Wow, someone pulled off that synthesis? I'm impressed!
For those who are wondering if this has any practical applications, the answer is almost certainly no. At best, someone might look at the synthetic pathways used to produce perfluorocubane to attempt to make something similar. It has really unusual spectroscopic and physical properties, which is pretty cool, but mostly in the sense of being a curiosity rather than being something you can do something with.
Imagine this as being the chemistry version of someone managing to get Doom to run on an electric toothbrush or something. It's interesting and amusing to know it's possible, but you're never actually going to start using your Sonicare for gaming.
It's a Time Cube. In a single rotation of the octafluorocubane, each Time corner point rotates through the other 3-corner Time points, thus creating 16 corners, 96 hours and 4-simultaneous 24-hour Days within a single rotation.
There's no Doctor, only corner Cubics, rotating life's 4 corner stage metamorphosis. 4 corner head has 1 corner face, 4 face life. Educated fools can't comprehend Cubicism.
Regular cubane and related compounds have been investigated as race fuels. The bond angles means that extra energy is stored (basically via tension in the bonds due to those extreme angles) compared to 4 ethane molecules (which add up to the same number of carbon atoms, hydrogen atoms, and bonds as one cubane molecule). So your race car could weigh less while still having just as much fuel energy. I think most race series have standardized fuel across competitors now so it’s unlikely anyone will continue with the research.
Could this thing be attached to a solid substrate, perhaps a semiconductor, and remain in place? Like in a computer chip
What about using that free electron in the middle to do computing? Perhaps a quantum computer or something
I mean that's what reminded me: quantum computers often trap a charged particle, perhaps an ion or electrons, and use it to store qubits. This stuff here seems to be a perfect electron trap. Or isn't it?
(note, I'm just throwing ideas in the air, I know almost nothing of chemistry, semiconductors or quantum computers)
Not far from reality, indeed. Every time you have some molecule with a free electron, you can perform Electron Spin Resonance on it. You take a small amount of the molecule, put in a strong magnectic field, and with microwave you could drive the transition between the down and up state (parallel and antiparallel to the magnetic field). However, with a conventional spectrometer you can't control a single spin, because its signal would be tremendosly low, you would need at least ~10^13 molecules (maybe even less nowadays). If you want to use a single molecule, you need to connect to some kind of nanofabricated structure, in order to control and read it out. It's feasible, many works showed that, but very very difficult to engineer. You could spend most of your phd trying that (a pretty common tale in the field).
That's actually not a terrible idea! But sadly the ion seems to be unstable, which means ithe electron is not 'trapped' and rather free to interact with it's cage.
Wouldn’t having an ion like this be useful? I’m not an expert in Chemistry, but most ions will either return or gain an electron at the first opportunity. This compound, on the other hand, likes having an extra electron.
Yeah, reading this article I was amused with the author's writing style and reminded of the "Things I Won't Work With" blog. Lo and behold, it's the same guy.
Hydrofluoric acid, mentioned in the article, is terribly toxic stuff. I can see why he doesn't want to work with it. A drop of the concentrated liquid on the skin can kill. Unfortunately, I think it's critical to the semiconductor industry and there's nothing that could conceivably replace it.
> A drop of the concentrated liquid on the skin can kill.
A small amount of hydrofluoric acid on the skin isn't that much worse than any other acid on the skin. It gives you a chemical burn and you certainly don't want any of this stuff near your eyes, but it is by no means instant death. We're not talking dimethylmercury or arsine gas levels of toxicity.
The problem with HF is that it penetrates tissues and eats calcium so you don't get the pain reception telling you how much HF you actually just got exposed to. That is REALLY DANGEROUS. You can have been exposed to a lot of HF vapor or liquid and not know.
Consequently, you have to treat every HF exposure as potentially lethal because:
1) you might have gotten a much bigger exposure than you think
2) HF consumes your calcium which can stop your heart long after your initial treatment if you don't replenish the calcium after a large exposure.
It is quite toxic, but a drop on skin being lethal is a bit of an exaggeration. If you get any on you, you probably have to talk to experts to address it properly. If you spill a lot on yourself it is indeed a medical emergency.
What happens is your body has to neutralize the acid that very freely absorbs into you through skin contact, and hours later when/if the amount you took exceeds your (mostly) kidney's ability to maintain pH/ion balances, your nerves stop firing for lack of calcium to enable the electrical activity and your heart stops beating normally, then at all.
We know how to treat it now, but originally it was, yes, quite a bit of bad news. So much so that it was used as an esoteric murder weapon in a mystery novel.
I think part of the, hrm, atmosphere of terror surrounding it is the delayed onset of symptoms, in the rabies "by the time you can tell, you're in deep kaka" sense. That and its ability to just slide through a lot of protection.
I read that, then I saw this guys youtube channel: https://youtu.be/gQnmP7UD_zk?t=253 on the bright side I've found something I have not been desensitized to no matter how many time I've watched it.
1. Quantum mechanics predicts that the target molecule can accommodate an electron inside (electron-in-a-cube).
2. A sample of the target molecule was prepared, and yes, it involved elemental fluorine, a very difficult substance to handle safely and one notorious for nonproductively chewing up just about everything you give it.
3. Analytical results were consistent with the structure.
4. The substance's electrochemistry at low temperatures was consistent with the uptake of an electron at the predicted potential. Fine structure of results are consistent with the electron-in-a-cube idea. At room temperature, the results indicate decomposition.
5. Bonus: the electrochemical results suggest the electron-in-a-cube assembly is rotating unexpectedly.
This is a really good example of basic science in action. Observation (some molecules envelop other molecules), generalization (maybe a molecule could envelop an electron), hypothesis (calculations suggest this envelope in particular would work, and would yield these specific observations), experiment (figure out how to make the thing, make it, then measure the predicted properties), update hypothesis (in this case, the electron-in-a-cube is rotating unexpectedly).
It's also a good example of why it's a good idea to do experiments you think will "work". Sometimes they don't work and your hypothesis does in fact suck. Sometimes they work exactly as you expect and you can add that to the pile of evidence you already have in support of the hypothesis. And sometimes you get a surprise.
Just checking, this experiment *confirms* that there's a lone electron inside the cubane cage?
- "At very low temperatures (77K, matrix isolation) in an ESR apparatus, though, you can indeed see the spectrum of the predicted "electron in a cube", split just the way that you would have drawn it out."
(It's written for an audience who doesn't need to be reminded that "ESR" means Electron Spin Resonance, and that is not me!)
Octanitrocubane also exists (first synthesized in 1999), and is the high explosive with the highest known detonation velocity. I think the bond strain in the cubane structure is a large factor in that.
Also related, Tom (Explosions & Fire/Extractions & Ire) has an in progress series of synthesising cubane (not octanitrocubane), in his shed. Whilst not as energetic as octanitrocubane, it is still an interesting molecule.
I love how excited the author is about this post. It sounds like some promising discoveries are in the works.
Of course I have no idea what any of this means. Maybe somebody could share a layman's explanation? What would be the benefit of "hold a free electron in the middle of that cube"?
His excitement is due to the unlikeliness of the result, more than its usefulness. All of the compounds discussed are amazingly reactive, and working with them, even in a lab, is incredibly difficult.
Matter is made up of atoms. Each atom has a nucleus and a cloud of electrons around it. Inside the nucleus we have some number of protons and neutrons. The number of protons determines which element it is. The number of protons + neutrons is basically how heavy it is - that's called an isotope. Isotopes don't matter for chemistry, so we'll ignore that.
For example if you have 6 protons then you're the 6th element. Namely carbon. And 9 electrons gives the 9th element, fluorine. Also protons carry a positive charge, so you'd generally have the same number of electrons as protons. But not always. If an atom or molecule has a different number of electrons and proteins then it is called an ion. More on that soon.
Next up, we have quantum mechanics. In a classical world, the electrons would want to go to the nucleus to hang out with the protons. In a quantum mechanical world, uncertainty in position times uncertainty in momentum has a minimum. Since electrons are light, if we know that an electron is in the nucleus, it probably has a momentum so big that it will soon NOT be in the nucleus. Therefore the best that the electron can do is be somewhere in a kind of probability cloud around the nucleus. Those clouds are called orbitals.
The exact shapes of those clouds have been worked out, and are called orbitals. Orbitals form into shells. Each orbital can contain 0, 1 or 2 electrons. Each shell has a finite (usually fairly short) list of orbitals in it, and all of this has been worked out. This is why the periodic table (see https://en.wikipedia.org/wiki/Periodic_table again) is arranged into columns. Each column usually has the same stuff in its outer shell, and therefore is likely to do somewhat similar things chemically.
Most of chemistry comes from one rule. Atoms like having their outer shell either totally empty, or totally full. They have 2 ways to do. The first is the ionic bond. That's where one atom gives another an electron, making both into ions. The ions then hang out together and are called a salt. The second is a covalent bond, where 2 atoms share an electron each to give each an extra part time electron, making both happy. In the periodic table the farther towards the right and top you are, the more you want a full outer shell. And the farther towards the left and bottom you are, the more you are willing to give up electrons if someone asks.
In fact the elements on the left side care so little for their outer electrons that, when they get together, they let their outer electrons wander around freely. Those electrons make things shiny, and conduct a current when they all move together. Those are metals. By contrast the ones on the right are non-metals - they can steal from metals or share with each other. How many depends on which column they are in.
The very last column is the noble gases. They have a full outer shell and would like it to remain that way, thank you very much. So they don't get involved in this chemistry nonsense.
Now let's talk about the stuff involved in this article.
Fluorine, element 9, is the farthest to the top and right you can get without being a noble gas. It wants one electron and is vicious about getting it. Trying to get it do something unusual usually requires making it temporarily very unhappy. An unhappiness that it is perfectly willing to resolve by reacting with the chemist. This is not an idle threat - histories of fluorine usually start with a list of famous chemists who were killed or maimed in this way. However once it has reacted, it is often very stable. We stick fluoride into toothpaste and cook with teflon - both of which contain fluorine.
Carbon, element 6, comes 3 columns before. Its outer shell has 3 fewer electrons, so it wants 3 more. Making 4 bonds. But where fluorine is vicious, carbon is polite. This makes carbon the tinker toy of complex chemistry. Which is how it became the backbone of pretty much everything required for life as we know it.
Now what does this compound look like?
Let's start with a box. At each corner you put a carbon. Each corner is connected by edges to 3 other corners. That leaves each carbon short one bond. So we stick one fluorine off of each corner. That gives us the diagram at the top right of the article.
Now remember that fluorine is vicious, while carbon is polite. Yes, each fluorine is sharing an electron with a carbon, but it is rather unequal. The electron hangs out with the fluorine a lot more than with the carbon. Therefore the fluorines wind up negatively charged (the extra electron spends more time with them). The carbon atoms therefore wind up with a corresponding positive charge. And all of these positive charges, in theory, make the very center of the box a perfect place for a passing electron to take up residence. An electron that is not part of any atom, just sitting there enjoying a nice home. That extra free electron where an electron normally wouldn't be makes the whole thing an ion.
So it is cool that the theory works out. But in order to do it, some chemist had to do stuff with fluorine that nobody sane wants to happen anywhere near them, let alone be actually doing doing in a lab.
My B.S. in chemistry is 25 years old, and I still got the story despite not working in the field [edit:sp]since. It should make sense if you've had organic and qualitative analytical chemistry, which are sophomore- and junior-level undergrad classes. Given his audience, that's pretty reasonable.
I don't have any chemistry background but my SO has an MS in chemistry and has experience with synthesis and nanomaterial analysis. I was able to follow along decently.
In my read of things it is pretty astounding whenever someone can convincingly prove they've actually synthesized any nanomaterial.
Every field does this trolling in some form. The sentence "The proof is trivial and left as an exercise to the reader." should be familiar for everyone who studied Math.
Hey, I'm reading a Springer book now, and it's not so bad. It's humbly titled "All of Statistics", and I think I understand at least 2/3 of it. So far.
This is an area where comment threads can shine. For most questions, if you ask it early enough then odds are that you'll get a good explanation from someone.
I never took anything past high school chemistry and I managed to understand it. It's not really that abstruse. My background is a bunch of wikipedia articles and chemistry youtube videos.
Just to weigh in as a chemist. A high level of skill and patience went into the creation of this. Fluorine is one of the nastiest things youll find in a lab. HF is no joke.
A long time ago, I asked my high school chemistry teacher why we use hydrochloric acid instead of hydrofluoric acid. Wouldn't the stronger electronegativity of fluorine react more efficiently?
It's always such a joy reading these posts. I'm not a chemist, although my father would have loved me to be, but the sheer style and erudition, makes them compulsive reading
There is a video series on YouTube of an organic chemistry PhD student attempting to synthesise cubane in his garage from readily accessible materials. It may put this feat into a bit of perspective as a non-chemist.
What are the potential applications? I read the article, it was pretty interesting but I only saw things that would be odd to an expert (which I am not). Sure it’s a cool shape, but what does it do?
It seems that it was evidence for theoretical approaches to predict molecule bond behavior. The author mentions DFT, which I assume stands for Density Functional Theory.
Not sure about practical applications, its an advancement in basic science since its never been made before (and its hard to make) and there were interesting theoretical predictions made regarding the bonding configuration that were verified with measurements upon the successful synthesis.
Can someone explain exactly how weird it is? It sounds like a monster was created but I don’t really understand its properties beyond it being very acidic (?)
You have a sterically strained carbon structure (it does NOT want to make a cube). Then you saturate it with the one of the most aggressive atoms in existence, all without blowing up the carbon structure or your lab.
It's probably happier that way, honestly. Like how fluorine is an insanely reactive species, and fluoride is pretty chill. Like he says, all those fluorine nuclei are pulling the electrons in the C-F bonds waaaay over to their side, leaving the inside of the molecule relatively positive. Think of the hydrogen bonding you see between water molecules, but on steroids.
Maybe I’m slow here, but the authors said they couldn’t get a molecular ion in mass spec, but the ESR shows an electron in the center like would be expected for an anion? Is that a radical? Did they mean they couldn’t get a cation?
Mass spec depends on the ion surviving the passage through an electron beam. They can't get a molecular ion because it blows apart in the process - they just get the fragments.
Normally, you get the big fragments and at least some of the whole molecule ions. Not here. Too unstable.
Not all mass spec use an electron beam (in fact I think most do not), one of the most common for analyzing organic molecules uses electro-spray ionization (ESI) and it is relatively gently but I assume you are generally correct in that they couldn't get the whole molecule to fly, it either didn't ionize or fragmented.
Thank you. It's been a good while since I studied how mass spec actually works. And the ones we used were not new at the time (they were from a local company that donated their older machines to my university). Maybe I only remember how ours worked.
The organic chem students didn't get to use the nice computerized FFT NMR machine that was in the basement - that was for analytical chem students and research projects. No, the NMR's you got to use in organic just scanned each frequency and had a plotter that traced your result on paper.
I did think that the single peak on both fluorine and carbon NMR was pretty cool.
If I'm reading the article right, the material is not stable (and also very very difficult to make). So I'm guessing this is probably just an interesting project to check how well current atomic bonding models fit reality.
Fulminates and Azides are known for their physical sensitivity, they're the primary explosive used for the primers in gun cartridges. Azides are generally more sensitive than fulminates - mercury fulminate is an older primer compound where mercury azides are quite unstable and reactive.
Azidoazole Azide is basically an azide group bonded to an azole ring... azole is like pentane except with a nitrogen ring. So basically just one giant pile of nitrogen bonds looking for a reason to un-bond.
See also, Hexanitrohexaazaisowurtzitane, although the name isn't nearly as suggestive, but that's a nice little molecular diagram right there too lol. "Thrillingly nitrogenated", would probably be the description.
Ignition! is one of my all time favourite reads, that I picked up from a previous comment similar to this - highly recommend if it piques the interest of any passer bys
I have a conjecture that if you visit some exotic materials' Wikipedia page and in top right corner is not something you can touch, it's probably a scam.
For those who are wondering if this has any practical applications, the answer is almost certainly no. At best, someone might look at the synthetic pathways used to produce perfluorocubane to attempt to make something similar. It has really unusual spectroscopic and physical properties, which is pretty cool, but mostly in the sense of being a curiosity rather than being something you can do something with.
Imagine this as being the chemistry version of someone managing to get Doom to run on an electric toothbrush or something. It's interesting and amusing to know it's possible, but you're never actually going to start using your Sonicare for gaming.