Structural characterization of a fluorescein hydrazone molecular switch with application towards logic gates

Villada, Juan D.; D’Vries, Richard F.; Macías, Mario A.; Zuluaga, Fabio; Chaur, Manuel N.

doi:10.1039/c8nj03817a

Cited by 12 publications

(6 citation statements)

References 56 publications

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“…Due to the relative rigidity of the Class a structure, the only possible way to bring metal centres of the two Pt(NCN) units to a distance of ∼3 Å is by bending the xanthene unit at the central C–O axis to give the S 0 -dimer structures. Formation of the bent conformer of xanthene has been reported earlier, 75 while similar bent conformers have been postulated or observed experimentally in analogous systems, such as in phenothiazine derivatives. 76…”

Section: Resultssupporting

confidence: 80%

Rigidly linked dinuclear platinum(ii) complexes showing intense, excimer-like, near-infrared luminescence

Pander,

Walden,

Salthouse

et al. 2023

J. Mater. Chem. C

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Section: Resultssupporting

confidence: 80%

Rigidly linked dinuclear platinum(ii) complexes showing intense, excimer-like, near-infrared luminescence

Pander,

Walden,

Salthouse

et al. 2023

J. Mater. Chem. C

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“…There was an ambiguity about whether the molecule might undergo a ring-opening of lactam in the Fe complex state as the ligand RSD-1 resembles rhodamine derivatives [64][65][66][67] (there are a few reports on rhodamine-based sensors that followed the spirolactam ring closed chelation mechanism). [68][69][70][71][72][73] In the case of spirolactam ring-opened sensors, the complex system showed the formation of a new band over 550 or 600 nm ranges in absorbance and emission. In the present system during complex formation there was no long shift in absorbance and the fluorescence emission was obtained around 420-455 nm.…”

Section: Binding Propertiesmentioning

confidence: 99%

Anthrone‐spirolactam and quinoline hybrid based sensor for selective fluorescent detection of Fe³⁺ ions

Darole

Leslee²,

Mukherjee

et al. 2020

Applied Organom Chemis

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The synthesis of a novel, and highly selective Fe3+ ion sensor based on anthrone‐spirolactam and its quinoline hybrid ligand is reported. The designed ligand displayed selective detection of Fe3+ ions with enhanced fluorescence emission. The complexation of Fe3+ ion led to a red shift of 32 nm from 420 nm to 452 nm, and a several fold increase in intensity with fluorescent green emission. The complexation (detection) of Fe3+ ions with ligand resulted in chelation enhanced fluorescence and intramolecular charge transfer through the inhibition of C=N isomerization. This hybrid sensor shows high sensitivity and selectivity, spontaneous response, and works on a wide pH range a minimum detection limit of 6.83 × 10−8 M. Importantly, the sensor works through the fluorescence turn‐on mechanism that overcomes the paramagnetic effect of Fe3+ ions. The binding mechanism between the ligand and the Fe3+ ions was established from the Job's plot method, optical studies, Fourier transfor infrared spectroscopy, NMR titration, fluorescence life‐time studies, and density functional theory optimization. The sensor displayed excellent results in the quantification of Fe3+ ions from real water samples. Furthermore, due to its biocompatibility nature, fluorescent spotting of Fe3+ ions in live cells revealed its bioimaging applications.

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“…The E→Z isomerization can also be accompanied by forming a weak coordination complex followed by the simultaneous release of the cation. The E→Z isomerization results from two different mechanisms, rotation, and inversion [ 24 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

et al. 2022

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The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activity of the Schiff base 4,4′-((1E,1′E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (compound 2). We have also isolated the side product compound 1 and characterized it using single X-ray crystallography. The crystal structure of compound 1 depicts that the ensuing C‒H···N hydrogen bonding interaction is presented and discussed herein. In addition, the calculations using density functional theory (DFT) approximation supported by experimental 1H and 13C NMR studies on the key compound 2 are reported. The results of theoretical and experimental 1H and 13C NMR were concordant. The antioxidant activity of compound 2 was determined by using 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS•+) radical cation assays and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Compound 2 demonstrated excellent antioxidant activity in ABTS assay (IC50 = 4.30 ± 0.21 µM) and DPPH assay (IC50 = 81.06 ± 0.72 µM) with almost no cytotoxicity below 25 µM.

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Structural characterization of a fluorescein hydrazone molecular switch with application towards logic gates

Cited by 12 publications

References 56 publications

Rigidly linked dinuclear platinum(ii) complexes showing intense, excimer-like, near-infrared luminescence

Rigidly linked dinuclear platinum(ii) complexes showing intense, excimer-like, near-infrared luminescence

Anthrone‐spirolactam and quinoline hybrid based sensor for selective fluorescent detection of Fe³⁺ ions

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

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Structural characterization of a fluorescein hydrazone molecular switch with application towards logic gates

Cited by 12 publications

References 56 publications

Rigidly linked dinuclear platinum(ii) complexes showing intense, excimer-like, near-infrared luminescence

Rigidly linked dinuclear platinum(ii) complexes showing intense, excimer-like, near-infrared luminescence

Anthrone‐spirolactam and quinoline hybrid based sensor for selective fluorescent detection of Fe3+ ions

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

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Product

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About

Anthrone‐spirolactam and quinoline hybrid based sensor for selective fluorescent detection of Fe³⁺ ions