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

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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, No. 217, 111405, 2023.

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

BibTeX

@article{59d9ca0ce71d475b92cfa46143d917c0,

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.",

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.",

year = "2023",

doi = "10.1016/j.dyepig.2023.111405",

language = "English",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

number = "217",

}

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.

PY - 2023

Y1 - 2023

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.

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UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001009396100001

U2 - 10.1016/j.dyepig.2023.111405

DO - 10.1016/j.dyepig.2023.111405

M3 - Article

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

IS - 217

M1 - 111405

ER -

ID: 40100747