Tripodal Squaramide Derivative as a Neutral Chloride Ionophore for Whole Blood and Sweat Chloride Measurement

Fan, Lingling; Xu, Ting-Ting; Feng, Junjun; Ji, Zihan; Li, Le; Shi, Xinhao; Tian, Chunxiu; Qin, Yu

doi:10.1002/elan.201900693

Cited by 9 publications

(8 citation statements)

References 49 publications

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“…Finally, the sensor was used for determining the iodide concentration in pharmaceutical formulations. Fan et al described a tripodal squaramide derivative as a new neutral ionophore for chloride ions . A tripodal structure of this ionophore makes it ideal for accommodating spherical anions, while squaramide groups can form four hydrogen bonds.…”

Section: Sensor Materialsmentioning

confidence: 99%

“…Fan et al described a tripodal squaramide derivative as a new neutral ionophore for chloride ions. 134 A tripodal structure of this ionophore makes it ideal for accommodating spherical anions, while squaramide groups can form four hydrogen bonds. The ionophore-based Cl −selective electrode exhibited a close to Nernstian response slope of 55 mV/decade in the concentration range of 10 −5 − 10 −1 M. The proposed ionophore was found to enhance the selectivity over the salicylate ion with a logarithmic selectivity coefficient estimated by the fixed interference method as low as −0.3.…”

Section: )mentioning

confidence: 99%

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Potentiometric Sensing

2020

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Section: Sensor Materialsmentioning

confidence: 99%

Section: )mentioning

confidence: 99%

Potentiometric Sensing

2020

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“…24 Moreover, the presence of the indole group as a substituent in the structure of acyclic squaramides was demonstrated to cause an enhancement of the anion recognition properties due to the cooperativity of the H-bond donor sites in stabilizing the formation of the host− guest adducts. 25 Based on these considerations, herein, we investigate a novel family of acyclic squaramide-based receptors L1−L5 tested as ionophores for the development of potentiometric sensors for NSAIDs detection in aqueous media through hydrogen-bond formation (Scheme 2). We demonstrate here that the selective potentiometric sensing of NSAIDs can be achieved by incorporating acyclic indolesubstituted squaramide-based ionophores inside solvent PVCbased polymeric membranes with a careful variation of the ionophore/anion-exchanger ratio.…”

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confidence: 99%

“…L1 and L2 were synthesized as previously reported. 25,27 The synthesis of L5 has also been recently described. 28 Receptors L3 and L4 were prepared by modification of the procedure reported in the literature and described in Scheme 3.…”

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confidence: 99%

Potentiometric Sensing of Nonsteroidal Painkillers by Acyclic Squaramide Ionophores

Picci,

Farotto,

Milia

et al. 2023

ACS Sens.

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We report here a small library of a new type of acyclic squaramide receptors (L1−L5) as selective ionophores for the detection of ketoprofen and naproxen anions (KF − and NS − , respectively) in aqueous media. 1 H NMR binding studies show a high affinity of these squaramide receptors toward KF − and NS − , suggesting the formation of H-bonds between the two guests and the receptors through indole and −NH groups. Compounds L1−L5 have been tested as ionophores for the detection of KF − and NS − inside solvent PVC-based polymeric membranes. The optimal membrane compositions were established through the careful variation of the ligand/tridodecylmethylammonium chloride (TDMACl) anion-exchanger ratio. All of the tested acyclic squaramide receptors L1−L5 have high affinity toward KF − and NS − and anti-Hofmeister selectivity, with L4 and L5 showing the highest sensitivity and selectivity to NS − . The utility of the developed sensors for a high precision detection of KF − in pharmaceutical compositions with low relative errors of analysis (RSD, 0.99−1.4%) and recoveries, R%, in the range 95.1−111.8% has been demonstrated. Additionally, the chemometric approach has been involved to effectively discriminate between the structurally very similar KF − and NS − , and the possibility of detecting these analytes at concentrations as low as 0.07 μM with R 2 of 0.947 and at 0.15 μM with R 2 of 0.919 for NS − and KF − , respectively, was shown.

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“…The response of the optodes is based on either ion exchange for cation-selective sensors or coextraction in the case of anion-selective sensors. ,, Numerous attempts at measuring hydrophilic anions such as chloride as well as highly lipophilic anions, such as thiocyanate or perchlorate in complex samples such as human saliva, serum, whole blood, and sweat, have been reported.…”

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confidence: 99%

Influence of Electrolyte Coextraction on the Response of Indicator-Based Cation-Selective Optodes

2020

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Here, we report on systematic investigation of the impact of coextraction of the aqueous electrolyte and anion interference on the response of cation-selective bulk optodes. It is evident that to deliberately manage the properties of chemical sensors and to apply them in routine analysis, one should have exhaustive insight into their operation mechanism. Despite the extensive research in the field of ionophore-based optodes and numerous attempts for their practical application, the understanding of how coextraction of an aqueous electrolyte influences its response characteristics has not been developed thus far. Meanwhile, the electrolyte coextraction determines the detection limits of analogous ion-selective electrodes. A theoretical model based on phase distribution equilibrium is proposed to quantitatively describe the effect of Donnan exclusion failure on the response of polymeric plasticized optodes. The theoretical conclusions are confirmed by the results obtained with Na+/pH-selective optodes based on a neutral chromoionophore as a model system in solutions containing anions of various lipophilicities (Cl–, NO3 –, I–, SCN–, and ClO4 –). For the first time, it is shown that coextraction leads to a significant shift of the response range of the optodes as well as to nonmonotonic response curves due to the transition from cationic to anionic response. An approach to estimate the coextraction constants of electrolytes from the optode response curves is proposed. The limitations in the applicability of optodes due to co-ion interference are explored. It is found that neglecting anion interference can cause dramatic errors in the results of analyses with optical sensors.

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Tripodal Squaramide Derivative as a Neutral Chloride Ionophore for Whole Blood and Sweat Chloride Measurement

Cited by 9 publications

References 49 publications

Potentiometric Sensing

Potentiometric Sensing

Potentiometric Sensing of Nonsteroidal Painkillers by Acyclic Squaramide Ionophores

Influence of Electrolyte Coextraction on the Response of Indicator-Based Cation-Selective Optodes

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