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. 2023 Jan 26;62(5):e202214653.
doi: 10.1002/anie.202214653. Epub 2022 Dec 22.

Furan-Extended Helical Rylenes with Fjord Edge Topology and Tunable Optoelectronic Properties

Teng Luo  1   2 , Yanpei Wang  1   2 , Jiahang Hao  1   2 , Ping-An Chen  3 , Yuanyuan Hu  3 , Bo Chen  4 , Jun Zhang  5 , Kun Yang  1   2 , Zebing Zeng  1   2
Affiliations

Furan-Extended Helical Rylenes with Fjord Edge Topology and Tunable Optoelectronic Properties

Teng Luo et al. Angew Chem Int Ed Engl. .

Abstract

Lateral furan-expansion of polycyclic aromatics, which enables multiple O-doping and peripheral edge evolution of rylenes, is developed for the first time. Tetrafuranylperylene TPF-4CN and octafuranylquaterrylene OFQ-8CN were prepared as model compounds bearing unique fjord edge topology and helical conformations. Compared to TPF-4CN, the higher congener OFQ-8CN displays a largely red-shifted (≈333 nm) and intensified absorption band (λmax =829 nm) as well as a narrowed electrochemical band gap (≈1.08 eV) due to its pronounced π-delocalization and emerging of open-shell diradicaloid upon the increase of fjord edge length. Moreover, strong circular dichroism signals in a broad range until 900 nm are observed for open-shell chiral OFQ-8CN, owing to the excellent conformational stability of its central bis(tetraoxa[5]helicene) fragments. Our studies provide insights into the relationships between edge topologies and (chir)optoelectronic properties for this novel type of O-doped PAHs.

Keywords: Diradicaloids; Edge Topology; Open-Shell Structure; Oxygen-Doping; Rylene.

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