Spreading behaviour of a series of amphiphilic [3 : 3] [60]fullerene hexakisadducts: a systematic study

Abstract

The spreading behaviour at the air-water interface of a series of [60]fullerene [3 : 3] hexakisadducts has been studied as a function of the hydrophobichydrophilic balance of the amphiphiles. More precisely, by changing both the nature and the size of the polar headgroup, by varying the nature of the chemical linker and/or spacer, by modifying the nature and/or the length of the spacer, it has been possible to perform a systematic study. The latter was carried out not only according to the pH of the aqueous subphase but also to its temperature highlighted various behaviours which in particular allowed to us to conclude that the optimal chemical design for this type of amphiphilic molecules is reached with the couples amine polar head/ester linker (Hexa-4) or carboxylic acid polar head/ amide linker (Hexa-5).

Synthesis of Amphiphilic [60]Fullerene [3:3]Hexakisadducts with Four Spherically Defined Addend Zones

“…19, 20 By varying both the hydrophilic and hydrophobic moieties of these amphiphiles, one can balance the hydrophilic/hydrophobic ratio very well and as a direct consequence the aggregation behavior of those amphiphiles in polar media. In a recent study, we investigated the spreading behavior at the air/water interface of a series of [3:3]hexakisadducts as a function of the hydrophobic/hydrophilic balance of the amphiphiles 21. For well‐tuned systems, we could observe the formation of structurally persistent micelles that contained a defined number of monomers.…”

Self- or Induced Organization of [60]Fullerene Hexakisadducts

“…Hirsch and Felder-Flesch have recently conducted a systematic study on the spreading behavior at the air-water interface of a series of [3:3] [60]fullerene hexakisadducts (6 to 12) as a function of the chemical design and hydrophobichydrophilic balance [54]. For this purpose, various structural parameters have been taken into account (Fig.…”