Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl
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 t...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/162215 |
| _version_ | 1826129201511530496 |
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| author | Li, Qiang-Qiang Hamamoto, Yosuke Kwek, Germain Xing, Bengang Li, Yongxin Ito, Shingo |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Li, Qiang-Qiang Hamamoto, Yosuke Kwek, Germain Xing, Bengang Li, Yongxin Ito, Shingo |
| author_sort | Li, Qiang-Qiang |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T07:36:49Z |
| format | Journal Article |
| id | ntu-10356/162215 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:36:49Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1622152022-10-10T04:27:04Z Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl Li, Qiang-Qiang Hamamoto, Yosuke Kwek, Germain Xing, Bengang Li, Yongxin Ito, Shingo School of Physical and Mathematical Sciences Science::Chemistry Buckybowl Corannulene 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. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) B. X. acknowledges the financial support from MOE Tier 1 RG6/20, A*Star SERC A1983c0028, and A20E5c0090. 2022-10-10T04:27:04Z 2022-10-10T04:27:04Z 2022 Journal Article 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-. https://dx.doi.org/10.1002/anie.202112638 1433-7851 https://hdl.handle.net/10356/162215 10.1002/anie.202112638 34863045 2-s2.0-85120920438 4 61 e202112638 en RG6/20 A1983c0028 A20E5c0090 Angewandte Chemie (International ed. in English) © 2021 Wiley-VCH GmbH. All rights reserved. |
| spellingShingle | Science::Chemistry Buckybowl Corannulene Li, Qiang-Qiang Hamamoto, Yosuke Kwek, Germain Xing, Bengang Li, Yongxin Ito, Shingo Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl |
| title | Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl |
| title_full | Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl |
| title_fullStr | Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl |
| title_full_unstemmed | Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl |
| title_short | Diazapentabenzocorannulenium: a hydrophilic/biophilic cationic buckybowl |
| title_sort | diazapentabenzocorannulenium a hydrophilic biophilic cationic buckybowl |
| topic | Science::Chemistry Buckybowl Corannulene |
| url | https://hdl.handle.net/10356/162215 |
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