Easily Vaporizable Ionic Liquids – No Contradiction!

Köckerling, Martin; Peppel, Tim; Thiele, Philipp; Verevkin, Sergey P.; Emel′yanenko, Vladimir N.; Samarov, Artemiy; Ruth, Wolfgang

doi:10.1002/ejic.201500391

Cited by 4 publications

(3 citation statements)

References 47 publications

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“…Structurally characterized examples thereof are known for compounds with tetracoordinate Si: [Me3Si(NMI)] + X − (X = Cl [19], Br [20]), [PhMe2Si(NMI)] + Cl − [21], [R2Si(NMI)2] 2+ 2Br − (R2 = Me2 [22], Et2 [23], -(CH2)5- [24]), with pentacoordinate Si: [R2Si(NMI)3] 2+ 2Br − (R2 = Et,H [23], Ph2 [23]) and with hexacoordinate Si: [23], Ph,H [23], Cl,Cl [26]), [R2Si(NMI)4] 2+ 2Cl − (R2 = Cl2 [26], H2 [26], -(CH2)4- [27]). Furthermore, some non-ionic hexacoordinate Si-NMI-complexes have been crystallographically confirmed (Si(o-C6H4O2)2(NMI)2 [28], XIX [29]), and an adduct of the composition MeSiCl3(NMI)2 is mentioned in the literature [30].…”

Section: Compounds Overviewmentioning

confidence: 99%

Lewis Acid-Base Adducts of α-Amino Acid-Derived Silaheterocycles and N-Methylimidazole

Seidel,

Gericke,

Kutzner

et al. 2023

Molecules

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In chloroform solution, the reaction of bis(tert-butylamino)dimethylsilane ((tBuNH)2SiMe2) and an α-amino acid (α-amino isobutyric acid, H2Aib; D-phenylglycine, H2Phg; L-valine, H2Val) in the presence of N-methylimidazole (NMI) gave rise to the formation of the pentacoordinate silicon complexes (Aib)SiMe2-NMI, (Phg)SiMe2-NMI and (Val)SiMe2-NMI, respectively. Therein, the amino acid building block was a di-anionic bidentate chelator at the silicon atom. In solution, the complexes were involved in rapid coordination–dissociation equilibria between the pentacoordinate Si complex (e.g., (Aib)SiMe2-NMI) and its constituents NMI and a five-membered silaheterocycle (e.g., (Aib)SiMe2), as shown by 29Si NMR spectroscopy. The energetics of the Lewis acid-base adduct formation and the competing solvation of the NMI molecule by chloroform were assessed with the aid of computational methods. In CDCl3 solution, deuteration of the silaheterocycle NH group proceeded rapidly, with more than 50% conversion within two days. Upon cooling to −44 °C, the chloroform solvates of the adducts (Aib)SiMe2-NMI and (Phg)SiMe2-NMI crystallized from their parent solutions and allowed for their single-crystal X-ray diffraction analyses. In both cases, the Si atom was situated in a distorted trigonal bipyramidal coordination sphere with equatorial Si–C bonds and an equatorial Si–N bond (the one of the silaheterocycle). The axial positions were occupied by a carboxylate O atom of the silaheterocycle and the NMI ligand’s donor-N-atom.

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Section: Compounds Overviewmentioning

confidence: 99%

Lewis Acid-Base Adducts of α-Amino Acid-Derived Silaheterocycles and N-Methylimidazole

Seidel,

Gericke,

Kutzner

et al. 2023

Molecules

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“…For instance, alkylimidazolium ILs can be thermally decomposed to their neutral precursors (imidazoles and alkyl halides), which evaporate and react back to the original IL upon condensation [49–51] . This concept has also been demonstrated for carbamate, [52] silylimidazolium, [53] and protic ILs [54] . In contrast to chemical distillation, IL‐CVD allows for the formation of well‐defined IL thin films.…”

Section: Figurementioning

confidence: 99%

Chemical Vapor Deposition of Ionic Liquids for the Fabrication of Ionogel Films and Patterns

et al. 2021

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Film deposition and high‐resolution patterning of ionic liquids (ILs) remain a challenge, despite a broad range of applications that would benefit from this type of processing. Here, we demonstrate for the first time the chemical vapor deposition (CVD) of ILs. The IL‐CVD method is based on the formation of a non‐volatile IL through the reaction of two vaporized precursors. Ionogel micropatterns can be easily obtained via the combination of IL‐CVD and standard photolithography, and the resulting microdrop arrays can be used as microreactors. The IL‐CVD approach will facilitate leveraging the properties of ILs in a range of applications and microfabricated devices.

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“…For instance, alkylimidazolium ILs can be thermally decomposed to their neutral precursors (imidazoles and alkyl halides), which evaporate and react back to the original IL upon condensation. [49][50][51] This concept has also been demonstrated for carbamate, [52] silylimidazolium, [53] and protic ILs. [54] In contrast to chemical distillation, IL-CVD allows for the formation of well-defined IL thin films.…”

mentioning

confidence: 91%

Chemical Vapor Deposition of Ionic Liquids for the Fabrication of Ionogel Films and Patterns

et al. 2021

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Easily Vaporizable Ionic Liquids – No Contradiction!

Cited by 4 publications

References 47 publications

Lewis Acid-Base Adducts of α-Amino Acid-Derived Silaheterocycles and N-Methylimidazole

Lewis Acid-Base Adducts of α-Amino Acid-Derived Silaheterocycles and N-Methylimidazole

Chemical Vapor Deposition of Ionic Liquids for the Fabrication of Ionogel Films and Patterns

Chemical Vapor Deposition of Ionic Liquids for the Fabrication of Ionogel Films and Patterns

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