The First Real Life Pictures EVER of Perfluorocubane

Take a look at the first pictures of perfluorocubane! In this video I discuss the recent synthesis of perfluorocubane.
I want to give a huge thank you to Midori Akiyama and Masafumi Sugiyama for allowing me to share their beautiful photos of perfluorocubane and its precursors. For inquiries regarding these images, please contact [e-mail]
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Links to articles discussed in this episode:
Perfluorocubane - www.doi.org/10...
PERFECT fluorination - www.doi.org/10...
Matrix radical cations - www.doi.org/10...
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[@gio9789]

at the beginning i was "oh these are just white crystals" but the end pictures where super cool, wow just wow, can't wait for explosion&fire to synthesize it's own cubane

[@Tabu11211]

S a m e!

[@YounesLayachi]

I legit thought this was a Ex&F video when I clicked xD

[@moosauceable]

He needs more reptile lamps.

[@TrojanHell]

@@YounesLayachi Same lmao

[@garycard1456]

He's almost there- just some 'yellow chem issues'

[@fedorkochemasov4533]

E&F shaking and crying

[@sealpiercing8476]

The yields are familiar though

[@gamingmarcus]

I still can't believe that "nuke it with F2" is actually a viable synthetic strategy for fluorination.

[@That_Chemist]

yeah its pretty wild!

[@dexter2392]

So dangerous tho.

[@cezarcatalin1406]

@@That_Chemist I wonder, if decarboxylation is easy on highly fluorinated acids, why didn’t they try something like Kochi decarboxylation-fluorination or some Hunsdiecker-type reaction ?

[@garycard1456]

One would think that, considering fluorine's veryaggressive oxidising action, the cubane would literally combust, forming (I imagine) a mixture of soot (C), HF and perhaps some fluorocarbon compounds. So, it was not possible to fluorinate cubane directly. The successful method was ingenious and clever.

[@tsm688]

nuke it with f2, it's the only way to be sure.

[@Mecharuva]

I’m not a chemist. I’m a truck driver and occasionally a computer tinkerer. I have no clue why this video was recommended to me, and I only understood about half of the words, but I watched the whole thing and all I can say is: those cubes are spiffy af.

[@That_Chemist]

Glad you were able to find the channel :)

[@LiborTinka]

I love when chemistry become more accessible as more authors share more of their work openly instead of keeping it behind the walled garden of academia.

[@GODDAMNLETMEJOIN]

I love molecules that are so extreme that electrons just say, "Chemistry is boring and physics is way more fun. I'm done with this 2c2e stuff, I'm just going to vibe in this nice electropositive space you've built for me."

[@That_Chemist]

To be fair it is only marginally more energetically favourable than lithium metal

[@milesmccollough5507]

@@That_Chemist you've gotta give it to a perfluoroalkane that can accomplish that.

[@nutzeeer]

@@That_Chemist a space is more favourable for pure negativite charge than an element, let that sink in

[@defenestrated23]

Pimp my Orbitals

[@minecraftify95]

quantum physics

[@kevinknutson4596]

Seriously, a big shout out to the authors for being open to show stuff like this off for us! Big love from weird chemistry youtube nerds to all the professionals.

[@kkgt6591]

He doesn't even mention their names.

[@Nov1cegg]

Uhhh... he did

[@dobbi6083]

Most scientists are nerds and are happy to share their stuff, all that gatekeeping by publishers is just sad. If i made some nice crystals or visually appealing stuff during research and someone contacts me about it, bet i'd share the cool stuff and nerd about it.

[@lunafoxfire]

I'm not a chemist -- basically I just know high school chemistry -- so I was completely lost during the in depth analysis. But it's always fascinating to me to see just how good we are at manipulating molecules in very specific ways.

[@web1bastler]

Now we just need Ex&F to make Octonitrocubane!

[@That_Chemist]

Absolutely

[@WowUrFcknHxC]

He hasn't even finished Cubane yet though?

[@thedoublek4816]

@@WowUrFcknHxC No, the last time I was checking in, he was still stuck at the photochemistry stage (2nd or even 3rd video on that step already).

[@VerbenaIDK]

@@WowUrFcknHxC Nope, stuck in the photochemistry, he bought some uv leds and made a video making a set up with those in extractions & ire, it's been 3 months so pobably by now he must have atleast got an idea of what to do

[@TheBackyardChemist]

@@VerbenaIDK he burned the UV leds to fucking tar because he has no damn clue what a milliampere is

[@daggerpuppets]

Menger sponge Cubane when? Joke aside, this is incredible. Simply beautiful images, crystals, and results. Congratulations to the authors, this must’ve taken ages to complete. As a biochemical engineer, I don’t read a lot of pure chemistry papers, but stuff like this is amazing.

[@AssistantCoreAQI]

Perfluoromengerane.

[@petersmythe6462]

Sadly I don't think a Menger sponge cubane is possible.

[@terdragontra8900]

@@petersmythe6462 yeah i dont see how you could do it with only four bonds per carbon. sierpinskis carpet on the other hand... (may also not work for other reasons im guessing)

[@OrangeC7]

You joke now, but imagine that, a real-life Menger sponge that fractals all the way down to the molecular level. That would be awesome.

[@tubebrocoli]

So the electron actually goes in the cube and then stays there? That's wild, if a good way to get the electron out with electricity and without damaging the molecule is found, that's the kind of stuff that can potentially make better flash drives and possibly even help with making quantum computers.

[@Correct_Opinion]

Naughty electrons get put into the fluorine jail

[@aSpyIntheHaus]

I'm an engineer and a heavy diesel mechanic. I look at things like the Merlin V12 Engine or the SR71 and think, that is beautiful and an engineering marvel. In this regard, I'm going to have to entirely rely on your expertise when you say that little bit of sugary looking stuff is "The most beautiful crystal you've ever seen" because to me.... it looks like sugar. :)

[@rem520]

I really loved the segment describing its ability to form a radical anion by trapping an electron in a box. I cannot believe that I made the connection to my Physics II class where we just started electrostatics with charge densities, and described this to my professor for the class. The perfect chemical situation to describe a complex charge density equation and he seemed just completely nonplussed about it. My previous Ochem prof. was pretty excited to hear it at least.

[@DerHenker_]

this stuff is really sexy. but these yields give me flashbacks and nearly anxiety attacks. after weeks of work and 8-10 syntesis steps and the last step yields under 10 % and then you need to do all kinds of analysis and hopefully have enough for testing in your search for a malaria medication. Brrrrr

[@AlcharynMusic]

This feels like a spacecraft lifting into space. It's just staggering as you know how much time, effort and money was put on the table to create something like this. The pinnacle of science and technology being on display is absolutely mesmerising.

[@That_Chemist]

Exactly!

[@tdawgmaster1729]

Now I just have two questions: 1) Can it be (theoretically) polymerized? 2) Will it blend?

[@That_Chemist]

I hope so, and I hope so

[@victordonchenko4837]

CUBIC CARBON ALLOTROPE

[@auxchar]

@@That_Chemist And if it can be polymerized, can it be 3D printed into a cube?

[@TheTdw2000]

*DON'T BREATHE THIS*

[@brrrrrr]

@@auxchar CUBIC CUBANE

[@zonex001]

This is consistent with the fact that PTFE is easily negatively electrostatically charged by friction.

[@quint3ssent1a]

🤔🕸️🤔 Interdasting....

[@nobody8717]

makes me wonder if a big crystal of this could be used for capacitance mechanisms...

[@Kevinfreddo]

Oh this is so cool. An organic molecule with Oh point group and beautiful molecular orbitals! That stuff excites me so much. I’d love to see how cubanes react with metals!

[@jpolowin0]

That's really cool stuff. Thank you for sharing it. I'm trying to dredge up a memory from my qualifying-exam paper on intercalated graphenes, which at the time were fairly novel. If I'm remembering correctly, a lithium graphene was exposed to some kind of alkene, which entered the solid structure and was semi-reduced. ESR studies showed that the result had a charge of -½. I'm sure I've still got the paper around here somewhere; it was weird enough that I wouldn't have chucked it out.

[@pmathewizard]

POV: turning excess F grades to A+ in Chemistry

[@shabaabhasnatt8799]

How beautiful a single microscopic entity could be that It made a person's day, which is surely hard, to put simply. I am just mesmerized. I want to wish @That Chemist and @Masafumi Sugiyama, @Midori Akiyama a very good day. (sorry, for the crappy language)

[@grim1427]

Well Done Sir! Great presentation! *slow clap transitioning into a standing ovation* Bravo!

[@That_Chemist]

Thank you kindly!

[@CharTheDude]

explosions & fire is gonna flip when he sees this

[@LlamasAtMidnight]

This is too chemistry for me but I am sure that this is wonderful and exciting for people who understand

[@BackYardScience2000]

Explosions & Fire and Extractions & Ire fans be drooling right now.....

[@tomkerruish2982]

Would perfluorododecahedrane make a good lubricant? I've got a mental image of nanoscopic Teflon-coated ball bearings. I have no intuition for chemical dynamics, however, so the answer might be, "Yes, it's a good lubricant, unless you drop it or heat it over -50⁰C, when it explosively decomposes."

[@That_Chemist]

Probably, but it would just be a solid

[@tomkerruish2982]

@@That_Chemist Thank you for the reply! Well, there goes that zillion-dollar idea.

[@chemistryofquestionablequa6252]

@@tomkerruish2982 there are solid lubricants. Graphite comes to mind.

[@tomkerruish2982]

@@chemistryofquestionablequa6252 Yes, I suppose it's a question of how solid a solid it is... which is a matter far beyond my meager chemical knowledge to intuit.

[@chemistryofquestionablequa6252]

@@tomkerruish2982 yeah, mine too.

[@petevenuti7355]

forbidden salt, S-tier salt...

[@monosodium-glutamate]

1:18 Love the 60s

[@Arandom7.62x39]

"these are the most beautiful crystals I've ever seen"- jesse Pinkman

[@karthik24]

Absolutely stunning crystal pics. This is the best video.

[@TheBackyardChemist]

Here is an interesting thought, if an electron can get trapped in that cage, could an antiproton get trapped?

[@That_Chemist]

it would annihilate with an electron from the molecule

[@TheBackyardChemist]

@@That_Chemist anti*proton*

[@TheBackyardChemist]

@@That_Chemist an antiproton would only be able to annihilate with a proton or neutron, no reaction with electrons

[@CED99]

Yes, an antiproton with a negative charge would repel a negatively charged electron

[@Ewr42]

@@TheBackyardChemist there is a reaction actually Electric repulsion bc they're both negative, so they wouldn't even touch without a particle accelerator to force them together But I do imagine that it would need extremely stable matter so we don't have stray alpha particles and neutrons Maybe a few neutrons are impossible to prevent and instead of that leading to a failure of containment it could just mean that the fuel gets depleted by itself with time(idk what the N(3q)+₱(3(5?)q)(or P+₱) annihilation would do to the chemical bonds holding it together at that distance, maybe it's stable, maybe it causes a chain reaction that annihilates everything till there's only an electronic plasma of atomless free electrons(??) and photons, probably more likely to break everything whilst exploding till there's nothing but tar left from all the different compounds made by having the molecules physically ripped apart(or would the energy need to specifically affect the electrons in the outer layer for that?) Anyway, I have no answers, just more questions and a lot of speculations I guess we'll keep on having no answer till someone at CERN or other antimatter producing facility has the idea to use it like that and tests it Imagine it ends up producing strange matter But if it works I think it'd be like a semi-conductor? I can imagine ways to make it useful by accelerating it parallel(I'd say perpendicular but ⅔of the faces are parallel) to the faces of the cubane into a diode-like valve (not tesla) against ionic hydrogen that'd be naturally accelerated against it in the same electric field and extracting the energy somehow(maybe like they do it in tokamaks for normal fusion, or simply thermonuclear-like) Can't think of an antimatter propulsion system tho(and I'm pretty sure I just watched smth in depth about it like yesterday, but I can't remember a thing) But nuclear anti-fusion seems trivial enough, so it'd be antimatter fueled if the energy is applied to an ionic propulsion rocket engine(which thank God I don't know how they work, else I'd be having even more ideas about it) What I'm saying is that it would be dumb and extremely dangerous, but extremely powerful and useful But again, dangerous on so many levels, specially if it DOES work.

[@jhyland87]

Thank you for getting those pics and sharing. This is amazing :-)

[@niconeuman]

That EPR spectrum is very nice!

[@calumpatel4956]

AHHH EXCELLENT! Absolutely gorgeous crystals and what a project!

[@wokkawicca]

Perfluorocubane is a cool compound and a great synthetic achievement--but I must say if these are truly the most beautiful crystals you've ever seen, then you may want to survey a few more crystals! 😀

[@danielharris4373]

Need more paper based videos. Love em and keep up the good work

[@That_Chemist]

if you have good suggestions, send them my way via DM on discord or twitter!

[@SwampMonster1]

I keep coming back to this video, it’s such a breathtaking crystal.

[@aldenconsolver3428]

Excellent dude, that is really cool. Their eloquent manipulation of the structure is amazing. Where do you think they are going from here? (the geologist)

[@That_Chemist]

I hope they make it into the next gemstone

[@xmantheeevee]

I don't understand half of the chemistry jargon but there are cool cubic crystalloids so you've got me hooked

[@RespectTheChemistry]

Fluorine is so cool. It's the most piratical of atoms

[@indigobebop2751]

could there be cubane derivatives that are made up of lots of cubanes? like a big cube made of 81 cubanes? i think thatd be very cool 🤣

[@That_Chemist]

I hope so! I would love to see a polymer of cubanes or hypercubanes

[@aloysiuskurnia7643]

Ah heck no not the rubik's cubane

[@indigobebop2751]

@@aloysiuskurnia7643 🤣🤣🤣

[@noecarrier5035]

Hypercubane with a 4D rotating core. Makes the flask float and is prone to spontaneously disappearing and reappearing later in different locations. Really hard to store!

[@nitroflux_o1040]

The great wall of cubane

[@einbeere4646]

Holy sh*t thats incredible! Thanks for sharing this, it made my day! 🔥🤩👌

[@pr0hobo]

they look like octahedrons but those are the invers of cubes so still pretty cool

[@word6344]

I wish bond strain didn't get in the way of octahedrane existing for long

[@SteamShinobi]

Your adoration for perfluorocubane is amazing. Keep up the good work.

[@brucecheesman2781]

This is a very detailed analysis of the synthesis of perfluorocubane and subsequent spectroscopic and X-ray characterisation.

[@sivalley]

Next challenge: perfluoro-tesserane

[@Flesh_Wizard]

Yeah you experiment with it for a while and it suddenly disappears

[@azxde9266]

Beautiful cubes!

[@brettmoore3194]

Very cool indeed. Thanks. You should be a organic chemistry teacher. I found it intriguing that material science has found a way to develop theoretical crystalline shapes. I think piezo will be the future if it wasn't already done in the past.

[@That_Chemist]

Glad you enjoyed it!

[@jonweinraub]

It’s amazing what we can do but also see. Wasn’t there a picture going around that showed the atomic structure that looked like what’s drawn in my textbook? It’s just crazy!

[@ericvosselmans5657]

Fantastic to see. Wonderful!

[@truncated_sleigh]

I was reading that the molecule can undergo a reduction process (C8F8-) that results in a free electron being trapped inside the cubic structure.

[@That_Chemist]

It’s an oversimplification, but sort of it does

[@SomnolentFudge]

I want a large monocrystal of this for a pendant.

[@That_Chemist]

same - imagine the bling!

[@Jokke13th]

Excellent video and topic! I loved this one. Keep up the wonder work! Thank you! 🤩

[@stevengill1736]

Nice!! I wonder why the mp was so spread out?

[@joshuaworley3898]

Could you react it with NaN3 and produce Cubaneoctoazide and NaF?

[@That_Chemist]

Maybe with an appropriate Lewis acid

[@californium-2526]

Octaazidocubane, for when you really don't want the cube to exist.

[@tschadschi1010]

I don't think so. SN2 shouldn't be possible and the energy barrier for SN1 would be incredible high because how unstable that resulting carbon cation would be (and F- isn't a good leaving group).

[@samspeed6271]

Beautiful. Absolutely beautiful. They're cubes! They're bloody cubes! Yeah, the normal zoom pics just show a white powder, it doesn't do it justice. But the pics where we can see the crystals, they're cubes with little ball feet on em! The optical microscope picture was beautiful. A very interesting video.

[@guyincognito.]

Table salt might blow your mind.

[@divlols4887]

I like the thumbnail, good change!

[@That_Chemist]

Thanks!

[@evilotis01]

i look forward to Explosions & Fire synthesising this from Melbourne Bitter and pool chemicals from Bunning's

[@petevenuti7355]

OG, seems like everyone's using the comments of this video to kick Tom! And Cobalt 60.... If Tom tries gamma rays over his AliExpress rejected looking UV light, he won't turn into the hulk, hopefully maybe grimace and not a SpongeBob 😜 Cat ion in the Matrix... sounds like a *potential* anime... And yeah, dam good forbidden salt, S-tier salt...

[@tomhutchins7495]

I only took chemistry to school level and still read the title as "the first images of excuse me what?"

[@spinjector]

I think I can hear that "Explosions & Fire" guy screaming from here (in Australian). 😆

[@MrBradshawbenjamin]

You got the hook up! Thank you for this!

[@Falco.]

You can feel the excitement in his voice

[@YounesLayachi]

I like how "PerFect fluorination" has a "PerF" like PerFluoroCubane :D

[@petrosthegoober]

Those cubes are just *chefs kiss*

[@paprikalp7989]

Can't wait for IUPAC rules on how to number substituents

[@word6344]

yea how is it 1,4 when they're on complete opposite vertices of the cube?? And then there's those carboranes that look like the dice from dungeons and dragons...how would substituents on those work???

[@GODDAMNLETMEJOIN]

They're numbered so that you can walk around the cube in a loop and come back to where you started. 1 and 4 are opposites on an eight membered ring.

[@alexandredevert4935]

Australian Outback Shed chemistry brought me here. I only have notions of chemistry, making such molecules is just magic to me.

[@zonex001]

I want to see octanitrocubane.

[@koukouzee2923]

This is beautiful

[@donovanschafer8620]

“I didn’t highlight this because it is well know that…” right yes I definitely knew exactly what he meant

[@cognetbenjami.1112]

One off your Best vidéo

[@That_Chemist]

Thank you!

[@nitroflux_o1040]

Someone flourinated a cube!

[@meme__supreme3373]

this week on chemistry analysis or a snippet of a quote from some random dude from the 90s: "Radical Cation in The Matrix"

[@McJaews]

I've watched a bunch of chemistry videos on KZbin. This video is by far the most dense with words I have never heard before. The entire thing could be one big elaborate shit post and I wouldn't be able to tell. But I'm going to assume it's genuine, and I congratulate the chemists on their achievement. It sounds like it was a very difficult thing to do.

[@That_Chemist]

It’s legit!

[@AmaroqStarwind]

WolframAlpha lets you create structural diagrams of molecules that don't exist, so if you ever wanted to know what Phosphomethane or Tetraglucosylhydrazine probably looks like...

[@ugiswrong]

This seems like a reasonable alternative to sugar

[@darren_anscombe]

I can see Explosions and Fire taking a deep interest in this. Great job.

[@idothings6685]

I'm pretty sure Tom from extractions&ire will synthesize cubane in 2056.

[@TubeNutriDoc]

Interesting and provocative. How are these crystals expected to perform and be utilized in the social fabrics of daily life?

[@mitchellp7305]

Those crystals are incredible. Wow!

[@kaboom4679]

Gorgeous crystal . It's hip to be square !

[@darewin3847]

Explosions and fire would love that

[@ligmabaldrich485]

Thought I was gonna see cubane for the first time on E&F's channel, but I guess ThatChemist beat him to it

[@That_Chemist]

[@maxmanlyman2438]

Impressive work. Only thing I wonder is whats up with the high mp range? All other analytical data looks great like there is the possibility of not detecting certain contaminants with 19F NMR but if it were contaminated the crystallography data wouldn't be this neat. Bit puzzling. As adding an electron is likely the most difficult ionization for MS I"m not surprised that they couldn't detect it, makes me wonder if there is a MALDI technique capable of doing it.

[@That_Chemist]

I haven’t ever had success with low molecular weight MALDI

[@crabmansteve6844]

So clean and white!

[@ricksanchez9669]

i always wonder what these exotic molecules taste like. Too bad you would probably only get to taste one.

[@kalidwapur]

Those are very satisfying NMR spectra.

[@That_Chemist]

absolutely!

[@1.4142]

I especially liked the white powder

[@demidrol5660]

Now I want to exchange F to Cl and see the crystal again, also the CN group shoud fit perfect at this place

[@jacoboleary9076]

Octanitrocubane sounds like it belongs on Derek Lowe's Things I Won't Work With

[@thunderclipper]

my brain melted watching this video

[@captainmcawesome7908]

While this is major cool, you gotta be careful to not become the "hey, you do want to promote my upcoming paper)"-guy 😅

[@That_Chemist]

I approached them, not the other way around

[@polygorg]

CUBANE

[@samanthaw.8560]

"Gen x is easily decarboxylated" oh god I should warn my mother

[@That_Chemist]

lmao

[@knyggaplease1222]

I can't be the only one unreasonably relieved that the title wasn't clickbait. 🤔🧐😏

[@selfloathinggameing]

That's a cursed freaking molecule

[@-kenik9629]

I can just imagine a fireball throwing wizard having his brain deflate while watching this.

[@spokehedz]

Forbidden Salt/Sugar/MSG

[@jimsvideos7201]

What a time to be alive.