Friday, December 08, 2006

van Gogh in Angewandte

Recently, a group at the Moscow State University published some synthetic work in Angewandte (DOI: 10.1002/anie.200602190).

It is a quite simply (and high yielding) route to a new funky heterocyclic circulene starting from the commercially available 3,4-dibromothiophene (even though, it doesn't seem clear to me, how they convince four thiophenes to make a macrocycle and not doing a lot of other stuff during the Yamamoto coupling):

The circulene is just as soluble as a brick, though. But if they (or others) can come up with some soluble derivatives or analogues - similar to what was done to kick off the research in hexa-peri-hexabenzocoronenes (HBCs) at the Max Planck Institute in Mainz by Professor Klaus Müllen - then a lot of cool applications are possible, I think...

3 comments:

Daniel Sejer said...

That's a funky looking molecule man. I'm glad I didn't have to assign the NMR spectra. The 1H-NMR would have been a real killer. I'm not really familiar with the properties of these circulenes. For what applications do you think they may be useful? D!

Tynchtyk said...

Nice to see a work from my university being highlighted in the blogosphere

Christian Bech said...

Maybe "applications" is a strong word, but disc-shaped molecules like this tend to pi-stack (face-to-face, like a stack of plates). Therefore, you can play around with the self-organizing properties and due to the intermolecular pi-pi interactions, it is likely that charges can be transported along a "stack". Ideally, it could be a player in the big molecular electronics game.