In the present investigation, a series of new aromatic aldehyde based chemosensors (S1-S4) have been sensibly designed and synthesized by the simple condensation reaction and their anion sensing properties were investigated. The compounds were characterized by spectroscopic techniques such as FT-IR, UV–Visible, ¹H NMR, ¹³C NMR and ESI-MS. The probes exhibited high sensitivity and selectivity towards fluoride and cyanide ions over the anions such as Br⁻, HSO⁻₄, Cl⁻, OH⁻, I⁻, NO⁻₂ and NO⁻₃ in dry DMSO and DMSO-water mixture (DMSO: H₂O 9:1 v/v). The binding mechanism of fluorometric chemosensors with Nsingle bondHsingle bondF and Nsingle bondHsingle bondCN ion was determined based on ¹H NMR titration and were also theoretically supported by DFT (Density functional theory) calculation. The stoichiometry and binding constant (Ka) of the host-guest complexes formed were determined by the Benesi–Hildebrand (B–H) plot and Job's method respectively. Finally, economically visible paper-based colorimetric “test stripes” of (S1-S4) were fabricated to the detection of F⁻ and CN⁻ ions in 100% aqueous solution.