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Issue 1, 2016
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Synthesis of open-shell ladder π-systems by catalytic C–H annulation of diarylacetylenes

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Abstract

A new open-shell ladder-shaped π-system has been synthesized. Pentaleno[1,2-b:4,5-b′]difluorene derivatives, 8 fused ring systems bearing 5- and 6-membered rings, were constructed from alkynylfluorenone through a reaction sequence including Pd-catalyzed C–H/C–H annulation. X-ray crystallography and ESR spectroscopy revealed the open-shell character of these ladder-shaped molecules, which derives from their extended π-electron conjugation. Absorption peaks in the near IR region as well as narrow redox potentials observed by cyclic voltammetry indicated small optical and fundamental energy gaps of these fused ring systems.

Graphical abstract: Synthesis of open-shell ladder π-systems by catalytic C–H annulation of diarylacetylenes

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Publication details

The article was received on 09 Sep 2015, accepted on 20 Oct 2015 and first published on 22 Oct 2015


Article type: Edge Article
DOI: 10.1039/C5SC03391H
Citation: Chem. Sci., 2016,7, 650-654
  • Open access: Creative Commons BY license
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    Synthesis of open-shell ladder π-systems by catalytic C–H annulation of diarylacetylenes

    T. Maekawa, H. Ueno, Y. Segawa, M. M. Haley and K. Itami, Chem. Sci., 2016, 7, 650
    DOI: 10.1039/C5SC03391H

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