Self-Assembly of [60]Fullerene−Thiol Derivatives on Mercury Surfaces

Abstract

Herein we report the first self-assembly of fullerene-thiol conjugates (1 and 2) on thin mercury films (TMF) deposited on a glassy carbon electrode (GCE). The fullerene-containing SAMs were investigated by cyclic voltammetry and water contact angle measurements. Two reversible, surface-confined redox couples were obtained for the fullerene-containing SAMs on TMF/GCE in CH(2)Cl(2) solution. The surface coverage of both fullerene derivatives 1 and 2 on TMF/GCE was measured to be in the range of (1.7-1.8) x 10(-10) mol cm(-2). Both SAMs of 1 and 2 partially blocked the electron transfer across the electrode in aqueous solution. The contact angle measurements performed on TMFs clearly showed an enhancement of the surface hydrophobicity upon formation of the fullerene-containing monolayer.

Nanometer‐Sized Fluorous Fullerene Vesicles in Water and on Solid Surfaces

“…When we spin coated the vesicle solution in water ([ 1 a ]=2.0 m M ) on indium tin oxide (ITO) and dried it at room temperature, the hydrophilic surface of ITO became as water‐repellent as a poly(tetrafluoroethylene) (PTFE, Teflon) surface. Thus, the water contact angle of ITO ((4.4±0.4)°) after treatment with the fluorous vesicle solution became (111.7±1.3)° (Figure 3 a), which is comparable to that of Teflon ((108–114)°)11 and is much larger than that of a fullerene‐modified self‐assembled monolayer ((100±3)°)12 and the phenyl‐vesicle‐covered ITO surface ((73.9±0.6)°; Figure 3 b). The water‐repellent property was maintained even after repeated rinsing with water (i.e., the vesicles became insoluble in water after drying) and after storing in air at room temperature for several months.…”

Electrochemistry of redox-active self-assembled monolayers

“…Potential-induced ion gating attributed to SAM defects are reported [294]. A C 60 -alkane thiol monolayer on a Hg film electrode showed electrochemical blocking of redox species in solution and a high degree of hydrophobicity [175]. SECM was used to evaluate pinholes in a SAM of alkane thiols of different chain lengths (CH 3 (CH 2 ) n SH; n = 8, 10, 11, 15) on Au and Hg surfaces using FcCH 2 NHCO(CH 2 ) 12 SH and ferrocene-terminated polynorbornyl (FcNB) thiols [102].…”

Fullerene Derivatives That Bear Aliphatic Chains as Unusual Surfactants: Hierarchical Self‐Organization, Diverse Morphologies, and Functions

“…[36] www.chemeurj.org ic chains. In addition, C 60 is less hydrophobic than the hydrocarbon group; the C 60 film has lower water contact angles than the alkane monolayer (75-1008 for C 60 and 1108 for alkane film), [50][51][52][53][54][55][56] and in situ X-ray reflectivity of the Langmuir monolayer of 2 indicated that the C 60 moieties are located adjacent to the water (Figure 2a). [48] Accordingly, in a relatively polar environment, unlike that of ionic C 60 amphiphile (Scheme 1), the C 60 group form the surface of the assembly.…”