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A new flexible anthracene linked benzimidazolium-based receptor 1 has been designed, synthesized and its binding properties have been studied by NMR, UV–vis and fluorescence spectroscopic techniques. While the receptor 1 exhibits a greater change in emission in the presence of tetrabutylammonium dihydrogenphosphate in CH3CN over the other anions studied, iodide is selectively preferred in CHCl3 containing 0.1% CH3CN. Upon complexation of dihydrogen phosphate and iodide, the emission of 1 gradually decreased without showing any other characteristic change in the spectra. Hydrogen bonding and charge–charge interactions interplay simultaneously in a cooperative manner for selectivity in the binding process.