Aggregation behavior of alkyl triphenyl phosphonium bromides in aprotic and protic ionic liquids

The aggregation behavior of alkyltriphenylphonium bromides, C n TPB (n = 12 and 14), has been investigated in two different room-temperature ionic liquids (ILs), the aprotic 1-butyl-3-metyllimidazolium tetrafluoroborate ([bmim][BF4]), and the protic ethylammonium nitrate (EAN). The critical micelle concentration was determined by the surface tension measurements. The calculated thermodynamic parameters based on surface tension measurements at various temperatures indicate that the micellization for C n TPB in both aprotic [bmim][BF4] and protic EAN is enthalpy-driven. But stronger solvophobic interactions presented between C n TPB and protic EAN than aprotic [bmim][BF4]. 1H NMR spectra were further conducted to reveal that ethylammonium cation can insert into the micelle while imidazole cation only locates among the head groups of C n TPB.