Synthesis, optical, electrochemical and theoretical studies of 2,3-Di(pyridin-2-yl)quinoxaline amine derivatives as blue-orange emitters for organic electronics

Mahadik, Suraj S.; Garud, Dinesh R.; Pinjari, Rahul V.; Kamble, Rajesh M.

doi:10.1016/j.molstruc.2021.131541

Cited by 18 publications

(4 citation statements)

References 69 publications

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“…The application of this protocol allowed the conversion of previously obtained unstable α-hydroxy-1,2-diketone 14a – l into the corresponding quinoxalines 15a – l ( Scheme 5 ). As it was shown earlier, acetic acid is the optimal solvent for the studied compounds and this solvent is also widely used for the condensation of α-diketones with 1,2-phenylenediamine [ 37 – 40 ]. We suggested that it is possible to exclude isolation of unstable α-hydroxy-1,2-diketones 14 and thereby reduce losses at this step.…”

Section: Resultsmentioning

confidence: 99%

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

Milyutin¹,

Komogortsev²,

Lichitsky³

et al. 2022

Beilstein J. Org. Chem.

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The photochemical properties behavior of 3-hydroxy-4-pyranone containing terarylenes with a pyrazole bridge fragment were studied. It was shown that UV-induced 6π-electrocyclization of the 1,3,5-hexatriene system was not observed for the considered objects molecules. At the same time, the phototransformation of such systems proceeds exclusively in the direction of the contraction of the pyranone ring leading to unstable α-hydroxydiketones. For the first time the possibility of isolation of the resulting α-hydroxydiketones in pure form was demonstrated. Wherein, it was shown that relatively low stable α-hydroxydiketones can be trapped by reaction with 1,2-phenylenediamine. The general method for the preparation of the corresponding quinoxalines on the basis of the aforementioned condensation was implemented. It was demonstrated that the studied photoreaction does not depend on the type of pyrazole bridge. The structures of three of synthesized products were established by X-ray diffraction.

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Section: Resultsmentioning

confidence: 99%

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

Milyutin¹,

Komogortsev²,

Lichitsky³

et al. 2022

Beilstein J. Org. Chem.

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“…[60][61][62] The molecules studied in the literature show that the localization on N-naphthalene is to be the HOMO level of Naphthalene and the donor part of the molecules. [63][64][65]…”

Section: Theoretical Calculations Of Homo-lumo Energy Levelsmentioning

confidence: 99%

The Effect of the Interface Layer on the Electronic Parameters of the Light Emitting Electrochemical Cell (LEC) Device Based on Iridium (III) Complex that Calculated by Different Methods

Havare¹,

Alsaeedi²

2023

ECS J. Solid State Sci. Technol.

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We report a calculation of the electronic parameters and some optical measurement results of a light-emitting electrochemical cell (LEC), one of the most basic forms of electroluminescent films by modifying 4-(4-methoxy-N-naphthalen-1-ylanilino) benzoic acid (MA) as a hole injection layer doped with an emissive layer that is ionic transition metal complex (Ir[dF(CF3)ppy]2(dtbpy))PF6-(Ir-iTMC). The electronic parameters of LEC device were computed using three different methods; Cheung and Cheung’s, Conventional Schottky and Norde, to evaluate the ideality factor (n), the barrier height (ϕ) and the series resistance (Rs) of the LEC device. The formation on indium tin oxide (ITO) substrate was analyzed by atomic force microscopy. The HOMO-LUMO energy level and electronic charge distribution of the MA molecule were computed theoretically using Chemissian software. The MA's HOMO-LUMO energy level is determined to be EHOMO=-5.27 eV and ELUMO=-1.40 eV. The ITO surface has been modified with the self-assembled monolayers technique as an interlayer to improve the surface working function by simplifying hole injection from the ITO anode to the hole transport layer in the LEC. The Ir- iTMC complexes containing Π-conjugated bridging ligand shown better external quantum efficiency, reaching to 1.49%.

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“…29 Recently, indoloquinoxaline molecules have been utilized as active materials in organic solar cells and organic light-emitting diodes due to their excellent emission and electron transport properties and high thermal stability and durability. [30][31][32] In the case OFETs, indole-fused or quinoxaline-fused heteroaromatic systems have been studied, but indole-fused quinoxaline systems have not been explored. The high-performance hole transport transistors are made of the indolo[3,2-b] indole-based p-conjugated molecule-fused heteroaromatic core showing a hole mobility of up to m h = 0.9 cm 2 V À1 s À1 .…”

Section: Introductionmentioning

confidence: 99%

π-Extended indoloquinoxaline functionalized triarylamines with ethynyl and tetracyanobutadiene bridges for p-channel and ambipolar OFETs

Devibala,

Balambiga,

Imran

et al. 2024

New J. Chem.

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Synthesis, optical, electrochemical and theoretical studies of 2,3-Di(pyridin-2-yl)quinoxaline amine derivatives as blue-orange emitters for organic electronics

Cited by 18 publications

References 69 publications

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

The Effect of the Interface Layer on the Electronic Parameters of the Light Emitting Electrochemical Cell (LEC) Device Based on Iridium (III) Complex that Calculated by Different Methods

π-Extended indoloquinoxaline functionalized triarylamines with ethynyl and tetracyanobutadiene bridges for p-channel and ambipolar OFETs

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