How does β-cyclodextrin affect oxygen solubility in aqueous solutions of sodium perfluoroheptanoate?

Dias, Alfredo M. P. G.; Andrade-Dias, Cristiano; Lima, Sérgio; Coutinho, João A. P.; Teixeira‐Dias, J. J. C.; Marrucho, Isabel M.

doi:10.1016/j.jcis.2006.07.074

Cited by 6 publications

(5 citation statements)

References 46 publications

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“…It is well-known that the physicochemical properties (stability, solubility, surface tension, etc.) of the guest molecules in the bound state are dramatically altered for inclusion complexes with β-CD. − However, the relationship between the mode of preparation of these complexes and their structure in the solid state are poorly understood and require further study. An understanding of the structure, dynamics, and molecular recognition properties of such solid-state complexes is afforded by multinuclear NMR studies described herein.…”

Section: Resultsmentioning

confidence: 99%

“…A comparison of the cmc values for PFOA (∼0.0105 M), SPFO (sodium perfluorooctanoate, 0.032 M), and sodium octanoate (∼0.4 M) − illustrates the differences in surface activity between PFCs and hydrocarbon surfactants. The solution and colloidal behavior of surface-active agents may be attenuated by their complexation with host compounds such as cyclodextrins. − Cyclodextrins (CDs) are macrocyclic (1→4)-linked oligomers of α- d -glucopyranose, and the most commonly studied CDs are α-, β-, and γ-CD, consisting of 6-, 7-, and 8-glucopyranose units, respectively . β-CD displays the remarkable ability of forming stable inclusion complexes with perfluorinated alkanes, partially because of the good “size-fit” complementarity of the guest and the host.…”

Section: Introductionmentioning

confidence: 99%

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Formation of Host-Guest Complexes of β-Cyclodextrin and Perfluorooctanoic Acid

et al. 2011

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Structural characterization and dynamic properties of solid-state inclusion complexes of β-cyclodextrin (β-CD) with perfluorooctanoic acid (PFOA) were investigated by (19)F/(13)C solid-state and (19)F/(1)H solution NMR spectroscopy. The complexes in the solid state were prepared using dissolution and slow cool methods, where thermal analyses (DSC and TGA), PXRD, and FT-IR results provided complementary support that inclusion complexes were formed between β-CD and PFOA with variable stoichiometry and inclusion geometry. (19)F DP (direct polarization) and (13)C CP (cross-polarization) with magic-angle spinning (MAS) solids NMR, along with (19)F/(1)H solution NMR were used to characterize the complexes in the solid and solution phases, respectively. The dynamics of the guest molecules in the inclusion complexes (ICs) were studied using variable temperature (VT) (19)F DP/MAS NMR experiments in the solid state. The guest molecules were observed to be in several different molecular environments, providing strong evidence of variable host-guest stoichiometry and inclusion geometry, in accordance with the preparation method of the complex and the conformational preference of PFOA. It was concluded from PXRD that β-CD and PFOA form inclusion complexes with "channel-type" structures. Variable spin rate (VSR) (19)F DP/MAS NMR was used to assess the phase purity of the complexes, and it was revealed that slow cooling resulted in relatively pure phases. In the solution state, (1)H and (19)F NMR complexation-induced chemical shifts (CISs) of β-CD and PFOA, respectively, provided strong support for the formation of 1:1 and 2:1 β-CD/PFOA inclusion complexes. The dynamics of the guest molecule in the β-CD/PFOA complexes in D(2)O solutions were probed using VT (19)F NMR and revealed some guest conformational and exchange dynamics as a function of temperature and the relative concentrations of the host and guest.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Formation of Host-Guest Complexes of β-Cyclodextrin and Perfluorooctanoic Acid

et al. 2011

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“…To circumvent this difficulty and increase the amount of non-selfassociated decanoic acid in water, α-cyclodextrin was added to the solution. Cyclodextrins tend to include the hydrophobic moiety of an amphiphilic guest of suitable size and are able to influence the guest self-association behavior, by interfering with the formation of the aggregates [34][35][36]. Setting Since this experimental observation cannot be theoretically reproduced on the basis of the inclusion of decanoic acid molecules in αCD alone, it should be concluded that the protons bonded to C2 and C10 are not inside the αCD cavity.…”

Section: Concentration Dependence Of the Chemical Shift Variationsmentioning

confidence: 98%

From simple amphiphilic to surfactant behavior: Analysis of 1H NMR chemical shift variations

Andrade-Dias¹,

Lima²,

Teixeira‐Dias³

2007

Journal of Colloid and Interface Science

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“…These compounds have been widely used in applications ranging from pharmaceuticals to surface-active agents − despite their potential adverse health risks as endocrine disruptors, and both infertility and immunotoxin agents. − The fate and transport pathways of PFCs in various environments and ecosystems are poorly understood despite the numerous studies over the past decade. In part, this may be due to the variation in the physicochemical properties of PFCs, such as surface activity, chemical mobility, and their chemical stability, as compared with their hydrocarbon analogues. , In previous studies, − cyclodextrins (CDs) were reported to attenuate the surface activity of PFCs due to the formation of stable noncovalent host/guest complexes between the apolar PFC guest and the apolar CD interior. An improved understanding of the structure of β-CD/PFC inclusion complexes (ICs) will contribute to the knowledge related to the physical and biophysical processes involving the fate and transport of PFCs in the environment.…”

Section: Introductionmentioning

confidence: 99%

Characterization and Dynamic Properties for the Solid Inclusion Complexes of β-Cyclodextrin and Perfluorooctanoic Acid

et al. 2013

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The structural characterization and dynamic properties of solid-state inclusion complexes (ICs) formed between β-cyclodextrin (β-CD; host) and perfluorooctanoic acid (PFOA; guest) were investigated using (13)C NMR spectroscopy. The 1:1 and 2:1 host/guest solid-state complexes were prepared using a modified dissolution method to obtain complexes with high phase purity. These complexes were further characterized using differential scanning calorimetry (DSC), FT-IR spectroscopy, powder X-ray diffraction (PXRD), (19)F directpolarization (DP), and (13)C cross-polarization (CP) with magic-angle spinning (MAS) NMR spectroscopy. The (19)F → (13)C CP results provided unequivocal support for the formation of well-defined inclusion compounds. The phase purity of the complexes formed between β-CD and PFOA were assessed using the (19)F DP NMR technique at variable temperature (VT) and MAS at 20 kHz. The complexes were found to be of high phase purity when prepared in accordance with the modified dissolution method. The motional dynamics of the guest in the solid complexes were assessed using T1/T2/T1ρ relaxation NMR methods at ambient and VT conditions. The relaxation data revealed reliable and variable guest dynamics for the 1:1 versus 2:1 complexes at the VTs investigated. The motional dynamics of the guest molecules involve an ensemble of axial motions of the whole chain and 120° rotational jumps of the methyl (CF3) group at the termini of the perfluorocarbon chain. The axial and rotational dynamics of the guest in the 1:1 and 2:1 complexes differ in distribution and magnitude in accordance with the binding geometry of the guest within the host.

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How does β-cyclodextrin affect oxygen solubility in aqueous solutions of sodium perfluoroheptanoate?

Cited by 6 publications

References 46 publications

Formation of Host-Guest Complexes of β-Cyclodextrin and Perfluorooctanoic Acid

Formation of Host-Guest Complexes of β-Cyclodextrin and Perfluorooctanoic Acid

From simple amphiphilic to surfactant behavior: Analysis of 1H NMR chemical shift variations

Characterization and Dynamic Properties for the Solid Inclusion Complexes of β-Cyclodextrin and Perfluorooctanoic Acid

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