3-(Dicyanomethylidene)indan-1-one-Functionalized Calix[4]arene-Calix[4]pyrrole Hybrid: An Ion-Pair Sensor for Cesium Salts

Abstract

A chromogenic calix[4]arene-calix[4]pyrrole hybrid ion pair receptor bearing an indane substituent at a beta-pyrrolic position has been prepared. On the basis of solution phase UV-vis spectroscopic analysis and H-1 NMR spectroscopic studies carried out in 10% methanol in chloroform, receptor 1 is able to bind only cesium ion pairs (e.g., CsF, CsCl, and CsNO3) but not the constituent cesium cation (as its perchlorate salt) or the F-, Cl-, or NO3- anions (as the tetrabutylammonium salts). It thus displays rudimentary AND logic gate behavior. Receptor 1 shows a colorimetric response to cesium ion pairs under conditions of solid-liquid (nitrobenzene) and liquid-liquid (D2O-nitrobenzene-d(s)) extraction.