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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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Article information


Submitted
09 Sep 2015
Accepted
20 Oct 2015
First published
22 Oct 2015

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

Chem. Sci., 2016,7, 650-654
Article type
Edge Article
Author version available

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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