Sumanene-carbazole conjugate with push-pull structure and its chemoreceptor application.

Autor: Ufnal D; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego Str. 3, 00-664 Warsaw, Poland. artur.kasprzak@pw.edu.pl., Cyniak JS; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego Str. 3, 00-664 Warsaw, Poland. artur.kasprzak@pw.edu.pl., Krzyzanowski M; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego Str. 3, 00-664 Warsaw, Poland. artur.kasprzak@pw.edu.pl., Durka K; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego Str. 3, 00-664 Warsaw, Poland. artur.kasprzak@pw.edu.pl., Sakurai H; Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, 565-0871 Osaka, Japan.; Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICSOTRI), Osaka University, Suita 565-0871, Osaka, Japan., Kasprzak A; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego Str. 3, 00-664 Warsaw, Poland. artur.kasprzak@pw.edu.pl.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2024 Jun 26; Vol. 22 (25), pp. 5117-5126. Date of Electronic Publication: 2024 Jun 26.
DOI: 10.1039/d4ob00539b
Abstrakt: The first-of-its-kind tetra-substituted sumanene derivative, featuring the push-pull chromophore architecture, has been successfully designed. The inclusion of both strong electron-withdrawing (CF 3 ) and electron-donating (carbazole) moieties in this buckybowl compound has enhanced the charge transfer characteristics of the molecule. This enhancement was supported by ultraviolet-visible (UV-Vis) and emission spectra analyses along with density functional theory (DFT) calculations. The application of the title sumanene-carbazole push-pull chromophore as a selective recognition material for cesium cations (Cs + ) was also presented. The title compound exhibited effective and selective Cs + -trapping ability, characterized by a high apparent binding constant value (at the level of 10 5 ) and a low limit of detection (0.09-0.13 μM). Owing to the tuned optical properties of the title push-pull chromophore, this study marks the first time in sumanene-tethered chemoreceptor chemistry where efficient tracking of Cs + binding was possible with both absorption and fluorescence spectroscopies. This work introduces a new approach toward tuning the structure of bowl-shaped optical chemoreceptors.
Databáze: MEDLINE
Externí odkaz: