Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Context: Organic cocrystals have a wide range of applications in the field of optics due to their photo responsive property. We present here a newly synthesized phenazine 2-hydroxynaphthalene (1:1) cocrystal, its structural and theoretical calculations which tend to the nonlinear optical property. In the crystal structure of the title cocrystal, the phenazine and 2-hydroxynaphthalene molecules from one- and two-dimensional supramolecular frameworks via O‒H…N hydrogen bonds and C‒H…N, C‒H…π interaction, respectively. The phenazine molecules from an infinite off-set stacking through π…π interaction in the three-dimensional molecular packing of the title cocrystal. The contribution of intermolecular interaction in the three-dimensional molecular packing and the interaction energy calculation is studied by the Hirshfeld surface analysis. The molecular geometry retrieved from the experimental X-ray diffraction analysis is in good agreement with the theoretically calculated parameters. Further, the molecular electrostatic potential (MEP) and frontier molecular orbital (FMO) analysis have been carried out to study the charge distribution and molecular reactive mechanism. Third-order nonlinear optical property of the cocrystals has been analyzed by Z-scan measurements. The determined nonlinear optical absorption coefficient value 6.442 × 10 (m/W) and the nonlinear refractive index value - 5.535 × 10 (m/W) suggest that the crystalline solid can be a good choice of potential nonlinear optical material.
Method: The crystal structures of phenazine 2-hydroxynaphthalene cocrystal was solved by direct methods procedure using SHELXS program and refined by full-matrix least square procedure on F using SHELXL-2018 program on Olex2 software. The computational calculation has been carried out using DFT/B3LYP quantum chemical function with triple zeta 6-311 + + basis set in the ground state molecular stability using Gaussian 09W program suite. The Hirshfeld surface analysis mapping, associated 2D fingerprint plot, and intermolecular molecular interaction energy calculations were carried out using CrystalExplorer (version 21.5) software.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1007/s00894-024-06128-3 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Design and synthesis of PDSPTCF as an influential Brønsted-Lewis acidic catalyst for the producing benzo[a]benzo[6,7]chromeno[2,3-c]phenazines.
Sci Rep
December 2024
Department of Nuclear and Renewable Energy, Ural Federal University Named After the First President of Russia Boris Yeltsin, Ekaterinburg, Russia, 620002.
Initially, 4,4'-(1,4-phenylene)di(sulfonic)pyridinium tetrachloroferrate (PDSPTCF) as a novel organic-inorganic hybrid salt was synthesized and identified by elemental mapping, energy-dispersive X-ray spectroscopy, inductively coupled plasma atomic emission spectrometer, Raman spectroscopy, Fourier-transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, vibrating-sample magnetometry, and thermal gravimetric (TG) techniques. Then, the catalytic performance of this hybrid salt was assessed for the producing benzo[a]benzo[6,7]chromeno[2,3-c]phenazine derivatives via one-pot multicomponent domino reaction (MDR) of benzene-1,2-diamine, 2-hydroxynaphthalene-1,4-dione and aldehydes under optimal conditions (70 °C, solvent-free, 5 mol% PDSPTCF) in short reaction times and high yields. Highly efficacy of the PDSPTCF for the production of benzo[a]pyrano[2,3-c]phenazines can be assigned to the synergistic effect of Lewis and Brønsted acids, and having two positions of each acid (i.
View Article and Find Full Text PDFA facile and green procedure in preparing dibenzo-chromeno-phenazine-diones using an effectual and recyclable Brønsted acidic ionic liquid.
Sci Rep
November 2024
Medical Laboratory Technique College, The Islamic University, Najaf, Iraq.
First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass, C NMR, F NMR, H NMR and FT-IR data. Further, it was successfully applied in the preparation of dibenzo-chromeno-phenazine-dione derivatives (1a-12a, 9-15 min, 90-98%) via one-pot multicomponent domino reaction among 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes under optimal conditions (5 mol% of PBPBSDT, solvent-free, 60 °C). The proper reproducibility of the PBPBSDT homogeneous catalyst (5 times), solvent-free medium, reasonable TON (Turnover Number) and TOF (Turnover Frequency) numbers, the non-metallic framework of the catalyst, and the formation of C-N, C = N, C-C, C = C, C-O bonds in a single operation are the distinct advantages of this protocol.
View Article and Find Full Text PDFRational analysis of hydrogen bonding interaction in phenazine, 2-hydroxynaphthalene (1:1) cocrystal: from molecular modeling to photophysical properties.
J Mol Model
September 2024
Department of Physics, Presidency College, Chennai, Tamil Nadu, 600005, India.
Article Synopsis
- A newly synthesized phenazine 2-hydroxynaphthalene cocrystal demonstrates promising nonlinear optical properties due to its structural arrangement facilitated by various intermolecular interactions.
- Experimental and theoretical analyses, including X-ray diffraction and DFT calculations, confirm that the molecular geometry aligns well with predicted values.
- Z-scan measurements yield nonlinear optical absorption and refractive index values, highlighting the cocrystal's potential as an effective nonlinear optical material.
Synthesis of benzo[]furo[2, 3-]phenazine derivatives through an efficient, rapid and via microwave irradiation under solvent-free conditions catalyzed by HPWO@FeO-ZnO for high-performance removal of methylene blue.
Artif Cells Nanomed Biotechnol
December 2021
Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran.
A rapid, one-pot synthesis of eight benzo[]furo[2,3-]phenazine derivatives has been achieved in moderate to good yields in good yields a multi-component of 2-hydroxynaphthalene-1,4-dione, arylglyoxal, indole (H, CH) in the presence of HPWO@FeO-ZnO magnetic core-shell nanoparticles (MCNPs) under solvent-free conditions using microwave irradiation. The catalyst was synthesised and characterised by X-ray diffraction, EDX, TEM, FESEM, TGA, VSM and atomic force microscope. As an application for the synthesised nanocatalyst, degradation of methylene blue as heavy-mass organic pollution was measured.
View Article and Find Full Text PDFAn Efficient, Green, Microwave-assisted Synthesis of Benzo[a]furo[2, 3-c]phenazine Derivatives with TiO-SOH as Cost-effective and Recyclable Catalyst under Solventfree Conditions.
Curr Org Synth
August 2021
Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran.
Background: A rapid, efficient, and environmentally benign procedure for the synthesis of novel furo [2,3-c]phenazine derivatives has been developed via reactions of 2-hydroxynaphthalene-1,4-dione, arylglyoxals, and indole in the presence of TiO-SOH-catalyst (TSAC) as a recyclable heterogeneous catalyst under solventfree conditions using microwave irradiation.
Introduction: This study describes a successful approach for the synthesis of 2-(4-bromophenyl)-1-(1H-indol-3- yl) benzo[a]furo[2,3-c] phenazine in the presence of TiO-SOH-catalyst using microwave irradiation.
Objectives: In this paper, we report an efficient and convenient method for the synthesis of phenazine derivatives from benzo[a]phenazin-5-ol, arylglyoxal derivatives, and indoles in the presence of TiO-SOH-catalyst under microwave irradiation.