Contorted polycyclic aromatic hydrocarbons: Materials for the future

Marilyn Monroe once sang that ‘diamonds are a girl’s best friend.’  If that is the case then it could be said that graphene, another form of carbon, has become the scientist’s best friend.  The relatively recent explosion of research conducted on graphene has been remarkable, and in 2010 resulted in a Nobel Prize for Andre Geim and Konstantin Novoselov at the University of Manchester.

Energy minimized structure from DFT calculations for a large PAH with the hydrogens removed.

Graphene can be thought of as the largest member of the polycyclic aromatic hydrocarbon (PAH) family, molecules made up of fused aromatic rings.  The interest in these carbon-based materials arises from their amazing electronic and optical properties.  The smaller members of the PAH family provide chemists an opportunity to create molecules of fixed and uniform dimensions, something which is challenging when making graphene.  Furthermore, by synthesising PAHs in a logical, stepwise fashion, we can adapt their properties to suit our own needs.

In a recent Chemical Science Edge article, the groups of Hexing Li (Shanghai Normal University) and Colin Nuckolls (Columbia University) have shown that they can construct large polycyclic aromatic hydrocarbons (PAHs) in a relatively straightforward and high yielding process. As might have been expected, such a large aromatic molecule is not particularly soluble but, emphasising the utility of their method, they are able to overcome this by adding groups to the molecule which make it more soluble.  The versatility of their approach will surely lead to the creation of even larger PAHs which will eventually serve to bridge the gap between these small molecules to the extended structures of graphene.

Interested in more?  Read this HOT Chem Sci Edge article now!

Supersized contorted aromatics
Shengxiong Xiao, Seok Ju Kang, Ying Wu, Seokhoon Ahn, Jong Bok Kim, Yueh-Lin Loo, Theo Siegrist, Michael L. Steigerwald, Hexing Li and Colin Nuckolls
Chem. Sci., 2013, 4, 2018-2023
DOI: 10.1039/C3SC50374G

Ruaraidh McIntosh is a guest web-writer for Chemical Science.  His research interests include supramolecular chemistry and catalysis.  When not working as a Research Fellow at Heriot-Watt University, Ruaraidh can usually be found in the kitchen where he has found a secondary application for his redoubtable skills in burning and profanity.

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