Synthesis and photophysical studies of novel 4-aryl substituted 2-phenyl-, 2-(fluoren-2-yl)- and 2-cymantrenylquinazolines

Носова, Э. В.; Moshkina, Tatyana N.; Lipunova, G. N.; Kelbysheva, E. S.; Loim, N. M.; Слепухин, П. А.; Charushin, Valery N.; Бакланова, И. В.

doi:10.1016/j.mencom.2018.01.010

Cited by 8 publications

(8 citation statements)

References 16 publications

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“…For a given quinazoline core, when changing arylamino donor from Ph 2 N to Et 2 N, there is a hypsochromic shift of emission maxima (26–34 nm), indicating a better donor ability of the diphenylamino group in considered system. The described findings fully correlate with previously published results for related 2,4‐disubstituted quinazolines [9,15] …”

Section: Resultssupporting

confidence: 91%

“…The LUMO energy of 5 a – g are in the range of −1.61 to −1.77 eV. In general, the LUMO level has the highest value compared to unsubstituted or fluoro‐substituted counterparts [9,15] corresponding to electron‐donating influence of methyl or methoxy group. The band gaps computed for the derivatives 5 a – g are in the range of 3.25–3.70 eV being the lowest for derivatives with diphenylamino donor moiety.…”

Section: Resultsmentioning

confidence: 98%

“…The 4‐bromoquinazolines 4 a – c were obtained similar to the previously described method [15] . The products were isolated by column chromatography on silica gel using EtOAc as an eluent.…”

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: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 98%

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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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“…Contrary, carbazolyl-derivatives 4c , 5c and 6c demonstrate opposite result. Such an influence of the carbazolyl-phenyl residue may be due to the destruction of the conjugation resulting from the withdrawal of the phenylene fragment from the quinazoline plane as it was previously noted for 4-(4-(9 H -carbazol-9-yl)phenyl)-2-phenyl and 2-quinolyl quinazolines [ 37 , 38 ].…”

Section: Resultsmentioning

confidence: 89%

Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines

et al. 2022

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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.

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“…The synthesis of the 2,4‐disubstituted quinazolines 1 and 2 is summarized in Scheme . Compounds 8a,b were obtained in three steps following the method similar to reported previously . The condensation of anthranilamide 4 with 4‐cyanobenzaldehyde ( 5a ) or 4‐trifluoromethylbenzaldehyde ( 5b ) and subsequent oxidation with copper(II) chloride led to quinazoline‐4e(3 H )‐ones 7a,b .…”

Section: Resultsmentioning

confidence: 99%

Electron‐Withdrawing Substituted Quinazoline Push‐Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second‐Order Nonlinear Optical Properties

et al. 2020

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A series of chromophores bearing 4‐cyanoquinazoline, 2‐(4‐cyanophenyl)quinazoline or 2‐(4‐trifluorophenyl)quinazoline electron–acceptor (A) and 5‐(4‐aminophenyl)thiophen‐2‐yl or 4‐aminophenyl electron‐donor (D) units has been designed. The influence of the electron‐withdrawing substituent on the pyrimidine core as well as the nature of the amino electron donating group has been studied by cyclic voltammetry, UV/Vis and emission spectroscopy. Whereas 2‐(4‐cyanophenyl)quinazoline and 2‐(4‐trifluorophenyl)quinazoline derivatives are highly luminescent in chloroform solution, 4‐cyanoquinazolines are poorly emissive. Interestingly all compounds are luminescent in the solid state with the emission ranging from blue to red. The second order nonlinear optical properties were studied using electric field induced second harmonic generation (EFISH) method. Quantum‐chemical calculations corroborate the aforementioned experimental results.

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Synthesis and photophysical studies of novel 4-aryl substituted 2-phenyl-, 2-(fluoren-2-yl)- and 2-cymantrenylquinazolines

Cited by 8 publications

References 16 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

Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines

Electron‐Withdrawing Substituted Quinazoline Push‐Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second‐Order Nonlinear Optical Properties

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