Solution-Processable Buckybowls

  • Author: European Journal of Organic Chemistry
  • Published Date: 16 September 2021
  • Copyright: Wiley-VCH GmbH
thumbnail image: Solution-Processable Buckybowls

Related Societies

Diindeno(1,2,3,4-defg:1',2',3',4'-mnop)chrysene (DIC, pictured in red) is one of the buckminsterfullerene fragments commonly referred to as "buckybowls". Buckybowls have a curved π-surface, leading to unique optoelectronic properties. Other examples of buckybowls are, i.e., corannulenes and sumanenes. There are only a few known syntheses of DIC with no option of installing functional groups. Functionalizing DIC could improve its solubility and allow the optimization of the buckybowl's properties for applications.


Tetsuo Iwasawa, Ryukoku University, Otsu, Japan, and colleagues have developed a solution-phase synthesis of multi-substituted DIC (pictured). The team used distorted dibenzo[g,p]chrysenes bearing four bromines, four methoxy ethers, and four alkyl groups (either iPr or tBu) as a precursor. Palladium-mediated ring-closing reactions then led to the desired buckybowls in yields up to 69 % for the iPr-substituted variant and up to 25 % for the tBu-substituted product.


The team performed the syntheses of both derivatives on a gram scale. Crystallographic analyses confirmed their bowl-like shapes. The researchers also demonstrated that the synthesized scaffold can be further transformed and functionalized, providing a basis for the continued exploration of this type of buckybowl.


 

 

 

 

Article Views: 2441

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