The efficient synthesis of four mesitylene-based receptors 1-4 and their potentiometric response characteristics to alkali metal, alkaline earth metal, and transition metal ions, under various pH conditions are outlined. Receptor 1-based electrode exhibited more sensitive response to Ag+ ion (49 mV/decade of range from 10-6 to 10-2 M) than the 2-based electrode (47 mV/decade of range from 3 ´ 10-5 to 10-2 M), while the 3- and 4-based ones revealed sub-Nernstian below 40 mV/pAg+. All electrodes showed substantial responses to Ag+ ion under acidic condition, but there was almost nil-response to other transition metal ions (Fe2+, Co2+, Zn2+, Ni2+, Pb2+, Cd2+, Cu2+ and Hg2+). The association constant of receptor 1 toward Ag+ ion, measured by 1H NMR titration, showed the largest value (200 M-1) among the tested receptors. The results were interpreted with semi empirically-modeled structures.