ESIPT reaction of potential bioactive heterocyclic Schiff base: Atomic visualization coupled with in vitro spectroscopy

Jadhao, Manojkumar; Joshi, Ritika; Kumar, H.M. Suresh; Das, Chayan; Ghosh, Sujit Kumar

doi:10.1016/j.jphotochem.2016.04.020

Cited by 14 publications

(13 citation statements)

References 38 publications

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“…It is pertinient to mention here that the Schiff bases exhibit ESIPT reactions resulting in tautomeric species, especially in non‐polar media [18,55] with a larger Stokes shift. The stokes shift observed in the DHHC molecule is much lesser as compared to the reported ESIPT probes.…”

Section: Resultsmentioning

confidence: 93%

“…Furthermore, in water, the excitation spectra observed monitoring 430 nm emission are excitation independent, indicating that the proton transfer band (at 430 nm) originated from the same ground state species. As a result, the lowest energy emission band at 430 nm in water possibly arises from the keto‐tautomer that is exclusively formed by solvent‐assisted ESPT reaction [18] …”

Section: Resultsmentioning

confidence: 99%

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Water‐Assisted Photoinduced Tautomerization in a Potential Bioactive Semicarbazone Schiff Base

Singh,

Teena,

Ganorkar

et al. 2023

ChemistrySelect

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This article epitomizes the design and synthesis of a potential bioactive Semicarbazone Schiff base (E)‐2‐(4‐(diethylamino)‐2‐hydroxybenzylidene)hydrazine‐1‐carboxamide (DHHC) and its water assisted photoinduced tautomerization. DHHC is feebly emissive in non‐polar solvents but the fluorescence intensity intensifies (at 406 nm) in alcohols possibly due to intermolecular H‐bonding. However, in protic polar water, the scenario is markedly different, the fluorescence intensity decreases a bit as compared to alcohols and the emission maxima shifted from 406 nm to 430 nm probably due to solvent (water) assisted excited state proton transfer reaction (ESPT). In contrast to the reported excited state intramolecular proton transfer reaction (ESIPT) in various compounds, DHHC on photoexcitation loses a proton from its phenolic ‐OH group to the water molecule, which insists a subsequent proton transfer from the hydronium ion to the imine nitrogen of DHHC resulting 24 nm red‐shifted fluorescence emission from the tautomeric species of DHHC, in aqueous media. The mechanism of ESPT reaction is explained theoretically through the reaction kinetics of the DHHC‐water complex (in ratio 1 : 3) in an explicit CPCM solvent model. The illustration of the findings may open up enormous possibilities for Semicarbazone Schiff bases to be used as a probe for water sensing inside biomacromolecules like proteins and enzymes.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Water‐Assisted Photoinduced Tautomerization in a Potential Bioactive Semicarbazone Schiff Base

Singh,

Teena,

Ganorkar

et al. 2023

ChemistrySelect

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“…The optimized geometries of bis-NAPPD and bis-NAPPD-Al 3+ complex are shown in Figure 11 All of these data indicate that this optimized structure could form intramolecular hydrogen bonds and generate an ESIPT process. [44][45][46] In the complex, the central Al 3+ ion is tetracoordinated with N1, N2, and the deprotonated O1 and O2 of the bis-NAPPD ligand. The bond distances of Al−O1, Al−O2, Al−N1, and Al−N2 are 1.757, 1.760, 1.978, and 1.945 Å, respectively.…”

Section: Density Functional Theory Studiesmentioning

confidence: 99%

Novel 2‐hydroxynaphthalene‐based fluorescent turn‐on sensor for highly sensitive and selective detection of Al³⁺ and its application in imaging in vitro and in vivo

Wang

Zou

et al. 2020

Applied Organom Chemis

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Excessive aluminum exposure in the human body has been held responsible for multiple adverse effects, and existing data underscore the significance of aluminum detection in environmental and biological systems. Developing high‐performance Al3+ fluorescent chemosensors can revolutionize our understanding of the physiological and pathological processes of Al3+ ions. Herein, we reported a highly sensitive and selective Schiff base fluorescence sensor, bis‐NAPPD (1,1'‐((1E,1'E)‐(pyridine‐2,3‐diylbis(azanylylidene))bis(methanylylidene))bis(naphthalen‐2‐ol)), which can recognize Al3+ ions and exhibits a remarkable turn‐on dual emission response (by ~23 fold) with a low nanomolar level detection limit (1.67 × 10−8 M) in methanol. Furthermore, the binding behavior and the turn‐on fluorescence probing mechanism of bis‐NAPPD were illustrated in detail by UV–vis titration, 1H NMR, and ESI‐MS spectroscopy as well as density functional theory calculations. Notably, bis‐NAPPD showed great potential for tracing Al3+ distribution in cells and living zebrafish larvae, and can also be applied in the fluorimetric detection of aluminum in sucralfate tablets with good precision and satisfactory accuracy, which may represent a promising Al3+ probe in bioimaging and biomedical applications.

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“…Herein, we report two new cobalt( ii ) complexes based on a ligand system that has been well studied in terms of its spectroscopic properties. 14–16 Both complexes show pseudotetrahedral coordination at the cobalt( ii ) ion with negligible dihedral twist distortion of the two chelate planes. Nonetheless, comparatively large magnetic anisotropy barriers are observed to reported SIMs with absent dihedral twist, 8 which is also evidenced by frequency-domain Fourier-transform (FD-FT) THz-EPR spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

Kink distortion of the pseudo-S₄ axis in pseudotetrahedral [N₂O₂] bis-chelate cobalt(ii) single-ion magnets leads to increased magnetic anisotropy

Lima¹,

Pohle²,

Böhme³

et al. 2023

Dalton Trans.

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ESIPT reaction of potential bioactive heterocyclic Schiff base: Atomic visualization coupled with in vitro spectroscopy

Cited by 14 publications

References 38 publications

Water‐Assisted Photoinduced Tautomerization in a Potential Bioactive Semicarbazone Schiff Base

Water‐Assisted Photoinduced Tautomerization in a Potential Bioactive Semicarbazone Schiff Base

Novel 2‐hydroxynaphthalene‐based fluorescent turn‐on sensor for highly sensitive and selective detection of Al³⁺ and its application in imaging in vitro and in vivo

Kink distortion of the pseudo-S₄ axis in pseudotetrahedral [N₂O₂] bis-chelate cobalt(ii) single-ion magnets leads to increased magnetic anisotropy

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ESIPT reaction of potential bioactive heterocyclic Schiff base: Atomic visualization coupled with in vitro spectroscopy

Cited by 14 publications

References 38 publications

Water‐Assisted Photoinduced Tautomerization in a Potential Bioactive Semicarbazone Schiff Base

Water‐Assisted Photoinduced Tautomerization in a Potential Bioactive Semicarbazone Schiff Base

Novel 2‐hydroxynaphthalene‐based fluorescent turn‐on sensor for highly sensitive and selective detection of Al3+ and its application in imaging in vitro and in vivo

Kink distortion of the pseudo-S4 axis in pseudotetrahedral [N2O2] bis-chelate cobalt(ii) single-ion magnets leads to increased magnetic anisotropy

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Novel 2‐hydroxynaphthalene‐based fluorescent turn‐on sensor for highly sensitive and selective detection of Al³⁺ and its application in imaging in vitro and in vivo

Kink distortion of the pseudo-S₄ axis in pseudotetrahedral [N₂O₂] bis-chelate cobalt(ii) single-ion magnets leads to increased magnetic anisotropy