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Updated: Jul 28, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Pyrrole-Fused Azacoronene Analog with Sulfur Embedded in the Outer Periphery
Masayoshi Takase1,2, Aiki Sagawa1, Shigeki Mori2,3
1Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan.
Abstract:
The synthesis of sulfur-embedded hexapyrrolohexaazacoronene (HPHAC) analog 2 and its corresponding desulfurized and rearranged compounds was achieved from tetrafluoroisothianaphthene. Structures of all the new π-skeletons were determined by X-ray crystallography. Comparison of the electronic spectrum of 2 with those of its derivatives revealed less involvement of the sulfur atom in π-conjugation. Similar to the reference HPHAC (1), compound 2 and its derivatives exhibited reversible oxidation behavior. The aromaticity of both neutral and dication states has been investigated through DFT calculations.
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