Advanced Tinkering - 2023-05-19
In today's video I will show you the synthesis of Octasilacubane using t-Butyltrichlorosilane, Sodium and 12-Crown-4 ether. So to say the inorganic equivalent of the well known Cubane. Since the reactants and the product are air sensitive, I will do the whole synthesis using the Schlenk technique. That is, I will work under inert gas to prevent contact of the chemicals with oxygen and moisture. The product will be beautiful purple crystals. I will use the product in another synthesis to create the stable radical anion. I am sorry for the bad audio. I really need to get a lavalier microphone. I hope you can still enjoy the video. If you want, you can join my patreon to help me working on my projects. I would really appreciate it! https://www.patreon.com/AdvancedTinkering If you want to support my channel and need chemicals, you can use my discount code "Tinkering2023" when ordering from Laboratoriumdiscounter: www.laboratoriumdiscounter.nl Music: Local Forecast – Elevator by “Kevin Macleod” Chapter: 00:00 Introduction 00:58 Explanation of the Schlenk-Setup 06:46 Weighing in the t-Butyl trichlorosilane 09:21 Assembling the reaction apparatus 11:46 Transferring the toluene 17:30 Transferring the 12-crown-4 ether 19:00 Cutting and adding the sodium 19:55 Adding the t-Butyl trichlorosilane 21:19 Starting the reaction 22:32 Filtering the product 28:42 Yield 29:44 Fluorescence of the product 31:19 Recrystallisation
This looks way too professional. Cubane chemistry should be done in a rat-infested shed.
100%. And if the route doesn't involve following the yellow tar road, I don't even wanna know about it
laugh ending in a rattling cough
F this, let‘s nitrate McAss!
😂
Absolutely beautiful synthesis! I had a lot of fun doing this with you!
Same! It was a great day! Can't wait to see your video and especially to try and improve the method we tested.
Unstoppable home chem duo!
I feel like youtube is just taunting Tom at all things cubical. 😂
It honestly didn't have anything to do with Tom :D
But if it gets him to finish his synthesis, even better ;)
I love me some weird shaped molecules
Weirdly shaped molecules are the best!
Please do the tert-butyl trichlorosilane synthesis, it sounds quite interesting.
Noted ;) I also want to do the t-BuLi synthesis because it's one of the chemicals needed for the t-BuSiCl3 synthesis. Maybe I will make a video series out of it.
@@AdvancedTinkering Excellent! I knew I was right when I set my notifications to all!
@@AdvancedTinkering you have nerves of steel. t-BuLi has earned a fearsome reputation.
@@davidfetter Yeah, I've never had the chance to play with any myself. Even just the juvenile fun of squirting it into the air is enough reason to want it though!!!
@@AdvancedTinkering I tried to share a link under my "tesseractane" comment but it's auto deleted it. I promise it's not only safe, but hilarious. Was hoping you could allow it just this once?
hätte nicht gedacht hier auf YT noch jemals vernünftige Inerttechnik zu sehen :D
Amazing work, the final product looks gorgeous!
Thanks!
Wow. What a video. And the unexpected Advanced Tinkering face reveal! Love the style of this video: really cool synthesis, Schlenk setup, explanation, and production all around. Sounds exhausting but fun! Really well done both of you.
And hopefully Laboratoriumdiscounter one day ships to the US it looks great 🤞
we are working on it ;) not everything will be available, but we are working on it.....
@@Laboratoriumdiscounter exciting! And happy to be a beta tester 😉
What a difference to the procedure in the aussie shed :D
Oh the shade.. THE SHADE 😂😂😂😂😂
Wow, but this is 1 of the most complex Chemistry experiments I've ever seen.
This is like hardcore overclocking chemistry!
Great video and explanations! That's a pretty cool setup you have!
Thanks! I got most of it from a retired chemist for very little money. Very cool guy :)
I just hope that I will have a dedicated location at some point where I can keep everything assembled. It took quite some time to get the stuff to elias and set it up.
Das deutsche Aufregen ist definitiv ein Highlight 😂 Auf jeden Fall sehr Wirksam für einen Deutschen Zuschauer für mich um die Aufmerksamkeit wieder auf das Video zu ziehen, falls es mal wieder in den Hintergrund gerückt ist... Sehr gutes Video!
This apparatus is so genius! I had no idea it existed. Thank you for showing the apparatus and this cool experiment!
Beutiful synthesis and beautiful crystalls. I really wish i had this much space...
Thanks! Sadly, it isn't my space and elias also can't use it permanently. We set up everything, did the synthesis and took it down again. All in one weekend.
Love it!
Im gonna color code my lines tomorrow. Great idea.
This video has gone down in my chemistry hall of fame! One of the best I have ever seen on youtube!
Thank you! I appreciate it!
Binge watching your videos back to back- and adding comments for the algorithm~! 🌻👍 Keep up the great content!
Thanks! I appreciate it!
Really loved the explanation of the whole setup!
Amazing!
Very very cool
Cool Video!
Rich people glass. Awesome job!
Ein Schlenk Setup ohne Abzug und Haubenvorrichtung. Wild!
Und ziemlich nice! AC at home. Casual stuff 😂
Super! Thank you very much!
"Poor man's glovebox" 😅
I like such stuff. Like my poor man's reflux condenser i often use for quick experiments: some icewater in a round bottom flask 👍
Can you also check out the fluorescence of the recrystallized product? I'd expect it to be a lot better than that of the initial particle sizes.
I will definitely check that out. I also want to test if the fluorescence changes at even colder temperatures. With my cryocooler I should be able to get down to at least 30 K.
@@AdvancedTinkering You could try a 405nm laser source as well...
Thanks!
Thank you, for the super thanks!
What a pro. This is the most impressive chemistry channel I've ever seen on Youtube.
Hi, I just finished my master´s in theoretical chemistry about descriptors for the electronic structure of electrides and as you probably already know F8C8@e- is one of them. So I got quite curious when you talked about your future project of reducing your compound to a radical anion, because I already simulated the electronic structure of such systems. But so far I was not aware of any synthetic approach. Could you please let me know if you found some literature on this topic. And if you like to include some DFT calculations to your videos I would be happy to help out. Best wishes from Münster :)
This is the paper I was referring to: https://doi.org/10.1002/anie.201500523
I have to admit that computational chemistry is not my strength. Just out of curiosity I did some calculations in gaussian regarding the Ocasilacubane. But I would be lying if I said I was able to interpret the results besides getting some neat visualizations of the orbitals.
If you want, you can write me an email at AdvancedTinkering@yahoo.com
Some calculations would definitely be a neat thing.
Regarding the C8F8@e-: Are you referring to the "Electron in a cube: Synthesis and characterization of perfluorocubane as an electron acceptor" paper?
Beste Grüße aus Hessen :)
@@AdvancedTinkering Yes! That is exactly what I was looking for, thank you so much :)
The electronic structure of electrides is indeed quite intricate and a bit tricky to simulate via the common hybrid functionals (e.q. B3LYP) due to the inherent delocalization error and the usage of diffuse basis set functions for the ghost atom…but that´s the reason why I love this topic so much. Some of the problems can be overcome by relaxed spin densities form post-Hartree-Fock methods…but that is maybe a story for an other day :D
Yes, you are absolutely correct that is the paper I was referring to and I am currently absolutely amazed by the fact that there is a silica-analog.
Viele Grüße (aktuell) aus den Allgäuer Hochalpen :)
PS: Die Mail mit den Details zu den Rechnungen die ich mir überlegt habe geht gleich raus, ich freu mich schon über die Diskussion mit dir.
Ich kam mir schon toll vor, dass ich eine zuhause fehlende Schlenkline einfach an der Uni für YouTube nutzen kann ABER nein du hast einfach eine Zuhause.... Feier ich😂🤌
Alter deine Glovebox ist ja mal richtig genial :D
Haha, danke! Hat leider nicht so gut funktioniert wie gehofft :D
It’s still an organic compound though! Anyway it is fascinating! Great video! ⚗😊
where the carbons at?
@@brandonbennett3082 In t-Bu rests.
@@crabcrab2024 oh duh
32:10 🤩 crystals
Absolutely wonderful synthesis! Congratulations! Also, the video as a whole was truly a pleasure to watch! P.s. it's good to see the man behind the tinkering finally!
Thank you a lot! I am really happy you enjoyed the video!
Insane, just insane. I must say, though, it is pretty kind of silicon to be so happy to form a cube.
Very nice. Makes me want to go back to the lab and synthesize something. Assembling batteries gets boring after a while 😕
Sehr nice
Danke dir!
0:26 I can feel the dissapointment from the other side of the globe.
Ah, now we‘re talking.
Ar is pretty expensive, in the industry you’ll more often see N2 than Ar.
A good glovebox will set you back. The „real“ gloves are very expensive as is everything manufactured to a high standard.
We used to use two pairs for good measure depending on the conditions in our boxes. That‘s an enormous pain, especially because one is already wearing a pair of surgical gloves.. Makes three.
If you want to get that up to an acceptable level you can contact me if you have any questions. There are some issues with pressure control within such a small volume that make handling it even more a nuisance.
The gloveboxes we had were the size you showed in the Cs lab 😍
Cheerio
Wery nice and interesting video! And i love thet you speeking English!! 👍🏻
Thank you!
@@AdvancedTinkering nooo thank you 🙌🏻🙏🏻🤲🏻
This was excellent - really enjoyed your thorough and well explained/performed chemistry! I was wondering whether you might consider making a video on preparing a Suzuki catalyst under Shlenk conditions (e.g. palladium tetrakis triphenylphosphine) and perhaps performing the Suzuki coupling? This was one of the only videos i had found on Youtube with proper Shlenk demonstration :)
Thank you very much!
As soon as I find the space to set up the Schlenk setup permanently, and I find the time, I can try to make a video about it.
Sehr cool! Deutlich schöner als das organische Cuban👍👍
3:04 is there another name for that one way glass valve? Looks pretty handy to have in the lab. I always pick up some little tidbits from you. I’ve been around organic chemistry labs for a while, but never filtered the drying agent through cotton for example. Love your stuff!
OK, those crystals are just GORGEOUS!! I would love to see if they could be grown larger - perhaps via re-dissolving them in toluene to make a saturated solution, then slowly evaporating the solvent off? Safely somehow haha.
Anyways this was ace, definitely subbing to see the next video. I came here half expecting to see a troll on Ex and Ire, but yeh this was just some really cool chemistry a slightly more advanced crack shed. Nice.
Thank you a lot! Yes, I also thought about growing bigger crystals. But I can't think of a practical way to slowly evaporate the toluene under an inert gas atmosphere. And you would need a lot of toluene. For the 470 mg I needed 500 mL of boiling toluene. It seemed to be basically insoluble when cold.
It may be possible to cool the boiling solution very slowly. A few degrees per day maybe.
@@AdvancedTinkering ahh true, I didn't even think about how clear the solution was once it had cooled down. It really doesn't look like theres any in there at room temps! Slow cooling would definitely be the method then I reckon. It could be useful to know at what temperature the crystals began forming - it might be that the solubility drops too rapidly to exert any real control over growth.
@@AdvancedTinkering Alcohol is always the answer.
Nice video! Did you weigh tare your flask and stopper when it was filled with argon (since the density difference to air is not neglectible in a 100 mL flask on your rxn scale) and already greased? Its also kind of weird to only determine the yield before recryst and i would take up the crown ether beneath the inverted "Ar funnel" if you made the effort of setting it up for the Na weighing anyway. Other than that you did a nice job making the best out of the setup. Septa would be a worthwile addition as it would make the flushing of syrringse with Ar much easier and it would also enable you to do cannula transfers which can be much more convenient. Looking forward to watch more of your content!
Thanks! Yes, the tara was determined with argon inside the flask and a greased stopper. We first weight the flask with the product under vacuum and then realized why the yield was relatively low.
The yield before recrystallization was the one I mentioned because it's also the one mentioned in the original literature and thus the only one to compare it to.
I also determined the yield after recrystallization and it was considerably lower (~0.3 g; I currently dont have my notes with me, so I can't say exactly).
Yeah you are right, using the inverted funnel for the 12-crown-4 ether would have been a good idea.
Finally! There it is! The octasilacubane! 👍
@suddendeath2000 - 2023-05-19
Oh no, no one tell Extractions&Ire!
@RostNicht - 2023-05-19
actually, someone really should...😉
@nilsnippe4359 - 2023-05-19
It's amazing what you can do with proper laboratory equipment, though this definitely lacks the shed-chemistry vibes
@matthewnardin7304 - 2023-05-19
@@nilsnippe4359honestly I'll be way more impressed when E&I finally gets it with hardware he pulled out of a dump.
@ExtractionsAndIre - 2023-05-20
Please, I am immediately aware of all cube based content online
@hgbugalou - 2023-05-20
He's our backyardchemtube daddy.