Design and Synthesis of Kekulè and Non-Kekulè Diradicaloids via the Radical Periannulation Strategy: The Power of Seven Clar’s Sextets

• Published in: Journal of the American Chemical Society Vol. 144; no. 51; pp. 23448 - 23464
• Main Authors: Kuriakose, Febin, Commodore, Michael, Hu, Chaowei, Fabiano, Catherine J., Sen, Debashis, Li, Run R., Bisht, Shubham, Üngör, Ökten, Lin, Xinsong, Strouse, Geoffrey F., DePrince, A. Eugene, Lazenby, Robert A., Mentink-Vigier, Frederic, Shatruk, Michael, Alabugin, Igor V.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.12.2022; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; EDGE STATE; GRAPHENE NANORIBBONS; POLYCYCLIC AROMATIC-HYDROCARBON; GROUND-STATE; RYLENE RIBBONS; 2ND HYPERPOLARIZABILITIES; SINGLET FISSION; OPEN-SHELL; INDEPENDENT CHEMICAL-SHIFTS; BOTTOM-UP SYNTHESIS

This work introduces an approach to uncoupling electrons via maximum utilization of localized aromatic units, i.e., the Clar’s π-sextets. To illustrate the utility of this concept to the design of Kekulé diradicaloids, we have synthesized a tridecacyclic polyaromatic system where a gain of five Cla...