Synthesis, Spectroscopic and Computational Studies of Charge-Transfer Complexation Between 4-Aminoaniline and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Lakkadi, Arunapriya; Baindla, Naveen; Tigulla, Parthasarathy

doi:10.1007/s10953-017-0685-9

Cited by 20 publications

(6 citation statements)

References 28 publications

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“…The ( Figure 2 b) represents photometric titration plots in both polar solvents. 24 Here, the results from both ACN and MeOH indicates the molar ratio of [(4-DMAP)/(DDQ)] complex is 1:1.…”

Section: Results and Discussionmentioning

confidence: 91%

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New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

et al. 2021

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A combined experimental and theoretical study of the electron donor 4-dimethylaminopyridine (4-DMAP) with the electron acceptor 2, 3-dichloro-5, 6-dicyano- p -benzoquinone (DDQ) has been made in acetonitrile (ACN) and methanol (MeOH) media at room temperature. The stoichiometry proportion of the charge transfer (CT) complex was determined using Job’s and photometric titration methods and found to be 1:1. The association constant ( K CT ), molar absorptivity (ε), and spectroscopic physical parameters were used to know the stability of the CT complex. The CT complex shows maximum stability in a high-polar solvent (ACN) compared to a less-polar solvent (MeOH). The prepared complex was characterized by Fourier transform infrared, NMR, powder X-ray diffraction, and scanning electron microscopy–energy-dispersive X-ray analysis. The nature of DNA binding ability of the complex was probed using UV–visible spectroscopy, and the binding mode of the CT complex is intercalative. The intrinsic binding constant ( K b ) value is 1.8 × 10 6 M –1 . It reveals a primary indication for developing a pharmaceutical drug in the future due to its high binding affinity with the CT complex. The theoretical study was carried out by density functional theory (DFT), and the basis set is wB97XD/6-31G(d,p), with gas-phase and PCM analysis, which supports experimental results. Natural atomic charges, state dipole moments, electron density difference maps, reactivity parameters, and FMO surfaces were also evaluated. The MEP maps indicate the electrophilic nature of DDQ and the nucleophilic nature of 4-DMAP. The electronic spectrum computed using time-dependent DFT (TD-DFT) via a polarizable continuum salvation approach, PCM/TD-DFT, along with natural transition orbital analysis is fully correlated with the experimental outcomes.

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“…The ( Figure 2 b) represents photometric titration plots in both polar solvents. 24 Here, the results from both ACN and MeOH indicates the molar ratio of [(4-DMAP)/(DDQ)] complex is 1:1.…”

Section: Results and Discussionmentioning

confidence: 91%

“…Similar results were obtained when applying Job’s method at 436 and 444 nm in ACN and MeOH solvents. The (Figure b) represents photometric titration plots in both polar solvents . Here, the results from both ACN and MeOH indicates the molar ratio of [(4-DMAP)/(DDQ)] complex is 1:1.…”

Section: Results and Discussionmentioning

confidence: 95%

New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

et al. 2021

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“…The samples form charge transfer (CT) complexes with DDQ in the liquid medium, leading to modifications in their magnetic, dielectric, and optical properties. 55 The outstanding optical sensitivity in visible and ultraviolet areas suggests they could be used in photodetectors and optoelectronic applications.…”

Section: Resultsmentioning

confidence: 99%

Structural, Optical, and Magnetic Properties of Nitrogen-Doped Graphene Oxide Synthesized by Hydrothermal Method

Sreenivas¹,

Suvarna²,

Lavanya³

et al. 2023

ECS J. Solid State Sci. Technol.

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The study examines how different nitrogen doping concentrations affect hydrothermally synthesized graphene oxide's properties using various analytical techniques. Two analytical spectroscopic techniques were used to investigate UV-Visible spectroscopy in dispersed samples, namely bromo phenol blue (BPB) and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The results showed that the doped graphene samples absorb most light in the visible range between 476 and 568 nm in the presence of BPB, and the band gap values obtained using Tauc's formalism ranged from 2.65 to 4.03 eV. In the presence of DDQ reagent, the formation of charge transfer complexes led to sharp absorption peaks in the ultraviolet region around 310 nm wavelength and a range of energy band gap values between 3.77 and 3.98 electron volts. Empirical relations-based calculation of the refractive index (n) for nitrogen-doped graphene displayed optical absorption potential in the visible and UV ranges. Pyrrolic-N bonding dominance in samples was shown by X-ray photoelectron spectroscopy. The VSM results demonstrated that the sample with the highest percentage of Pyrrolic-N exhibited the highest saturation magnetization (0.23 emu/gm) and coercive field (66.6 H Oe). The improved magnetic properties and optical band gap values observed in nitrogen-doped graphene oxide make them promising materials for use in magneto-optical devices.

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“…Job's Continuous Plot of Variation Technique. Job's procedure 28 was followed for the stoichiometric determination of the charge transfer reaction involving OPD and DDQ molecules in selected polar solvents. The highest absorbance at 0.5 mole fraction/DDQ value indicates the development of 1:1 [(OPD)(DDQ)] complex.…”

Section: ■ Conclusionmentioning

confidence: 99%

Charge Transfer Complex betweenO-Phenylenediamine and 2, 3-Dichloro-5, 6-Dicyano-1, 4-Benzoquinone: Synthesis, Spectrophotometric, Characterization, Computational Analysis, and its Biological Applications

et al. 2022

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UV–vis electronic absorption spectroscopy was used to investigate the new molecular charge transfer complex (CTC) interaction between electron donor O -phenylenediamine (OPD) and electron acceptor 2,3-dichloro-5,6-dicyano- p -benzoquinone (DDQ). The CTC solution state analysis was carried out by two different polarities. The stoichiometry of the prepared CTC was determined by using Job’s, photometric, and conductometric titration methods and was detemined to be 1:1 in both solvents (at 298 K). The formation constant and molar extinction coefficient were determined by applying the modified (1:1) Benesi–Hildebrand equation. The thermodynamic parameter Δ G ° result indicated that the charge transfer reaction was spontaneous.The stability of the synthesized CTC was evaluated by using different spectroscopic parameters like the energy, ionization potential, oscillator strength, resonance energy, dissociation energy, and transition dipole moment. The synthesized solid CTC was characterized by using different analytical methods, including elemental analysis, Fourier transform infrared, nuclear magnetic resonance, TGA-DTA, and powder X-ray diffraction. The biological evolution of the charge transfer (CT) complex was studied by using DNA binding and antibacterial analysis. The CT complex binding with calf thymus DNA through an intercalative mode was observed from UV–vis spectral study. The CT complex produced a good binding constant value (6.0 × 10 5 L.mol –1 ). The antibacterial activity of the CT complex shows notable activity compared to the standard drug, tetracycline. These results reveal that the CT complex may in future be used as a bioactive drug. The hypothetical DFT estimations of the CT complex supported the experimental studies.

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Synthesis, Spectroscopic and Computational Studies of Charge-Transfer Complexation Between 4-Aminoaniline and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Cited by 20 publications

References 28 publications

New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

Structural, Optical, and Magnetic Properties of Nitrogen-Doped Graphene Oxide Synthesized by Hydrothermal Method

Charge Transfer Complex betweenO-Phenylenediamine and 2, 3-Dichloro-5, 6-Dicyano-1, 4-Benzoquinone: Synthesis, Spectrophotometric, Characterization, Computational Analysis, and its Biological Applications

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