New Macrocyclic Diamides as Neutral Ionophores for Highly Selective and Sensitive PVC‐Membrane Electrodes for Be²⁺ Ion

Abstract

Five recently synthesized macrocyclic diamides were investigated to characterize their ability as beryllium ion carriers in potentiometric PVC-membrane electrodes. The electrodes based on 1, 15-diaza-3,4;12,13-dibenzo-5,8,11-trioxabicyclo[13,2,2] heptadecane-2,14-dione exhibited a Nernstian response for Be 2 ion over wide concentration ranges (from 3.0 Â 10 À6 to 3.0 Â 10 À2 M for polymeric membrane electrode, PME, and from 5.0 Â 10 À7 to 2.0 Â 10 À2 M for coated glassy carbon electrode, CGCE) and very low detection limits (2.0 Â 10 À6 M for PME and 4.0 Â 10 À7 M for (CGCE). The electrodes possess low resistances, fast responses, satisfactory reproducibilities and, most importantly, good selectivities relative to a variety of other common cations. The potentiometric response of the electrodes is independent of pH of test solution in the pH range of 4.0 ± 7.5. The proposed sensors were used to determine beryllium ion in water samples.

Highly Selective and Sensitive Membrane Sensors for Copper(II) Ion Based on a New Benzo‐Substituted Macrocyclic Diamide 6,7,8,9,10‐Hexahydro‐2H‐1,13,4,7,10‐benzodioxatriazacyclopentadecine‐3,11(4H,12H)‐dione

“…In recent years we have reported the successful use of some different size lipophilic benzo-substituted macrocyclic diamides as ion carriers in constructions of PVC-based selective electrodes for Cu 2þ [23], Zn 2þ [24], Hg 2þ [25], Sr 2þ [26] and Ca 2þ [27], Cs þ [28], Co 2þ [29], Ag þ [30] and Be 2þ [31]. The in-built configuration rigidity induced by Nsubstituted amides in the periphery of benzo-macrocycles invokes pre-organization leading to ionophoric selectivity of the benzo-substituted macrocyclic diamides incorporated in plasticized PVC-membranes [23 -32].…”

One decade of research on ion-selective electrodes in Iran (1996–2006)

“…As seen in Table 1, most of the alkaline earth metal ions were based on crown ether derivatives [11,[13][14][15][16][17][18]24]. However other compounds like 3,4-di[2-(2-tetrahydro-2H-pyranoxy)] ethoxy styrene-styrene copolymer [12], 2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecane-12-carbaldehyde-12-(2,4-dinitro-phenyl)hy [17], 1,13-diaza-3,4;12,13-dibenzo-5,8,11-trioxabicyclo [13,2,2]heptadecane-2,14-dione [23], a synthesized benzo-9-crown-3 derivative [19], 1,4-diaza-2,3;8,9-dibenzo-7,10-dioxacyclododecane-5,12-dione [20], 2-[(2-hydroxyphenyl)imino]-1,2-diphenylethanone [21], dimethyl-1-(4-nitrobenzoyl)-8-oxo-2,8-dihydro-1H-pyrazolo [5,1-a] iso-indole-2,3-dicarboxylate [22], 1,13-diaza-2,3;11,12-dibenzo-4,7,10-trioxacyclopentadecane-14,15-dione [23] have also been reported to show selectivities to these ions.…”

“…However other compounds like 3,4-di[2-(2-tetrahydro-2H-pyranoxy)] ethoxy styrene-styrene copolymer [12], 2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecane-12-carbaldehyde-12-(2,4-dinitro-phenyl)hy [17], 1,13-diaza-3,4;12,13-dibenzo-5,8,11-trioxabicyclo [13,2,2]heptadecane-2,14-dione [23], a synthesized benzo-9-crown-3 derivative [19], 1,4-diaza-2,3;8,9-dibenzo-7,10-dioxacyclododecane-5,12-dione [20], 2-[(2-hydroxyphenyl)imino]-1,2-diphenylethanone [21], dimethyl-1-(4-nitrobenzoyl)-8-oxo-2,8-dihydro-1H-pyrazolo [5,1-a] iso-indole-2,3-dicarboxylate [22], 1,13-diaza-2,3;11,12-dibenzo-4,7,10-trioxacyclopentadecane-14,15-dione [23] have also been reported to show selectivities to these ions. The sensors are mostly PMEs, GCEs, and even carbon paste electrodes with near to ideal slopes [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25]. The most sensitive alkaline earth sensor has been reported to be a Sr 2+ sensor having a potential slope of 30 mV dec -1 of concentration, which was based on 1,13-diaza-2,3,11,12-dibenzo-4,7,10-trioxacyclopentadecane 14,15-dione [23] as the selective ion carrier, while the loest detection limit belongs to a Be 2+ selective 2,6-diphenyl-4-benzo-9-crown-3-pyridine sensor that was about 4.0 × 10 -8 M [16].…”

“…Other sensors include Eu 3+ [171,172], Gd 3+ [173][174][175][176], Tb 3+ [177,178], Dy 3+ [179,180], Ho 3+ [181,182], Er 3+ [183], Tm 3+ [184,185], Yb 3+ [186][187][188] PMEs, in addition to one Lu 3+ PME [189] and two uranyl PMEs and GCE [190,191]. The minimum detection limit among all of these sensors is reported to be 7.0 × 10 -8 for uranyl ion [191], which is a 2,2'- …”

Novel PVC-membrane potentiometric sensors based on a recently synthesized sulfur-containing macrocyclic diamide for Cd2+ ion. Application to flow-injection potentiometry

“…The in-built configuration rigidity induced by N-substituted amides present in periphery of benzomacrocycles invokes preorganization leading to ionophoric selectivity [6][7][8]. In past decade, we have synthesized and used several novel benzo-substituted macrocyclic diamide derivatives as suitable ionophores in the preparation of highly selective potentiometric sensors for Zn 2+ [9], Sr 2+ [10,11], Hg 2+ [12], Cs + [13], Ca 2+ [14], Ag + [15], Co 2+ [16], Be 2+ [17], UO 2 2+ [18], Cu 2+ [19].…”