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Updated: Dec 30, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis, Photophysical Characterization, and Self-Assembly of Hexa-peri-hexabenzocoronene/Benzothiadiazole
Yunbin Hu1, Lukas F Dössel1, Xiao-Ye Wang1
1Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.
Abstract:
Hexa-peri-hexabenzocoronene (HBC) substituted by six benzothiadiazole (BTZ) units with ethynylene bridges is synthesized as a new donor-acceptor (D-A) motif. The C≡C bridges significantly reduce the dihedral angles between HBC and BTZ, and thus, lead to a planar molecular conformation as predicted by density functional theory calculations. The optoelectronic properties are investigated by UV/Vis absorption and emission spectroscopies with absorption and emission maxima at 424 and 650 nm, respectively, demonstrating the tunable electronic structures of HBC through the attachment of electron-withdrawing BTZ units. Two-dimensional wide-angle X-ray scattering analysis shows that the molecules self-assemble into liquid-crystalline columns with high stability over a wide temperature range. Scanning tunneling microscopy reveals the formation of ordered bilayers of the D-A molecules with star-shaped structures.
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