Issue 25, 2024

Sumanene–carbazole conjugate with push–pull structure and its chemoreceptor application

Abstract

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 (CF3) 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 105) 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.

Graphical abstract: Sumanene–carbazole conjugate with push–pull structure and its chemoreceptor application

Supplementary files

Article information

Article type
Paper
Submitted
03 Apr 2024
Accepted
14 May 2024
First published
15 May 2024
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2024,22, 5117-5126

Sumanene–carbazole conjugate with push–pull structure and its chemoreceptor application

D. Ufnal, J. S. Cyniak, M. Krzyzanowski, K. Durka, H. Sakurai and A. Kasprzak, Org. Biomol. Chem., 2024, 22, 5117 DOI: 10.1039/D4OB00539B

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