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Updated: Aug 18, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Furan-Extended Helical Rylenes with Fjord Edge Topology and Tunable Optoelectronic Properties
Teng Luo1,2, Yanpei Wang1,2, Jiahang Hao1,2
1Shenzhen Research Institute of Hunan University, Shenzhen, 518000, P. R. China.
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.
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