Here are some tips for the column: 1) Do a solid addition : Weigh the crude residue, dilute it with DCM, then add silica, 4 times the mass of crude. Evaporate the DCM 2) Use more solvent in the slurry : When you pack your silica gel, leave the stopcock open, add the slurry, push a good pressure or air in it. When the gel stops moving, it is packed. By using more solvent, you'll make sure that the packing is perfect without cracking the silica. 3) Leave a good 5 inches of solvent on top of the silica at all times : If you always have 5 inches of solvent, you will never disturb the silica when adding more solvent. 4) Don't use sand : Once the gel is packed, leave the 5 inches of solvent, then directly add your crude on silica that you prepared on step 1. Use a pasteur pipette and spray solvent inside the column where your crude is sticking 5) Use pure hexanes when packing : By using pure hexanes, you product will never elute prematurely, and gives you the opportunity to wash off any grease or apolar contaminants first. 6) Use a gradient of solvents : Find the solvent system that gives you 0.3 Rf. Then, calculate 4 different concentrations that are lower. For example, for a separation using 50% EA in hexanes, prepare 4 erlenmeyers with 10, 20, 30 and 40% EA. For 1 gram of crude, use 150 mL of solvent for each concentrations. The first 3 concentrations will not elute your compound, so drain directly in a big 1L flask. Elute concentration 4, collect in tubes, then you can go with your 0.3 Rf solvent. Your product will come out REALLY pure. A good rule of thumb: you want to have no more than 1 inch of the crude on silica in your column. It is much easier this way than doing a liquid addition. I see that you use way too little silica for the amount of crude. Your yields are often low because you have way too much product for the amount of silica. Here you have ~50 grams of crude. You should use 20 to 100g of silica per 1g of crude. That's why your yield is so low. You should be getting at least 20 grams of pure bipyridine. Try smaller scale, better column purification, and you would get >70% yields. In this video, 1.6L for 50g is impossible : most of your compound is still stuck in the silica. I hope it helps! 😀 Cheers
Even better than dry loading with silica is dry loading with celite. You will get much better resolution that way because the crude product mixture won't stick to it.
@@Abdcwyxz Personally I never measure out the celite. I just use the minimum amount to facilitate the transfer of the product, but if that ratio works with the silica, I don't see why it wouldn't with celite. I highly recommend it because your product shouldn't stick to the celite like it does to the silica, which results in much tighter bands and better separation. Let me know how it works out for you if you try it :)
Quality control, proper purification, some qualitative tests, all while still being concise quick and easy to listen to... That really makes you stand out from most other chemistry videos! Okay there are a lot of others that still make good videos, but frankly most others, for all practical purposes, are just another AMSR , long winded, or meant for elementary school kids... And if there's anything you feel you left out to keep it so concise, you could always put that in the description or comments... Basically , well done! thank you!
You definitely deserve great sponsors! Your videos are superb. And, I can't believe how many steps this reaction has! You were patient enough to finish it and it ended up excellently!
Nice work on the synthesis! One thing to note though, is that the complex doesn't show fluorescence, but phosphorescence. It's a very important difference for many applications of Ru bipy, actually :D
Yes I used the phosphorescence of this complex to determine the amount of dissolved oxygen in my solvent. Oxygen quenches the triplet state that leads to phosphorescence.
I had to make deuterated Raney nickel once, it was very expensive having to digest it with NaOD and washing it with like a liter of D2O to get it neutral lol
Recently I have been doing a lot of research into dye sensitized solar cells. Coincidentally, the main photosensitive component in this cell is this Ruthenium bipyridine complex. So imagine my surprise to see this video in my feed today. Interesting vid, I really enjoyed it.
Mate, I need a mechanism. You can't just throw that bipy is formed by raney nickel just like that😢. Why is it inserting into the bond? What's the second pyridine doing? Is the nickel consumed? I NEED ANSWERS
Mechanism probably consists of pyridine coordinating to Ni through N, followed by CH activation (oxidative addition at Ni0) via sigma like nickelate intermediate, repeat, reductive elimination
@@SixTough not exactly sure. I know terpyridines (terpy) and higher order polypyridines are much more difficult to make and much more expensive. If I had to guess Bipy is a much stronger ligand then pyridine, possibly holding Ni in place (chelated by both N atoms) and preventing subsequent CH activation and coupling.
This is super cool! I am actually doing a research project at my university where I am making a bisbipyridine complex that can enantioselectively coordinate to metals, and the first metal I am going to try is ruthenium.
And similar idea would be making dinitro-diamino-platinum, it's one of the few Pt salts that can be used in electroless Pt plating (using hydrazine as reducing agent, said to be able to make perfect pitless Pt coated electrodes for electrochemistry experiments). Next to that it it the direct precursor to Pt ligands used in cancer treatment.
Well done. This is a very nice but expensive synthesis considering the relatively low yields in combination with the Ru market price. Have you collected the liquids to recover the Ru one day?
As always very nice video and chemistry! You plan to do something with Rubypy3? Photochemistry just asks to be used (oxidation with air by singlet oxygen formed thanks to complex). I made in past similar complex for such things. From your latest videos I see you watched main academic lab illness: column chromatography XD
And if anyone can think of anything less expensive to do such with that doesn't involve a rare earth... I'm sure the whole field of chemistry would appreciate that...
@@sheastewart7608 this video from Ben sticks with me ruclips.net/video/iwj78pR46zM/видео.html I think the surface structure could be similarly engineered leading to interesting catalytic effects, I would place money on zirconium, but I've heard the same about tungsten
@@Chemiolis I did know that about ruthenium but I was checking if the compound may eliminate that effect through lack of further reactivity. However, as a pigment, it seems to have a similar effect to quantum dots. It may have usefulness in consumer electronics. Regardless, apologies if what I say doesn't make full sense, chemistry is not my first language.
![Making Dibenzo[a,e]cyclooctene - an Emerging Ligand?](http://i.ytimg.com/vi/_2FNaCZldE4/mqdefault.jpg)
Here are some tips for the column:
1) Do a solid addition : Weigh the crude residue, dilute it with DCM, then add silica, 4 times the mass of crude. Evaporate the DCM
2) Use more solvent in the slurry : When you pack your silica gel, leave the stopcock open, add the slurry, push a good pressure or air in it. When the gel stops moving, it is packed. By using more solvent, you'll make sure that the packing is perfect without cracking the silica.
3) Leave a good 5 inches of solvent on top of the silica at all times : If you always have 5 inches of solvent, you will never disturb the silica when adding more solvent.
4) Don't use sand : Once the gel is packed, leave the 5 inches of solvent, then directly add your crude on silica that you prepared on step 1. Use a pasteur pipette and spray solvent inside the column where your crude is sticking
5) Use pure hexanes when packing : By using pure hexanes, you product will never elute prematurely, and gives you the opportunity to wash off any grease or apolar contaminants first.
6) Use a gradient of solvents : Find the solvent system that gives you 0.3 Rf. Then, calculate 4 different concentrations that are lower. For example, for a separation using 50% EA in hexanes, prepare 4 erlenmeyers with 10, 20, 30 and 40% EA. For 1 gram of crude, use 150 mL of solvent for each concentrations. The first 3 concentrations will not elute your compound, so drain directly in a big 1L flask.
Elute concentration 4, collect in tubes, then you can go with your 0.3 Rf solvent. Your product will come out REALLY pure.
A good rule of thumb: you want to have no more than 1 inch of the crude on silica in your column. It is much easier this way than doing a liquid addition.
I see that you use way too little silica for the amount of crude. Your yields are often low because you have way too much product for the amount of silica.
Here you have ~50 grams of crude. You should use 20 to 100g of silica per 1g of crude. That's why your yield is so low. You should be getting at least 20 grams of pure bipyridine. Try smaller scale, better column purification, and you would get >70% yields. In this video, 1.6L for 50g is impossible : most of your compound is still stuck in the silica.
I hope it helps! 😀
Cheers
Even better than dry loading with silica is dry loading with celite. You will get much better resolution that way because the crude product mixture won't stick to it.
@@literallyabee Hi!
Never heard about that! I might try it this week if I have a chance!
It's the same ratio? 4g of celite per gram of crude?
@@Abdcwyxz Personally I never measure out the celite. I just use the minimum amount to facilitate the transfer of the product, but if that ratio works with the silica, I don't see why it wouldn't with celite. I highly recommend it because your product shouldn't stick to the celite like it does to the silica, which results in much tighter bands and better separation. Let me know how it works out for you if you try it :)
Quality control, proper purification, some qualitative tests, all while still being concise quick and easy to listen to...
That really makes you stand out from most other chemistry videos!
Okay there are a lot of others that still make good videos, but frankly most others, for all practical purposes, are just another AMSR , long winded, or meant for elementary school kids...
And if there's anything you feel you left out to keep it so concise, you could always put that in the description or comments...
Basically ,
well done!
thank you!
Well done, there was a lot of steps involved but you condensed it all nicely in 10 minutes
You definitely deserve great sponsors! Your videos are superb. And, I can't believe how many steps this reaction has! You were patient enough to finish it and it ended up excellently!
Nice work on the synthesis! One thing to note though, is that the complex doesn't show fluorescence, but phosphorescence. It's a very important difference for many applications of Ru bipy, actually :D
Yes I used the phosphorescence of this complex to determine the amount of dissolved oxygen in my solvent. Oxygen quenches the triplet state that leads to phosphorescence.
I had to make deuterated Raney nickel once, it was very expensive having to digest it with NaOD and washing it with like a liter of D2O to get it neutral lol
I'm ngl i heard NaOD for the first time
did you make the NiAl alloy yourself?
@@bromisovalum8417 no, I wouldn't even know how to haha, you can buy it commercially in different ratios and stuff
That was really cool. I especially loved the bright-red glow of the ruthenium complex.
Really a great help for synthetic people. Wish to see more videos on metal complexes, especially on cyclometallated iridium complexes.
Recently I have been doing a lot of research into dye sensitized solar cells. Coincidentally, the main photosensitive component in this cell is this Ruthenium bipyridine complex. So imagine my surprise to see this video in my feed today. Interesting vid, I really enjoyed it.
Mate, I need a mechanism. You can't just throw that bipy is formed by raney nickel just like that😢. Why is it inserting into the bond? What's the second pyridine doing? Is the nickel consumed? I NEED ANSWERS
It is used as a solvent, a lot of bipy is adsorbed on Ray-Ni
Mechanism probably consists of pyridine coordinating to Ni through N, followed by CH activation (oxidative addition at Ni0) via sigma like nickelate intermediate, repeat, reductive elimination
@@brandonwatson883 how does it stop at two then?
@@SixTough not exactly sure. I know terpyridines (terpy) and higher order polypyridines are much more difficult to make and much more expensive. If I had to guess
Bipy is a much stronger ligand then pyridine, possibly holding Ni in place (chelated by both N atoms) and preventing subsequent CH activation and coupling.
@@brandonwatson883 Thank you, that sounds reasonable
I learned about Ru(bipy)3 in freshman chemistry class. It's chiral too!!
Every time I want to make an inorganic catalyst I should see this 👌 good job
This is super cool! I am actually doing a research project at my university where I am making a bisbipyridine complex that can enantioselectively coordinate to metals, and the first metal I am going to try is ruthenium.
I'm making this for my inorganic lab today!
I just made the Ruthenium complex of bipyridine in my lab this week! It looked exactly like the one you made as well! We used NaBF4 instead though.
Just wonderful! Great! Congratulations!
This is actually a complex I’ve synthesized in my inorganic lab class. It’s very pretty complex
Beautiful complex and awesome work!
9:34 Looks like fire under water - I love that.
That's the salery for so much effort.
Sorry, my comment has disappeared/seems to be deleted. So I don't know to what you are referring to.
I remember having made thin film LED's with this stuff...nice orange glow.
Really nice video! This complex can be also used as redox indicator.
We used the Ru complexes for oxygen sensors in the 90´s.
Holy crud! Fun to watch but I will definitely buy 2,2-bipyridine when I need it. :)
I've worked with ruthenium complexes in my masters research. But instead of 2,2' bipyridine, it's another one; 2,2' dipyridylamine.
This complex can also exhibit chemilumescence upon reduction from Ru(III) to Ru(II).
Super! Thank you very much! Chlorofil?
I wonder how long your whole set up smelled like pyridine, such a pungent smell. Great video btw!
And similar idea would be making dinitro-diamino-platinum, it's one of the few Pt salts that can be used in electroless Pt plating (using hydrazine as reducing agent, said to be able to make perfect pitless Pt coated electrodes for electrochemistry experiments). Next to that it it the direct precursor to Pt ligands used in cancer treatment.
How did your flask break? Did it have a crack? That is so unfortunate
Well done. This is a very nice but expensive synthesis considering the relatively low yields in combination with the Ru market price. Have you collected the liquids to recover the Ru one day?
I haven’t, it wasn’t really worth my time. Such little Ru isn’t really that expensive.
dios que divertido se ve, daría todo en mi vida para poder sintetizar este complejo
is the solid triboluminescent?
As always very nice video and chemistry! You plan to do something with Rubypy3? Photochemistry just asks to be used (oxidation with air by singlet oxygen formed thanks to complex). I made in past similar complex for such things.
From your latest videos I see you watched main academic lab illness: column chromatography XD
And if anyone can think of anything less expensive to do such with that doesn't involve a rare earth... I'm sure the whole field of chemistry would appreciate that...
@@petevenuti7355 you mean Chemiolis using something more approachable for hobby chemist?
@@petevenuti7355 A TiO2 surface funtionalized with certain ligands can also generate singlet oxygen via energy transfer.
@@sheastewart7608 this video from Ben sticks with me ruclips.net/video/iwj78pR46zM/видео.html
I think the surface structure could be similarly engineered leading to interesting catalytic effects, I would place money on zirconium, but I've heard the same about tungsten
I remember Isaac Asimov chanting: para-dimethyl-amino-benzaldehyde in iambic pentameter.
Is this toxic? If not, it looks to be a good red pigment.
Ruthenium is really expensive and really toxic.
It looks amazing, but really shouldn't be used as a pigment
Bipyridine and its complexes are quite toxic through skin contact and ingestion, they complex with the metals ur body needs to function :-)
@@Chemiolis I did know that about ruthenium but I was checking if the compound may eliminate that effect through lack of further reactivity. However, as a pigment, it seems to have a similar effect to quantum dots. It may have usefulness in consumer electronics.
Regardless, apologies if what I say doesn't make full sense, chemistry is not my first language.
"To the middle adapter, a 500mil flask is connected" O-S-V. English is weird.
Awesome video. Keep up the good work :)
very nice!
The most exspensive hippie light😂🎉, what happens when the uv light is concentrated,. Like a uv laser...
bipy