Isatin‐Triazole‐Functionalized Rhodamine: A Dual Sensor for Cu<sup>2+</sup> and Fe<sup>3+</sup> Ions and Its Application to Cell Imaging

Gahlyan, Parveen; Bawa, Rashim; Jain, Hemant Kumar; Dalela, Manu; Joshi, Ankita; Ramachandran, C.; Prasad, Ashok K.; Kaur, Arunjit; Kumar, Rakesh

doi:10.1002/slct.201901374

Cited by 13 publications

(11 citation statements)

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“…We have synthesized a colorimetric and fluorimetric sensor L1 by Cu(I) catalyzed, click chemistry approach between 3',6'-bis Rhodamine B (1) reacted with hydrazine hydrate in presence of ethanol yielded 2-amino-3',6'-bis(diethylamino) spiro[isoindoline-1,9'-xanthen]-3-one (2) which was then treated with propargyl bromide in presence of K 2 CO 3 to afford 3',6'-bis (diethylamino)-2-(prop-2-yn-1-ylamino)spiro [isoindoline-1,9'-xanthen]-3-one (3). [31] The synthesis of azido glycerol (2-azidopropane-1,3-diol) was successfully obtained using previously reported method. [32][33]…”

Section: Resultsmentioning

confidence: 99%

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu²⁺

et al. 2021

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A glycerol-triazole tethered rhodamine based colorimetric and fluorimetric sensor 3',6'-bis(diethylamino)-2-(((1-(1,3-dihydroxypropan-2-yl)-1H-1,2,3-triazol-4-yl)methylene)aminospiro [isoindoline-1,9'-xanthen]-3-one (L1) is designed and synthesized for the selective recognition of Cu 2 + ion. The sensor L1 allows naked eye detection of Cu 2 + ion with a fast response (< 1 min). Among the various metal ions tested, the sensor L1 shows selective binding with Cu 2 + through turn-on fluorescence mechanism. The sensor shows 1 : 2 binding stoichiometry with binding constant, K a = 1.1 × 10 6 M À 2 as revealed by job's plot & Benesi-Hildebrand plot (BÀ H plot), respectively. The detection limit of L1 with Cu 2 + ion is found to be 3.3 μM. Further, the experimental results are also validated using density functional theoretical (DFT) study. The optimized geometries indicates that the formation of the L1-Cu 2 + complex is thermodynamically favourable by ΔG = À 11.7 kcal/mol. The HOMO-LUMO gap of the ligand L1 is found to be 3.49 eV, which decreases to 1.76 eV upon complexation with copper.

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Section: Resultsmentioning

confidence: 99%

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu²⁺

et al. 2021

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“…To achieve this, the colorimetric and spectral changes of PPS–arginine (10 : 5 μM) were observed in the presence of 5 μM of other amino acids. 28 …”

Section: Methodsmentioning

confidence: 99%

Pyranopyrazole based Schiff base for rapid colorimetric detection of arginine in aqueous and real samples

et al. 2022

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“…Therefore, many researchers have focused on the development of an applicable and reliable approach for the detection of Cu 2+ and Fe 3+ by using a chemosensor. 26 − 28 …”

Section: Introductionmentioning

confidence: 99%

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu²⁺ and Fe³⁺ and Its Application in Drinking Water and Rice Quality Monitoring

et al. 2022

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A spirooxazine derivative, PheSPO (3,3-dimethyl-1-phenethylspiro[indoline-2,3′-naphtho[2,1- b ][1,4]oxazine]), as a dual-sensing probe for Cu 2+ and Fe 3+ was synthesized, and its structure was confirmed by 1 H NMR, 13 C NMR, HRMS, and single-crystal X-ray diffraction. The results reveal that the PheSPO probe is selective to both Cu 2+ and Fe 3+ through distinct colorimetric responses in acetonitrile. The sensing performance of PheSPO toward Cu 2+ was investigated, and upon addition of Cu 2+ , an instant change in color from colorless to bright yellow with a strong absorption band at 467 nm was observed. Due to a dual-sensing behavior, PheSPO also exhibits a unique response toward Fe 3+ that can be discovered from a color change from colorless to red at an absorption wavelength of 514 nm. Based on spectroscopic analyses and density functional theory calculations, the 1:1 stoichiometric complexation of PheSPO with the targeted metal ions was proposed and the binding constants of 1.95 × 10 3 M –1 for Cu 2+ and 1.29 × 10 3 M –1 for Fe 3+ were obtained. In addition, the detection limits of PheSPO for Cu 2+ and Fe 3+ were 0.94 and 2.01 μM, respectively. To verify its applicability in real samples, PheSPO was further explored for quantitative determination of both Cu 2+ and Fe 3+ in spiked drinking water. The results showed that the recoveries of Cu 2+ and Fe 3+ examined using the PheSPO probe were found comparable to those obtained from atomic absorption spectroscopy. Moreover, the PheSPO strip test was developed, and its utilization for qualitative detection of Fe 3+ in real rice samples was demonstrated.

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Isatin‐Triazole‐Functionalized Rhodamine: A Dual Sensor for Cu²⁺ and Fe³⁺ Ions and Its Application to Cell Imaging

Cited by 13 publications

References 69 publications

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu²⁺

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu²⁺

Pyranopyrazole based Schiff base for rapid colorimetric detection of arginine in aqueous and real samples

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu²⁺ and Fe³⁺ and Its Application in Drinking Water and Rice Quality Monitoring

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Isatin‐Triazole‐Functionalized Rhodamine: A Dual Sensor for Cu2+ and Fe3+ Ions and Its Application to Cell Imaging

Cited by 13 publications

References 69 publications

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu2+

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu2+

Pyranopyrazole based Schiff base for rapid colorimetric detection of arginine in aqueous and real samples

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu2+ and Fe3+ and Its Application in Drinking Water and Rice Quality Monitoring

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Product

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Isatin‐Triazole‐Functionalized Rhodamine: A Dual Sensor for Cu²⁺ and Fe³⁺ Ions and Its Application to Cell Imaging

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu²⁺

Glycerol‐Triazole Conjugated Rhodamine as Colorimetric and Fluorimetric Sensor for Cu²⁺

Spirooxazine-Based Dual-Sensing Probe for Colorimetric Detection of Cu²⁺ and Fe³⁺ and Its Application in Drinking Water and Rice Quality Monitoring