+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

The first (ferrocenylmethyl)imidazolium and (ferrocenylmethyl)triazolium room temperature ionic liquids



The first (ferrocenylmethyl)imidazolium and (ferrocenylmethyl)triazolium room temperature ionic liquids



Inorganic Chemistry 43(11): 3406-3412



N-(Ferrocenylmethyl)imidazole (3a), 1-(ferrocenylmethyl)-1,2,4-triazole (3b), 1,1'-bis[(1H-imidazol-1-yl)methyl]ferrocene (8a), 1,1'-bis([1H-(2-methyl)imidazol-1-yl]methyl]ferrocene (8b), and 1,1'-bis[(1H-1,2,4-triazol-1-yl)methyl]ferrocene (8c) were synthesized in moderate yields. These compounds were quaternized with methyl iodide to form 1-(ferrocenylmethyl)-3-methylimidazolium iodide (4a), 1-(ferrocenylmethyl)-4-methyl-1,2,4-triazolium iodide (4b), 1,1'-bis([1-(2,3-dimethyl)imidazolium]methyl)ferrocene diiodide (9b), and 1,1'-bis([1-(4-methyl)-1,2,4-triazolium]methyl)ferrocene diiodide (9c), respectively, in excellent yields. Compounds 4a, 4b, 9b, and 9c were metathesized with bis(trifluoromethanesulfonyl)amide to give high yields of 5a, 5b, 10b, and 10c. With potassium hexafluorophosphate, 9b forms 10d. Salts 5a, 5b, and 10c are the first room-temperature ionic liquids with cations containing an organometallic moiety that exhibit T(g) values well below room temperature, i.e., -32, -16, and -11 degrees C. The compounds were characterized by (1)H, (19)F, and (13)C NMR, MS, and elemental analyses. T(g) values and melting points were determined by DSC. T(d) values (5% weight loss temperature) were recorded by TGA. X-ray single-crystal structures show that 9c and 10d crystallize in the triclinic space group P.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 050635894

Download citation: RISBibTeXText

PMID: 15154802

DOI: 10.1021/ic049961v


Related references

1,3-Di(Ferrocenylmethyl)Imidazolium and 1-Ferrocenylmethyl-3-Alkylimidazolium Salts: A High Yield and Facile Synthesis. Synthetic Communications 30(10): 1865-1878, 2000

Picosecond time-resolved fluorescence study on solute-solvent interaction of 2-aminoquinoline in room-temperature ionic liquids: aromaticity of imidazolium-based ionic liquids. Journal of Physical Chemistry. B 111(18): 4914-4919, 2007

Ferrocenylmethyl mercaptan and methyl ferrocenylmethyl sulfide. Russian Chemical Bulletin 14(9): 1662-1664, 1965

1-Ferrocenylmethyl-3-(2,4,6-trimethylbenzyl)-1H-imidazolidin-3-ium iodide and trans-bis(3-benzyl-1-ferrocenylmethyl-1H-imidazolidin-2-ylidene)diiodidopalladium(II). Acta Crystallographica. Section C Crystal Structure Communications 68(Pt 2): M48-M52, 2012

The chemistry of the C2 position of imidazolium room temperature ionic liquids. Current Organic Synthesis 4(4): 381-389, 2007

Dielectric response of imidazolium-based room-temperature ionic liquids. Journal of Physical Chemistry. B 110(25): 12682-8, 2006

Shear relaxation of imidazolium-based room-temperature ionic liquids. Journal of Physical Chemistry. B 114(24): 8126-8133, 2010

Stability of superoxide ion in imidazolium cation-based room-temperature ionic liquids. Journal of Physical Chemistry. a 113(5): 912-916, 2009

What is the origin of the prepeak in the X-ray scattering of imidazolium-based room-temperature ionic liquids?. Journal of Physical Chemistry. B 114(50): 16838-16846, 2010

Effects of imidazolium room temperature ionic liquids on the fluorescent properties of norfloxacin. Luminescence 27(6): 495-500, 2013

Terahertz and Infrared Spectroscopy of Room-Temperature Imidazolium-Based Ionic Liquids. Journal of Physical Chemistry. B 119(51): 15696-15705, 2015

The reduction of oxygen in various room temperature ionic liquids in the temperature range 293-318 K: exploring the applicability of the Stokes-Einstein relationship in room temperature ionic liquids. Journal of Physical Chemistry. B 113(26): 8953-8959, 2009

Scope and limitations of imidazolium-based ionic liquids as room temperature glycosylation promoters. Carbohydrate Research 345(1): 45-49, 2010

Direct synthesis of ferrocenylmethylphosphines from ferrocenylmethyl alcohols and their application as ligands for room temperature Pd(0)-catalyzed Suzuki cross-couplings of aryl bromides. Organic Letters 5(3): 297-300, 2003

Electrochemistry of heme proteins entrapped in DNA films in two imidazolium-based room temperature ionic liquids. Bioelectrochemistry 91: 8, 2013