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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Triple Helicene Cage: Three-Dimensional π-Conjugated Chiral Cage with Six [5]Helicene Units
Tomoya Matsushima1, Shoko Kikkawa2, Isao Azumaya2
1Department of Biomolecular Science, Faculty of Science and Research Center for, Materials with Integrated Properties Toho University Miyama 2-2-1, Funabashi Chiba 274-8510 Japan.
Abstract:
A three-dimensional π-conjugated chiral cage with six [5]helicene units (a triple helicene cage) was synthesized for the first time. Taking advantage of the Yamamoto coupling reaction, the triflate-substituted triple [5]helicene, a strained and preorganized precursor, was dimerized to afford the target compound. Single-crystal X-ray diffraction analysis revealed the unique structural features of the triple helicene cage: a cage-shaped rigid structure with outer helical grooves and an inner chiral cavity. All-P and all-M enantiomers were separated successfully by HPLC over a chiral column and their chiroptical properties were characterized by circular dichroism spectra.
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