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Scientists finally make 'triangulene,' which is good, we think

It won't cooperate long enough for us to measure its properties, so nobody has any idea what to do with it, but it sure does aim to misbehave.
By Jessica Hall
graphene hexagons

Chemists have made another compound nobody has any idea what to do with. The new weirdness is called triangulene, a cousin of graphene that's been theorized for decades but never successfully synthesized. What do we do with it? How do we handle it? What are its properties? Other than that it's badly behaved, and that it could have implications for future electronics, nobody knows -- not even the chemists who made it.

On paper, triangulene is made of six benzene rings, put together edge-on to make a flat triangular flake of a molecule that has a seemingly innocuous set of unpaired electrons. It's expected to be magnetic, and it would tessellate into a sheet of graphene, if you could convince it to stick together and do so -- its authors call triangulene molecules "graphene fragments." But you can't convince triangulene to do much of anything. Its makers only managed to make one molecule of the stuff at a time, and that with atomically precise tools. They couldn't synthesize it in the usual "take A, add B, stir" way chemists use, because it's too unstable -- they had to use the ultra-fine gold tip of a scanning probe microscope to individually flick away two hydrogen molecules from the dihydro form of the triangulene molecule, which left the naked electrons. And even under such tender, loving care, the stuff wouldn't sit still for any length of time.

Triangulene.

The reason for its instability is also why we're having such trouble describing it. It's all because of that pair of extra electrons: the little dots in the image above. Chemistry has a couple major ways it uses to describe how electrons do what they do, and triangulene occupies a weird superstate of being both and yet neither(Opens in a new window), at the same time. It's a little like how light can act like both a particle and a wave. Triangulene acts like it has both a delocalized pi cloud of electrons and also a discrete resonant single- and double-bond structure (double bonds, hence the -ene). The two extra electrons want to be subsumed into the resonant structure, but because you just cannot force carbon to make five bonds, the electrons aren't going to get what they want.

What happens to them? Well, they try to slipstream into the resonant structure anyway, and that doesn't work. So they go for the delocalized-cloud-of-electrons approach, hoping to blend into the crowd. It's like the chemistry equivalent of going to a party and just talking to the host's dog all night. [I have literally done this. -Ed] But that doesn't work either, because there's nowhere in the cloud for them to settle in. Flipping feverishly back and forth in this meta-unstable state means that triangulene is the opposite of inert. That pair of extra electrons just zooms around, stuck in a higher-energy state, so triangulene reacts with anything it encounters. Including any stray oxygen molecules that got into the testing chamber. The longest-lived sample they made persisted for all of four days before it reacted away, although that may have been because of pseudo-resonant interactions with the metal plate on which it was synthesized.

The icing on the proverbial cake is that the scientists who made triangulene have no idea how to handle it nor what to do with it. They remark that a thorough investigation of exactly what those electrons are doing is "beyond the scope of this paper(Opens in a new window)." Because the electrons are sort of participating in quantum spin weirdness, there has been some speculation(Opens in a new window) that their property of spin could make them useful in quantum computing. This, to me, seems like trying to call in a Bradley APC to take out a spider in the corner of your garage: it's physically possible, but it's unwieldy, it'll be too expensive, and nobody in the spider-removal field even thinks it's a good idea because they already have different, purpose-built tools.

Just for laughs -- in the course of reading about triangulene, I discovered that triangulene isn't the only super fun chemical that scientists produced with no idea how to use, contain, or even investigate. For one -- good old nitric acid was once an unknown enough quantity to convince chemists to just drip the stuff onto various substances, to see what it would do. (Either that, or nobody was making their apprentices watch those terrible lab safety videos...) One chemist, seeing a label that said nitric acid acts upon copper, wished to know what it would do. He discovered that "...nitric acid not only acts upon copper but it acts upon fingers. The pain led to another unpremeditated experiment. I drew my fingers across my trousers and another fact was discovered. Nitric acid acts upon trousers.(Opens in a new window)"

Beyond that, though, you really should go read Derek Lowe's remarks on azoazide azides, which are compounds fabricated by a lab in Germany where people get paid to synthesize the craziest, nastiest, most insanely explosive crap they can dream up. They managed to make a chemical so outrageously explosive that they literally could not measure its properties because it kept blowing up the spectrometers(Opens in a new window) every time they tried.

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