Synthesis and Crystal Structure of Dimorphic Dibenzo[cde,opq]rubicene

Dibenzo[cde,opq]rubicene has been synthesized by an eight‐step reaction sequence including an iron‐mediated [2+2+1] cycloaddition and a flash vacuum pyrolysis as key steps. Two crystal modifications of the S‐shaped, planar polycyclic aromatic hydrocarbon have been obtained and characterized by X‐ray...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-10, Vol.25 (60), p.13759-13765
Main Authors: Suresh, Joghee R., Whitener, Glenn, Theumer, Gabriele, Bröcher, Dirk J., Bauer, Ingmar, Massa, Werner, Knölker, Hans‐Joachim
Format: Article
Language:English
Subjects:
cycloadditions
flash vacuum pyrolysis
polycyclic aromatic hydrocarbons
polymorphism
X-ray diffraction
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Summary:Dibenzo[cde,opq]rubicene has been synthesized by an eight‐step reaction sequence including an iron‐mediated [2+2+1] cycloaddition and a flash vacuum pyrolysis as key steps. Two crystal modifications of the S‐shaped, planar polycyclic aromatic hydrocarbon have been obtained and characterized by X‐ray diffractometry. An uncurved C30 fragment of C70 fullerene: Dibenzo[cde,opq]rubicene as a fragment of C70 fullerene was synthesized using an iron‐mediated [2+2+1] cycloaddition and flash vacuum pyrolysis. Two structural modifications were obtained showing perfectly planar single molecules in different packing modes.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201902915