Planarization of negatively curved [7]circulene on a graphene monolayer

Author(s)
Karton, Amir
Publication Date
2023-05-01
Abstract
<p>[7]Circulene (C<sub>28</sub>H<sub>14</sub>) is the smallest saddle-shaped [<i>n</i>]circulene with negative Gaussian curvature. The electronic properties of highly curved π-systems change upon planarization, and therefore the induced planarization of these systems has attracted considerable attention in recent years. Here we use dispersion-corrected density functional theory (DFT) calculations (at the PW6B95-D4/def2-QZVP level) to show that the highly nonplanar [7] circulene adopts a completely planar equilibrium structure upon adsorption on a nanographene (modeled as C<sub>96</sub>H<sub>24</sub>). This planarization is rooted in strong dispersion and electrostatic interactions between the [7]circulene and C<sub>96</sub>H<sub>24</sub> (est. as △E<i><sub>e,int</sub></i> = 166.9 kJ mol<sup>− 1</sup> ), which are significantly stronger than the planarization energy of the free [7]circulene (est. as △E<i><sub>e,planar</sub></i> = 40.0 kJ mol<sup>− 1</sup> ). Upon planarization, the magnetic nature of [7]circulene changes from nonaromatic to antiaromatic. Thus, this graphene-induced planarization provides a novel approach for a reversible nonaromatic/antiaromatic molecular switch.</p>
Citation
Chemical Physics, v.569, p. 1-5
ISSN
1873-4421
0301-0104
Link
Publisher
Elsevier BV
Title
Planarization of negatively curved [7]circulene on a graphene monolayer
Type of document
Journal Article
Entity Type
Publication

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