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Modeling competitive guest binding to β-cyclodextrin molecular printboards
Tyndall National Institute, University College Cork.
2006 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 110, no 33, p. 16640-16645Article in journal (Refereed) Published
Abstract [en]

Anchoring of functionalized guest molecules to self-assembled monolayers (SAMs) is key to the development of molecular printboards for nanopatterning. One very promising system involves guest binding to immobilized β-cyclodextrin (β-CD) hosts, with guest:host recognition facilitated by a hydrophobic interaction between uncharged anchor groups on the guest molecule and β-CD hosts self-assembled at gold surfaces. We use molecular dynamics free energy (MDFE) simulations to describe the specificity of guest:β-CD association. We find good agreement with experimental thermodynamic measurements for binding enthalpy differences between three commonly used phenyl guests: benzene, toluene, and t-butylbenzene. van der Waals interaction with the inside of the host cavity accounts for almost all of the net stabilization of the larger phenyl guests in β-CD. Partial and full methylation of the secondary rim of β-CD decreases host rigidity and significantly impairs binding of both phenyl and larger adamantane guest molecules. The β-CD cavity is also very intolerant of guest charging, penalizing the oxidized state of ferrocene by at least 7 kcal/mol. β-CD hence expresses moderate specificity toward uncharged organic guest molecules by van der Waals recognition, with a much higher specificity calculated for electrostatic recognition of organometallic guests.

Place, publisher, year, edition, pages
2006. Vol. 110, no 33, p. 16640-16645
Identifiers
URN: urn:nbn:se:ltu:diva-6947DOI: 10.1021/jp062553nLocal ID: 545e8ce6-19a0-4fc6-88dd-94ad1b600289OAI: oai:DiVA.org:ltu-6947DiVA: diva2:979833
Note
Upprättat; 2006; 20130302 (andbra)Available from: 2016-09-29 Created: 2016-09-29 Last updated: 2017-11-24Bibliographically approved

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CiteExportLink to record
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