Molecular solubilization of fullerene C₆₀ in water by γ-cyclodextrin thioethers

Abstract

SummaryVarious hydrophilic γ-cyclodextrin (CD) thioethers, containing neutral or ionic side arms were found to form molecular disperse solutions of C60 in water reaching concentrations of 15 mg/L. Equilibrium state was approached after seven days without the use of organic cosolvents. The 1:2 stoichiometry of the C60/γ-CD thioether complexes was demonstrated by a parabolic phase-solubility diagram. In contrast, native γ-CD forms nanoparticles with C60. Particle sizes of C60 were determined by dynamic light scattering.

Oligo- and poly(fullerene)s for photovoltaic applications: Modeled electronic behaviors and synthesis

“…The positions of addition to C 60 are shown in Figure (a). It should be noted that C 60 , while generally thought insoluble in THF, can also, at very low concentrations, give a peak at around 400 nm . In general, it was expected that 1,4‐bis adducts would result from the ATRAP due to steric effects.…”

“…It should be noted that C 60 , while generally thought insoluble in THF, can also, at very low concentrations, give a peak at around 400 nm. 75 In general, it was expected that 1,4-bis adducts would result from the ATRAP due to steric effects. Zooming in the specific region of around 445 nm of Figure 3(b), one can find the same characteristic broad peak described by Okamura et al 72 and Kadish, [76][77][78][79] and considered a diagnostic indicator of the synthesis of 1,4-bis-attacked fullerene moieties.…”

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

“…Recently, we synthesized a series of highly water-soluble per-6-deoxy-thioethers of β- and γ-CD, which are able to solubilize hydrophobic, nearly insoluble guest molecules, such as camptothecin [20], 1,4-dihydroxyanthraquinone [21], betulin [22], benzene and cyclohexane derivatives [23], and even C 60 [24] in water. Furthermore, their respective γ-CD thioethers form highly water-soluble 1:2 complexes with polycyclic aromatics, such as naphthalene, anthracene ( ANT ), and acenaphthylene ( ACE ) [25].…”

Mechanochemical Preparation of Stable Sub‐100 nm γ‐Cyclodextrin:Buckminsterfullerene (C60) Nanoparticles by Electrostatic or Steric Stabilization

“…The resulting solutions were analysed by UV/Vis spectroscopy demonstrating the ability of all hosts to complex C 60 due to the presence of its characteristic absorbance bands. In addition, applying the Lambert–Beer law allowed the quantification of the C 60 content in solution by using the known molar extinction coefficient of ϵ (335 nm)=51 900 m −1 cm −1 . From the C 60 concentration in a 1 mg mL −1 solution of each complex, we were able to calculate the weight percentage of C 60 , the yield of C 60 incorporation in each of the formulations and the ratio of CD to C 60 in the obtained nanoparticle formulations (Table ).…”