Unsymmetrical and symmetrical azines toward application in organic photovoltaic

Jarczyk-Jedryka, Anna; Bijak, Katarzyna; Sęk, Danuta; Siwy, Mariola; Filapek, Michał; Małecki, Jan Grzegorz; Kula, Sławomir; Lewińska, Gabriela; Nowak, E.; Sanetra, J.; Janeczek, Henryk; Smolarek, Karolina; Maćkowski, Sebastian; Schab‐Balcerzak, Ewa

doi:10.1016/j.optmat.2014.10.065

Cited by 14 publications

(7 citation statements)

References 72 publications

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“…They also found wide applications as sensors, NLO materials, image recording materials, conducting polymers, dye lasers, etc. Facile reduction under relatively mild reduction potential makes this class of compounds suitable as hole transport materials in various optoelectronic devices . Azines are also used as building blocks to synthesize different covalent organic frameworks and other supramolecular architectures with multitasking abilities …”

Section: Introductionmentioning

confidence: 99%

Iron-Catalyzed Metal–Ligand Cooperative Approach toward Sustainable Synthesis of Azines and N-Acylhydrazones in Air

2022

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Herein, we describe a metal–ligand cooperative approach for the sustainable synthesis of various aldazines, ketazines, and N-acylhydrazones via dehydrogenative functionalization of alcohols with hydrazine hydrate using a simple, easy-to-prepare iron catalyst featuring a redox noninnocent tridentate arylazo backbone. Our catalyst is compatible with both primary and secondary alcohols to produce a wide variety of substituted aldazines, ketazines, and N-acylhydrazones in good isolated yields in air. A series of control experiments are performed to elucidate the reaction mechanism.

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Section: Introductionmentioning

confidence: 99%

Iron-Catalyzed Metal–Ligand Cooperative Approach toward Sustainable Synthesis of Azines and N-Acylhydrazones in Air

2022

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“…Among the types of Schiff bases, polyazines are significantly used as nonlinear optical materials (NLO) because of their optical transparency [13]. They are of particular importance in the development of light-based technology for communication and computing [14]. These compounds have pharmacological and biological properties and close relationships with their structures, which act as anti-inflammatory, analgesic, antibacterial, antifungal, antitumor, anti-HIV and antimicrobial agents [15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Yahyaoui

Bouchama²,

Anak³

et al. 2019

Journal of Molecular Structure

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In this paper, we report the synthesis of new unsymmetrical azines Schiff bases. These compounds were prepared by condensation of hydrazine with different aldehydes and ketones to give (E) -2-hydroxynaphthalene-1-carbaldehyde [(1E) -2-thienylmethylene] hydrazone compound (I) and (Z) -2 -[(E) -1-(2-hydroxyphenyl) ethylidenehydrazin-1-ylidene] -1,2diphenylethanone compound (II). The method adopted consists in reacting the two different carbonyl compounds simultaneously in one step in a stepwise manner reported which is practical and cost-effective. The reaction with a minor modification in operating conditions proceeded efficiently and with excellent performance. The structure of each of the two compounds (I) and (II) was determined by the X-ray diffraction technique performed on single crystals. The asymmetric unity of the two molecules consists of one asymmetry-independent molecule. In addition, hydrogen bonds C-H ... π are observed in the compound (II). We then present a detailed DFT study based on B3LYP / 6-31G (d, p) geometric structures of compounds (I); (II) and another compound (III) also another asymmetric azine (Z) -2 -[(E) -2-benzylidenehydrazine-1-ylidene] -1,2diphenylethanone whose crystal structure is reported. The fundamental vibration wave numbers are calculated and a good agreement between the observed and calculated wave numbers is obtained. The study was extended to the HOMO-LUMO analysis to calculate the energy gap. The calculated HOMO and LUMO energy reveals that the charge is transferred into the molecule.

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“…An appropriate substituent on R1 and R2 positions can lead to different applications . These compounds have presented a broad spectrum of biological activities, such as anticonvulsant, antibacterial, anti-inflammatory, antioxidant, and antitumoral. ,− Also, due to their supramolecular versatility, azines can exhibit nonlinear optical and optoelectronic properties. − In particular, the azo group (NN) has shown important features to increase the nonlinear optical properties of azo-enaminone compounds. − …”

Section: Introductionmentioning

confidence: 99%

Contribution of Directional Dihydrogen Interactions in the Supramolecular Assembly of Single Crystals: Quantum Chemical and Structural Investigation of C₁₇H₁₇N₃O₂ Azine

Almeida

Carvalho

Napolitano

et al. 2017

Crystal Growth & Design

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Crystalline systems can be organized from several types of intermolecular interactions, among which classical and weak H-bonds are the most common, playing a very important role in the supramolecular assembly. However, in recent years a number of works have considered the influence of the homonuclear dihydrogen interaction, which had been neglected for a long time, to describe the supramolecular assembly of single crystals. In the C17H17N3O2 azine of the present study, a nonclassical dihydrogen interactions (C–H···H–C contact) have appeared in the crystal structure with a fundamental contribution toward the stability of crystalline packing. Nonetheless, an X-ray structural analysis is not conclusive to assess the real importance of the C–H···H–C contact. In order to characterize the nature and implications of C–H···H–C contacts concomitant with the classical interactions, the crystallized compound was evaluated by Hirshfeld surface, Quantum Theory of Atoms in Molecules, natural bond orbital, and Car–Parrinello molecular dynamics. The results establish that these interactions really exist, and their extension is responsible for the cooperative effect on the stability of crystalline packing. We expect that a more thorough understanding and description of homonuclear dihydrogen interactions in the supramolecular assembly of C17H17N3O2 can assist in the crystal engineering of small molecules, offering progress on physical–chemistry parameters of biological and material processes.

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Unsymmetrical and symmetrical azines toward application in organic photovoltaic

Cited by 14 publications

References 72 publications

Iron-Catalyzed Metal–Ligand Cooperative Approach toward Sustainable Synthesis of Azines and N-Acylhydrazones in Air

Iron-Catalyzed Metal–Ligand Cooperative Approach toward Sustainable Synthesis of Azines and N-Acylhydrazones in Air

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Contribution of Directional Dihydrogen Interactions in the Supramolecular Assembly of Single Crystals: Quantum Chemical and Structural Investigation of C₁₇H₁₇N₃O₂ Azine

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Unsymmetrical and symmetrical azines toward application in organic photovoltaic

Cited by 14 publications

References 72 publications

Iron-Catalyzed Metal–Ligand Cooperative Approach toward Sustainable Synthesis of Azines and N-Acylhydrazones in Air

Iron-Catalyzed Metal–Ligand Cooperative Approach toward Sustainable Synthesis of Azines and N-Acylhydrazones in Air

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

Contribution of Directional Dihydrogen Interactions in the Supramolecular Assembly of Single Crystals: Quantum Chemical and Structural Investigation of C17H17N3O2 Azine

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Contribution of Directional Dihydrogen Interactions in the Supramolecular Assembly of Single Crystals: Quantum Chemical and Structural Investigation of C₁₇H₁₇N₃O₂ Azine