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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Regioselectivity and Rearrangement in the Scholl Reaction: π-Extended Helicenes
Ziyang Cao1, Zixian Wu1, Zheng Zhou2
1School of Chemistry and Chemical Engineering, Southeast University, Nanjing, Jiangsu211189, China.
Abstract:
We synthesize three aryl-substituted [6]helicene derivatives and investigate their reactivity in the Scholl reaction. The phenylnaphthyl substrate exhibits unique regioselectivity and rearrangement involving competing 1,2-aryl migrations, as elucidated by density functional theory calculations. The obtained π-extended helicenes are characterized by X-ray diffraction. 1 featuring a perylenyl moiety displays bathochromically shifted absorption and emission compared to triple helicenes 2-4. Circular dichroism and circularly polarized luminescence spectra demonstrate that optically pure 1 and 3 show absorption and luminescence dissymmetry factors of 10-3.
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