Cyanohydridoborate Anions: Synthesis, Salts, and Low‐Viscosity Ionic Liquids

Bischoff, Lisa A.; Drisch, Michael; Kerpen, Christoph; Hennig, Philipp T.; Landmann, Johannes; Sprenger, Jan A. P.; Bertermann, Rüdiger; Grüne, Matthias; Yuan, Qinqin; Warneke, Jonas; Wang, Xue‐Bin; Ignat'ev, Nikolai V.; Finze, Maik

doi:10.1002/chem.201804698

Title: Cyanohydridoborate Anions: Synthesis, Salts, and Low‐Viscosity Ionic Liquids

Journal Article · Mon Feb 11 00:00:00 EST 2019 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201804698· OSTI ID:1494206

Bischoff, Lisa A. ^[1]; Drisch, Michael ^[1]; Kerpen, Christoph ^[1]; Hennig, Philipp T. ^[1]; Landmann, Johannes ^[1]; Sprenger, Jan A. P. ^[1]; Bertermann, Rüdiger ^[1]; Grüne, Matthias ^[2]; Yuan, Qinqin ^[3]; Warneke, Jonas ^[4]; Wang, Xue‐Bin ^[3]; Ignat'ev, Nikolai V. ^[5];

^[1]

Institut für nachhaltige Chemie &, Katalyse mit Bor (ICB), Institut für Anorganische Chemie Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany
Institut für Organische Chemie &, Center for Nanosystems Chemistry Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany
Physical Sciences Division Pacific Northwest National Laboratory 902 Battelle Boulevard, P.O. Box 999, MSIN K8-88 Richland WA 99352 USA
Department of Chemistry Purdue University 560 Oval Drive West Lafayette IN 47907 USA
Institut für nachhaltige Chemie &, Katalyse mit Bor (ICB), Institut für Anorganische Chemie Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany, Consultant Merck KGaA 64293 Darmstadt Germany

Abstract High‐yield syntheses up to molar scales for salts of [BH(CN) ₃ ] ⁻ ( 2 ) and [BH ₂ (CN) ₂ ] ⁻ ( 3 ) starting from commercially available Na[BH ₄ ] (Na 5 ), Na[BH ₃ (CN)] (Na 4 ), BCl ₃ , (CH ₃ ) ₃ SiCN, and KCN were developed. Direct conversion of Na 5 into K 2 was accomplished with (CH ₃ ) ₃ SiCN and (CH ₃ ) ₃ SiCl as a catalyst in an autoclave. Alternatively, Na 5 is converted into Na[BH{OC(O) R } ₃ ] ( R =alkyl) that is more reactive towards (CH ₃ ) ₃ SiCN and thus provides an easy access to salts of 2 . Some reaction intermediates were identified, for example, Na[BH(CN){OC(O)Et} ₂ ] (Na 7 b ) and Na[BH(CN) ₂ {OC(O)Et}] (Na 8 b ). A third entry to 2 and 3 uses ether adducts of BHCl ₂ or BH ₂ Cl such as the commercial 1,4‐dioxane adducts that react with KCN and (CH ₃ ) ₃ SiCN. Alkali metal salts of 2 and 3 are convenient starting materials for organic salts, especially for low viscosity ionic liquids (ILs). [EMIm] 3 has the lowest viscosity and highest conductivity with 10.2 mPa s and 32.6 mS cm ⁻¹ at 20 °C known for non‐protic ILs. The ILs are thermally, chemically, and electrochemically robust. These properties are crucial for applications in electrochemical devices, for example, dye‐sensitized solar cells (Grätzel cells).

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Sponsoring Organization:: USDOE

OSTI ID:: 1494206

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Vol. 25 Journal Issue: 14; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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