Related Experiment Video
Updated: Jan 6, 2026

Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes
Published on: January 10, 2017
Efficient enantiorecognition of amino acids under a stimuli-responsive system: synthesis, characterization and
Datong Wu1, Fei Pan, Gao-Chao Fan
1Jiangsu Key Laboratory of Advanced Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China. yzkongyomg@cczu.edu.cn.
Abstract:
In this study, an electroactive rotaxane, (S,S)-crown-3, consisting of a polymeric chiral ionic liquid as a flexible axle and 18-crown-6 as the wheel, was designed and synthesized. It is worth noting that a stimuli-responsive system was developed, in which the wheel could switch its location between the chiral carbamido group and ionic pair of the ionic polymers under an external force. Next, (S,S)-crown-3 was employed as a modification on the surface of glassy electrode. In contrast to previous study, the developed probe presented a clear discrimination of an electrochemical signal in the absence of Cu(ii). Under the external force (different pH values), l-isomers of amino acids (tryptophan, tyrosine, and cysteine) could form stable host-guest interactions with the chiral carbamido group, producing higher peak currents than the d-isomers. Compared to the absence of the crown, (S,S)-crown-3 showed much better recognition efficiency. The value of IL/ID for tryptophan could reach 39.8. In brief, the present study describes a powerful method for the synthesis of an electroactive rotaxane with great enantiorecognition capability.
Related Concept Videos
Properties of Enantiomers and Optical Activity
Prochirality
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Stereochemical Effects of Enolization
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

