(A)symmetric chromophores based on cyano and fluorine-substituted 2,3-bis(5-arylthiophen-2-yl)quinoxalines: Synthesis, photophysical properties and application prospects

Moshkina, Tatyana N.; Носова, Э. В.; Kopotilova, Alexandra E.; Ośmiałowski, Borys; Reguant, Alejandro I.; Слепухин, П. А.; Lipunova, G. N.; Taniya, Olga S.; Kalinichev, Alexey A.; Чарушин, В. Н.

doi:10.1016/j.dyepig.2022.110434

Cited by 10 publications

(5 citation statements)

References 77 publications

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“…For two‐photon excitation fluorescence measurements a femtosecond laser system RAPOP‐100 (manufactured by Avesta‐Project) of the resource center “Laser and optical methods for studying substances” at St. Petersburg State University was used. Detailed method of calculations of the two‐photon absorption and emission cross sections, as well as the setup diagram, can be found in previous publications [9,32] …”

Section: Methodsmentioning

confidence: 99%

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Methyl‐ and Methoxy‐substituted 2‐(Pyridin‐2‐yl)‐4‐(4‐aminophenyl)quinazolines: Synthesis and Photophysical Properties

Kopotilova,

Valieva,

Kudryashova

et al. 2024

Asian J Org Chem

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A series of 2‐(2‐pyridyl)quinazoline luminophores containing donor aryl fragment at position 4 and methyl or methoxy groups at benzene ring has been synthesized by efficient three‐step route. The linear optical properties have been studied by UV/Vis absorption and photoluminescence spectra in two solvents. We revealed that introduction of additional methyl group or the replacement of methyl substituents with methoxy ones lead to sequentially shift of absorption and emission maximum to blue region. 9H‐Carbazol‐9‐yl‐containing derivative is characterized by hypsochromically shifted absorption band compared to NEt2 and NPh2 counterparts. Unlike 9H‐carbazol‐9‐yl‐derivative, Et2N‐ and Ph2N‐bearing quinazolines demonstrate considerable decrease in quantum yield values when going from toluene to MeCN. Solvatochromic properties have been explored, the pronounced bathochromic shift was observed in fluorescence spectra with the increase of solvents polarity. Moreover, the compounds show significant shift of emission band with the increase of water fraction in DMSO/H2O mixture. Two‐photon optical properties were also studied, the two‐photon absorption cross‐sections in MeCN and toluene reached 120 GM and 210 GM, respectively. The presence of additional methyl group has little impact on δTPA, while introduction of methoxy substituents dramatically decreases TPA cross sections. Additionally, a quantum‐chemical calculations of synthesized compounds were performed to support the experimental data.

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Section: Methodsmentioning

confidence: 99%

“…Detailed method of calculations of the two-photon absorption and emission cross sections, as well as the setup diagram, can be found in previous publications. [9,32]…”

Section: Photophysical Characterizationmentioning

confidence: 99%

Methyl‐ and Methoxy‐substituted 2‐(Pyridin‐2‐yl)‐4‐(4‐aminophenyl)quinazolines: Synthesis and Photophysical Properties

Kopotilova,

Valieva,

Kudryashova

et al. 2024

Asian J Org Chem

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“…The replacement of difluoroquinoxaline with cyanoquinoxaline improved the nonlinear optical properties, highlighting the importance of tailoring electron acceptor strength. Furthermore, the ability to induce changes in emission properties through mechanical stimulation offers exciting possibilities for optomechanical applications [68].…”

Section: Quinoxalines As Chromophoresmentioning

confidence: 99%

Quinoxaline derivatives as attractive electron-transporting materials

Abid,

Ali,

Gulzar

et al. 2023

Beilstein J. Org. Chem.

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This review article provides a comprehensive overview of recent advancements in electron transport materials derived from quinoxaline, along with their applications in various electronic devices. We focus on their utilization in organic solar cells (OSCs), dye-sensitized solar cells (DSSCs), organic field-effect transistors (OFETs), organic-light emitting diodes (OLEDs) and other organic electronic technologies. Notably, the potential of quinoxaline derivatives as non-fullerene acceptors in OSCs, auxiliary acceptors and bridging materials in DSSCs, and n-type semiconductors in transistor devices is discussed in detail. Additionally, their significance as thermally activated delayed fluorescence emitters and chromophores for OLEDs, sensors and electrochromic devices is explored. The review emphasizes the remarkable characteristics and versatility of quinoxaline derivatives in electron transport applications. Furthermore, ongoing research efforts aimed at enhancing their performance and addressing key challenges in various applications are presented.

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“…More recently, work on V-shaped D–A–D chromophores, where 1,5-thiophenylene acts as a π-conjugated spacer unit and either 6-cyano or 6,7-difluoroquinoxaline functioned as electron-acceptors have also been reported. 9…”

Section: Introductionmentioning

confidence: 99%

“…More recently, work on V-shaped D-A-D chromophores, where 1,5-thiophenylene acts as a π-conjugated spacer unit and either 6-cyano or 6,7-difluoroquinoxaline functioned as electron-acceptors have also been reported. 9 While there are no reports on the coordination chemistry of thiophene-quinoxaline hybrid ligands, there are numerous examples, that date back to the 1970s, of organometallic complexes that contain a metalated thiophene unit. For example, 2-(2′-thienyl)pyridine was initially demonstrated as a ligand for Pt(II).…”

Section: Introductionmentioning

confidence: 99%

2-(Thienyl)quinoxaline derivatives and their application in Ir(iii) complexes yielding tuneable deep red emitters

Fitzgerald,

Payce,

Horton

et al. 2023

Dalton Trans.

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(A)symmetric chromophores based on cyano and fluorine-substituted 2,3-bis(5-arylthiophen-2-yl)quinoxalines: Synthesis, photophysical properties and application prospects

Cited by 10 publications

References 77 publications

Methyl‐ and Methoxy‐substituted 2‐(Pyridin‐2‐yl)‐4‐(4‐aminophenyl)quinazolines: Synthesis and Photophysical Properties

Methyl‐ and Methoxy‐substituted 2‐(Pyridin‐2‐yl)‐4‐(4‐aminophenyl)quinazolines: Synthesis and Photophysical Properties

Quinoxaline derivatives as attractive electron-transporting materials

2-(Thienyl)quinoxaline derivatives and their application in Ir(iii) complexes yielding tuneable deep red emitters

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