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Title: Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl
Authors: Li, Qiang-Qiang
Hamamoto, Yosuke
Kwek, Germain
Xing, Bengang
Li, Yongxin
Ito, Shingo
Keywords: Science::Chemistry
Issue Date: 2022
Source: Li, Q., Hamamoto, Y., Kwek, G., Xing, B., Li, Y. & Ito, S. (2022). Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl. Angewandte Chemie (International Ed. in English), 61(4), e202112638-.
Project: RG6/20
Journal: Angewandte Chemie (International ed. in English)
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 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.
ISSN: 1433-7851
DOI: 10.1002/anie.202112638
Rights: © 2021 Wiley-VCH GmbH. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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