Orientational effect of surface-confined cyclodextrin on the inclusion of bisphenols.

Abstract

The molecular recognition of various kinds of bisphenols (BPs) and a bisphenol A-polymer conjugate (BPA-polymer) by a self-assembled monolayer (SAM) of thiolated beta-cyclodextrin (CD) on a gold electrode was examined using cyclic voltammetry (CV). Based on the inhibitory effect of BPs on the inclusion of hydroquinone (HQ) as a probe by the surface-confined CD, the association constants (K(assoc)) of BPs with the immobilized beta-CD were estimated. The K(assoc) values for BPs with the SAM of 3-dithiobis(undecanoylamido)-3-deoxy-beta-cyclodextrin (DTUA-beta-CD) were smaller than those in the free beta-CD system reported previously. A similar tendency was obtained when 6-(lipoylamido)-6-deoxy-beta-cyclodextrin (LP-beta-CD) was used in place of DTUA-beta-CD. The K(assoc) values for all the BPs except for bisphenol B with the SAM of LP-beta-CD were always larger than those with the SAM of DTUA-beta-CD, due to a difference in the orientation of the beta-CD moiety in the SAMs. Furthermore, adsorption and desorption processes of the BPA-polymer from the surface-confined beta-CD was followed using local surface plasmon resonance spectroscopy.

• Authors: Hiroshi Endo, Tadashi Nakaji-Hirabayashi, Shinta Morokoshi, Makoto Gemmei-Ide, Hiromi Kitano
• Journal: Langmuir : the ACS journal of surfaces and colloids (Langmuir) Vol. 21 Issue 4 Pg. 1314-21 (Feb 15 2005) ISSN: 0743-7463 [Print] United States
• PMID: 15697276 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Amides
• Cyclodextrins
• Phenols
• Gold

Topics

• Amides (chemistry)
• Circular Dichroism
• Cyclodextrins (chemistry)
• Electrodes
• Gold
• Molecular Structure
• Oxidation-Reduction
• Phenols (chemistry)