Distinct Helical Molecular Orbitals through Conformational Lock*.

Chemistry : a European Journal
Ani OzcelikJ Lorenzo Alonso-Gómez

Abstract

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 in 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. 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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Aug 21, 2019·Chemistry : a European Journal·Vanessa C Arias-CoronadoSandra Bolaño
Feb 14, 2020·Chirality·Ani OzcelikJ Lorenzo Alonso-Gómez

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Citations

Jun 5, 2021·Chemical Communications : Chem Comm·Marc H Garner, Clemence Corminboeuf
Jul 17, 2021·The Journal of Physical Chemistry Letters·P BaronasS Juršėnas
Oct 1, 2020·Organic Letters·Marc H Garner, Clemence Corminboeuf
Sep 8, 2021·The Journal of Physical Chemistry. a·William Bro-JørgensenGemma C Solomon

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