Surface-Induced Diastereomeric Complex Formation of
a Nucleoside at the Liquid/Solid Interface: Stereoselective Recognition
and Preferential Adsorption

Guo, Zongxia; Cat, Inge De; Averbeke, Bernard Van; Ghijsens, Elke; Lin, Jianbin; Xu, Hong; Wang, Guojie; Hoeben, Freek
J. M.; Tomović, Željko; Lazzaroni, Roberto; Beljonne, David; Meijer, E. W.; P. H. J. Schenning, Albertus; Feyter, Steven De

doi:10.1021/ja402914m.s001

Surface-Induced Diastereomeric Complex Formation of a Nucleoside at the Liquid/Solid Interface: Stereoselective Recognition and Preferential Adsorption

journal contribution

posted on 2013-07-03, 00:00 authored by Zongxia Guo, Inge De Cat, Bernard Van Averbeke, Elke Ghijsens, Jianbin Lin, Hong Xu, Guojie Wang, Freek J. M. Hoeben, Željko Tomović, Roberto Lazzaroni, David Beljonne, E. W. Meijer, Albertus P. H. J. Schenning, Steven De Feyter

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.