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3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties. / Kopotilova, Alexandra E.; Moshkina, Tatyana N.; Nosova, Emiliya V. et al.
In: Molecules, Vol. 28, No. 4, 1937, 02.2023.

Research output: Contribution to journal › Article › peer-review

Harvard

Kopotilova, AE, Moshkina, TN, Nosova, EV, Lipunova, GN, Starnovskaya, ES, Kopchuk, DS, Kim, GA, Gaviko, VS, Slepukhin, PA & Charushin, VN 2023, '3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties', Molecules, vol. 28, no. 4, 1937. https://doi.org/10.3390/molecules28041937

APA

Kopotilova, A. E., Moshkina, T. N., Nosova, E. V., Lipunova, G. N., Starnovskaya, E. S., Kopchuk, D. S., Kim, G. A., Gaviko, V. S., Slepukhin, P. A., & Charushin, V. N. (2023). 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties. Molecules, 28(4), [1937]. https://doi.org/10.3390/molecules28041937

Vancouver

Kopotilova AE, Moshkina TN, Nosova EV, Lipunova GN, Starnovskaya ES, Kopchuk DS et al. 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties. Molecules. 2023 Feb;28(4):1937. doi: 10.3390/molecules28041937

Author

Kopotilova, Alexandra E. ; Moshkina, Tatyana N. ; Nosova, Emiliya V. et al. / 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties. In: Molecules. 2023 ; Vol. 28, No. 4.

BibTeX

@article{07955ce205274991ab0ff1887a9834a7,
title = "3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties",
abstract = "Amino-[1,1′]-biphenyl-containing 3-aryl-[1,2,4]triazolo[4,3-c]quinazoline derivatives with fluorescent properties have been designed and synthesized. The type of annelation of the triazole ring to the pyrimidine one has been unambiguously confirmed by means of an X-ray diffraction (XRD) method; the molecules are non-planar, and the aryl substituents form the pincer-like conformation. The UV/Vis and photoluminescent properties of target compounds were investigated in two solvents of different polarities and in a solid state. The samples emit a broad range of wavelengths and display fluorescent quantum yields of up to 94% in toluene solutions. 5-(4{\textquoteright}-Diphenylamino-[1,1′]-biphenyl-4-yl)-3-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-c]quinazoline exhibits the strongest emission in toluene and a solid state. Additionally, the solvatochromic properties were studied for the substituted [1,2,4]triazolo[4,3-c]quinazolines. Moreover, the changes in absorption and emission spectra have been demonstrated upon the addition of water to MeCN solutions, which confirms aggregate formation, and some samples were found to exhibit aggregation-induced emission enhancement. Further, the ability of triazoloquinazolines to detect trifluoroacetic acid has been analyzed; the presence of TFA induces changes in both absorption and emission spectra, and acidochromic behavvior was observed for some triazoloquinazoline compounds. Finally, electronic-structure calculations with the use of quantum-chemistry methods were performed for synthesized compounds.",
author = "Kopotilova, {Alexandra E.} and Moshkina, {Tatyana N.} and Nosova, {Emiliya V.} and Lipunova, {Galina N.} and Starnovskaya, {Ekaterina S.} and Kopchuk, {Dmitry S.} and Kim, {Grigory A.} and Gaviko, {Vasiliy S.} and Slepukhin, {Pavel A.} and Charushin, {Valery N.}",
note = "The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program) is gratefully acknowledged.",
year = "2023",
month = feb,
doi = "10.3390/molecules28041937",
language = "English",
volume = "28",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "4",

}

RIS

TY - JOUR

T1 - 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties

AU - Kopotilova, Alexandra E.

AU - Moshkina, Tatyana N.

AU - Nosova, Emiliya V.

AU - Lipunova, Galina N.

AU - Starnovskaya, Ekaterina S.

AU - Kopchuk, Dmitry S.

AU - Kim, Grigory A.

AU - Gaviko, Vasiliy S.

AU - Slepukhin, Pavel A.

AU - Charushin, Valery N.

N1 - The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program) is gratefully acknowledged.

PY - 2023/2

Y1 - 2023/2

N2 - Amino-[1,1′]-biphenyl-containing 3-aryl-[1,2,4]triazolo[4,3-c]quinazoline derivatives with fluorescent properties have been designed and synthesized. The type of annelation of the triazole ring to the pyrimidine one has been unambiguously confirmed by means of an X-ray diffraction (XRD) method; the molecules are non-planar, and the aryl substituents form the pincer-like conformation. The UV/Vis and photoluminescent properties of target compounds were investigated in two solvents of different polarities and in a solid state. The samples emit a broad range of wavelengths and display fluorescent quantum yields of up to 94% in toluene solutions. 5-(4’-Diphenylamino-[1,1′]-biphenyl-4-yl)-3-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-c]quinazoline exhibits the strongest emission in toluene and a solid state. Additionally, the solvatochromic properties were studied for the substituted [1,2,4]triazolo[4,3-c]quinazolines. Moreover, the changes in absorption and emission spectra have been demonstrated upon the addition of water to MeCN solutions, which confirms aggregate formation, and some samples were found to exhibit aggregation-induced emission enhancement. Further, the ability of triazoloquinazolines to detect trifluoroacetic acid has been analyzed; the presence of TFA induces changes in both absorption and emission spectra, and acidochromic behavvior was observed for some triazoloquinazoline compounds. Finally, electronic-structure calculations with the use of quantum-chemistry methods were performed for synthesized compounds.

AB - Amino-[1,1′]-biphenyl-containing 3-aryl-[1,2,4]triazolo[4,3-c]quinazoline derivatives with fluorescent properties have been designed and synthesized. The type of annelation of the triazole ring to the pyrimidine one has been unambiguously confirmed by means of an X-ray diffraction (XRD) method; the molecules are non-planar, and the aryl substituents form the pincer-like conformation. The UV/Vis and photoluminescent properties of target compounds were investigated in two solvents of different polarities and in a solid state. The samples emit a broad range of wavelengths and display fluorescent quantum yields of up to 94% in toluene solutions. 5-(4’-Diphenylamino-[1,1′]-biphenyl-4-yl)-3-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-c]quinazoline exhibits the strongest emission in toluene and a solid state. Additionally, the solvatochromic properties were studied for the substituted [1,2,4]triazolo[4,3-c]quinazolines. Moreover, the changes in absorption and emission spectra have been demonstrated upon the addition of water to MeCN solutions, which confirms aggregate formation, and some samples were found to exhibit aggregation-induced emission enhancement. Further, the ability of triazoloquinazolines to detect trifluoroacetic acid has been analyzed; the presence of TFA induces changes in both absorption and emission spectra, and acidochromic behavvior was observed for some triazoloquinazoline compounds. Finally, electronic-structure calculations with the use of quantum-chemistry methods were performed for synthesized compounds.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85149054297

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000941783500001

U2 - 10.3390/molecules28041937

DO - 10.3390/molecules28041937

M3 - Article

VL - 28

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 4

M1 - 1937

ER -

ID: 35467334