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Author: Subject: Some C60 Chemistry
walruslover69
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[*] posted on 20-11-2018 at 11:09


wikipedia has a great chart

in g/L
1-chloronaphthalene 51
1-methylnaphthalene 33
tetrahydronaphthalene 16
carbon disulfide 8
1,2,3-tribromopropane 8
xylene 5
bromoform 5
cumene 4
toluene 3
benzene 1.5
carbon tetrachloride 0.447
chloroform 0.25
n-hexane 0.046
cyclohexane 0.035
tetrahydrofuran 0.006
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Tsjerk
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[*] posted on 20-11-2018 at 11:47


Ok, then I get the soxhlet method over just soaking and filtering.
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walruslover69
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[*] posted on 20-11-2018 at 13:04


The chromatography step seems very important as to separate other fullerenes and side products.
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VSEPR_VOID
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[*] posted on 20-11-2018 at 16:50


Quote: Originally posted by fusso  
Yes I know I mean the R-C6H5 should lose 1 H when it react with C60 in a friedel craft to form C60-C6H4-R isnt it?


The extra hydrogen also bonds to the C60 cage giving C60Hn(C6H4-R)n where n has been reported to be primarily 12.

I may have had a typo there or something got lost in translation, my bad.

Quote: Originally posted by walruslover69  
How do you control the number of adducts that attach to the C60?


For the reaction I am doing you can not, or it has not been discovered how.

12 just is the most common number of additions, with 16 being reported in very small amounts.

Quote: Originally posted by Tsjerk  
Ok, then I get the soxhlet method over just soaking and filtering.


Yes, if you use a solvent like toluene, chloroform, or benzene it will be very easy. In addition you can use the same equipment and reagents (in addition to some charcoal and alumina) to purify your fullerenes so you only get C60, and not C60 and C70.

[Edited on 21-11-2018 by VSEPR_VOID]




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DrP
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[*] posted on 21-11-2018 at 01:01


Quote: Originally posted by VSEPR_VOID  
C60 behaves as a super electron deficient polyalkene. It undergoes a variety of reactions to form many adducts. For example, C60 is very reactive with grignard reagents.

Most reactions with C60 are driven forward because of strain relief from the double bonds becoming single bonds. This however, can be counter acted by the eclipsing of the added groups causing more steric strain. An example of this is polyhydrogenated C60. C60H60 is not stable and does not form, but C60H36 is the most stable hydrogenated derivative. It has just enough 1,2 additions (which reduce the strain caused by double bonds) to counteract the strain from eclipsed hydrogens.

C60, in addition to having a very reactive exterior, has endohedral chemistry as well. Because of steric hindrance, the inside of C60 acts as a sort of chemical Feriday cage. As a result, exotic or reactive species (such as nitrogen radicals) can be trapped inside and studied.

Right now a lot of research is being conducted on opening holes in the C60 cage, inserting an element or molecule inside, then closing that hole.



Awesome - thanks for that info. I think the chemistry of it has progressed since I first heard about it. There was a lot of hype about how amazing it would be.... I guess nano tubes get more study due to ease of loading them up and getting stuff out compared to trying to put stuff into a bucky ball and get it out again. There seems to be more hype for nano tubes and grapheme over bucky balls now. I like the radical trap idea... no idea how you'd get something inside it though.




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VSEPR_VOID
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[*] posted on 21-11-2018 at 13:22


Nanotubes and graphene are definitely cool, but nanotubes are difficult to purify and both nanotubes and graphene are hard to produce at any meaningful size.

Fullerenes on the other hand are easy to make and purify. I think that we as amateurs could really to some neat things with them.

One aspect that should interest amateurs is that many fullerene derrivatives are both easy to make and have never been made before. Take for example my amine adduct, first in the world.




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mayko
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[*] posted on 9-2-2019 at 09:50


An interesting fullerene paper I ran across:

Zhu, S.-E., Li, F., & Wang, G.-W. (2013). Mechanochemistry of fullerenes and related materials. Chemical Society Reviews, 42(18), 7535. http://doi.org/10.1039/c3cs35494f

Quote:

The low or lack of solubility of fullerenes, carbon nanotubes and graphene/graphite in organic solvents and water severely hampers the study of their chemical functionalizations and practical applications. Covalent and noncovalent functionalizations of fullerenes and related materials via mechanochemistry seem appealing to tackle these problems. In this review article, we provide a comprehensive coverage on the mechanochemical reactions of fullerenes, carbon nanotubes and graphite, including dimerizations and trimerizations, nucleophilic additions, 1,3-dipolar cycloadditions, Diels–Alder reactions, [2 + 1] cycloadditions of carbenes and nitrenes, radical additions, oxidations, etc. It is intriguing to find that some reactions of fullerenes can only proceed under solvent-free conditions or undergo different reaction pathways from those of the liquid-phase counterparts to generate completely different products. We also present the application of the mechanical milling technique to complex formation, nanocomposite formation and enhanced hydrogen storage of carbon-related materials.




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