Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200 FB-3001, Leuven, Belgium.
J Am Chem Soc. 2013 Jul 3;135(26):9811-9. doi: 10.1021/ja402914m. Epub 2013 Jun 19.
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.
为了实现表面介导的对映选择性吸附，通过扫描隧道显微镜和分子建模研究了手性寡聚（对苯撑乙烯基）（OPV3T）与核苷在液/固界面的自组装。OPV3T 对映体形成镜像相关的六聚体蔷薇花样图案。DNA 核苷胸腺嘧啶不能自组装成稳定的吸附层，但与 OPV3T 在表面共吸附，导致 OPV3T 从蔷薇花样到二聚体的图案转变，以及手性表达的变化。OPV3T 和胸腺嘧啶对映体之间的非对映选择性识别可用于在非手性表面上用 OPV3T 对映体作为拆分剂拆分胸腺嘧啶对映体。系统研究了摩尔比和浓度对自组装和手性拆分的影响。由于 OPV3T 和胸腺嘧啶在溶液中没有相互作用，因此液/固界面成为手性拆分胸腺嘧啶对映体的平台。
