Chemistry with a Twist
  • Chemistry with a Twist
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    • Chiroptical Systems >
      • Helical Molecular Orbitals
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      • Metallacycles & More
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Helical Molecular Orbitals

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Distinct helical molecular orbitals through conformational lock: Several theoretical studies have proposed strategies to generate helical molecular orbitals (Hel-MOs) in [n]cumulenes and oligoynes. While chiral even-[n] cumulenes feature Hel-MOs, odd-[n] cumulenes may also present them if the terminal groups lie on different planes. However, the proposed systems have been either experimentally unfeasible or resulted in opposite pseudo-degenerated Hel-MOs. We hereby demonstrate the introduction of a remarkable energy difference between helical orbitals of opposite twist by fixing the torsion angle between the terminal groups in butadiyne fragments. In order to experimentally lock the conformation of the terminal groups, we designed and synthesized cyclic architectures by combining acetylenes with chiral spirobifluorenes. The high stability of these systems with distinct helical orbitals allowed their isolation and full characterization. In our view, these results constitute a step further in the development of real systems presenting helical molecular orbitals.

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  • Chemistry with a Twist
  • People
  • Research
    • Chiroptical Systems >
      • Helical Molecular Orbitals
      • Chiroptical Systems due to Chiral Axes
      • Chiroptical Symmetry Analysis
      • Chiroptical Surfaces & More
    • Metallaaromatic Systems >
      • Metallacycles & More
      • Metallaaromatic Systems
      • Metallaaromatic Biaryl Atropisomers
      • Metallaaromatic Spirobifluorenes
    • Simulations
    • Lab on a Chip
  • Publications
    • Articles
    • Conferences
    • Outreach
  • Funding
  • Contact
    • Links