Highly sensitive colorimetric and fluorometric anion sensors based on mono and di-calix[4]pyrrole substituted diketopyrrolopyrroles

Four novel deeply coloured and highly fluorescent anion sensors have been developed by coupling calix[4]pyrrole with two different diketopyrrolopyrroles. The sensors showed both colorimetric and fluorometric sensitization by selective anions. Complexation properties of the receptors with anions like halides, acetate, phosphate, sulphate, hydrogen sulphate, perchlorate and cyanide were investigated by UV-vis spectroscopy and fluorescence spectroscopy. Sharp visual colour changes as well as complete fluorescence quenching was observed in the presence of selective anions like fluoride, acetate, phosphate and cyanide. Visual detection of sensing properties was achievable up to anion concentration of 1.15 ppm for detection in visible light and 0.025 ppm under UV light. One of the sensor, namely S1, showed a dramatic colour change in the presence of CN- ion. Furthermore, a cheap and highly efficient procedure for bulk scale synthesis of monoiodo-octamethylcalix[4]pyrrole, which is one of the main building blocks for the design of calix[4]pyrrole based sensors has been developed. (C) 2015 Elsevier B.V. All rights reserved.