[Et4N]2[TCNE]2 (TCNE = tetracyanoethylene) - an example of an exceptionally long 2.827 Ã CC bond

Journal ArticleInterest in organic compounds exhibiting unusually long CC bonds has been the subject of several recent studies.1-3 The longest sp3-sp3 C-C single bond reported to date is 1.73 A°,1,2 whereas several [TCNE]22- (TCNE = tetracyanoethylene) dimers have been recently reported to form cation-assisted, long, two-electron (pi*-pi*) CC bonds involving four carbon atoms. These CC bonds range from 2.833 to 3.09 A°. The cations range from electrostatically bonded Tl+4 and K+5 to large, bulky, non-coordinating cations such as [Cr(C6H6)2]+,6 [Fe(C5H4)2C3H6]+,7 and [TDAE]2+ [TDAE = (Me2N)2- CC(NMe2)2].4,8 Herein we report the structure, IR and UV-Vis spectroscopic properties of [Et4N]2[TCNE]2, a new example of the [TCNE]22- dimer, which exhibits the shortest (pi*-pi*) CC bond for this family of compounds

Isolation of two salts from the reduction of TCNE with [(n-C3H7)4N]I. A further example of long 2.87 Ã pi-C-C bonding in pi-[TCNE]22-

Journal ArticleReduction of tetracyanoethylene, TCNE, with tetrakis(n-propyl)ammonium iodide, [Pr4N]I, results in a new example of long pi*-CC bonded pi-[TCNE]22- dimers with a 2.870(4) A(°) intradimer CC bond, which is structurally and spectroscopically characterized. This reaction also results in isolation of [Pr4N]2[TCNE][I3] possessing isolated [TCNE][I3] possessing isolated [TCNE].- radical anions

Charge transfer complexes of 2,4,6-tricyano-s-triazine with tetrathiafulvalene (TTF) and N,N,N' ,N'-tetramethyl-p-phenylenediamine (TMPD)

Journal ArticleReaction of 2,4,6-tricyano-s-triazine (TCT) with tetrathiafulvalene (TTF) and N,N,N',N'-tetramethylp-phenylenediamine (TMPD) leads to 1 : 1 charge transfer complexes. The crystal structures of the TTF[TCT], as well as the decomposition product due to hydrolysis of the [TMPD][TCT], i.e. HTMPD]+[2,4-dicyano-6-oxy-s-triazine]-, are reported and spectroscopically characterized

Vibrational spectra of imidazolium tetrafluoroborate ionic liquids

Abstract The Raman and infrared spectra of a series of 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids ([C2

The large scale synthesis of pure imidazolium and pyrrolidinium ionic liquids,

Ionic liquids are being employed in almost all areas of chemistry and materials, yet there are inherent issues which arise if the utmost care is not taken in the preparation and purification of these materials. They are not easily synthesized and purified using the existing methods. We describe a reliable method for producing large quantities of high quality ionic liquids. Additionally, we show that imidazoliums are not 'special' due to their 'inherently fluorescent' nature, that spectroscopically clean imidazoliums are attainable, and most classes of ionic liquids do exhibit fluorescent backgrounds when extreme care is not taken during their synthesis and purification

Fulleride-Based Ionic Liquids

A room temperature fulleride-based ionic liquid has been developed and characterized. Utilizing the trihexyl(tetradecyl) phosphonium cation, the ionic liquid [PC 6 C 6 C 6 C 14 ] 3 [C 60 ]Cl was synthesized, and distinctly shows spectroscopic characteristics of the [C 60 ] 2-anion. The glass transition of the ionic liquid occurs well below room temperature at -56°C, but it still retains an extremely high viscosity at room temperature. Attempts were made to obtain the pure fulleride salt [PR 4 ] 3 [C 60 ], but nearly always results in the binary fulleride-chloride salt

Limited thermal stability of imidazolium and pyrrolidinium ionic liquids

a b s t r a c t Ionic liquids, with their vast applications, have been touted as being thermally stable to very high temperatures. However, decomposition not detected by standard TGA and NMR techniques are observed with spectroscopic techniques sensitive enough to see small amounts of impurities. Decomposition temperatures of common ionic liquids appear to occur at hundreds of degrees below those temperatures previously reported