Positional Isomeric Symmetric Dipodal Receptors Dangled with Rotatable Binding Scaffolds: Fluorescent Sensing of...

Three simple dipodal artificial acyclic symmetric receptors, SDO, SDM, and SDP, driven by positional isomerism based on xylelene scaffolds were designed, synthesized, and characterized by ¹H NMR, ¹³C NMR, and mass spectroscopy techniques. Probes SDO, SDM, and SDP demonstrated selective detection of Ag⁺ metal ions and amino acid l-histidine in a DMSO-H₂O solution (1:1 v/v, HEPES 50 mM, pH = 7.4). The detection of Ag⁺ metal ions occurred in three ways: (i) inhibition of the photoinduced electron-transfer (PET) process, (ii) blueshifted fluorescence enhancement via the intramolecular charge-transfer (ICT) process, and (iii) restricted rotation of the dangling benzylic scaffold following coordination with a Ag⁺ metal ion. Job's plot analysis and quantum yields confirm the binding of probes to Ag⁺ in 1:1, 1:2, and 1:2 ratios with LODs and LOQs found to be 1.3 μM and 3.19 × 10^-7 M, 6.40 × 10^-7 and 2.44 × 10 ^-6 M, and 9.76 × 10^-7 and 21.01 × 10^-7 M, respectively. ¹H NMR titration, HRMS, ESI-TOF, IR analysis, and theoretical DFT investigations were also used to establish the binding stoichiometry. Furthermore, the probes were utilized for the detection of Ag⁺ ions in water samples, food samples, soil analysis, and bacterial imaging in Escherichia coli cells and a molecular logic gate was constructed.