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Extended Quinolizinium-Fused Corannulene Derivatives: Synthesis and Properties

Huang, Lin; Wang, Qing; Fu, Peng; Sun, Yuzhu; Xu, Jun; Browne, Duncan L; Huang, Jianhui; (2024) Extended Quinolizinium-Fused Corannulene Derivatives: Synthesis and Properties. JACS Au 10.1021/jacsau.4c00105. (In press). Green open access

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Abstract

Reported here is the design and synthesis of a novel class of extended quinolizinium-fused corannulene derivatives with curved geometry. These intriguing molecules were synthesized through a rationally designed synthetic strategy, utilizing double Skraup–Doebner–Von Miller quinoline synthesis and a rhodium-catalyzed C–H activation/annulation (CHAA) as the key steps. Single-crystal X-ray analysis revealed a bowl depth of 1.28–1.50 Å and a unique “windmill-like” shape packing of 12a(2PF6–) due to the curvature and incorporation of two aminium ions. All of the newly reported curved salts exhibit green to orange fluorescence with enhanced quantum yields (Φf = 9–13%) and improved dispersibility compared to the pristine corannulene (Φf = 1%). The reduced optical energy gap and lower energy frontier orbital found by doping extended corannulene systems with nitrogen cations was investigated by UV–vis, fluorescence, and theoretical calculations. Electrochemical measurements reveal a greater electron-accepting behavior compared with that of their pyridine analogues. The successful synthesis, isolation, and evaluation of these curved salts provide a fresh perspective and opportunity for the design of cationic nitrogen-doped curved aromatic hydrocarbon-based materials.

Type: Article
Title: Extended Quinolizinium-Fused Corannulene Derivatives: Synthesis and Properties
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/jacsau.4c00105
Publisher version: http://dx.doi.org/10.1021/jacsau.4c00105
Language: English
Additional information: This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. The images or other third-party material in this article are included in the Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/
Keywords: Nitrogen doped PAHs, corannulene, nitrogen cations, intermolecular packing, photophysical properties
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10190115
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