Synthesis and physical properties of tris(dialkylamino)cyclopropenium dicyanamide ionic liquids

RSC Adv. 2018 Aug 7;8(50):28313-28322. doi: 10.1039/c8ra05558k.

Abstract

The synthesis and properties of 16 tris(dialkylamino)cyclopropenium (TDAC) cations with the dicyanamide (DCA) anion, [N(CN)2]-, are described. D 3h- and C 3h-symmetric cations ([C3(NR2)3]DCA (R = Me, Et, Pr, Bu, Pent, Hex, Dec) and [C3(NRMe)3]DCA (R = Bu, St), respectively) were synthesised by reaction of C3Cl5H with the corresponding amine. Reaction of the alkoxydiaminocyclopropenium salt [C3(NEt2)2(OMe)]+ with amines led to a series of C 2v-symmetric salts [C3(NEt2)2(NR2)]DCA (R = Me, Bu, Hex) and two C s-symmetric salts and [C3(NEt2)2(NRMe)]DCA (R = Me, Bu). Similarly, [C3(NMe2)2(OMe)]+, was used to prepare the C s-symmetric salts [C3(NMe2)2(NRMe)]DCA (R = Pr, Bu). In addition to characterisation by NMR, mass spectrometry and microanalysis, the salts were characterised by DSC, TGA, density, viscosity, conductivity and miscibility/solubility studies. Comparisons have been made with similar series of bistriflimide (NTf2 -) salts that have been previously reported to see whether the same trends are observed with a different anion.