Evaluation of naked-eye sensing and anion binding studies in meso-fluorescein substituted one-walled calix[4]pyrrole (C4P)

Abstract

In this paper, we have design, synthesized and fully characterized a new meso-fluorescein substituted one-walled calix[4]pyrrole (C4P7), obtained from simple and easily available starting materials such as fluorescein, 4-hydroxyacetophenone and pyrrole. The anion sensing studies reveal that the C4P7 system displays selective and sensitive naked-eye sensing towards fluoride, phosphate, and acetate anions with the limit of detection of 4.27 mg L⁻¹, 6.4 mg L⁻¹, and 5.94 mg L⁻¹, respectively. Moreover, the C4P7 receptor displays good results of binding (host–guest, 1 : 1) towards a variety of anions. The 1 : 1 binding stoichiometry was further confirmed by means of Job's plots. TD-DFT calculations showed that the HOMO–LUMO gap decreases in all the complexes (C4P7@anions) in comparison to the free C4P7 system. The authors are of the opinion that this work may provide a good platform to explore calix[4]pyrrole chemistry in the arena of recognition/sensing of biologically significant analytes in future studies.