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Picene, u-cene, we all scream for picene March 11, 2010

Posted by fetzthechemist in Musings, PAHs.

Picene, the five-ring alternant ortho-fused PAH, has been found to superconduct when doped with metal atoms.

Why picene? Well, it is bent and ortho-fused. What does that mean electronically? Each of its rings, the two on the end and the middle one, are fully aromatic – in a Clar sextet fashion. The other two rings then only contain one pi bond. This pattern alternates. the bent seven ring dibenzo[c,m]picene ought to be even better…..but it cannot be gotten off the shelf or readily synthesized.

Another PAH that ought to superconduct like picene is easier to make. Dibenzo[cd,lm]perylene has those three sextets and two pairs of bridging, peripheral rings with one single nomd. It can be made in multigram quantities by condensing perinaphthenone.



1. psi*psi - March 11, 2010

Cute! Got a reference for that?

2. fetzthechemist - March 11, 2010

The thing I saw about picene was in the March 8th C&R News. The syntheses for dibenzo[cd,lm]perylene are covered in Ron Harvey’s PAH synthesis book from Wiley about a dozen years ago.

(BTW, did you see my comment about NSF GRFs being twice as many?)

3. psi*psi - March 15, 2010

No, I didn’t! That’s good news…well…maybe good news…I have another few weeks of waiting.

4. Rhenium - March 16, 2010

I’ve been looking at picene for a while, it even has it’s own Merck entry. It should love DNA just as much as metals…

Posting the references would be awesome…

5. Rhenium - March 16, 2010

NATURE| Vol 464|4 March 2010| doi:10.1038/nature08859

and the synthesis of the “pero-pyrene”
J. Am. Chem. Soc., 2003, 125 (42), pp 12829–12835
DOI: 10.1021/ja035968k

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