This is adamantane:


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Adamantane is an unusual molecule that can actually be found in high abundance in some oil wells. It can also be made from the hydrogenated dimer of cyclopentadiene by a simple rearrangement process using heat and a catalyst. That's to say, most people think adamantane is pretty expensive, but it's actually not. Pound for pound, in fact, it does things no other pendent group on a polymer can possibly do.

It's cousin to molecules containing two, three or more adamantanes fused together, which can also be found in some oil wells. They're collectively called "diamondoids" since they're actually natural precursors to diamond. They just haven't been exposed to as much heat and pressure to finish the job to being the diamonds we find deep underground. In one sense, then, adamantane is the monomer and repeat unit of diamond.

So what's so interesting about adamantane by itself? Sure, it looks like the repeat unit of that massively crosslinked material we call diamond, but does it do anything useful for polymers? Great question, glad you asked, and it turns out the answer is a resounding "YES!" And now you might ask "How does it do whatever it does you're so excited about?"

Well, that's the whole point of this page, now isn't it? Let's start with a simple polymer made from adamantyl acrylate. This acrylate is made by reacting adamantol, the hydroxy-substituted adamantane, with either acryloyl chloride or acrylic anhydride (see below). Using a base and catalyst helps, but in any event, the monomer is easy to make and purify. In fact, you can make a lot of monomers for a whole lot of different kinds of polymers from adamantol, adamantamine and bromoadamantane, all simple derivatives easy to make.

And here's another interesting fact about adamantane in all it's glory and unusual properties: there are several amine derivatives with have antiviral activity. That is, they are some of the few chemicals we know of that can actually fight viruses. In fact, the simple amine-substituted adamantane (below) not only fights viral infections, it helps with Parkinson's disease as well, for reasons no one seems to fully understand. But hey, if it works, let's use it while we figure out how so we can make it work better, no?

      
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