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

AbstractA series of novel 2‐(2‐pyridyl)quinazoline luminophores containing a 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 its 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 have been 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 value, while introduction of methoxy substituents dramatically decreases TPA cross sections. Additionally, a quantumchemical calculations of synthesized compounds were performed to support the experimental data.

Authors
Kopotilova Alexandra E.1 , Valieva Maria I.1, 2 , Kudryashova Ekaterina A.1 , Starnovskaya Ekaterina S.1 , Moshkina Tatyana N.1 , Nosova Emiliya V.1, 2 , Taniya Olga S.1 , Kalinichev Alexey A.3 , Novikov Alexander S. 3, 4 , Kopchuk Dmitry S.1, 2 , Slepukhin Pavel A.1, 2 , Charushin Valery N.1, 2
Publisher
John Wiley and Sons Inc
Number of issue
7
Language
English
Status
Published
Volume
13
Year
2024
Organizations
  • 1 Department of Organic and Biomolecular Chemistry Ural Federal University 19 Mira Str. Yekaterinburg 620002 Russia
  • 2 Postovsky Institute of Organic Synthesis Ural Division of the Russian Academy of Sciences 22 S. Kovalevskoy Str. Yekaterinburg 620219 Russia
  • 3 Institute of Chemistry Saint Petersburg State University 7/9 Universitetskaya Nab. Saint Petersburg 199034 Russia
  • 4 Research Institute of Chemistry Рeoples' Friendship University of Russia (RUDN University) 6 Miklukho-Maklaya St. Moscow 117198 Russia
Date of creation
17.10.2024
Date of change
17.10.2024
Short link
https://repository.rudn.ru/en/records/article/record/157640/
Share

Other records