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  • Diazapentabenzocorannuleniu...
    Li, Qiang‐Qiang; Hamamoto, Yosuke; Kwek, Germain; Xing, Bengang; Li, Yongxin; Ito, Shingo

    Angewandte Chemie International Edition, January 21, 2022, Letnik: 61, Številka: 4
    Journal Article

    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 a 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‐shaped 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. Two exceeds one: Diazapentabenzocorannulenium, a cationic corannulene derivative bearing an internal imidazolium core, was prepared by a bottom‐up synthetic strategy. The introduction of positive charge and two nitrogen atoms into corannulene resulted in remarkable molecular properties, such as the formation of charge‐segregated one‐dimensional columns, high dispersibility in water, and selective introduction into the mitochondria of tumor cells.