[tommac]

A little back ground I was originally a biology major I really didn't care for the subject or research so I focused a lot and math and chemistry. I'm working now on a grad degree in chemistry, and doing research under the engineering department. The lab I'm working in used to have a materials engineer who focused on polymers, but now he's gone. The majority of the students I'm working with are electrical engineers. I've had two good years of chemistry, but barely covered polymers I think it was organic II and this consisted of identify monomers. I wanted to know:



Is it possible for quinine to undergo polymerization using ammonia per sulfate and Tetramethylethylenediamine AKA TEMED.

If not could use TiCl3

Thanks

[baum0372]

How do you expect this to polymerize?  It seems to me the ammonium persulfate is a source of radicals, and the TEMED will be incorporated into the polymer?  Based on the structure of quinine I don't see too many groups that are actively going to polymerize.  But if you mix radicals with a diamine and toss in some quinine, I'm sure that are a lot of possible reactions that are going to occur to give some insoluble junk.  Can you elaborate more?

[tommac]

Hey baum0372,

Thanks for the reply.

I work with acrylate polymer gel. I was trying to fictionalize the gel with quinine. I was looking at the polymerization of styrene to polystyrene. The mechanism looks like it place at a terminal alkene. I thought since that since  had a terminal alkene the mechanism would be similar. The mechanism is on youtube http://www.youtube.com/watch?v=2iHRJPnB0EM the only difference is that they use a different initiator.

The TEMED is used as an accelerator. I use it when the gels i make are thermosensitive, and I cant use heat.

[Arkcon]

Hey baum0372,

Thanks for the reply.

I work with acrylate polymer gel.

Many biologists do.

I was trying to fictionalize the gel with quinine.

Was that a typo?

I was looking at the polymerization of styrene to polystyrene. The mechanism looks like it place at a terminal alkene. I thought since that since  had a terminal alkene the mechanism would be similar. The mechanism is on youtube http://www.youtube.com/watch?v=2iHRJPnB0EM the only difference is that they use a different initiator.


The TEMED is used as an accelerator. I use it when the gels i make are thermosensitive, and I cant use heat.

That was a little slow for me to watch.  Try to find a textbook on styrene and acrylate polymerization, see if they're really as similar as you suggest.

[wildfyr]

Quinine will not under go radical polymerization at that double bond, the radical generated is too unstable. If you look at styrene or methylmethacrylate you can see how the radical generated is stabilized by delocalization and/or sterics. You have two routes you can pursue to make a quinine functionalized polymer, neither of which is guaranteed to maintain the exact biological activity of quinine (which I what I'm assuming you want). The first is to use that alkene or the alcohol to couple quinine to a simple monomer (such as reacting the alcohol of the quinine with methacroyl chloride). The other would be to do postpolymerization modification. In that case, you could take a simple monomer like 4-vinylbenzyl chloride, and (attempt) to react it with again, the hydroxy on quinine, which to me is the simplest handle on the molecule. You could also use an activated ester functionality like NHS or PFPA to make this reaction easier, if more synthetically involved up front to make those ester monomers.

Another handle could be to try what would be a longer synthesis and do hydrosilation with that double bond, or some sort of olefin metathesis. Theres room to do other things, but these are the standard ways to make polymers with exotic functionalities.