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Imidazolium 2-substituted 4,5-dicyanoimidazolate ionic liquids: synthesis, crystal structures and structure-thermal property relationships

  • Thirty six novel ionic liquids (ILs) with 1-butyl-3-methylimidazolium and 3-methyl-1-octylimidazolium cations paired with 2-substitited 4,5-dicyanoimidazolate anions (substituent at C2=chloro, bromo, methoxy, vinyl, amino, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and phenyl) have been synthesized and characterized by using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and single-crystal X-ray crystallography. The effects of cation and anion type and structure on the thermal properties of the resulting ionic liquids, including several room temperature ionic liquids (RTILs) are examined and discussed. ILs exhibited large liquid and crystallization ranges and formed glasses on cooling with glass transition temperatures in the range of -22 to -68 degrees C. The effects of alkyl substituents of the imidazolate anion reflected the crystallization, melting points and thermal decomposition of the ILs. The Coulombic packing force, van der Waals forces and size ofThirty six novel ionic liquids (ILs) with 1-butyl-3-methylimidazolium and 3-methyl-1-octylimidazolium cations paired with 2-substitited 4,5-dicyanoimidazolate anions (substituent at C2=chloro, bromo, methoxy, vinyl, amino, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and phenyl) have been synthesized and characterized by using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and single-crystal X-ray crystallography. The effects of cation and anion type and structure on the thermal properties of the resulting ionic liquids, including several room temperature ionic liquids (RTILs) are examined and discussed. ILs exhibited large liquid and crystallization ranges and formed glasses on cooling with glass transition temperatures in the range of -22 to -68 degrees C. The effects of alkyl substituents of the imidazolate anion reflected the crystallization, melting points and thermal decomposition of the ILs. The Coulombic packing force, van der Waals forces and size of the anions can be considered for altering the thermal transitions. Three crystal structures of the ILs were determined and the effects of changes to the cations and anions on the packing of the structure were investigated.show moreshow less

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Metadaten
Author:Suvendu Sekhar Mondal, Holger Mueller, Matthias Junginger, Alexandra Kelling, Uwe SchildeORCiDGND, Veronika StrehmelORCiDGND, Hans-Juergen Holdt
DOI:https://doi.org/10.1002/chem.201304934
ISSN:0947-6539 (print)
ISSN:1521-3765 (online)
Pubmed Id:http://www.ncbi.nlm.nih.gov/pubmed?term=24888334
Parent Title (English):Chemistry - a European journal
Publisher:Wiley-VCH
Place of publication:Weinheim
Document Type:Article
Language:English
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
Tag:crystal structures; imidazole; ion exchange; ionic liquids; pi-pi stacking
Volume:20
Issue:26
Pagenumber:12
First Page:8170
Last Page:8181
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert