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1H- and 2H-1,2,3-triazoles hybrids: Comparative study of photophysical properties. / Safronov, Nikita E.; Tsyrenova, Biligma D.; Minin, Artem S. et al.

In: Dyes and Pigments, Vol. 217, 111405, 09.2023.

Research output: Contribution to journalArticlepeer-review

Harvard

Safronov, NE, Tsyrenova, BD, Minin, AS, Benassi, E, Nenajdenko, VG & Belskaya, NP 2023, '1H- and 2H-1,2,3-triazoles hybrids: Comparative study of photophysical properties', Dyes and Pigments, vol. 217, 111405. https://doi.org/10.1016/j.dyepig.2023.111405

APA

Safronov, N. E., Tsyrenova, B. D., Minin, A. S., Benassi, E., Nenajdenko, V. G., & Belskaya, N. P. (2023). 1H- and 2H-1,2,3-triazoles hybrids: Comparative study of photophysical properties. Dyes and Pigments, 217, [111405]. https://doi.org/10.1016/j.dyepig.2023.111405

Vancouver

Safronov NE, Tsyrenova BD, Minin AS, Benassi E, Nenajdenko VG, Belskaya NP. 1H- and 2H-1,2,3-triazoles hybrids: Comparative study of photophysical properties. Dyes and Pigments. 2023 Sept;217:111405. doi: 10.1016/j.dyepig.2023.111405

Author

Safronov, Nikita E. ; Tsyrenova, Biligma D. ; Minin, Artem S. et al. / 1H- and 2H-1,2,3-triazoles hybrids: Comparative study of photophysical properties. In: Dyes and Pigments. 2023 ; Vol. 217.

BibTeX

@article{5442d391dd3f42dc95bae6bd7360c93d,
title = "1H- and 2H-1,2,3-triazoles hybrids: Comparative study of photophysical properties",
abstract = "The photophysical properties of three types of hybrid molecules, containing two 1,2,3-triazole isomers with different spatial arrangements and set of surrounding substituents, were investigated. The effect of the heterocyclic scaffold construction and the nature and position of the substituents were revealed by spectral and computational investigations. UV–Vis absorption spectra showed maxima with high molar extinction coefficients. Moderate blue emission (QYs up to 42.2%) and average fluorescence life-time of 1.05–4.53 ns were determined. Positive solvatochromism and intramolecular charge transfer were detected and confirmed by the quantum mechanical calculations. A peculiar effect of a hydrogen bond formation was registered in MeOH, EtOH, i-PrOH, ethylene glycol (EG) solutions and water mixtures. The compounds exhibited an Aggregation Induced Emission Enhancement (AIEE) effect in DMSO-H2O mixtures with a 1.3–3.1 fold increase of QYs and a 1.1–2.8 fold increase of fluorescence life-time. Molecular geometries and electronic characteristics were studied at (Time Dependent) Density Functional Theory ((TD-)DFT) level. The biological behavior of 2H-bis[1,2,3]triazolo)[5,1-a:4′,5′-c]isoquinolines was studied by means of confocal microscopy experiments, which showed that these compounds successfully penetrate the cell membranes, accompanied by bright emission in the cytoplasmic region of the confocal micrographs.",
keywords = "1,2,3-Triazole, AIEE-Effect, Absorption, Fluorescence, Quantum mechanical calculation",
author = "Safronov, {Nikita E.} and Tsyrenova, {Biligma D.} and Minin, {Artem S.} and Enrico Benassi and Nenajdenko, {Valentine G.} and Belskaya, {Nataliya P.}",
note = "To reveal the role of the intra- and intermolecular interactions on the photophysical properties of BT, BTIs and BTOs, the map of the molecular electrostatic potential (MEP) may provide a useful visual support (Fig. 6) [55]. Highly positive MEP regions (depicted in blue color) indicate electron deficiency, whereas highly negative MEP regions (depicted in red color) indicate an excess of electrons. The negative MEP regions (of strongest attraction to positively charged species) were found around the nitrogen atom of the triazole's cycles which are possible binding sites with the labile protons (Fig. 6). The positive MEP regions were found around the hydrogen atoms of the aromatic cycles A, B, C. For BTIs and BTOs, another negative MEP regions appeared, due to the presence of substituents (MeO and CN).This work was performed using the equipment of the Shared Research Centre of Scientific Equipment SRC IIP UrB RAS. We also gratefully acknowledge the Siberian Supercomputer Centre of the ICMMG SB RAS for providing supercomputer facilities. Публикация для корректировки.",
year = "2023",
month = sep,
doi = "10.1016/j.dyepig.2023.111405",
language = "English",
volume = "217",
journal = "Dyes and Pigments",
issn = "0143-7208",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - 1H- and 2H-1,2,3-triazoles hybrids: Comparative study of photophysical properties

AU - Safronov, Nikita E.

AU - Tsyrenova, Biligma D.

AU - Minin, Artem S.

AU - Benassi, Enrico

AU - Nenajdenko, Valentine G.

AU - Belskaya, Nataliya P.

N1 - To reveal the role of the intra- and intermolecular interactions on the photophysical properties of BT, BTIs and BTOs, the map of the molecular electrostatic potential (MEP) may provide a useful visual support (Fig. 6) [55]. Highly positive MEP regions (depicted in blue color) indicate electron deficiency, whereas highly negative MEP regions (depicted in red color) indicate an excess of electrons. The negative MEP regions (of strongest attraction to positively charged species) were found around the nitrogen atom of the triazole's cycles which are possible binding sites with the labile protons (Fig. 6). The positive MEP regions were found around the hydrogen atoms of the aromatic cycles A, B, C. For BTIs and BTOs, another negative MEP regions appeared, due to the presence of substituents (MeO and CN).This work was performed using the equipment of the Shared Research Centre of Scientific Equipment SRC IIP UrB RAS. We also gratefully acknowledge the Siberian Supercomputer Centre of the ICMMG SB RAS for providing supercomputer facilities. Публикация для корректировки.

PY - 2023/9

Y1 - 2023/9

N2 - The photophysical properties of three types of hybrid molecules, containing two 1,2,3-triazole isomers with different spatial arrangements and set of surrounding substituents, were investigated. The effect of the heterocyclic scaffold construction and the nature and position of the substituents were revealed by spectral and computational investigations. UV–Vis absorption spectra showed maxima with high molar extinction coefficients. Moderate blue emission (QYs up to 42.2%) and average fluorescence life-time of 1.05–4.53 ns were determined. Positive solvatochromism and intramolecular charge transfer were detected and confirmed by the quantum mechanical calculations. A peculiar effect of a hydrogen bond formation was registered in MeOH, EtOH, i-PrOH, ethylene glycol (EG) solutions and water mixtures. The compounds exhibited an Aggregation Induced Emission Enhancement (AIEE) effect in DMSO-H2O mixtures with a 1.3–3.1 fold increase of QYs and a 1.1–2.8 fold increase of fluorescence life-time. Molecular geometries and electronic characteristics were studied at (Time Dependent) Density Functional Theory ((TD-)DFT) level. The biological behavior of 2H-bis[1,2,3]triazolo)[5,1-a:4′,5′-c]isoquinolines was studied by means of confocal microscopy experiments, which showed that these compounds successfully penetrate the cell membranes, accompanied by bright emission in the cytoplasmic region of the confocal micrographs.

AB - The photophysical properties of three types of hybrid molecules, containing two 1,2,3-triazole isomers with different spatial arrangements and set of surrounding substituents, were investigated. The effect of the heterocyclic scaffold construction and the nature and position of the substituents were revealed by spectral and computational investigations. UV–Vis absorption spectra showed maxima with high molar extinction coefficients. Moderate blue emission (QYs up to 42.2%) and average fluorescence life-time of 1.05–4.53 ns were determined. Positive solvatochromism and intramolecular charge transfer were detected and confirmed by the quantum mechanical calculations. A peculiar effect of a hydrogen bond formation was registered in MeOH, EtOH, i-PrOH, ethylene glycol (EG) solutions and water mixtures. The compounds exhibited an Aggregation Induced Emission Enhancement (AIEE) effect in DMSO-H2O mixtures with a 1.3–3.1 fold increase of QYs and a 1.1–2.8 fold increase of fluorescence life-time. Molecular geometries and electronic characteristics were studied at (Time Dependent) Density Functional Theory ((TD-)DFT) level. The biological behavior of 2H-bis[1,2,3]triazolo)[5,1-a:4′,5′-c]isoquinolines was studied by means of confocal microscopy experiments, which showed that these compounds successfully penetrate the cell membranes, accompanied by bright emission in the cytoplasmic region of the confocal micrographs.

KW - 1,2,3-Triazole

KW - AIEE-Effect

KW - Absorption

KW - Fluorescence

KW - Quantum mechanical calculation

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85159639577&origin=inward&txGid=8862a2b446e5e335a1e624c011954ea4

UR - https://www.mendeley.com/catalogue/e7ee19eb-d100-3a54-8951-aa7abd20ca38/

U2 - 10.1016/j.dyepig.2023.111405

DO - 10.1016/j.dyepig.2023.111405

M3 - Article

VL - 217

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 111405

ER -

ID: 59292891