Rhodamine based chemosensor for trivalent cations: Synthesis, spectral properties, secondary complex as sensor for arsenate and molecular logic gates

Dey, Sudipto; Sarkar, Subhashis; Maity, Dinesh; Roy, Partha

doi:10.1016/j.snb.2017.02.094

Cited by 75 publications

(26 citation statements)

References 72 publications

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“…Specifically, such compounds have been studied as dark or light‐controlled chemosensors for metal ions and Al 3+ in particular . There is always a demand for reliable and facile sensors for salts and compounds of Al …”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11][12][13][14][15] There is always a demand for reliable and facile sensors for salts and compounds of Al. [16][17][18][19][20] The focus of our research was the kinetics and mechanism of complex formation of Al 3+ with 1',3',3'trimethylspiro[2H-1-benzopyran-2,2'-indoline] (SP)/MC in ethanol (EtOH), methanol (MeOH), and MeOH/H 2 O mixtures (up to 0.5 mole fraction). Previous studies of spirocompounds as chemosensors for Al 3+ demonstrated the formation of relatively labile complexes (LCs) МС-Al 3+.…”

Section: Introductionmentioning

confidence: 99%

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New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

Levin

Belikov

Левина

et al. 2019

J of Physical Organic Chem

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Ultraviolet‐visible (UV‐vis) absorption, flash photolysis, and 1H and 13C NMR spectroscopy were used to investigate the mechanism of formation and structure of complexes in the 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (SP, also well known as BIPS) with Al3+ (inorganic salts) in ethanol (EtOH), methanol (MeOH), and in aqueous MeOH solutions. A labile (equilibrium constants ≤ 5000 M−1) complex of SP and Al3+ with broad absorption band in the UV‐vis with λmax = 380 nm appeared promptly in the presence of an excess of Al3+. The slow formation of a stable complex (SC) between Al3+ and two merocyanine (MC) forms of SP with an intensive absorption band at λmax = 430 nm is observed with a yield of 1.0 upon keeping the solutions of these two compounds at constant concentration ratio [Al3+] ≥[SP]/2 in the dark. The rate constants of such SC formation were close to the corresponding rate constant of the transformation of SP into MC in the dark (5.0×10−5‐1×10‐3 s‐1, depending upon the solvent). The photolysis of the SC with visible light (λ > 400 nm) results in the total conversion of the SC into SP. The SC forms promptly after the addition of Al3+ at concentrations of the same order as those of MC. This method allows detection of [Al3+] to concentrations as low as 50 nM. The kinetics and thermodynamic parameters of the SP and MC reactions and of their complex formation with Al3+ are discussed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

Levin

Belikov

Левина

et al. 2019

J of Physical Organic Chem

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“…Whereas systems 1 (Figure ) and 2 (Figure ), and the various other kinetically controlled molecular keypad locks that respond to chemical inputs demonstrate well the generality of this approach, they also reveal a few limitations of this technology. The difficulty of predicting the relative stability of the metastable species, for example, complicates rational design, whereas using an excitation beam as an additional input provides an inelegant means of enhancing password lengths without improving the efficiency of the molecular “processor”.…”

Section: Molecular Logic Gate‐based User Authorization Systemsmentioning

confidence: 99%

“…The latter are macroscopic analytical devices that, similar to the way the olfactory system operates, can interact non‐specifically with a wide range of analytes and discriminate among them by creating a wide range of unique identification patterns . Hence, the main difference between 8 and the molecular keypad locks discussed before is that instead of generating a single digital output (0 or 1) for each code entry, it associates each password with a unique emission “signature” that enables it to authorize multiple users.…”

Section: User Authorization By Pattern‐generating Fluorescent Molecumentioning

confidence: 99%

User Authorization at the Molecular Scale

2017

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Electronic user authorization systems help us maintain our privacy in many aspects of everyday life. However, the increasing difficulty to secure access and/or information digitally has inspired chemists to devise alternative, molecular approaches, in which users are identified by chemical means. The potential advantages of using molecular user authentication systems over conventional electronic devices are their versatility and unusual operating principles, which complicate replicating and, consequently, breaking into molecular security devices. Their molecular scale is another unique property that enables hiding such systems and, consequently, applying steganography as an additional layer of protection. Although the area of molecular‐based user authorization is still in its infancy, the development of various molecular keypad locks and, more recently, a password‐protected molecular cryptographic machine, indicate the possibility of protecting information at the molecular scale.

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“…We therefore examined the existing chemical sensors developed for Pi detection, as a novel sensing scaffold for arsenate detection. Our developed binuclear zinc complex served as the first turn-on fluorescence molecular sensor for arsenate under neutral aqueous solution [11][12][13][14][15] . However in the arsenate-phosphate coexisting environment, a novel strategy which can suppress the Pi detection while maintaining the arsenate sensing capability would be definitely required.…”

mentioning

confidence: 99%

Masking Phosphate with Rare-Earth Elements Enables Selective Detection of Arsenate by Dipycolylamine-ZnII Chemosensor

Mekjinda

Phunnarungsi

Ruangpornvisuti

et al. 2020

Sci Rep

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Functional reassessment of the phosphate-specific chemosensors revealed their potential as arsenate detectors. A series of dipicolylamine (Dpa)-Zn ii chemosensors were screened, among which acridine Dpa-Zn ii chemosensor showed the highest capability in sensing arsenate. the presence of excess Zn ii improved sensitivity and strengthened the binding between acridine Dpa-Zn ii complex to arsenate as well as phosphate. However, due to their response to phosphate, these sensors are not suited for arsenate detection when phosphate is also present. This study demonstrated for the first time that rare-earth elements could effectively mask phosphate, allowing the specific fluorescence detection of arsenate in phosphate-arsenate coexisting systems. in addition, detection of arsenate contamination in the real river water samples and soil samples was performed to prove its practical use. this sensor was further employed for the visualization of arsenate and phosphate uptake in vegetables and flowering plants for the first time, as well as in the evaluation of a potent inhibitor of arsenate/phosphate uptake. Arsenic is a chemical analog of phosphorus that belongs to the same periodic group and shares a number of similarities with phosphorus, including the same number of valence electrons and nearly identical electronegativity (2.18 for As and 2.19 for P) 1. Phosphorus-and arsenic-derived oxoanions, importantly inorganic phosphate (Pi) and arsenate, also exhibit similar properties 2 , such as tetrahedral geometry and close bond lengths (1.69A° and 1.52A° for arsenate (HAsO 4 −) and phosphate (HPO 4 −), respectively) 3 Their acid counterparts also have similar dissociation constants (pK a 2.26, 6.76, and 11.29 for the arsenic acid compared with 2.16, 7.21, and 12.32 for phosphoric acid) 1 , thus possessing the same net charge acr.oss pH values. These salient physiochemical similarities to phosphate make arsenate highly toxic to humans. In addition, arsenate is a confirmed carcinogen and the most significant chemical contaminant in drinking-water worldwide 4. Detection of arsenate has been conventionally conducted by atomic absorption spectrometry (AAS) and inductively coupled plasma mass spectrometry (ICPMS) 5-10. However, the techniques require laborious sample preparation and cannot be employed to visualize biological phenomena in situ. To overcome this problem, several arsenate-specific chemosensors were developed 11-15 , but they were only compatible with organic or aqueous-organic media and can be unstable in water 16. Egdal et al. (2009) reported the divanadyl complex which was able to selectively bind to arsenate over Pi in aqueous solution, but it was optimal at a slightly acidic pH (pH = 3) 17. Therefore, for the purpose of arsenate detection in drinking water and biological systems, a chemosensor that is stable in neutral aqueous solution would be more attractive. Because of the significant roles in biological and environmental systems of the Pi anion, considerable efforts have been devoted to developing methods to d...

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Rhodamine based chemosensor for trivalent cations: Synthesis, spectral properties, secondary complex as sensor for arsenate and molecular logic gates

Cited by 75 publications

References 72 publications

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

User Authorization at the Molecular Scale

Masking Phosphate with Rare-Earth Elements Enables Selective Detection of Arsenate by Dipycolylamine-ZnII Chemosensor

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Rhodamine based chemosensor for trivalent cations: Synthesis, spectral properties, secondary complex as sensor for arsenate and molecular logic gates

Cited by 75 publications

References 72 publications

New stable colored complex of Al3+ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

New stable colored complex of Al3+ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

User Authorization at the Molecular Scale

Masking Phosphate with Rare-Earth Elements Enables Selective Detection of Arsenate by Dipycolylamine-ZnII Chemosensor

Contact Info

Product

Resources

About

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)