Energetics of small molecule and water complexation in hydrophobic calixarene cavities

Langmuir : the ACS Journal of Surfaces and Colloids
Justin M NotesteinEnrique Iglesia

Abstract

Calixarenes grafted on silica are energetically uniform hosts that bind aromatic guests with 1:1 stoichiometry, as shown by binding energies that depend upon the calixarene upper rim composition but not on their grafted surface density (0.02-0.23 nm(-2)). These materials are unique in maintaining a hydrophilic silica surface, as probed by H2O physisorption measurements, while possessing a high density of hydrophobic binding sites that are orthogonal to the silica surface below them. The covalently enforced cone-shaped cavities and complete accessibility of these rigidly grafted calixarenes allow the first unambiguous measurements of the thermodynamics of guest interaction with the same calixarene cavities in aqueous solution and vapor phase. Similar to adsorption into nonpolar protein cavities, adsorption into these hydrophobic cavities from aqueous solution is enthalpy-driven, which is in contrast to entropy-driven adsorption into water-soluble hydrophobic hosts such as beta cyclodextrin. The adsorption thermodynamics of several substituted aromatics from vapor and liquid are compared by (i) describing guest chemical potentials relative to pure guest, which removes differences among guests because of aqueous solvation and van ...Continue Reading

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Citations

Aug 25, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Anthony B ThompsonJustin M Notestein
Apr 19, 2011·Chemical Communications : Chem Comm·John S HartJason B Love
Dec 18, 2013·ACS Applied Materials & Interfaces·Anthony B ThompsonJustin M Notestein
Sep 7, 2017·Chemical Communications : Chem Comm·Christian SchöttleAlexander Katz
Mar 23, 2018·Beilstein Journal of Organic Chemistry·Marco Russo, Paolo Lo Meo
Aug 27, 2011·Chemical Society Reviews·Hyun Jung KimJong Seung Kim
Feb 13, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Nina KorbakovShlomo Yitzchaik

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