Utilization of a Crown Ether/Amine-Type Rotaxane as a Probe for the Versatile Detection of Anions and Acids by Thin-Layer Chromatography.

A crown ether/amine-type [2]rotaxane was synthesized and utilized as a probe for the detection of acids and anions. The addition of acids to the amine-type [2]rotaxane solution generated corresponding crown ether/ammonium-type [2]rotaxanes, which were purified by silica gel column chromatography as ammonium salts. The isolated yields of the [2]rotaxanes, possessing a variety of anions, depended on the acidity and polarity of the counter anions. The behaviours of the ammonium-type [2]rotaxanes on thin-layer chromatography (TLC) silica gel reflected the properties of the counter anions. The treatment of the amine-type [2]rotaxane with acids afforded the corresponding ammonium-type [2]rotaxanes bearing several different anions. The ammonium-type [2]rotaxanes behaved similarly to the purified [2]rotaxanes on the TLC silica gel. Furthermore, we succeeded in the analysis of anions using mixtures of the amine-type [2]rotaxane and salts in an appropriate solvent. We demonstrated the detection of anions by the combination of TLC and the utilization of the [2]rotaxane probe.