Diazapentabenzocorannulenium: A Hydrophilic/Biophilic Cationic Buckybowl

Q.-Q. Li, Y. Hamamoto, G. Kwek. B. Xing,* Y. Li, S. Ito*
Angew. Chem. Int. Ed. 2022, 61, e202112638. DOI: 10.1002/anie.202112638

Abstract: Polycyclic aromatic molecules are promising functional materials for a wide range of applications, especially in organic electronics. However, their largely hydrophobic nature has impeded further applications. As such, imparting high solubility/hydrophilicity to polycyclic aromatic molecules leads to breakthrough in this research field. Herein, we report the synthesis of diazapentabenzocorannulenium, a cationic nitrogen-embedded buckybowl bearing a central imidazolium core, by a bottom-up strategy from polycyclic aromatic azomethine ylide. X-ray crystallography analyses have revealed a bowl-shape molecular structure that is capable of forming charge-segregated one-dimensional columns by bowl-in-bowl packing. In addition to its fluorescence capabilities and high dispersibility in water, the molecule was found to selectively localize in the mitochondria of various tumor cells, showing potential as viable mitochondria-selective fluorescent probes.

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