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Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim

Dicationic ionic liquids are being developed and are found to have better properties than common room temperature ionic liquids. By comparison, they posses higher melting temperature, wider electrochemical window and stronger ion conductivity rather than RTILs. Previous reports suggest that dicatio...

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Main Author: Abd Rahim, Munirah Sufiyah
Format: Thesis
Published: 2012
Subjects:
Q Science (General)
QD Chemistry
Online Access:http://studentsrepo.um.edu.my/4196/1/MSc_Thesis_Munirah_Sufiyah.pdf
http://studentsrepo.um.edu.my/4196/
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spelling my.um.stud.41962014-10-03T09:05:17Z Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim Abd Rahim, Munirah Sufiyah Q Science (General) QD Chemistry Dicationic ionic liquids are being developed and are found to have better properties than common room temperature ionic liquids. By comparison, they posses higher melting temperature, wider electrochemical window and stronger ion conductivity rather than RTILs. Previous reports suggest that dicationic ionic liquids have potential applications as solvent in organic synthesis, dye sensitized solar cells, phase transfer catalyst, lubricants, surfactants and as a stationary phase in gas liquids chromatography column. Eight series of dicationic ionic liquids were successfully synthesized by reacting α,α-dibromo-p-xylene with tertiary amines (pyridine, 1-methylpyrrolidine, 1-butylpyrrolidine, triethylamine, 1- methylpiperidine, 1-methylmorphline, N,N-dimethylethanoamine and N,Ndiethylethanoamine) at the 1,4-position, forming symmetrical cations with bromide, hexafluorophosphate and bis(trifluoromethanesulfonyl)imide as the counter-anions. Dicationic ionic liquids were successfully synthesized with yield of more than 85%, through conventional methods (quaternization reaction followed by anion exchange). Counter-anion plays an important role in determining thermal properties of dicationic ionic liquids. Bromide moieties have poorer thermal stability compared with hexafluorophosphate moieties. On the other hand, bis(trifluoromethanesulfonyl)imide moieties are the most thermally stable dicationic ionic liquids while having the lowest melting point. Few bis(trifluoromethanesulfonyl)imide salts melt at temperature below 100°C which is in good agreement with the definition of ionic liquids. All dicationic ionic liquids appear as solid at ambient temperature and were purified through recrystallization with an appropriate solvent. Upon recrystallization, nine dicationic ionic liquids afforded single crystal suitable for X-ray crystallography 3 measurement. The molecular structure of crystals are solved, refined, and found to be in good agreement with the expected structures. Based on the chromatographic analysis, hexafluorophosphate and bis(trifluoromethanesulfonyl)imide moieties have extremely low bromide and water content. 2012 Thesis NonPeerReviewed application/pdf http://studentsrepo.um.edu.my/4196/1/MSc_Thesis_Munirah_Sufiyah.pdf Abd Rahim, Munirah Sufiyah (2012) Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim. Masters thesis, University of Malaya. http://studentsrepo.um.edu.my/4196/
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Student Repository
url_provider http://studentsrepo.um.edu.my/
topic Q Science (General)
QD Chemistry
spellingShingle Q Science (General)
QD Chemistry
Abd Rahim, Munirah Sufiyah
Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim
description Dicationic ionic liquids are being developed and are found to have better properties than common room temperature ionic liquids. By comparison, they posses higher melting temperature, wider electrochemical window and stronger ion conductivity rather than RTILs. Previous reports suggest that dicationic ionic liquids have potential applications as solvent in organic synthesis, dye sensitized solar cells, phase transfer catalyst, lubricants, surfactants and as a stationary phase in gas liquids chromatography column. Eight series of dicationic ionic liquids were successfully synthesized by reacting α,α-dibromo-p-xylene with tertiary amines (pyridine, 1-methylpyrrolidine, 1-butylpyrrolidine, triethylamine, 1- methylpiperidine, 1-methylmorphline, N,N-dimethylethanoamine and N,Ndiethylethanoamine) at the 1,4-position, forming symmetrical cations with bromide, hexafluorophosphate and bis(trifluoromethanesulfonyl)imide as the counter-anions. Dicationic ionic liquids were successfully synthesized with yield of more than 85%, through conventional methods (quaternization reaction followed by anion exchange). Counter-anion plays an important role in determining thermal properties of dicationic ionic liquids. Bromide moieties have poorer thermal stability compared with hexafluorophosphate moieties. On the other hand, bis(trifluoromethanesulfonyl)imide moieties are the most thermally stable dicationic ionic liquids while having the lowest melting point. Few bis(trifluoromethanesulfonyl)imide salts melt at temperature below 100°C which is in good agreement with the definition of ionic liquids. All dicationic ionic liquids appear as solid at ambient temperature and were purified through recrystallization with an appropriate solvent. Upon recrystallization, nine dicationic ionic liquids afforded single crystal suitable for X-ray crystallography 3 measurement. The molecular structure of crystals are solved, refined, and found to be in good agreement with the expected structures. Based on the chromatographic analysis, hexafluorophosphate and bis(trifluoromethanesulfonyl)imide moieties have extremely low bromide and water content.
format Thesis
author Abd Rahim, Munirah Sufiyah
author_facet Abd Rahim, Munirah Sufiyah
author_sort Abd Rahim, Munirah Sufiyah
title Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim
title_short Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim
title_full Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim
title_fullStr Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim
title_full_unstemmed Synthesis and characterization of phenylene-based dicationic ionic liquids / Munirah Sufiyah Abd Rahim
title_sort synthesis and characterization of phenylene-based dicationic ionic liquids / munirah sufiyah abd rahim
publishDate 2012
url http://studentsrepo.um.edu.my/4196/1/MSc_Thesis_Munirah_Sufiyah.pdf
http://studentsrepo.um.edu.my/4196/
_version_ 1738505649574117376
score 13.211869

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