two equivalents of ferrocene or decamethylcobaltocene. [TCNQ·4 B(C6F5)3]− and [TCNQ·4 B(C6F5)3]2− are rare cases of redox-active weakly-coordinating anions. [ABSTRACT FROM AUTHOR]

Published
2022
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50. Isolation and structural characterization of eightfold protonated octacyanometalates [M(CNH)8]4+ (M=MoIV, WIV) from superacids

Author

Sellin, Malte, Marvaud, Valérie, and Malischewski, Moritz

Subjects
isocyanide ligands, 500 Naturwissenschaften und Mathematik::540 Chemie::546 Anorganische Chemie, superacidic systems, Communication, protonation, hydrogen bonds, cyanides, Communications, Cyanometalates
Abstract

Octacyanometalates K4[Mo(CN)8] and K4[W(CN)8] are completely protonated in superacidic mixtures of anhydrous hydrogen fluoride and antimony pentafluoride. The resulting hydrogen isocyanide complexes [Mo(CNH)8]4+ [SbF6]− 4 and [W(CNH)8]4+ [SbF6]− 4 are the first examples of eight‐coordinate homoleptic metal complexes containing hydrogen isocyanide (CNH) ligands. The complexes were crystallographically characterized, revealing hydrogen‐bonded networks with short N⋅⋅⋅H⋅⋅⋅F contacts. Low‐temperature NMR measurements in HF confirmed rapid proton exchange even at −40 °C. Upon protonation, ν(C≡N) increases of about 50 cm−1 which is in agreement with DFT calculations., Give me eight! All eight cyano groups in the octacyanometalates Mo(CN)8 4− and W(CN)8 4− are protonated under superacidic conditions without formation of HCN. Instead homoleptic complexes of Mo4+ and W4+ with eight hydrogen isocyanide ligands are formed and could be fully characterized.

Published
2020
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