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Updated: May 9, 2025

Preparation of Carbon Nanosheets at Room Temperature
Published on: March 8, 2016
Synthesis of zwitterionic open-shell bilayer spironanographenes
Juan Lión-Villar1, Jesús M Fernández-García1, Samara Medina Rivero2
1Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Madrid, Spain.
None:
Molecular nanographenes (NGs) are nanoscale graphene fragments obtained by organic synthetic protocols. Here we report the bottom-up synthesis of two spiro-NGs formed by two substituted hexa-peri-hexabenzocoronenes (HBCs), spiro-NG and F-spiro-NG. The X-ray crystal structure of the deca-tert-butyl-functionalized spiro-NG shows a bilayer disposition of the HBCs in face-to-face contact. By contrast, F-spiro-NG, which features tert-butyl substituents on one HBC unit, and fluorine on the other HBC unit, is an electron donor-acceptor bilayer NG. The structural assembly of the donor and acceptor graphenic layers enables an electron-transfer process that leads to the formation of a zwitterionic open shell, paramagnetic species constituted by a radical cation and a radical anion located in the donor and the acceptor HBCs, respectively. Magnetic and spectroelectrochemical experiments, together with theoretical calculations, support the persistent/dominant charge-separated nature of F-spiro-NG. Furthermore, photoconductivity measurements show a significant increase of the charge carrier mobility in the case of F-spiro-NG (Σμ = 6 cm2 V-1 s-1) compared with spiro-NG.
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