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. 2021 Mar 29;60(14):7796-7801.
doi: 10.1002/anie.202014621. Epub 2021 Feb 26.

Double π-Extended Undecabenzo[7]helicene

Ying Chen  1 , Chaojun Lin  1 , Zhixing Luo  1 , Zhibo Yin  1 , Haonan Shi  1 , Yanpeng Zhu  1 , Jiaobing Wang  1
Affiliations

Double π-Extended Undecabenzo[7]helicene

Ying Chen et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: PAH; chiral nanographene; chiroptical property; extended conjugation; helicene.

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