Sumanene-carbazole conjugate with push-pull structure and its chemoreceptor application.
Dominika UfnalJakub S CyniakMaurycy KrzyzanowskiKrzysztof DurkaHidehiro SakuraiArtur KasprzakPublished in: Organic & biomolecular chemistry (2024)
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.
Keyphrases
- density functional theory
- molecular dynamics
- cystic fibrosis
- high resolution
- molecular docking
- dna binding
- loop mediated isothermal amplification
- ionic liquid
- single molecule
- cancer therapy
- solar cells
- magnetic resonance
- computed tomography
- diffusion weighted imaging
- mass spectrometry
- drug delivery
- electron microscopy
- energy transfer
- water soluble
- crystal structure