Double π‐Extended Undecabenzo[7]helicene

• Published in: Angewandte Chemie International Edition Vol. 60; no. 14; pp. 7796 - 7801
• Main Authors: Chen, Ying, Lin, Chaojun, Luo, Zhixing, Yin, Zhibo, Shi, Haonan, Zhu, Yanpeng, Wang, Jiaobing
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 29.03.2021
• Subjects: Chemistry; Chemistry, Multidisciplinary; chiral nanographene; chiroptical property; extended conjugation; helicene; PAH; Physical Sciences; Science & Technology; helicene; chiral nanographene; PAH; chiroptical property; extended conjugation
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202014621

This work reports the first double π‐extended undecabenzo[7]helicene 1, which is a large chiral nanographene, composed of 65 fused rings and 186 conjugated carbon atoms. The molecular identity of 1 has been confirmed by single crystal X‐ray diffraction. A wine coloured solution of 1 in dichloromethane absorbs light from ultraviolet to the near infrared, featuring an extremely large molar absorption coefficient of 844 000 M−1 cm−1 at 573 nm. Optically pure 1 shows a record high electronic circular dichroism intensity in the visible spectral range (|Δϵ|=1375 M−1 cm−1 at 430 nm) known for any discrete polycyclic aromatic hydrocarbon. These unusual photophysical properties of 1 contrast sharply with those of a mono‐undecabenzo[7]helicene derivative 2. More than double: This paper presents the first double π‐extended undecabenzo[7]helicene. It is a chiral nanographene, displaying an extremely strong light absorption capability with a record high ECD intensity in the visible spectral range known for any discrete PAH compound.