Synthesis of open-shell ladder π-systems by catalytic C-H annulation of diarylacetylenes

A new open-shell ladder-shaped π-system has been synthesized. Pentaleno[1,2- :4,5- ']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...

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Published inChemical science (Cambridge) Vol. 7; no. 1; pp. 650 - 654
Main Authors Maekawa, Takehisa, Ueno, Hiroshi, Segawa, Yasutomo, Haley, Michael M, Itami, Kenichiro
Format Journal Article
LanguageEnglish
Published England 01.01.2016
Subjects
Chemical reactions
Conjugation
Derivatives
Electrode potentials
Ladders
Organic chemistry
Palladium
Voltammetry
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Summary:A new open-shell ladder-shaped π-system has been synthesized. Pentaleno[1,2- :4,5- ']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.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc03391h