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