A new highly selective “off–on” typical chemosensor of Al3+, 1-((Z)-((E)-(3,5-dichloro-2-hydroxybenzylidene)hydrazono)methyl) naphthalene-2-ol, an experimental and in silico study

Anshori, Jamaludin Al; Ismalah, Daliah; Abror, Ajar Faflul; Zainuddin, Achmad; Yusuf, Muhammad; Maharani, Rani; Hidayat, Ace Tatang

doi:10.1039/d1ra08232a

Cited by 16 publications

(7 citation statements)

References 58 publications

(89 reference statements)

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“…There are several chemosensors for Al 3+ in the literature. 11,13,[44][45][46][47][48][49][50][51][52][53][54][55] Some parameters of recently published chemosensors for Al 3+ are summarized in Table 1. Most of them have been synthesized by Schiff-base condensation reactions (exception: entry 5).…”

Section: Comparative Discussionmentioning

confidence: 99%

Imaging of Al³⁺in plant roots by the interaction with a bisphenol A-based chemosensor

et al. 2023

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Section: Comparative Discussionmentioning

confidence: 99%

Imaging of Al³⁺in plant roots by the interaction with a bisphenol A-based chemosensor

et al. 2023

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“…To understand the ground state and excited state behaviors of the receptor OX(HA) 2 and their complexes were acquired by carrying out the calculations for Density Functional Theory (DFT) with the Gaussian 09 software package [42] . For the geometry optimization calculations, the effective core potential LanL2DZ basis sets were assigned to the nonmetal elements (C, H, O, N, and S) and the metal elements, respectively, using Becke's three‐parameter exchange functions (B3) and the Lee‐Yang‐Parr correlation function (LYP) [43] …”

Section: Methodsmentioning

confidence: 99%

Oxalohydrazide‐Based Chemosensor for Detection of Cu²⁺/Fe³⁺ Ions and Its Application in Live Cell Imaging

Murugaperumal,

Rajendran,

Nallathambi

et al. 2024

ChemistrySelect

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The N1,N2‐diphenyloxalohydrazide OX(HA)2 chemosensor was synthesized and used as a colorimetric and fluorescent receptor to detect Cu2+ and Fe3+ ions in the presence of other metal ions. A range of physicochemical approaches were utilized to characterize the symmetrical oxalohydrazide‐based receptor, including FT‐IR, 1H and 13C NMR, TGA, and mass spectrometry. According to single crystal X‐ray diffraction investigation, OX(HA)2 crystallizes in monoclinic with space group C2/c. UV‐Vis and fluorescence spectroscopy were used to thoroughly explore OX(HA)2’s sensing capabilities towards diverse cations. Using measurements of fluorescence intensity, the binding constant for OX(HA)2 with Cu2+/Fe3+ ions was calculated to be 2.78×103 M−1 and 1.12×103 M−1 with the lower detection limit of 0.43 μM and 0.2 μM respectively. With a 1 : 1 binding mechanism validated by Job's plot, mass spectral analysis, FT‐IR spectra, and density functional theory, the dual‐sensing receptor exhibits remarkable selectivity and sensitivity towards Cu2+ and Fe3+ ions. The average fluorescence lifetimes of OX(HA)2, OX(HA)2+Cu2+, and OX(HA)2+Fe3+ were calculated to be 2.19 ns, 1.73 ns, and 1.26 ns, respectively. This fluorescence lifetime measurement results strongly support the complexation of Cu2+ and Fe3+. When Cu2+ and Fe3+ ions bind with OX(HA)2, they induce the ‘Turn‐Off’ signal. Then, fluorescence imaging of the OX(HA)2 receptor in MDA‐MB‐231 demonstrated that the receptor holds a lot of promise for usage in bioimaging and their IC50 value for cytotoxicity is 96.96 μg. Furthermore, fluorescence microscopy experiments demonstrate that OX(HA)2 can be utilized as a fluorescent probe for detecting Cu2+ and Fe3+ ions in living cells, making it potentially helpful as an anticancer medication.

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“…Thus, several groups from all over the world are actively working on the development of fluorescence sensors for the sensing of various metal ions. Various fluorophoric platforms such as naphthalene, [2] coumarin, [3] rhodamine, [4] bisphenol A, [5] pyrene, [6] 2,6-diformyl-4-methyl-phenol, [7] etc. [8] have been used for the construction of chemosensors for different metal ions.…”

Section: Introductionmentioning

confidence: 99%

Detection of the +3 Oxidation State of Metal Ions with the Aid of a Rhodamine‐Based Dye and Applications in Construction of Complex Logic Circuits and Living Cell Imaging

Ghosh,

Hazra,

Bari

et al. 2024

ChemistrySelect

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Detection of correct oxidation state of a metal ion is important to understand its speciation and redox properties. Some of rhodamine derivatives can identify Al3+, Cr3+ and Fe3+ as the trivalent cations. We have synthesized a rhodamine derivative, HL‐qui, from the reaction of N‐(rhodamine‐6G)lactam‐ethylenediamine with quinoline‐2‐carboxaldehyde for the colorimetric as well as fluorogenic detection of all of metal ions with +3 oxidation state such as Al3+, Cr3+, Fe3+, Ga3+, In3+, Tl3+ and Gd3+. In the presence of these trivalent cations, colorless and nonfluorescent HL‐qui turns pink and strongly fluorescent in HEPES buffer (10 mM) in H2O/ethanol=1/9 (v/v) (pH 7.4) as its spirolactam ring gets open to show the changes in color and fluorescence properties. High sensitivity of the probe towards the cations is reflected from the limit of detection values that are in nM range. To the best of our knowledge, there is no such report where fluorescence sensing has been utilized to determine oxidation state. This multi‐ion sensing feature has been used for fabrication of multi input‐output based logic circuit using Boolean algebraic method. It has been used in imaging of metal ions in living cell (L6 cells).

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A new highly selective “off–on” typical chemosensor of Al³⁺, 1-((Z)-((E)-(3,5-dichloro-2-hydroxybenzylidene)hydrazono)methyl) naphthalene-2-ol, an experimental and in silico study

Abstract: A new promising fluorescent chemosensor of Al3+ based on a 2-hydroxynaphthaldehyde skeleton was successfully synthesized through double imine formation and demonstrated excellent sensing properties through the ESIPT inhibition mechanism.

Cited by 16 publications

References 58 publications

Imaging of Al³⁺in plant roots by the interaction with a bisphenol A-based chemosensor

Imaging of Al³⁺in plant roots by the interaction with a bisphenol A-based chemosensor

Oxalohydrazide‐Based Chemosensor for Detection of Cu²⁺/Fe³⁺ Ions and Its Application in Live Cell Imaging

Detection of the +3 Oxidation State of Metal Ions with the Aid of a Rhodamine‐Based Dye and Applications in Construction of Complex Logic Circuits and Living Cell Imaging

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A new highly selective “off–on” typical chemosensor of Al3+, 1-((Z)-((E)-(3,5-dichloro-2-hydroxybenzylidene)hydrazono)methyl) naphthalene-2-ol, an experimental and in silico study

Abstract: A new promising fluorescent chemosensor of Al3+ based on a 2-hydroxynaphthaldehyde skeleton was successfully synthesized through double imine formation and demonstrated excellent sensing properties through the ESIPT inhibition mechanism.

Cited by 16 publications

References 58 publications

Imaging of Al3+in plant roots by the interaction with a bisphenol A-based chemosensor

Imaging of Al3+in plant roots by the interaction with a bisphenol A-based chemosensor

Oxalohydrazide‐Based Chemosensor for Detection of Cu2+/Fe3+ Ions and Its Application in Live Cell Imaging

Detection of the +3 Oxidation State of Metal Ions with the Aid of a Rhodamine‐Based Dye and Applications in Construction of Complex Logic Circuits and Living Cell Imaging

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A new highly selective “off–on” typical chemosensor of Al³⁺, 1-((Z)-((E)-(3,5-dichloro-2-hydroxybenzylidene)hydrazono)methyl) naphthalene-2-ol, an experimental and in silico study

Imaging of Al³⁺in plant roots by the interaction with a bisphenol A-based chemosensor

Imaging of Al³⁺in plant roots by the interaction with a bisphenol A-based chemosensor

Oxalohydrazide‐Based Chemosensor for Detection of Cu²⁺/Fe³⁺ Ions and Its Application in Live Cell Imaging