Persistent prevalence of supramolecular architectures of novel ultrasonically synthesized hydrazones due to hydrogen bonding [X–H⋯O; X=N]: Experimental and density functional theory analyses

Khalid, Muhammad; Ali, Akbar; Asim, Sumreen; Tahir, Muhammad Nawaz; Khan, Muhammad Usman; Vieira, Lucas Campos Curcino; Torre, Alexander F. de la; Usman, Muhammad

doi:10.1016/j.jpcs.2020.109679

Cited by 58 publications

(24 citation statements)

References 61 publications

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“…The simplest relation between the properties of the intermolecular BCP and the corresponding interaction energy is the Espinosa equation [ 85 ]. While its use in the intramolecular context is disputed [ 30 ], it is generally accepted in the intermolecular case [ 90 , 91 , 92 , 93 , 94 ]. In the current study, we applied this methodology to the selected non-equilibrated structures of dimers taken directly from the X-ray data.…”

Section: Resultsmentioning

confidence: 99%

Revealing Intra- and Intermolecular Interactions Determining Physico-Chemical Features of Selected Quinolone Carboxylic Acid Derivatives

Wojtkowiak¹,

Jezierska²,

Panek³

2022

Molecules

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The intra- and intermolecular interactions of selected quinolone carboxylic acid derivatives were studied in monomers, dimers and crystals. The investigated compounds are well-recognized as medicines or as bases for further studies in drug design. We employed density functional theory (DFT) in its classical formulation to develop gas-phase and solvent reaction field (PCM) models describing geometric, energetic and electronic structure parameters for monomers and dimers. The electronic structure was investigated based on the atoms in molecules (AIM) and natural bond orbital (NBO) theories. Special attention was devoted to the intramolecular hydrogen bonds (HB) present in the investigated compounds. The characterization of energy components was performed using symmetry-adapted perturbation theory (SAPT). Finally, the time-evolution methods of Car–Parrinello molecular dynamics (CPMD) and path integral molecular dynamics (PIMD) were employed to describe the hydrogen bond dynamics as well as the spectroscopic signatures. The vibrational features of the O-H stretching were studied using Fourier transformation of the autocorrelation function of atomic velocity. The inclusion of quantum nuclear effects provided an accurate depiction of the bridged proton delocalization. The CPMD and PIMD simulations were carried out in the gas and crystalline phases. It was found that the polar environment enhances the strength of the intramolecular hydrogen bonds. The SAPT analysis revealed that the dispersive forces are decisive factors in the intermolecular interactions. In the electronic ground state, the proton-transfer phenomena are not favourable. The CPMD results showed generally that the bridged proton is localized at the donor side, with possible proton-sharing events in the solid-phase simulation of stronger hydrogen bridges. However, the PIMD enabled the quantitative estimation of the quantum effects inclusion—the proton position was moved towards the bridge midpoint, but no qualitative changes were detected. It was found that the interatomic distance between the donor and acceptor atoms was shortened and that the bridged proton was strongly delocalized.

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Section: Resultsmentioning

confidence: 99%

Revealing Intra- and Intermolecular Interactions Determining Physico-Chemical Features of Selected Quinolone Carboxylic Acid Derivatives

Wojtkowiak¹,

Jezierska²,

Panek³

2022

Molecules

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“…Chromophore orbitals with the highest occupied (HOMO) and lowest unoccupied (LUMO) energies have a considerable effect on the charge transport, electronic, and absorption attributes. − Charge transport and electronic density distribution patterns are characterized by Frontier molecular orbitals (FMOs). − A molecule accompanied by a small band gap is highly polarizable and has low kinetic stability but great chemical reactivity (i.e., it is a soft molecule) …”

Section: Resultsmentioning

confidence: 99%

Bithieno Thiophene-Based Small Molecules for Application as Donor Materials for Organic Solar Cells and Hole Transport Materials for Perovskite Solar Cells

et al. 2021

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This quantum mechanical study focuses on the designing of twelve (MPAM1–MPAM12) bithieno thiophene (BTTI) central core-based small molecules to explore optoelectronic properties as donor candidates for organic solar cells (OSCs) and hole transport materials (HTMs) accompanied by enhanced charge mobility for perovskite solar cells (PSCs). MPAM1–MPAM6 have been designed by the substitution of thiophene-bridged end-capped acceptors on both side terminals of reference ( MPAR). MPAM7–MPAM12 are tailored by adopting the same tactic on one side terminal only. MPW1PW91/6-311G (d,p) has been employed for all computational simulations. MPAM12 revealed the highest λ max at 639 nm in dichloromethane (DCM) solvent with the lowest E g of 1.78 eV and dipole moment (20.74 D) in the solvent phase, showing excellent miscibility as compared to the reference. All designed chromophores (MPAM1–MPAM12) demonstrated higher estimated V OC and power conversion efficiency (PCE) when compared to MPAR , suggesting their prominent operational efficiency. Among all, MPAM4 manifested the highest PCE (47.86%). MPAM2 portrayed the highest electron mobility (0.0041573 eV) and MPAM3 exhibited the highest hole mobility (0.0047178 eV). The outcomes highlight the adequacy of the planned strategies, paving a new route for the development of small-molecule HTMs for PSCs and donor contributors for OSCs.

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“…In 2021, de la Torre (Universidad de Concepción, Chile), in collaboration with research groups from Pakistan and Brazil [46] , published a series of novel pyridine-based hydrazone derivatives ( 129 ) synthesized vi a ultrasonic energy at room temperature ( Scheme 35 ). Besides, the hydrazone structures were unambiguously confirmed by spectral analysis, X-ray crystallography and comprehensive computational analysis.…”

Section: Ultrasound-assisted Organic Synthesismentioning

confidence: 99%

The use of ultrasound in the South Cone region. Advances in organic and inorganic synthesis and in analytical methods

Fiego

Lorenzetti

Silbestri

et al. 2021

Ultrasonics Sonochemistry

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Persistent prevalence of supramolecular architectures of novel ultrasonically synthesized hydrazones due to hydrogen bonding [X–H⋯O; X=N]: Experimental and density functional theory analyses

Cited by 58 publications

References 61 publications

Revealing Intra- and Intermolecular Interactions Determining Physico-Chemical Features of Selected Quinolone Carboxylic Acid Derivatives

Revealing Intra- and Intermolecular Interactions Determining Physico-Chemical Features of Selected Quinolone Carboxylic Acid Derivatives

Bithieno Thiophene-Based Small Molecules for Application as Donor Materials for Organic Solar Cells and Hole Transport Materials for Perovskite Solar Cells

The use of ultrasound in the South Cone region. Advances in organic and inorganic synthesis and in analytical methods

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