A Reinvestigation of the Ionic Liquid Diisopropylethylammonium Formate by NMR and DFT Methods

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

The complex between diisopropylethylamine (DIPEA) and formic acid has been reinvestigated. Mixing the compounds in the ratio 1:1 leads to a phase separation in which the upper phase is DIPEA, the lower phase is the “ionic liquid” named DIPEF. A combined NMR and DFT study shows that the lower phase primarily is formic acid:formate and diisopropyl-ammonium ions in the ratio 2:1 (acid:base) plus the formic acid dimer. Addition of more acid leads to more and more of the acid dimer. The proton transfer in the system is 65-80%. The structural picture presented in this paper is very different from that presented elsewhere. However, the present picture should be considered using acids and bases with a pKa difference less than 8. The formic acid content in the DIPEF ionic liquid causes desorption of the dye-sensitized solar cell (DSC) dye N719 from the photo anode and DIPEF is therefore not a suitable electrolyte for DSCs.
OriginalsprogEngelsk
TidsskriftThe Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical
Vol/bind120
Sider (fra-til)11279-11286
Antal sider8
ISSN1520-6106
DOI
StatusUdgivet - 12 okt. 2016

Emneord

  • ionic liquid
  • NMR
  • rheology
  • DFT calculations
  • synthesis
  • proton transfer

Citer dette

@article{2898af56eefb4f829ed60ee60550fbbd,
title = "A Reinvestigation of the Ionic Liquid Diisopropylethylammonium Formate by NMR and DFT Methods",
abstract = "The complex between diisopropylethylamine (DIPEA) and formic acid has been reinvestigated. Mixing the compounds in the ratio 1:1 leads to a phase separation in which the upper phase is DIPEA, the lower phase is the “ionic liquid” named DIPEF. A combined NMR and DFT study shows that the lower phase primarily is formic acid:formate and diisopropyl-ammonium ions in the ratio 2:1 (acid:base) plus the formic acid dimer. Addition of more acid leads to more and more of the acid dimer. The proton transfer in the system is 65-80{\%}. The structural picture presented in this paper is very different from that presented elsewhere. However, the present picture should be considered using acids and bases with a pKa difference less than 8. The formic acid content in the DIPEF ionic liquid causes desorption of the dye-sensitized solar cell (DSC) dye N719 from the photo anode and DIPEF is therefore not a suitable electrolyte for DSCs.",
keywords = "ionic liquid, NMR, rheology, DFT calculations, synthesis, proton transfer, Ionic liquid, Infra red, proton transfer, NMR, DFT calculations, rheology, synthesis",
author = "Hansen, {Poul Erik} and Torben Lund and Jacob Krake and Jens Spanget-Larsen and S{\o}ren Hvidt",
year = "2016",
month = "10",
day = "12",
doi = "10.1021/acs.jpcb.6b08561",
language = "English",
volume = "120",
pages = "11279--11286",
journal = "Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical",
issn = "1520-6106",
publisher = "American Chemical Society",

}

TY - JOUR

T1 - A Reinvestigation of the Ionic Liquid Diisopropylethylammonium Formate by NMR and DFT Methods

AU - Hansen, Poul Erik

AU - Lund, Torben

AU - Krake, Jacob

AU - Spanget-Larsen, Jens

AU - Hvidt, Søren

PY - 2016/10/12

Y1 - 2016/10/12

N2 - The complex between diisopropylethylamine (DIPEA) and formic acid has been reinvestigated. Mixing the compounds in the ratio 1:1 leads to a phase separation in which the upper phase is DIPEA, the lower phase is the “ionic liquid” named DIPEF. A combined NMR and DFT study shows that the lower phase primarily is formic acid:formate and diisopropyl-ammonium ions in the ratio 2:1 (acid:base) plus the formic acid dimer. Addition of more acid leads to more and more of the acid dimer. The proton transfer in the system is 65-80%. The structural picture presented in this paper is very different from that presented elsewhere. However, the present picture should be considered using acids and bases with a pKa difference less than 8. The formic acid content in the DIPEF ionic liquid causes desorption of the dye-sensitized solar cell (DSC) dye N719 from the photo anode and DIPEF is therefore not a suitable electrolyte for DSCs.

AB - The complex between diisopropylethylamine (DIPEA) and formic acid has been reinvestigated. Mixing the compounds in the ratio 1:1 leads to a phase separation in which the upper phase is DIPEA, the lower phase is the “ionic liquid” named DIPEF. A combined NMR and DFT study shows that the lower phase primarily is formic acid:formate and diisopropyl-ammonium ions in the ratio 2:1 (acid:base) plus the formic acid dimer. Addition of more acid leads to more and more of the acid dimer. The proton transfer in the system is 65-80%. The structural picture presented in this paper is very different from that presented elsewhere. However, the present picture should be considered using acids and bases with a pKa difference less than 8. The formic acid content in the DIPEF ionic liquid causes desorption of the dye-sensitized solar cell (DSC) dye N719 from the photo anode and DIPEF is therefore not a suitable electrolyte for DSCs.

KW - ionic liquid

KW - NMR

KW - rheology

KW - DFT calculations

KW - synthesis

KW - proton transfer

KW - Ionic liquid

KW - Infra red

KW - proton transfer

KW - NMR

KW - DFT calculations

KW - rheology

KW - synthesis

U2 - 10.1021/acs.jpcb.6b08561

DO - 10.1021/acs.jpcb.6b08561

M3 - Journal article

VL - 120

SP - 11279

EP - 11286

JO - Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical

JF - Journal of Physical Chemistry Part B: Condensed Matter, Materials, Surfaces, Interfaces & Biophysical

SN - 1520-6106

ER -