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Issue 2, 2017
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Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes

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Abstract

Highly distorted polycyclic aromatic hydrocarbons (PAHs) are predicted to be attractive goals in nanoscience owing to the new properties they can exhibit. We have shown that a variety of functionalized distorted heptagon-containing nanographenes can be easily prepared from simple building blocks by a sequence of Co-catalyzed cyclotrimerization and cyclodehydrogenation reactions. The versatility of this strategy allows easy subsequent enlargement of these nanostructures by Ni-catalyzed cross-coupling and final cyclodehydrogenation reactions. Soluble extended distorted nanographenes 1 and 2 containing heptagon and an edge-shared pentagon–heptagon combination have been synthesized. High distortion of the polycyclic backbone of 2 caused by non-hexagonal rings and a helicene moiety was confirmed by X-ray crystallography. Experimental data reveal promising optical and electronic properties for distorted PAHs with long fluorescence lifetimes (up to 14.5 ns) and low band gaps (down to 2.27 eV). This straightforward and versatile synthetic strategy, the observed long fluorescence lifetimes and the small optical and electrochemical band gaps for the presented compounds may promote the future implementation of distorted graphene molecules in electronic devices.

Graphical abstract: Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes

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Publication details

The article was received on 30 Jun 2016, accepted on 30 Aug 2016 and first published on 31 Aug 2016


Article type: Edge Article
DOI: 10.1039/C6SC02895K
Citation: Chem. Sci., 2017,8, 1068-1074
  • Open access: Creative Commons BY license
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    Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes

    I. R. Márquez, N. Fuentes, C. M. Cruz, V. Puente-Muñoz, L. Sotorrios, M. L. Marcos, D. Choquesillo-Lazarte, B. Biel, L. Crovetto, E. Gómez-Bengoa, M. T. González, R. Martin, J. M. Cuerva and A. G. Campaña, Chem. Sci., 2017, 8, 1068
    DOI: 10.1039/C6SC02895K

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