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

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• 作者：Zongxia Guo ; Inge De Cat ; Bernard Van Averbeke ; Elke Ghijsens ; Jianbin Lin ; Hong Xu ; Guojie Wang ; Freek J. M. Hoeben ; 沤eljko Tomovi膰 ; Roberto Lazzaroni ; David Beljonne ; E. W. Meijer ; Albertus P. H. J. Schenning ; Steven De Feyter
• 刊名：The Journal of the American Chemical Society
• 出版年：2013
• 出版时间：July 3, 2013
• 年：2013
• 卷：135
• 期：26
• 页码：9811-9819
• 全文大小：661K
• 年卷期：v.135,no.26(July 3, 2013)
• ISSN：1520-5126

文摘

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.