A fan-shaped synthetic chiral nanographene

• Published in: Chinese chemical letters Vol. 34; no. 2; p. 107520
• Main Authors: Shi, Haonan, Xiong, Bangyuan, Chen, Ying, Lin, Chaojun, Gu, Jiajian, Zhu, Yanpeng, Wang, Jiaobing
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.02.2023
• Subjects: Chirality; Helicene; Molecular nanocarbon; Nanographene; Polycyclic aromatic hydrocarbon; Helicene; Nanographene; Molecular nanocarbon; Chirality; Polycyclic aromatic hydrocarbon
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2022.05.034

We report the synthesis and characterization of a fan-shaped chiral nanographene 1, which is composed of 6 hexabenzocoronene subunits with 216 conjugated carbon atoms. In the dehydrocyclization reaction, 38 CC bonds are formed simultaneously. 1 exhibits strong panchromatic absorption from the ultraviolet to the near-infrared, with an absorption coefficient of 209,000 L mol−1 cm−1 at 564 nm. Optically pure samples, obtained via chiral HPLC, show distinct ECD signals (|Δε| = 704 L mol−1 cm−1 at 405 nm). Upon excitation, 1 emits near-infrared fluorescence at 820 nm with a quantum yield of 5.5%. These photophysical properties of 1 were analyzed with the assistance of DFT calculations. [Display omitted] This work presents the synthesis and characterization of a fan-shaped chiral nanographene, which is composed of 6 hexabenzocoronene subunits with 216 conjugated carbon atoms.