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Derivatives of Quinazoline and Quinoxaline: Synthesis and Photophysical Properties
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Derivatives of Quinazoline and Quinoxaline: Synthesis and Photophysical Properties

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (15 December 2022) | Viewed by 5149

Special Issue Editors

Prof. Dr. Emiliya V Nosova

E-Mail Website
Guest Editor
Department of Organic and Biomolecular Chemistry, Ural Federal University, 19 Mira St., Ekaterinburg 620002, Russia
Interests: novel benzazines; cyclocondensation; cross-coupling reactions; luminophores; luminescent sensors; coordination chemistry; antitubercular and anticancer activity
Prof. Dr. Dmitry S. Kopchuk

E-Mail Website
Guest Editor
Laboratory of Coordination Compounds, Institute of Organic Synthesis of Ural Branch of Russian Academy of Sciences, 22/20 Kovalevskoy St., Ekaterinburg 620137, Russia
Interests: ligands; bipyridines; luminophores; 1,2,4-triaizines; luminescent sensors; PASE methods; metallocomplexes; metallopolymers

Special Issue Information

Dear Colleagues,

Benzodiazine-based chromophores are key materials utilised in optoelectronics. Intramolecular charge transfer (ICT) or push–pull chromophores based on quinazoline and quinoxaline cores are important diazine representatives and have been extensively used in light-emitting diodes, solar cells, organic field-effect transistors, non-linear optics, fluorescent optical chemosensors and other fields. Modification of the nature and arrangement of substituents as well as condensation with benzo- or hetero-rings are commonly used approaches for fine-tuning the desired properties of benzodiazine-based dyes. Of particular interest are quadrupolar V-shaped (or Y-shaped) quinoxaline-centred chromophores with a D-π-A-π-D architecture, as they attract considerable research interest due to a number of promising properties: linear and non-linear optical response, aggregation-induced emission enhancement (AIEE) or aggregation-induced emission (AIE), mechanochromic luminescence (MCL) as well as thermally activated delayed fluorescence (TADF).

This Special Issue aims to familiarize readers with the most modern trends and achievements in the field of quinazoline and quinoxaline chromophore design. Special focus is placed on both the synthetic chemistry, including approaches to modified push–pull molecules, oligomers, annelated or cyclometalated compounds, and the in-depth study of photophysical properties.

Prof. Dr. Emiliya V Nosova
Prof. Dr. Dmitry S. Kopchuk
Guest Editors

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Keywords

  • quinazoline
  • quinoxaline
  • intramolecular charge transfer
  • tunable luminescence
  • aggregation-induced emission
  • metallocomplexes
  • high-performance phosphorescence
  • π-conjugated polymers

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Published Papers (3 papers)

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Research

24 pages, 2200 KiB  
Article
Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level
by Alexey A. Kalinin, Liliya N. Islamova, Sirina M. Sharipova, Guzel M. Fazleeva, Alexey A. Shustikov, Adel I. Gaysin, Artemiy G. Shmelev, Anastasiya V. Sharipova, Tatyana A. Vakhonina, Olga D. Fominykh, Olga B. Babaeva, Ayrat R. Khamatgalimov and Marina Yu. Balakina
Molecules 2023, 28(2), 531; https://doi.org/10.3390/molecules28020531 - 5 Jan 2023
Cited by 5 | Viewed by 1503
Abstract
Novel D-π-A′-π-A chromophores with quinoxaline cores as auxiliary acceptors and various donor moieties (aniline, carbazole, phenothiazine, tetrahydroquinoline) containing bulky tert-butyldimethylsilyloxy (TBDMSO) groups and tricyanofuranyl (TCF) acceptors with bulky cyclohexylphenyl substituents were synthesized via eight- to nine-step procedures, and their photo-physical and thermal [...] Read more.
Novel D-π-A′-π-A chromophores with quinoxaline cores as auxiliary acceptors and various donor moieties (aniline, carbazole, phenothiazine, tetrahydroquinoline) containing bulky tert-butyldimethylsilyloxy (TBDMSO) groups and tricyanofuranyl (TCF) acceptors with bulky cyclohexylphenyl substituents were synthesized via eight- to nine-step procedures, and their photo-physical and thermal properties were investigated. The values of the chromophores’ first hyperpolarizabilities were calculated in the framework of DFT at the M06-2X/aug-cc-pVDZ computational level; the effect of the introduction of the TBDMSO group into the donor fragment is shown to be inessential, as this group is not coupled to the π-conjugated system of the chromophore. The chromophore with the tetrahydroquinoline donor has a first hyperpolarizability value of 937 × 10−30 esu, which is the highest for the studied chromophores. Atomistic modeling of composite materials with the studied chromophores as guests demonstrated that the presence of bulky substituent in the donor fragment prevents notable aggregation of chromophores, even at high chromophore content (40 wt.%). The nonlinear optical performance of guest–host materials with 25 and 40 wt.% of suggested chromophore content was studied using a second harmonic generation technique to give the NLO coefficient, d33 up to 52 pm/V. Full article
(This article belongs to the Special Issue Derivatives of Quinazoline and Quinoxaline: Synthesis and Photophysical Properties)
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18 pages, 3093 KiB  
Article
Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines
by Tatyana N. Moshkina, Emiliya V. Nosova, Julia V. Permyakova, Galina N. Lipunova, Ekaterina F. Zhilina, Grigory A. Kim, Pavel A. Slepukhin and Valery N. Charushin
Molecules 2022, 27(21), 7156; https://doi.org/10.3390/molecules27217156 - 22 Oct 2022
Cited by 3 | Viewed by 1699
Abstract
Design and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3H)-ones and 4-cyano-2-arylquinazolines with Et2N-, Ph2N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have been studied by UV/Vis absorption and fluorescence spectroscopy in solvents of different [...] Read more.
Design and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3H)-ones and 4-cyano-2-arylquinazolines with Et2N-, Ph2N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have been studied by UV/Vis absorption and fluorescence spectroscopy in solvents of different polarity (toluene and MeCN). 2-(Aryl/thiophen-2-yl)quinazolin-4(3H)-ones show fluorescence in blue-green region in toluene solution with quantum yields up to 89% in the case of 2-(4’-N,N-diphenylamino[1,1’-biphenyl]-4-yl)-quinazolin-4(3H)-one. Moreover, triphenylamino derivative based on quinazolin-4(3H)-one with para-phenylene linker displays the highest quantum yield of 40% in powder. The fluorescence QY of Et2N and Ph2N derivatives decrease when going from toluene to MeCN solution, whereas carbazol-9-yl counterparts demonstrate strengthening of intensity that emphasizes the strong influence of donor fragment nature on photophysical properties. 4-Cyanoquinazolines are less emissive in both solvents, as well as, in solid state. The introduction of cyano group into position 4 leads to orange/red colored powder and dual emission bands. Some molecules demonstrate the increase in emission intensity upon addition of water to MeCN solution. According to frontier molecular orbitals (HOMO, LUMO) calculations, the energy gap of 4-cyanoquinazoline decreases by more than 1 eV compared to quinazolin-4-one, that is consistent with experimental data. Full article
(This article belongs to the Special Issue Derivatives of Quinazoline and Quinoxaline: Synthesis and Photophysical Properties)
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18 pages, 1235 KiB  
Article
Design, Synthesis, Anti-Varicella-Zoster and Antimicrobial Activity of (Isoxazolidin-3-yl)Phosphonate Conjugates of N1-Functionalised Quinazoline-2,4-Diones
by Magdalena Łysakowska, Iwona E. Głowacka, Graciela Andrei, Dominique Schols, Robert Snoeck, Paweł Lisiecki, Magdalena Szemraj and Dorota G. Piotrowska
Molecules 2022, 27(19), 6526; https://doi.org/10.3390/molecules27196526 - 2 Oct 2022
Cited by 2 | Viewed by 1551
Abstract
Dipolar cycloaddition of the N-substituted C-(diethoxyphosphonyl)nitrones with N3-allyl-N1-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a N1-benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antiviral and antibacterial activities. Several compounds showed moderate inhibitory activities [...] Read more.
Dipolar cycloaddition of the N-substituted C-(diethoxyphosphonyl)nitrones with N3-allyl-N1-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a N1-benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antiviral and antibacterial activities. Several compounds showed moderate inhibitory activities against VZV with EC50 values in the range of 12.63–58.48 µM. A mixture of isoxazolidines cis-20c/trans-20c (6:94) was found to be the most active against B. cereus PCM 1948, showing an MIC value 0.625 mg/mL, and also was not mutagenic up to this concentration. Full article
(This article belongs to the Special Issue Derivatives of Quinazoline and Quinoxaline: Synthesis and Photophysical Properties)
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