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
@@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 ?
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.
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.
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.
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.
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.
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.
@@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
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.
@@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)
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. :)
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.
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.
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.
@@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.
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."
@@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.
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)
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.
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!
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
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).
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!
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???
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.
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.
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!
It's been explored theoretically, and there's some talk and information about it on sciencemadness from what I remember in the energetics section. People looking for a "perfect" explosive. Like That Chemist said, it can only exist at extreme low temperatures.
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)
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! 😀
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.
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...
![Seungmin "그렇게, 천천히, 우리(As we are)" | [Stray Kids : SKZ-PLAYER]](http://i.ytimg.com/vi/kAzmhLHePqU/mqdefault.jpg)
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
S a m e!
I legit thought this was a Ex&F video when I clicked xD
He needs more reptile lamps.
@@YounesLayachi Same lmao
He's almost there- just some 'yellow chem issues'
I still can't believe that "nuke it with F2" is actually a viable synthetic strategy for fluorination.
yeah its pretty wild!
So dangerous tho.
@@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 ?
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.
nuke it with f2, it's the only way to be sure.
E&F shaking and crying
The yields are familiar though
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.
Glad you were able to find the channel :)
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.
He doesn't even mention their names.
Uhhh... he did
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.
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.
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.
Naughty electrons get put into the fluorine jail
Now we just need Ex&F to make Octonitrocubane!
Absolutely
He hasn't even finished Cubane yet though?
@@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).
@@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
@@VerbenaIDK he burned the UV leds to fucking tar because he has no damn clue what a milliampere is
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.
Perfluoromengerane.
Sadly I don't think a Menger sponge cubane is possible.
@@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)
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.
Now I just have two questions:
1) Can it be (theoretically) polymerized?
2) Will it blend?
I hope so, and I hope so
CUBIC CARBON ALLOTROPE
@@That_Chemist And if it can be polymerized, can it be 3D printed into a cube?
*DON'T BREATHE THIS*
@@auxchar CUBIC CUBANE
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. :)
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.
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.
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.
Exactly!
POV:
turning excess F grades to A+ in Chemistry
Well Done Sir! Great presentation! *slow clap transitioning into a standing ovation* Bravo!
Thank you kindly!
explosions & fire is gonna flip when he sees this
Here is an interesting thought, if an electron can get trapped in that cage, could an antiproton get trapped?
it would annihilate with an electron from the molecule
@@That_Chemist anti*proton*
@@That_Chemist an antiproton would only be able to annihilate with a proton or neutron, no reaction with electrons
Yes, an antiproton with a negative charge would repel a negatively charged electron
@@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.
forbidden salt, S-tier salt...
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."
Probably, but it would just be a solid
@@That_Chemist Thank you for the reply! Well, there goes that zillion-dollar idea.
@@tomkerruish2982 there are solid lubricants. Graphite comes to mind.
@@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.
@@tomkerruish2982 yeah, mine too.
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)
Thank you for getting those pics and sharing. This is amazing :-)
This is consistent with the fact that PTFE is easily negatively electrostatically charged by friction.
🤔🕸️🤔
Interdasting....
makes me wonder if a big crystal of this could be used for capacitance mechanisms...
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.
Absolutely stunning crystal pics. This is the best video.
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!
AHHH EXCELLENT! Absolutely gorgeous crystals and what a project!
Explosions & Fire and Extractions & Ire fans be drooling right now.....
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
I only took chemistry to school level and still read the title as "the first images of excuse me what?"
Need more paper based videos. Love em and keep up the good work
if you have good suggestions, send them my way via DM on discord or twitter!
I like the thumbnail, good change!
Thanks!
Excellent video and topic! I loved this one. Keep up the wonder work!
Thank you! 🤩
Fantastic to see. Wonderful!
I want a large monocrystal of this for a pendant.
same - imagine the bling!
I keep coming back to this video, it’s such a breathtaking crystal.
Holy sh*t thats incredible! Thanks for sharing this, it made my day! 🔥🤩👌
That EPR spectrum is very nice!
One off your Best vidéo
Thank you!
"these are the most beautiful crystals I've ever seen"- jesse Pinkman
Beautiful cubes!
Could you react it with NaN3 and produce Cubaneoctoazide and NaF?
Maybe with an appropriate Lewis acid
Octaazidocubane, for when you really don't want the cube to exist.
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).
Your adoration for perfluorocubane is amazing. Keep up the good work.
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 🤣
I hope so! I would love to see a polymer of cubanes or hypercubanes
Ah heck no not the rubik's cubane
@@aloysiuskurnia7643 🤣🤣🤣
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!
The great wall of cubane
1:18 Love the 60s
I was reading that the molecule can undergo a reduction process (C8F8-) that results in a free electron being trapped inside the cubic structure.
It’s an oversimplification, but sort of it does
they look like octahedrons but those are the invers of cubes so still pretty cool
I wish bond strain didn't get in the way of octahedrane existing for long
Can't wait for IUPAC rules on how to number substituents
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???
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.
I don't understand half of the chemistry jargon but there are cool cubic crystalloids so you've got me hooked
Next challenge: perfluoro-tesserane
Yeah you experiment with it for a while and it suddenly disappears
Fluorine is so cool. It's the most piratical of atoms
This is beautiful
I want to see octanitrocubane.
This is too chemistry for me but I am sure that this is wonderful and exciting for people who understand
I can just imagine a fireball throwing wizard having his brain deflate while watching this.
This is a very detailed analysis of the synthesis of perfluorocubane and subsequent spectroscopic and X-ray characterisation.
You can feel the excitement in his voice
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.
Table salt might blow your mind.
But the most important question is - what happens if we snort it?
Where does the cube go
Fluorine poisoning, probably
I'm pretty sure Tom from extractions&ire will synthesize cubane in 2056.
Those cubes are just *chefs kiss*
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.
Glad you enjoyed it!
Tom is going to need a gamma ray source in his parent's shed.
Someone flourinated a cube!
“They would never trap an electron inside that electropositive molecular structure”
*spits out hypothetical cereal in shock*
The perflourocubane molecule is fascinating in its structure. But what does it do?
I can see Explosions and Fire taking a deep interest in this. Great job.
Australian Outback Shed chemistry brought me here. I only have notions of chemistry, making such molecules is just magic to me.
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!
“I didn’t highlight this because it is well know that…” right yes I definitely knew exactly what he meant
Is it possible for eight nitrogen atoms to exist in a cube structure like the carbons of cubane?
maybe at ultra low temperatures
If it's possible I would not want to be anywhere near at least some km from that thing being synthesized
@@That_Chemist cubazane go brrrr
@@DrKratso what's the problem? It's just four nitrogen molecules hanging out very near each other. Are you saying they might not want to hang out? ;)
It's been explored theoretically, and there's some talk and information about it on sciencemadness from what I remember in the energetics section. People looking for a "perfect" explosive. Like That Chemist said, it can only exist at extreme low temperatures.
"Gen x is easily decarboxylated" oh god I should warn my mother
lmao
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)
I hope they make it into the next gemstone
I think I can hear that "Explosions & Fire" guy screaming from here (in Australian). 😆
Love it!
This seems like a reasonable alternative to sugar
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! 😀
This is incredibly cool
make sure you share it!
What use could the Perfluorocubane have besides looking cool?
my brain melted watching this video
Amazing!
Glad you liked it :)
Nice!! I wonder why the mp was so spread out?
Those crystals are incredible. Wow!
I like how "PerFect fluorination" has a "PerF" like PerFluoroCubane :D
i look forward to Explosions & Fire synthesising this from Melbourne Bitter and pool chemicals from Bunning's
can we have a superacids tier list?
Good idea!
What a time to be alive.
Gorgeous crystal .
It's hip to be square !
Doesn't this molecule violently hate existing?
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.
I haven’t ever had success with low molecular weight MALDI
this week on chemistry analysis or a snippet of a quote from some random dude from the 90s: "Radical Cation in The Matrix"
doing great!
I can't be the only one unreasonably relieved that the title wasn't clickbait. 🤔🧐😏
What are the applications for this compound ?
I think one awesome application would be as a gemstone on a ring
Hey dude I took chemistry in high school, and I understood about 5% of what you said. I thought this was super interesting once I saw the end.
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...
Is it another step to synthetisze super grease?
Non-chemist scientist: Please tell me what’s interesting here besides the curiosity of making a weird molecule? Does it hold promise for something?
This is a great video about the F box
:(