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

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...

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Autores principales: Kopotilova, Alexandra E., Moshkina, Tatyana N., Nosova, Emiliya V., Lipunova, Galina N., Starnovskaya, Ekaterina S., Kopchuk, Dmitry S., Kim, Grigory A., Gaviko, Vasiliy S., Slepukhin, Pavel A., Charushin, Valery N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9963873/
https://www.ncbi.nlm.nih.gov/pubmed/36838924
http://dx.doi.org/10.3390/molecules28041937
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author Kopotilova, Alexandra E.
Moshkina, Tatyana N.
Nosova, Emiliya V.
Lipunova, Galina N.
Starnovskaya, Ekaterina S.
Kopchuk, Dmitry S.
Kim, Grigory A.
Gaviko, Vasiliy S.
Slepukhin, Pavel A.
Charushin, Valery N.
author_facet Kopotilova, Alexandra E.
Moshkina, Tatyana N.
Nosova, Emiliya V.
Lipunova, Galina N.
Starnovskaya, Ekaterina S.
Kopchuk, Dmitry S.
Kim, Grigory A.
Gaviko, Vasiliy S.
Slepukhin, Pavel A.
Charushin, Valery N.
author_sort Kopotilova, Alexandra E.
collection PubMed
description 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.
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spelling pubmed-99638732023-02-26 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. Lipunova, Galina N. Starnovskaya, Ekaterina S. Kopchuk, Dmitry S. Kim, Grigory A. Gaviko, Vasiliy S. Slepukhin, Pavel A. Charushin, Valery N. Molecules Article 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. MDPI 2023-02-17 /pmc/articles/PMC9963873/ /pubmed/36838924 http://dx.doi.org/10.3390/molecules28041937 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kopotilova, Alexandra E.
Moshkina, Tatyana N.
Nosova, Emiliya V.
Lipunova, Galina N.
Starnovskaya, Ekaterina S.
Kopchuk, Dmitry S.
Kim, Grigory A.
Gaviko, Vasiliy S.
Slepukhin, Pavel A.
Charushin, Valery N.
3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties
title 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties
title_full 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties
title_fullStr 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties
title_full_unstemmed 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties
title_short 3-Aryl-5-aminobiphenyl Substituted [1,2,4]triazolo[4,3-c]quinazolines: Synthesis and Photophysical Properties
title_sort 3-aryl-5-aminobiphenyl substituted [1,2,4]triazolo[4,3-c]quinazolines: synthesis and photophysical properties
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9963873/
https://www.ncbi.nlm.nih.gov/pubmed/36838924
http://dx.doi.org/10.3390/molecules28041937
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