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Cyclobishelicenes: shape-persistent figure-eight aromatic molecules with promising chiroptical properties

Abstract : Cyclobis[n]helicenes (n = 3 or 5) are chiral D2-symmetric p-conjugated macrocycles with stable lemniscular, or figure-eight, shapes. The conformational analysis of five different cyclobis[n]helicenes revealed that these molecules can only exist as their lemniscular conformers with high barriers to enantiomerization (>200 kJ.mol-1). The enantiomers of a cyclobis[5]helicene were resolved by HPLC and their unusual chiroptical properties were attributed to the inherent chirality of their macrocyclic figure-eight.
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Submitted on : Thursday, October 24, 2019 - 4:06:47 PM
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Antoine Robert, Guillaume Naulet, Harald Bock, Nicolas Vanthuyne, Marion Jean, et al.. Cyclobishelicenes: shape-persistent figure-eight aromatic molecules with promising chiroptical properties. Chemistry - A European Journal, Wiley-VCH Verlag, 2019, 25, pp.14364-14369. ⟨10.1002/chem.201902637⟩. ⟨hal-02265747⟩

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