Redox-Switched Amphiphilic Ionic Liquid Behavior in Aqueous Solution

Abstract

A new redox amphiphilic ionic liquid (AIL) containing ferrocene as a redox-active group was synthesized, 1-(11-ferrocenylundecyl)-3-methylimidazolium bromide (Fc11MIm+). Adsorption and aggregation of both reduced and oxidized forms of this ferrocenated AIL in aqueous solution were studied by surface tension measurements. The micellization was favored for the reduced ferrocenated AIL (Fc11MIm+) as compared with the oxidized ferrocenated AIL (Fc+11MIm+). Minimum areas at the air/aqueous solution interface were identical whereas limiting surface tensions were slightly different. This corroborated the formation of an expanded monolayer of redox active AIL at the interface. The electrochemical behavior of redox active AIL was investigated. The electrochemical responses of Fc11MIm+ aqueous solution interestingly differed, depending on its concentration. Below the cmc, the electrochemical reaction was dominated by ferrocenated AIL adsorbed onto the electrode surface; then above the cmc, it was controlled by the Fc11MIm+ diffusing to the electrode. For the latter, the electrochemical mechanism was suggested to couple with the disruption reaction of the reduced form micelles.

Synthesis and characterization of an electroactive ionic liquid based on the ferrocenylsulfonyl(trifluoromethylsulfonyl)imide anion

“…However, there are very few reports on electroactive ILs and there is a very narrow array of available structures and given that the design of a new RIL is hindered by a lack of knowledge of their structure-properties relationships [18][19][20][21][22][23][24]. In addition, the current library of RILs almost exclusively contains structures based on the modification of alkylimidazoliums, with some exceptions from reports on ferrocene-functionalized phosphonium IL [14,25] and metallocenium ILs [26,27].…”

Effect of cationic head group on micellization behavior of new amide-functionalized surface active ionic liquids

“…7,8 The large number of ILs that can be synthesized by judicious choice of cation, anion, and alkyl chain length of cation or anion is of huge importance in targeted synthesis of ILs for specific applications. 13 The studies concerning micellization behavior of SAILs in aqueous medium, or even in short chain ILs as base solvents, is gaining momentum at high speed. 13 The studies concerning micellization behavior of SAILs in aqueous medium, or even in short chain ILs as base solvents, is gaining momentum at high speed.…”

Amphiphile self-assembly based on ionic liquids

“…Structures of anionic surfactant ionic liquids [59,60] 液中的聚集行为. 此后, Yu课题组 [62] 又系统研究了 [72] Figure 7 (Color online) Schematic illustration of the proposed aggregation structures of [Fc11mim]Br in the reduced and oxidized forms [72] 十六烷基-1-(1-羟基异丙基)咪唑溴(S-3-hexadecyL 1 - Cl), 如图8所示 [76] .…”