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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 1 H NMR, 13 C 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−H 2 O 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 chargetransfer (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 +

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