Structural, Electronic and NLO Properties of 6-aminoquinoline: A DFT/TD-DFT Study

Pandey, Nupur; Mehata, Mohan Singh; Pant, Sanjay; Tewari, Neeraj

doi:10.1007/s10895-021-02788-z

Cited by 28 publications

(5 citation statements)

References 57 publications

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“…[60] Moreover, the TICT mechanism is supported by a tiny increase of the energy of the ICT absorption band (Δλ max < 25 nm), in contrast to a large red shift of the emission band as a function of the solvent orientation polarizability (Table 1; Table S3, and Figure S5, Supporting Information). The data in Table 1 and the solvatochromism analysis by the Lippert-Mataga and the Bilot-Kawski models [58,59,61,62] (Tables S4 and S5 and Figures S5 and S6, Supporting Information) suggest that the dipole moment of the ground state (µ g ) is almost insensitive to the solvent polarity, while, that of the excited state (µ e ), is strongly dependent on it. There is, indeed, a significant increase of its value, leading to large dipole moment differences, (Δµ = µ e − µ g ) (Table S6, Supporting Information), in agreement to other similar DAD compounds characterized by greater ICT character in the excited state.…”

Section: Introductionmentioning

confidence: 99%

Vis–NIR Electrochromism and NIR–Green Electroluminochromism in Dual Functional Benzothiadiazole‐Arylamine Mixed‐Valence Compounds

Corrente

González

Aktas

et al. 2022

Advanced Optical Materials

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Electrochromism/electrofluorochromism is the reversible tuning of the absorption/photoluminescence by redox processes. Dual functional electrochromic/electrofluorochromic materials can be exploited in, for example, smart windows, encryption/anticounterfeiting technologies, displays, and biomedical sensors. While electrofluorochromic materials showing tunable fluorescence intensity are relatively widespread, those with tunable color emission are not. Moreover, electrofluorochromic materials with tunable emission in the near‐infrared (NIR) range are seldom encountered. Here, this work shows a new molecular approach to afford both the above functionalities, in addition to red–NIR electrochromism, by combining the properties of highly stable arylamine radical cation mixed valence species, with those of donor–acceptor systems exhibiting the photoinduced twisted intramolecular charge transfer mechanism.

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Section: Introductionmentioning

confidence: 99%

Vis–NIR Electrochromism and NIR–Green Electroluminochromism in Dual Functional Benzothiadiazole‐Arylamine Mixed‐Valence Compounds

Corrente

González

Aktas

et al. 2022

Advanced Optical Materials

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“…Global chemical reactivity parametersglobal hardness, global softness, chemical potential, electron negativity, and global electrophilicity indexare calculated using Koopman’s theorem. , Table depicts the global chemical reactivity parameters. Electronegativity is a term used to describe an atom’s or functional groups’ ability to pull inbound electrons to itself .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

Rajan,

Karthikeyan,

Desikan

2024

ACS Omega

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Novel methylenedioxyphenyl-based amides, especially N-(4-methoxybenzyl)-6-nitrobenzo-[1,3]-dioxole-5-carboxamide (MDC) and N-(3-acetylphenyl)-6-nitrobenzo-[1,3]-dioxole-5-carboxamide (ADC), potential cardiovascular preventive agents, are successfully synthesized, and their chemical structures are verified by 1 H and 13 C NMR, Fourier transform infrared (FT-IR), high-resolution mass spectrometry (HRMS), and single-crystal Xray diffraction (SC-XRD) analyses. Data obtained from SC-XRD reveal that MDC and ADC are both monoclinic molecules with Z = 2 and 4, respectively. From density functional theory (DFT) calculations, 3.54 and 3.96 eV are the energy gaps of the optimized MDC and ADC structures, respectively. MDC and ADC exhibit an electrophilicity index value of more than 1.5 eV, suggesting that they can act as an electrophile, facilitating bond formation with biomolecules. Hirshfeld surface analysis demonstrates that more than 25% of atomic interactions in both MDC and ADC are from H•••H interactions. Based on pharmacokinetic predictions, MDC and ADC exhibit drug-like properties, and molecular docking simulations revealed favorable interactions with active site pockets. Both MDC and ADC achieved higher docking scores of −7.74 and −7.79 kcal/mol, respectively, with myeloperoxidase (MPO) protein. From docking results, MPO was found to be most favorable followed by dipeptidyl peptidase-4 (DPP-4) and α-glucosidase (α-GD). Antioxidant, anti-inflammatory, and in vitro enzymatic studies of MDC and ADC indicate that MDC is more selective toward MPO and more potent than ADC. The application of MDC to inhibit myeloperoxidase could be ascertained to reduce the cardiovascular risk factor. This can be supported from the results of computational docking (based on hydrogen bonding and docking score), in vitro antioxidant and anti-inflammatory properties, and MPO enzymatic inhibition (based on the percentage of inhibition and IC 50 values).

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“…Indeed, while the UV/Vis ground state absorption spectra of 2N6S and 6AQ show that 2N6S is in its ROH state and 6AQ is in its RN state (Figure 1b and c, black curves), the emission spectra, which probe the excited state, show that 2N6S is in its RO À * state and 6AQ is in its RNH + * state (Figure 1b and c, red curves). [30][31][32][33] Importantly, the emergence of the ionic forms following PA and PB excitation is only in the excited state.…”

Section: Resultsmentioning

confidence: 99%

Photocurrent Generation and Polarity Switching in Electrochemical Cells through Light‐induced Excited State Proton Transfer of Photoacids and Photobases**

et al. 2023

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Light is a common source of energy in sustainable technologies for photocurrent generation. To date, in such light‐harvesting applications, the excited electrons generate the photocurrent. Here, we introduce a new mechanism for photocurrent generation that is based on excited state proton transfer (ESPT) of photoacids and photobases that can donate or accept a proton, respectively, but only after excitation. We show that the formed ions following ESPT can either serve as electron donors or acceptors with the electrodes, or modify the kinetics of mass transport across the diffuse layer, both resulting in photocurrent generation. We further show that control of the current polarity is obtained by switching the irradiation between the photoacid and the photobase. Our study represents a new approach in photoelectrochemistry by introducing ESPT processes, which can be further utilized in light‐responsive energy production or energy storage.

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Structural, Electronic and NLO Properties of 6-aminoquinoline: A DFT/TD-DFT Study

Cited by 28 publications

References 57 publications

Vis–NIR Electrochromism and NIR–Green Electroluminochromism in Dual Functional Benzothiadiazole‐Arylamine Mixed‐Valence Compounds

Vis–NIR Electrochromism and NIR–Green Electroluminochromism in Dual Functional Benzothiadiazole‐Arylamine Mixed‐Valence Compounds

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

Photocurrent Generation and Polarity Switching in Electrochemical Cells through Light‐induced Excited State Proton Transfer of Photoacids and Photobases**

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