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Dimerization of indenocorannulene radicals: imposing stability through increasing strain and curvature

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Abstract

One-electron reduction of bowl-shaped indenocorannulene, C26H12, with Rb metal in THF affords [{Rb+(18-crown-6)}2(C26H12–C26H12)2−]·4THF, as confirmed by single-crystal X-ray diffraction. The product consists of a dimeric σ-bonded dianion (C–C, 1.568(7) Å) having two endo6 coordinated {Rb+(18-crown-6)} moieties (Rb–C, 3.272(4)–3.561(4) Å). The (C26H12–C26H12)2− dimer represents the first crystallographically confirmed example of spontaneous coupling for indenocorannulene monoanion radicals, C26H12˙. Comprehensive theoretical investigation of the new dimer confirms the single σ-bond character of the linker and reveals a significant increase of both thermodynamic and kinetic stability of [σ-(C26H12)2]2− in comparison with analogues formed by such π-bowls as corannulene and its dibenzo-derivative. The in-depth computational analysis and direct comparison of the series demonstrates the effect of curvature on radical coupling processes, allowing control over stability and reactivity of bowl-shaped π-radicals.

Graphical abstract: Dimerization of indenocorannulene radicals: imposing stability through increasing strain and curvature

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Article information


Submitted
08 Jun 2020
Accepted
14 Jul 2020
First published
22 Jul 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Dimerization of indenocorannulene radicals: imposing stability through increasing strain and curvature

A. Yu. Rogachev, Y. Zhu, Z. Zhou, S. Liu, Z. Wei and M. A. Petrukhina, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00686F

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