New Path to Stable Nanographenes

  • Author: Angewandte Chemie International Edition
  • Published Date: 19 October 2021
  • Copyright: Wiley-VCH GmbH
thumbnail image: New Path to Stable Nanographenes

Peri-acenes with extended zigzag edges can have unique electronic and magnetic properties, but higher peri-acenes generally have poor ambient stability. The introduction of heteroatoms, such as boron or nitrogen (N), to the zigzag edges of peri-acenes can stabilize them thermodynamically.


Xinliang Feng, Technische Universität Dresden, Germany, and colleagues have combined solution-based and surface-assisted synthesis to produce NBN-doped bis- and peri-tetracenes (NBN-BT and NBN-PT, pictured) that are stable in ambient conditions. NBN-BT was prepared via consecutive Suzuki coupling reactions (pictured below), followed by a reduction of the nitro groups and a twofold electrophilic borylation. A photocyclization of NBN-BT in the presence of propylene oxide and iodine then produced NBN-PT.

 


The team found that NBN-BT and NBN-PT can be oxidized to obtain dications, which have similar electronic structures to their all-carbon-based analogues bis-tetracene and peri-tetracene. The work provides a new path for the synthesis of stable zigzag-edged nanographenes with multi-NBN units.


 

 

Article Views: 2366

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

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH