3-Phenyl Derivatives of Trans-2-(Aryl/Pyridinyl)Vinyl-3H-Quinazolin-4-ones: Synthesis and Fluorescent Properties

This work was supported by Russian Foundation for Basic Research (grant № 18-03-00112)

2,5-DIARYL-[1,2,4]TRIAZOLO[1,5-c]QUINAZOLINES AS PROMISING FLUOROPHORES

This research was funded by Russian Scientific Foundation (grant number No. 23-73-01147)

THE DESIGN AND SYNTHESIS OF NOVEL 3,5-DIARYL[1,2,4]TRIAZOLO[4,3-C]QUINAZOLINE BASED FLUOROPHORES

This work was supported by the Russian Scientific Foundation (project 22-23-00006)

V-SHAPED FLUOROPHORES - 2,3-BIS(ARYLTHIENYL)QUINOXALINE DERIVATIVES: SYNTHESIS AND PHOTOPHYSICAL PROPERTIES

This work was supported by the Russian Scientific Foundation (project 21-13-00304)

SYNTHESIS OF (2-ARYLQUINAZOLIN-4-YL)HYDRAZONES OF 2-HYDROXYBENZALDEHYDES AS POTENTIAL PHOSPHOINOSITIDE 3-KINASE (IP3Kδ) AND CASEIN KINASE 2 (CK2) INHIBITORS

This work was supported by the Ministry of Science and Higher Education of Russian Federation, State Contract no FEUZ-2020-0058 (Н687.42Б.223/20)

3-ARYL-[1,2,4]TRIAZOLO[4,3-c]QUINAZOLINE DERIVATIVES: SYNTHESIS AND MODIFICATIONS

This work was supported by the Ministry of Science and Higher Education of Russian Federation, State Contract no FEUZ-2020-0058 (Н687.42Б.223/20)

5-AMINOBIPHENYL-SUBSTITUTED [1,2,4]TRIAZOLO[4,3-c]- AND [1,2,4]TRIAZOLO[1,5-c]QUINAZOLINES: SYNTHESIS AND PHOTOPHYSICAL PROPERTIES

This work was supported by the Russian Scientific Foundation (project 23-73-01147)

SYNTHESIS AND PHOTOPHYSICAL PROPERTIES OF 2-ARYL-4-(4-CYANOPHENYL)QUINAZOLINES

This work was supported by the Russian Scientific Foundation (project 22-23-00006)

2-AZINYL QUINAZOLINES: SYNTHESIS AND PHOTOPHYSICAL PROPERTIES

This work was supported by the Russian Scientific Foundation (project 22-23-00006)

Design, Synthesis, and Photophysical Properties of 5-Aminobiphenyl Substituted [1,2,4]Triazolo[4,3-<i>c</i>]- and [1,2,4]Triazolo[1,5-<i>c</i>]quinazolines

Two series of novel [1,2,4]triazolo[4,3-c]- and [1,2,4]triazolo[1,5-c]quinazoline fluorophores with 4′-amino[1,1′]-biphenyl residue at position 5 have been prepared via Pd-catalyzed cross-coupling Suzuki–Miyaura reactions. The treatment of 2-(4-bromophenyl)-4-hydrazinoquinazoline with orthoesters in solvent-free conditions or in absolute ethanol leads to the formation of [4,3-c]-annulated triazoloquinazolines, whereas [1,5-c] isomers are formed in acidic media as a result of Dimroth rearrangement. A 1D-NMR and 2D-NMR spectroscopy, as well as a single-crystal X-ray diffraction analysis, unambiguously confirmed the annelation type and determined the molecular structure of p-bromophenyl intermediates and target products. Photophysical properties of the target compounds were investigated in two solvents and in the solid state and compared with those of related 3-aryl-substituted [1,2,4]triazolo[4,3-c]quinazolines. The exclusion of the aryl fragment from the triazole ring has been revealed to improve fluorescence quantum yield in solution. Most of the synthesized structures show moderate to high quantum yields in solution. Additionally, the effect of solvent polarity on the absorption and emission spectra of fluorophores has been studied, and considerable fluorosolvatochromism has been stated. Moreover, electrochemical investigation and DFT calculations have been performed; their results are consistent with the experimental observation