Mechanistic study demonstrates unexpected aryl migrations during the Scholl reaction of helicenes, highlighting pathways for synthesizing chiral polycyclic aromatic hydrocarbons.
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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Cao et al. (2026) studied this question.
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