Synthesis of a Calix[4]arene Derivative for Isolation of a Stable Cation Radical Salt for Use as a Colorimetric Sensor of Nitric Oxide

We have designed and synthesized a modified calixarene derivative (1) that allows, for the first time, the isolation of a stable cation radical salt that binds a single molecule of nitric oxide deep within its cavity with remarkable efficiency (KNO >108 M-1), as demonstrated by isolation of a crystalline complex [1, NO]+ and its characterization by X-ray crystallography as well as by optical spectroscopy. Furthermore, the ready accessibility of the calixarene cation radical will allow the exploration of its use for developing efficient sensing devices for nitric oxide based on the accompanied color changes.