Tetrasubstituted cyclopentenone‐based fluorescent chemosensors for the selective detection of Fe<sup>3+</sup> and Cu<sup>2+</sup> ions

Balachandran, Aswathy L.; Deepthi, Ani; Suneesh, Chettiyam Veettil

doi:10.1002/bio.3695

Cited by 14 publications

(6 citation statements)

References 58 publications

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“…The slight increase in τ avg1 of Fe(III)– FCP4 compared to that of FCP4 confirmed the enhancement of rigidity through Fe(III) coordination (Table S22). Notably, IRF provided the best fit to the experimental data, as seen clearly from the residual plots (Figure S25). The Stern–Volmer constants ( K sv ) were 6.82 × 10 3 and 2.44 × 10 3 M –1 at λ em1 and λ em2 , respectively (Figures d and S24c–e).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

Mitra,

Sanfui,

Roy

et al. 2023

Macromolecules

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The design, synthesis, and optimization of excited-state intramolecular proton transfer (ESIPT)-associated dual-emissive aliphatic conductive polymer is one of the very challenging tasks, and has not been reported to date. Herein, aliphatic fluorescent conducting polymers (FCPs) are synthesized by polymerizing N-(monomethylol)acrylamide (MMA), acrylic acid (AA), and in situ-generated 3-N-(monomethylolacrylamido)propanoic acid (NMMAPA). Of different FCPs, the maximum population of heteroatomic nontraditional luminophores, i.e., secondary amide (−CONH), imidol (−CN(OH)), tertiary amide (−CON), and carboxylic acid (−COOH), in FCP4 is supported by the spectroscopic analyses, thermal profiles, fluorescence enhancements, and computational calculations. Thus, further investigations are made on FCP4 to explore the photophysical properties, check the suitability in dual metal ion sensing, and study the proton conductivity. The ESIPT-associated dual light emissions at 436 nm (λem1) and 573/617 nm (λem2) originate from FCP4 (amide)/FCP4 (amide)-aggregate and FCP4 (imidol)/FCP4 (imidol)-aggregate, respectively, and are supported by concentration-dependent emissions, time-correlated single photon counting studies, solvent polarity effects, and computational measurements. Regarding this, the high fluorescence quantum yields of 0.68 and 0.18 at λem1 and λem2, respectively, confirmed the ESIPT-associated strong dual emissions of FCP4. The UV spectrum within 264–300 nm, FTIR peak at 2165 cm–1, binding energies of −CN(OH)/–CN(OH) at 399.0/533.4 eV, and computational studies indicate the coexistence of FCP4 (amide)/FCP4 (amide)-aggregate and FCP4 (imidol)/FCP4 (imidol)-aggregate forms of FCP4. In FCP4, −CONH/–CN(OH)/–CON/–COOH/–CH2OH-associated dipolar and hydrogen-bonding interactions, n−π* transitions, and N-branching-associated rigidity contribute to ESIPT-associated amide–imidol phototautomerism, aggregation-enhanced emissions, dual light emissions, metal ion sensing, and conductivity. The strong coordinations of Fe(III) and Cr(III) with FCP4 (amide) and FCP4 (imidol), respectively, are supported by spectroscopic, thermal, and computational studies. The strong quenching efficiencies of Fe(III) and Cr(III) are indicated by the very low limits of detection of 0.1142 and 0.0534 ppb, respectively. The I–V and ac impedance spectroscopy data of FCP4 having 0.28 cm thickness and 1.72 cm2 area indicate high proton conductivities of 3.53 × 10–5 and 3.22 × 10–5 S cm–1 at pH = 7.0 and 8.0, respectively.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

Mitra,

Sanfui,

Roy

et al. 2023

Macromolecules

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“…The detection of specific metal ions using a chemosensor is a dynamic and interesting area at this time due to their environmental, clinical, biological, and practical applications. [ 1–3 ] Most metal ions make necessary contributions to determining and resolving anatomical functions in living systems; however, excessive quantities can cause toxic effects on human health and the environment. [ 4,5 ] An important trace element, nickel (Ni), plays a vital role in living organisms especially in the respiratory system, metabolism, and biosynthesis, with the addition of various industrial and commercial applications such as in nickel–cadmium (Ni–Cd) batteries, as precursors for catalysts, in paint as a pigment, and for machinery, electroplating, welding, utensils, etc.…”

Section: Introductionmentioning

confidence: 99%

2‐Amino‐5‐substituted‐1,3,4‐oxadiazole as chemosensor for Ni(II) ion detection: antifungal, antioxidant, DNA binding, and molecular docking studies

et al. 2022

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An oxadiazole derivative 2 was prepared by condensation reaction through cyclization of semicarbazone in the presence of bromine; the structural confirmation was supported by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, Fourier transform‐infrared spectroscopy, and liquid chromatography‐mass spectrometry. Its sensing ability towards Ni2+ ion was examined showing a binding constant of 1.04 × 105 compared with other suitable metal cations (Ca2+, Co2+, Cr3+, Ag+, Pb2+, Fe3+, Mg2+, and K+) using ultraviolet–visible (UV–vis) and fluorescence spectroscopic studies. The minimum concentration of Ni2+ ions and limit of detection was found to be 9.4 μM. A job's plot gave the binding stoichiometry ratio of oxadiazole derivative 2 vs Ni2+ ions as 2:1. Furthermore, the intercalative binding mode of oxadiazole derivative 2 with calf thymus DNA was supported by ultraviolet–visible (UV–vis) and fluorescent light, viscosity, cyclic voltammetry, time‐resolved fluorescence, and circular dichroism measurements. The molecular docking result gave the binding score for oxadiazole derivative 2 as −6.5 kcal/mol, which further confirmed the intercalative interaction. In addition, the antifungal activity of oxadiazole derivative 2 was also screened against several fungal strains (C. albicans, C. glabrata, and C. tropicalis) by broth dilution and disc diffusion methods. In antioxidant studies, the oxadiazole derivative 2 showed potential scavenging activity against 2,2‐diphenyl‐1‐picrylhydrazyl and H2O2 free radicals.

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“…Excessive accumulation of heavy metal ions (such as Cr 3+ , Hg 2+ , Cd 2+ , Cu 2+ , Ag + ) in water and soil with rapid industrial growth is causing harm to the health of living organisms and human body. [ 1–5 ] Among these heavy metal ions, copper ion is special as it is an essential trace element in the human body. Deficiency in copper ions can cause impaired growth, osteoporosis, and bone abnormalities.…”

Section: Introductionmentioning

confidence: 99%

One‐step preparation of red‐emitting carbon dots for visual and quantitative detection of copper ions

et al. 2020

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A one‐step solvothermal method for the preparation of carbon dots with red fluorescence (R‐CDs) was put forward, in which sodium citrate and formamide were chosen as precursors, while formamide was adopted as the solvent. The fluorescence emission peak of the as‐prepared R‐CDs remained the same (600 nm) when the excitation wavelength increased from 490 nm to 560 nm, and the fluorescence quantum yield is 35.3%. Furthermore, the fluorescence intensity of the as‐prepared R‐CDs could be selectively quenched by copper ions, and the mechanism of Cu2+ quenching R‐CDs is the combination of static and dynamic quenching. As a result, the R‐CDs were applied for the construction of a fluorescent sensor without any modification for the quantitative and visual detection of copper ions, which is a typical contaminant in water. The limit of detection for the fluorescent sensor was as low as 5 nmol/L, and it can be used to fast and directly confirm whether the content of copper ions in drinking water meets the criteria of the United States Environmental Protection Agency and the World Health Organization.

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Tetrasubstituted cyclopentenone‐based fluorescent chemosensors for the selective detection of Fe³⁺ and Cu²⁺ ions

Cited by 14 publications

References 58 publications

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

2‐Amino‐5‐substituted‐1,3,4‐oxadiazole as chemosensor for Ni(II) ion detection: antifungal, antioxidant, DNA binding, and molecular docking studies

One‐step preparation of red‐emitting carbon dots for visual and quantitative detection of copper ions

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Tetrasubstituted cyclopentenone‐based fluorescent chemosensors for the selective detection of Fe3+ and Cu2+ ions

Cited by 14 publications

References 58 publications

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

Synthesis of Intrinsically Dual-Emissive Aliphatic Conducting Polymer and ESIPT-Associated Switching of Amide-Aggregate to Imidol-Aggregate for Sensing of Cr(III) and Fe(III)

2‐Amino‐5‐substituted‐1,3,4‐oxadiazole as chemosensor for Ni(II) ion detection: antifungal, antioxidant, DNA binding, and molecular docking studies

One‐step preparation of red‐emitting carbon dots for visual and quantitative detection of copper ions

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Tetrasubstituted cyclopentenone‐based fluorescent chemosensors for the selective detection of Fe³⁺ and Cu²⁺ ions