Making 2,2'-Bipyridine and its Ruthenium Complex

2,2'-Bipyridine procedure:

Don't conduct any chemical reactions without proper and professional safety analysis and risk management. Measures taken can be invisible, not filmed, not properly visible on camera or misjudged by the viewer due to setup or video construction. Always conduct own appropriate measures regardless of video setup.

[petevenuti]

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!

[Abdcwyxz]

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

[VinsCool]

Well done, there was a lot of steps involved but you condensed it all nicely in 10 minutes

[Zenzicubic]

That was really cool. I especially loved the bright-red glow of the ruthenium complex.

[ABDULSALAM-qnin]

Really a great help for synthetic people. Wish to see more videos on metal complexes, especially on cyclometallated iridium complexes.

[tracybowling]

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!

[tggd]

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

[ashkanolad]

Every time I want to make an inorganic catalyst I should see this 👌 good job

[rayandfrances]

I learned about Ru(bipy)3 in freshman chemistry class. It's chiral too!!

[bubsygaming]

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.

[danielveldkamp]

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.

[palamalama]

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

[bdnugget]

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

[petkotzvetkov]

Just wonderful! Great! Congratulations!

[ssj]

I'm making this for my inorganic lab today!

[fododude]

Holy crud! Fun to watch but I will definitely buy 2, 2-bipyridine when I need it. :)

[bryanrivera]

This is actually a complex I’ve synthesized in my inorganic lab class. It’s very pretty complex

[jozefnovak]

Super! Thank you very much! Chlorofil?

[einfisch]

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.

[bedlaskybedla]

Really nice video! This complex can be also used as redox indicator.