朝向手性外消旋有机凝胶剂。

Towards racemizable chiral organogelators.

机构信息

Functional Organic Materials and Devices and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600MB Eindhoven, The Netherlands.

出版信息

Beilstein J Org Chem. 2010 Oct 6;6:960-5. doi: 10.3762/bjoc.6.107.

DOI:10.3762/bjoc.6.107

PMID:21085504

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2981819/

Abstract

A chiral organogelator has been synthesized that can be racemized and self-assembled in apolar solvents whilst at higher concentrations organogels are formed. Field emission scanning and transmission electron microscopy revealed the formation of bundle fibrils that are able to gelate the solvent. ¹H NMR studies showed hydrogen-bond interactions between the peptide head groups of neighbouring organogelator molecules. The enantiomerically pure organogelator can be racemized by the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) as was evident from chiral high-performance liquid chromatography analysis.

摘要

已经合成了一种手性有机凝胶剂，它可以在非极性溶剂中消旋和自组装，而在较高浓度下则形成有机凝胶。场发射扫描和透射电子显微镜显示形成了束状原纤维，能够使溶剂凝胶化。¹H NMR 研究表明，相邻有机凝胶剂分子的肽头基团之间存在氢键相互作用。对映体纯的有机凝胶剂可以通过碱 DBU（1,8-二氮杂双环[5.4.0]十一-7-烯）消旋，从手性高效液相色谱分析中可以明显看出。