Synthesis and thermophysical properties of ionic liquids: Cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids

Man Lung Kwan; Arsalan Mirjafari; John R. McCabe; Richard A. O'Brien; David F. Essi IV; Leah Baum; Kevin N. West; James H. Davis

doi:10.1016/j.tetlet.2012.09.101

Synthesis and thermophysical properties of ionic liquids: Cyclopropyl moieties versus olefins as T_m-reducing elements in lipid-inspired ionic liquids

Man Lung Kwan
, Arsalan Mirjafari
, John R. McCabe
, Richard A. O'Brien
, David F. Essi IV
, Leah Baum
, Kevin N. West
, James H. Davis

Chemistry

SUNY Oswego

John Carroll University
University of South Alabama

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

Cyclopropyl moieties embedded in the long aliphatic side chains of imidazolium-type ionic liquids are shown to be highly effective in lowering the T_m of such materials relative to counterparts bearing linear, saturated side chains. While not as efficient as olefins in bringing about this effect, ILs incorporating side-chain cyclopropanated modules are likely to be more resistant to aerobic degradation than those employing the former.

Original language	English
Pages (from-to)	12-14
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2012.09.101
State	Published - Jan 2 2013

Keywords

Cyclopropanation
Homeoviscous adaptation
Imidazolium
Ionic liquids
Lipids

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10.1016/j.tetlet.2012.09.101

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title = "Synthesis and thermophysical properties of ionic liquids: Cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids",

abstract = "Cyclopropyl moieties embedded in the long aliphatic side chains of imidazolium-type ionic liquids are shown to be highly effective in lowering the Tm of such materials relative to counterparts bearing linear, saturated side chains. While not as efficient as olefins in bringing about this effect, ILs incorporating side-chain cyclopropanated modules are likely to be more resistant to aerobic degradation than those employing the former.",

keywords = "Cyclopropanation, Homeoviscous adaptation, Imidazolium, Ionic liquids, Lipids",

author = "Kwan, \{Man Lung\} and Arsalan Mirjafari and McCabe, \{John R.\} and O'Brien, \{Richard A.\} and \{Essi IV\}, \{David F.\} and Leah Baum and West, \{Kevin N.\} and Davis, \{James H.\}",

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doi = "10.1016/j.tetlet.2012.09.101",

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T2 - Cyclopropyl moieties versus olefins as Tm-reducing elements in lipid-inspired ionic liquids

AU - Kwan, Man Lung

AU - Mirjafari, Arsalan

AU - McCabe, John R.

AU - O'Brien, Richard A.

AU - Essi IV, David F.

AU - Baum, Leah

AU - West, Kevin N.

AU - Davis, James H.

PY - 2013/1/2

Y1 - 2013/1/2

N2 - Cyclopropyl moieties embedded in the long aliphatic side chains of imidazolium-type ionic liquids are shown to be highly effective in lowering the Tm of such materials relative to counterparts bearing linear, saturated side chains. While not as efficient as olefins in bringing about this effect, ILs incorporating side-chain cyclopropanated modules are likely to be more resistant to aerobic degradation than those employing the former.

AB - Cyclopropyl moieties embedded in the long aliphatic side chains of imidazolium-type ionic liquids are shown to be highly effective in lowering the Tm of such materials relative to counterparts bearing linear, saturated side chains. While not as efficient as olefins in bringing about this effect, ILs incorporating side-chain cyclopropanated modules are likely to be more resistant to aerobic degradation than those employing the former.

KW - Cyclopropanation

KW - Homeoviscous adaptation

KW - Imidazolium

KW - Ionic liquids

KW - Lipids

UR - https://www.scopus.com/pages/publications/84870296723

U2 - 10.1016/j.tetlet.2012.09.101

DO - 10.1016/j.tetlet.2012.09.101

M3 - Article

SN - 0040-4039

VL - 54

SP - 12

EP - 14

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Synthesis and thermophysical properties of ionic liquids: Cyclopropyl moieties versus olefins as T_m-reducing elements in lipid-inspired ionic liquids

Abstract

Keywords

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