From Fenestrindane towards Saddle‐Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom

Two saddle‐shaped polycyclic aromatic compounds (8 a and 8 b) bearing an all‐cis‐[5.5.5.5]fenestrane core surrounded by an o,p,o,p,o,p,o,p‐cyclooctaphenylene belt were synthesized and characterized by NMR spectroscopy and mass spectrometry. The key step of this synthesis involves the formation of fo...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-09, Vol.56 (40), p.12356-12360
Main Authors: Wong, Wai‐Shing, Ng, Chun‐Fai, Kuck, Dietmar, Chow, Hak‐Fun
Format: Article
Language:English
Subjects:
Aromatic compounds
Crystallography
fenestrane
Fluorescence
Fluorescence spectroscopy
Magnetic resonance spectroscopy
Mass spectrometry
Mass spectroscopy
nanographene
NMR spectroscopy
polycyclic aromatic compounds
saddle-shaped structures
Scholl cyclization
X-ray crystallography
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Summary:Two saddle‐shaped polycyclic aromatic compounds (8 a and 8 b) bearing an all‐cis‐[5.5.5.5]fenestrane core surrounded by an o,p,o,p,o,p,o,p‐cyclooctaphenylene belt were synthesized and characterized by NMR spectroscopy and mass spectrometry. The key step of this synthesis involves the formation of four cycloheptatriene rings from the corresponding electron‐rich 1,4,9,12‐tetraarylfenestrindane derivatives 7 a and 7 b in Scholl‐type cyclizations. The structural details of the D2d‐symmetric saddle compound 8 a were determined by X‐ray crystallography, and the properties of 8 a and 8 b were studied by UV/Vis and fluorescence spectroscopy and cyclic voltammetry. Warped nanographene: Two fourfold bay‐bridged fenestrindane derivatives were prepared in good yields through a non‐classical Scholl‐type cyclization, paving the way to saddle‐shaped nanographenes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201707505