title: Surface-induced diastereomeric complex formation of a nucleoside at the liquid/solid interface: stereoselective recognition and preferential adsorption.
abstract: With the aim of achieving surface-mediated enantioselective adsorption, the self-assembly of chiral oligo(p-phenylenevinylene) (OPV3T) with nucleosides is investigated at the liquid/solid interface by means of scanning tunneling microscopy and molecular modeling. OPV3T enantiomers form mirror related hexameric rosette patterns. The DNA nucleoside, thymidine, does not self-assemble into stable adlayers but coadsorbs with OPV3T on the surface, leading to a pattern transformation of OPV3T from rosettes to dimers, and a change in chiral expression as well. Diastereoselective recognition between OPV3T and thymidine enantiomers can be used to resolve thymidine enantiomers at an achiral surface with an OPV3T enantiomer as the resolving agent. The impact of molar ratio and concentration on the self-assembly and chiral resolution is systematically investigated. Because there is no interaction between OPV3T and thymidine in solution, the liquid/solid interface acts as the platform for the chiral resolution of thymidine enantiomers.
authors.affiliation: Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200 FB-3001, Leuven, Belgium.
authors.forename: Zongxia
authors.initials: Z
authors.lastname: Guo
authors.forename: Inge
authors.initials: I
authors.lastname: De Cat
authors.forename: Bernard
authors.initials: B
authors.lastname: Van Averbeke
authors.forename: Elke
authors.initials: E
authors.lastname: Ghijsens
authors.forename: Jianbin
authors.initials: J
authors.lastname: Lin
authors.forename: Hong
authors.initials: H
authors.lastname: Xu
authors.forename: Guojie
authors.initials: G
authors.lastname: Wang
authors.forename: Freek J M
authors.initials: FJ
authors.lastname: Hoeben
authors.forename: Željko
authors.initials: Ž
authors.lastname: Tomović
authors.forename: Roberto
authors.initials: R
authors.lastname: Lazzaroni
authors.forename: David
authors.initials: D
authors.lastname: Beljonne
authors.forename: E W
authors.initials: EW
authors.lastname: Meijer
authors.forename: Albertus P H J
authors.initials: AP
authors.lastname: Schenning
authors.forename: Steven
authors.initials: S
authors.lastname: De Feyter
mesh_terms: D000327:Adsorption; D008958:Models, Molecular; D015394:Molecular Structure; D011145:Polyvinyls / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013499:Surface Properties; D013936:Thymidine / Q000737:chemistry*
chemical_list: D011145:Polyvinyls; C470024:poly(4-phenylenevinylene); D013936:Thymidine