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Issue 19, 2021
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“Broken-hearted” carbon bowl via electron shuttle reaction: energetics and electron coupling

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Abstract

Unprecedented one-step C[double bond, length as m-dash]C bond cleavage leading to opening of the buckybowl (π-bowl), that could provide access to carbon-rich structures with previously inaccessible topologies, is reported; highlighting the possibility to implement drastically different synthetic routes to π-bowls in contrast to conventional ones applied for polycyclic aromatic hydrocarbons. Through theoretical modeling, we evaluated the mechanistic pathways feasible for π-bowl planarization and factors that could affect such a transformation including strain and released energies. Through employment of Marcus theory, optical spectroscopy, and crystallographic analysis, we estimated the possibility of charge transfer and electron coupling between “open” corannulene and a strong electron acceptor such as 7,7,8,8-tetracyanoquinodimethane. Alternative to a one-pot solid-state corannulene “unzipping” route, we reported a nine-step solution-based approach for preparation of novel planar “open” corannulene-based derivatives in which electronic structures and photophysical profiles were estimated through the energies and isosurfaces of the frontier natural transition orbitals.

Graphical abstract: “Broken-hearted” carbon bowl via electron shuttle reaction: energetics and electron coupling

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Supplementary files

Article information


Submitted
09 Dec 2020
Accepted
30 Mar 2021
First published
08 Apr 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 6600-6606
Article type
Edge Article

“Broken-hearted” carbon bowl via electron shuttle reaction: energetics and electron coupling

G. A. Leith, A. M. Rice, B. J. Yarbrough, P. Kittikhunnatham, A. Mathur, N. A. Morris, M. J. Francis, A. A. Berseneva, P. Dhull, R. D. Adams, M. V. Bobo, A. A. Vannucci, M. D. Smith, S. Garashchuk and N. B. Shustova, Chem. Sci., 2021, 12, 6600
DOI: 10.1039/D0SC06755E

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    [Original citation] - Published by The Royal Society of Chemistry.

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