Indolyl imine substituted BODIPY systems; synthesis, photophysical, and biological properties
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60076658%3A12310%2F23%3A43906674" target="_blank" >RIV/60076658:12310/23:43906674 - isvavai.cz</a>
Výsledek na webu
<a href="https://www.sciencedirect.com/science/article/pii/S0040402023001497?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0040402023001497?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2023.133367" target="_blank" >10.1016/j.tet.2023.133367</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Indolyl imine substituted BODIPY systems; synthesis, photophysical, and biological properties
Popis výsledku v původním jazyce
In the study, 4,6-dimethoxy-2,3-diphenylindole-7-carbaldheyde 2, served as a valuable precursor for the reaction with both aniline and BODIPY-linked aniline, generated novel indolyl-imine Schiff base ligands 3 and 7. These indolyl-imine ligand systems were then employed to create the corresponding N-N six -membered boron complexes, 4 (precursor) and 8. The structure of novel compounds were confirmed by 1H and 13C NMR, and high-resolution mass spectrometry. The final evidences of indolyl-imine 7 and its corresponding boron complex 8 were further supported by the single X-ray crystal structures. Single crystal X-ray diffraction analysis revealed the formation of short "C-H center dot center dot center dot F", "C-H center dot center dot center dot p", "C-H center dot center dot center dot O" and "C-H center dot center dot center dot B" interactions, which led to the impressive supramolecular tubular-like (7) and helical (8) self -assemblies. The investigations of the UV-Vis absorption and fluorescence emission properties of the targeted compounds 4, 7 and 8 were carried out using absorption and fluorescence emission (2D and 3D) spectroscopic techniques. Fluorescence properties of the targeted compounds were found to be solvent -dependent. DFT optimized structures and the TD-DFT calculations were in alignment with the experi-mental studies. Additionally, the cytotoxic properties of the target compounds were examined in human breast cancer cells, MCF-7 in vitro as preliminary biological study.(c) 2023 Elsevier Ltd. All rights reserved.
Název v anglickém jazyce
Indolyl imine substituted BODIPY systems; synthesis, photophysical, and biological properties
Popis výsledku anglicky
In the study, 4,6-dimethoxy-2,3-diphenylindole-7-carbaldheyde 2, served as a valuable precursor for the reaction with both aniline and BODIPY-linked aniline, generated novel indolyl-imine Schiff base ligands 3 and 7. These indolyl-imine ligand systems were then employed to create the corresponding N-N six -membered boron complexes, 4 (precursor) and 8. The structure of novel compounds were confirmed by 1H and 13C NMR, and high-resolution mass spectrometry. The final evidences of indolyl-imine 7 and its corresponding boron complex 8 were further supported by the single X-ray crystal structures. Single crystal X-ray diffraction analysis revealed the formation of short "C-H center dot center dot center dot F", "C-H center dot center dot center dot p", "C-H center dot center dot center dot O" and "C-H center dot center dot center dot B" interactions, which led to the impressive supramolecular tubular-like (7) and helical (8) self -assemblies. The investigations of the UV-Vis absorption and fluorescence emission properties of the targeted compounds 4, 7 and 8 were carried out using absorption and fluorescence emission (2D and 3D) spectroscopic techniques. Fluorescence properties of the targeted compounds were found to be solvent -dependent. DFT optimized structures and the TD-DFT calculations were in alignment with the experi-mental studies. Additionally, the cytotoxic properties of the target compounds were examined in human breast cancer cells, MCF-7 in vitro as preliminary biological study.(c) 2023 Elsevier Ltd. All rights reserved.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10403 - Physical chemistry
Návaznosti výsledku
Projekt
—
Návaznosti
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Ostatní
Rok uplatnění
2023
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Tetrahedron Letters
ISSN
0040-4039
e-ISSN
—
Svazek periodika
137
Číslo periodika v rámci svazku
MAY 12 2023
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
10
Strana od-do
—
Kód UT WoS článku
000986849800001
EID výsledku v databázi Scopus
2-s2.0-85151457937