Synthesis, crystal structure analysis, spectral IR, UV–Vis, NMR assessments, electronic and nonlinear optical properties of potent quinoline based derivatives: Interplay of experimental and DFT study

Khalid, Muhammad; Ullah, Malik Aman; Adeel, Muhammad; Khan, Muhammad Usman; Tahir, Muhammad Nawaz; Braga, Ataualpa Albert Carmo

doi:10.1016/j.jscs.2018.09.006

Cited by 93 publications

(34 citation statements)

References 41 publications

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“…In the experimental UV-Vis spectrum recorded between 200 to 400 nm are observed maxima at 218, 253 and 328 nm and minima at 243 and 275 nm while the predicted visible absorption wavelengths and oscillator strength (f ) for both enantiomers of chloroquine can be observed in Table S11 . The positions of these bands are in agreement with those observed in other quinoline compounds [80]. The different bands observed in the experimental spectrum can be associated to the different transitions predicted by NBO calculations in aqueous solution, as detailed in Table S4.…”

Section: Electronic Spectrumsupporting

confidence: 85%

Properties and Molecular docking of Antiviral to COVID-19 Chloroquine combining DFT calculations with SQMFF approach

Brandán

Romano

Issaoui

et al. 2020

Preprint

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Structural, electronic, topological, vibrational and molecular docking studies have been performed for both enantiomeric S(-) and R(+) forms of potential antiviral to COVID-19 chloroquine (CQ) combining DFT calculations with SQMFF methodology. Hybrid B3LYP/6-311++G** calculations in gas phase and aqueous solution predict few energy differences between both forms. Solvation energies of S(-) and R(+) form are predicted in -55.07 and 59.91 kJ/mol, respectively. Low solvation energies of both forms are justified by the presence of only four donor and acceptor H bonds groups, as compared with other antiviral agents. MK charges on the Cl1, N2, N3 and N4 atoms and AIM calculations could support the high stability of R(+) form in solution according to the higher reactivity predicted for the S(-) form in this medium. Antiviral to COVID-19 niclosamide shows higher reactivity than both forms of CQ. Complete vibrational assignments of 153 vibration modes for both forms and scaled force constants have been reported here. Reasonable concordances were found between predicted and available 1H-NMR, 13C-NMR and UV-Vis spectra. Additionally, NMR and UV-visible spectra suggest the presence of two forms of CQ in solution. A molecular docking study was performed to identify the potency of inhibition of Chloroquine molecule against COVID-19 virus

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Section: Electronic Spectrumsupporting

confidence: 85%

Properties and Molecular docking of Antiviral to COVID-19 Chloroquine combining DFT calculations with SQMFF approach

Brandán

Romano

Issaoui

et al. 2020

Preprint

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“…When evaluating the computational error percentage, the values of the derived parameters for compound 3 (MFCTP) were close to the values found for similar structures, conrming the accuracy of the obtained results. [49][50][51][52] Urea is one of the classic compounds utilized in the research of the NLO characteristics of molecular systems. Thus, it was employed as a comparative threshold value.…”

Section: Second Harmonic Generationmentioning

confidence: 99%

Synthesis, FT-IR, structural, thermochemical, electronic absorption spectral, and NLO analysis of the novel 10-methoxy-10H-furo[3,2-g]chromeno[2,3-b][1,3]thiazolo[5,4-e]pyridine-2,10(3H)-dione (MFCTP): a DFT/TD-DFT study

Halim

Ibrahim

2021

RSC Adv.

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“…Recently, the demand for more efficient optoelectronic materials has skyrocketed. Numerous theoretical and experimental research groups focus on the development of nonlinear optical (NLO) materials [ 1 , 2 , 3 , 4 , 5 , 6 ] owing to their overwhelming potential in photonic-based technologies [ 7 , 8 ], including two-photon excitation fluorescence imaging [ 9 ], multidimensional optical-based data storage devices [ 10 ], optical communication [ 11 ], and numerous other optical devices [ 12 ]. Studies have also reported different NLO active materials, including molecular dyes and organic and inorganic polymers, as well as nanomaterials [ 13 , 14 , 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Key Electronic, Linear and Nonlinear Optical Properties of Designed Disubstituted Quinoline with Carbazole Compounds

et al. 2021

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Organic materials development, especially in terms of nonlinear optical (NLO) performance, has become progressively more significant owing to their rising and promising applications in potential photonic devices. Organic moieties such as carbazole and quinoline play a vital role in charge transfer applications in optoelectronics. This study reports and characterizes the donor–acceptor–donor–π–acceptor (D–A–D–π–A) configured novel designed compounds, namely, Q3D1–Q3D3, Q4D1–Q1D2, and Q5D1. We further analyze the structure–property relationship between the quinoline–carbazole compounds for which density functional theory (DFT) and time-dependent DFT (TDDFT) calculations were performed at the B3LYP/6-311G(d,p) level to obtain the optimized geometries, natural bonding orbital (NBO), NLO analysis, electronic properties, and absorption spectra of all mentioned compounds. The computed values of λmax, 364, 360, and 361 nm for Q3, Q4, and Q5 show good agreement of their experimental values: 349, 347, and 323 nm, respectively. The designed compounds (Q3D1–Q5D1) exhibited a smaller energy gap with a maximum redshift than the reference molecules (Q3–Q5), which govern their promising NLO behavior. The NBO evaluation revealed that the extended hyperconjugation stabilizes these systems and caused a promising NLO response. The dipole polarizabilities and hyperpolarizability (β) values of Q3D1–Q3D3, Q4D1-Q1D2, and Q5D1 exceed those of the reference Q3, Q4, and Q5 molecules. These data suggest that the NLO active compounds, Q3D1–Q3D3, Q4D1–Q1D2, and Q5D1, may find their place in future hi-tech optical devices.

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Synthesis, crystal structure analysis, spectral IR, UV–Vis, NMR assessments, electronic and nonlinear optical properties of potent quinoline based derivatives: Interplay of experimental and DFT study

Cited by 93 publications

References 41 publications

Properties and Molecular docking of Antiviral to COVID-19 Chloroquine combining DFT calculations with SQMFF approach

Properties and Molecular docking of Antiviral to COVID-19 Chloroquine combining DFT calculations with SQMFF approach

Synthesis, FT-IR, structural, thermochemical, electronic absorption spectral, and NLO analysis of the novel 10-methoxy-10H-furo[3,2-g]chromeno[2,3-b][1,3]thiazolo[5,4-e]pyridine-2,10(3H)-dione (MFCTP): a DFT/TD-DFT study

Key Electronic, Linear and Nonlinear Optical Properties of Designed Disubstituted Quinoline with Carbazole Compounds

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