| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - Photochemical Imprint of Molecular Recognition Sites inTwo-Dimensional Monolayers Assembled on AuElectrodes: Effects of the Monolayer Structures on theBinding Affinities and Association Kinetics to theImprinted Interfaces1
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - Photochemical imprint of molecular recognition sites for phenoxynaphthacene quinone (1a) in two-dimensional monolayers assembled on Au surfaces is accomplished. The photochemical imprint of themolecular recognition sites involves several steps: The primary step includes the assembly of the trans-phenoxynaphthacene quinone monolayer (2a), followed by the rigidification of the monolayer with long-chain alkanethiols that generates a densely packed quinone monolayer. The second process involves thephotoisomerization of the monolayer to the ana-quinone state (2b), followed by the nucleophilic displacementof the quinone with butylamine. The association of 1a to the imprinted sites and the dissociation of thehost substrate from the sites are followed by electrochemical means as well as by microgravimetric quartz-crystal-microbalance measurements. The binding of 1a to the imprinted recognition sites reveals selectivity,and structurally related substrates do not associate to the imprinted sites. The kinetics of association of1a to the imprinted sites and of the dissociation of 1a from the sites is affected by the length of therigidifying alkanethiols. As the alkanethiol is longer, the association of 1a to the sites and the dissociationof 1a from the recognition sites is slower. The slower association of 1a to perforated monolayers with along-chain alkanethiol (C18H37SH) is attributed to the blocking of the imprinted sites by the flexiblealkanethiol chains. The retardation of the dissociation of 1a from the imprinted sites rigidified by thelong-chain alkanethiols is attributed to the capping of the substrate by the long-chain thiols. The selectivityof the imprinted recognition sites is attributed to a structural fit of 1a to the imprinted hydrophobic contourand the synergetic stabilization of 1a in the site by complementary H-bonds.
|
| article type
| |
| is part of this journal
| |
