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Cited by 631

The DOI matches its Crossref record; 35 of the 35 references it cites were found in a registry or an index.

Amino Acid Ionic Liquids

Ohno, Hiroyuki, Fukumoto, Kenta·2007·Accounts of Chemical Research
DOI 10.1021/ar700053z
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Abstract

The preparation of ionic liquids derived from amino acids, and their properties, are outlined. Since amino acids have both a carboxylic acid residue and an amino group in a single molecule, they can be used as either anions or cations. These groups are also useful in their ability to introduce functional group(s). Twenty different natural amino acids were used as anions, to couple with the 1-ethyl-3-methylimidazolium cation. The salts obtained were all liquid at room temperature. The properties of the resulting ionic liquids (AAILs) depend on the side groups of the amino acids involved. These AAILs, composed of an amino acid with some functional groups such as a hydrogen bonding group, a charged group, or an aromatic ring, had an increased glass transition (or melting) temperature and/or higher viscosity as a result of additional interactions among the ions. Viscosity is reduced and the decomposition temperature of imidazolium-type salts is improved by using the tetrabutylphosphonium cation. The chirality of AAILs was maintained even upon heating to 150 degrees C after acetylation of the free amino group. The amino group was also modified to introduce a strong acid group so as to form hydrophobic and chiral ionic liquids. Unique phase behavior of the resulting hydrophobic ionic liquids and water mixture is found; the mixture is clearly phase separated at room temperature, but the solubility of water in this IL increases upon cooling, to give a homogeneous solution. This phase change is reversible, and separation occurs again by raising the temperature a few degrees. It is extraordinary for an IL/water mixture to display such behavior with a lower critical solution temperature. Some likely applications are proposed for these amino acid derived ionic liquids.

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Metadata

Authors
Ohno, H., & Fukumoto, K.
Venue
Accounts of Chemical Research
Publisher
American Chemical Society (ACS)
Published
2007-10-31
Volume
40
Issue
11
Pages
1122-1129
ISSN
  • 0001-4842 (ISSN-L)
  • 1520-4898
DOI
10.1021/ar700053z
OpenAlex
W1965902062
Cited by
631
References
35
FWCI
9.37
Type
journal article
Language
en
Open access
closed

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