Dimorphic Dibenzorubicene

  • ChemPubSoc Europe Logo
  • Author: Chemistry – A European Journal
  • Published Date: 01 November 2019
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Dimorphic Dibenzorubicene

Related Societies

Polycyclic aromatic hydrocarbons (PAHs) consisting only of fused aromatic rings are molecules with interesting structures. They occur as pollutants released by incomplete combustion processes. Due to their interesting optoelectronic properties, they can be used as materials for organic electronic devices (e.g., OLEDs). For further investigations, it is crucial to have reliable synthetic routes to these molecules.


Hans-Joachim Knölker, Technische Universität Dresden, Germany, and colleagues have developed a synthetic path to the prominent PAH dibenzo[cde,opq]rubicene (pictured). The team's eight-step synthesis relies on an iron-mediated [2+2+1] cycloaddition and a flash vacuum pyrolysis as key steps. A domino reaction consisting of Diels-Alder cycloaddition, CO extrusion, and aromatization has been used for the construction of the central benzene ring.


An X-ray crystal structure determination revealed two crystal modifications of dibenzo[cde,opq]rubicene with different packing modes (pictured in the background). According to the team, the synthesis should provide enough material for further studies, in particular, for environmental analytics. In addition, this synthetic strategy could pave the way for the synthesis of other PAHs.


 

 

Article Views: 438

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH