Talk:Fullerene

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Contents 1 Comment on the Potential of C-60 as an Inhibitor to the HIV Virus ? 2 Clarity 3 Bioterrorism 4 Bucky 5 Graphene 6 Discoverers 7 Stucture image 8 Why C60 is the most well known 9 Some comment triggered by health related article 10 Nomenclature 11 Picture of C70? 12 Harder than Diamond? 13 Fullerenes in Humour/Fiction 14 Mathematics of Fullerenes 15 Toxicity questions 16 Merge from popular culture 17 Possible Dangers: "our compounds" 18 Merge from Buckminster Fullerene 19 Category Chemical Elements 20 References #2 and #3 are dead links 21 Maximum Length of Carbon Nanotubes 22 non-planar? what gives?! 23 Buckyeggs 24 R.W. Henson 25 Buckyball and soccerball 26 Shungites

[edit] Comment on the Potential of C-60 as an Inhibitor to the HIV Virus ?

This seems worthy of mention; apparently the buckyball are bigger than charlies balls and can interfere with a crucial protease that the virus uses to reproduce.

http://www.chem.wisc.edu/~newtrad/CurrRef/BDGTopic/BDGtext/bmmbas.html

Infinitys 7th 20:22, 27 November 2006 (UTC)

[edit] Clarity

The smallest fullerene which does not contain any bordering pentagons (which is destabilizing - see pentalene?) is C₆₀, and it is also the best known.

What does the phrase does not contain any bordering pentagons mean? Buckyballs contain pentagonal carbon rings. And what's the deal with calling them destabilizing --destabilizing compared to what? Are you thinking of the aromatic stabilization of benzene's six-member ring? According to this, the smallest fullerene known is C₂₀ [1]

Finally, calling C₆₀ the "best known" seems kind of subjective, though it may be true. I think the fact that it might thethe best known or earliest discovered is an interesting comment on the culture of science, perhaps the role of aesthetic imagination and spectroscopic symmetry. -- dja

The C₆₀ fullerene has a mollecular shape which is comparable to that of a Soccer ball, in that the pentagonal sections deform, distort or destabalize an otherwise flat ridgid structure into a curved or spherical shape.

C₆₀ fullerenes may be the "Best known" of the fullerenes as there has been a quite considerable research effort in their development and their application especialy in the construction of carbon nanotubes, medical applications and materials such as fullerite (a C₆₀ based man-made material proported to be harder than diamond). -- ash

I changed the text according to most of the above. The comment that neighboring pentagons are destabilizing I left in, though. It means pretty much the opposite of stabilization as applied to benzene, namely that the whole structure is considerably less stable (higher energy) than one would otherwise expect, in this case thanks to bond angle strain. I think this is fairly common usage, but if you think you have a better way of saying the same feel free to change it. -- JG

The clarification about the pentagonal rings not sharing an edge is much better, thank you. The stabilization of benze is attributed to aromaticity, though, which is a concept hard (at least for me) to apply in the context of fullerenes and which, in any case, doesn't seem to be the same thing as bond angle strain. I guess that means I'll have to leave it be, for now.  ;-) -- dja

I just meant that stabilization and destabilization are opposing concepts, not that the causes are the same here. You're right, benzene is stabilized by aromaticity, and fullerenes are too. Bond strain is a different effect. --JG :)

I'm not a chemist, came to this article because my 14 year old son is interested. Offering comment here because this is unclear to me:

Buckminsterfullerene (IUPAC name (C₆₀-I_h)[5,6]fullerene) is the smallest fullerene in which no two pentagons share an edge (which can be destabilizing — see pentalene).

My response after reading this: WHAT can be destabilizing? "Sharing an edge"? Or, "No two pentagons sharing an edge"? Or being "the smallest fullerene"? The sentence is terribly obtuse — to the layman, at least. Richard Myers 23:10, 2 March 2007 (UTC)

The sentence is a bit ambiguous and could be improved. The answer is that having pentagons sharing an edge can be destabilizing. Buckminsterfullerene is stable, and also it is the smallest fullerene that is "stable enough", precisely because it is the smallest fullerene that can be build without having pentagons sharing an edge. Itub 09:41, 5 March 2007 (UTC)

[edit] Bioterrorism

I removed the words prevent bioterrorism from the section on medical uses of fullerenes, for two reasons. First, unless this technique can prevent all disease, I don't see how it can prevent bioterrorism. Second, even if the wording were toned down to something like help fight bioterrorism, it seems overly sensationalistic to mention it. It should be clear that fighting disease is one way of fighting bioterrorism; I don't see any need to mention it specifically here. (For instance, there is no mention of bioterrorism in the penicillin page.) -- Cwitty

There's no mention of there uses in the article.

[edit] Bucky

The terms "buckyball" and "buckytube" are used frequently enought that they deserve their place in Wikipedia's index. So I'm creating a page for each, and it will redirect here. In order to maintain the preferred practices with regard to such redirect pages, I'm also making sure that "buckyball" and "buckytube" are mentioned in the first paragraph, so that readers know they've found the right place.

Also, both terms have come to be used commonly enough that I don't think it is appropriate to suggest that they are used so in a joking way. Google either one and you'll find plenty of serious articles on the topic.

updated to include plane as the possible forms, see [2]. linked from here [3]. my first edit, hope i'm doing the right thing, if not, plz, let me know -- User:TrevorP

[edit] Graphene

The sentence on graphene as a fullerene is incorrect. This may have been taken from an article by the BBC, who got it wrong (why do journalists always seem to get things wrong when it comes to chemistry?). Graphene molecules are planar, and are essentially small fragments of single sheets of graphite. In fullerenes, however, the presence of pentagonal rings allow for curvature, so they curve back around on themselves to form a hollow enclosure. Graphenes do not do this, which is why they were given their own name instead of being called fullerenes. I have taken the liberty of removing the incorrect sentence. -- dryguy

Thanks - I thought that entry looked odd. Graphite, as layers of sheets of hexagons, has been known for quite a while. -- Solipsist 14:04, 22 Dec 2004 (UTC)

I have likewise modified the first sentence to remove rings and planes from the definition. True, there are all-carbon molecules which are rings, and some (nearly) all carbon molecules which are planes, but neither rings nor planes are hollow enclosures. --dryguy 03:29, 1 Jan 2005 (UTC)

Graphene is not even considered an allotrope of carbon because it is essentially 2 dimensional. Graphite is, because graphite is a 3 dimensional arrangement of graphene. Graphene is most definitely NOT a type of fullerene; only nanospheres and nanotubes fall into that category (organic and inorganic both, they were named because their structure resembles that of a geodesic sphere which bucky was famous for). -- AeoniosHaplo 21:45, 13 March 2007 (UTC)

[edit] Discoverers

Jim Heath and Sean O'Brian were from Rice. The last edit makes this unclear. Also, I really don't see what was accomplished by rearranging the names. I'm reverting to the previous edit, but I'm open to hear why you think it needed changing. --dryguy 03:26, 25 Jan 2005 (UTC)

The link to Jim Heath (the son of the big band leader Ted Heath) looks wrong to me. --JohnBates 07:13, 9 July 2006 (UTC)

[edit] Stucture image

In chemical structure diagrams, colors are often used to indicate the identity of atoms in the drawing. The practice is so common that there are even standards for the color used for some atoms (carbon = grey, oxygen = red, nitrogen = blue, etc.). For this reason, the changes to make the structure in the C₆₀ figure multi-colored incorrectly imply that C₆₀ contains elements other than carbon, which is not true. I'm reverting to the previous edit. --dryguy 12:21, 2 Feb 2005 (UTC)

Sadly, that image does not meet Wikipedia's copyright requirements, so it had to go. A desaturated version of the replacement is up. In the future, please check an image's status before including it. In this case, a more appropriate action would have been to remove the image until the modification could be made. iMeowbot~Mw 17:29, 2 Feb 2005 (UTC)

[edit] Why C₆₀ is the most well known

Regarding the above comment, C₆₀ is the "best known" because it is the most widely studied. This mostly has to do with the fact that C60 is essentially the only fullerene with interesting (read: useful) chemical properties. For example, the high symmetry of the C60 molecule allows it to accept up to six electrons per molecule with very little energy lost to bond-reorganization (it has a low reorganization energy associated with reduction). This property is almost entirely unique to C₆₀ and it allows C₆₀ to accept electrons and then readily pass them another molecule, which is the basis for organic photovolatic technology.

Anyway, the (scientific) literature is rife with C₆₀ and I think "best known" could simply be rephrased "best studied" and added back in as relavent information. Fearofcarpet 22:46, 17 Mar 2005 (UTC)

[edit] Some comment triggered by health related article

I did admire this post. [4] It may also be worth to watch out for the nano result coming out next week as the following post claim. [5]

[edit] Nomenclature

Please see the talk page on nanotubes, where there is some discussion about whether the opening definition of fullerene is correct. There is some concern that "fullerene" strictly refers to spherical closed-cage carbon molecules that have exactly 12 pentagons, which excludes from its definition the nanotubes. Thus nanotubes would be distinct (and considered another allotrope?). In loose speaking, many chemists will speak of "the fullerenes" and include carbon nanotubes, but this isn't necessarily following the strict definitions. Again, refer to the link and associated evidence, and see what you think. Kebes 22:11, 10 May 2005 (UTC)

[edit] Picture of C₇₀?

Does anyone have a picture of C₇₀, the egg shaped fullerene? -Hmib 00:34, 9 Jun 2005 (UTC)

Here's a site [6] -corky842

[edit] Harder than Diamond?

Is the Fullerene harder than diamond? And what is a fullerene? C₆₀ or any spherical completely carbon substance? Anyone knows the answer?

cjingren

No, fulerenes are not hard at all. They are mostly in form of black powder, soluble in some organic solvents such as toluene (C₆₀ forms purple solution). There are many "types" of fullerenes, buckminsterfullerene (C₆₀) is just one of them, but is the most stable and symmetric, it is the fist member of this familyto be prepared. Mykhal 15:35, 25 Jun 2005 (UTC)

Maybe the poster means this [7]? Also, a list of fullerenes would be nice... Samohyl Jan 07:50, 30 August 2005 (UTC)

A list of fullerenes? What would that include? There is an infinite number of them. Refer to the mathematical section for some examples of how many there are. Sdaug 08:01, 24 February 2006 (UTC)

[edit] Fullerenes in Humour/Fiction

I moved this here because these sections tend to grow out of control on the main page, and detract from the topic. DV8 2XL 01:31, 26 October 2005 (UTC)

• This is a bad idea, this section does belong in the Fullerene article (wiki is not an ordinary encyclopedia) or at least given it's own article with a SF category. Side note: Chemistry Wiki is imploding at the moment, more material deleted than contributions made. This is not the way to go forward V8rik 15:25, 26 October 2005 (UTC)
  • My feeling is this falls under the heading of Wikipedia is not an indiscriminate collection of information.

Too many time I have seen this type of section get so large that it becomes the major part of the article; a huge list looking more like a Google search for "topic +fiction" than anything that adds to the understanding of topic itself. DV8 2XL 16:33, 26 October 2005 (UTC)

• I agree with DV8 2XL. The fullerene article should be about fullerenes in the real world, not about fictional representations of fullerenes. Maybe this stuff can go somewhere, but please not in the main fullerene article. People come here to read about chemistry, not science fiction. Ed Sanville 01:11, 2 November 2005 (UTC)

In New Scientist there used to be a weekly column called Daedelus written by David Jones, which contained humourous descriptions of unlikely technologies. In 1966 the columnist included a description of the C₆₀ and other forms of graphite. This was meant as pure entertainment.

Also in the New Scientist magazine, a free book was enclosed entitled, "100 Things to Do Before You Die" and one of which was to kick a buckyball.

Science fiction writer Neal Stephenson uses buckyballs as nanotechnological containers in his 1995 cyberpunk/postcyberpunk novel The Diamond Age. Buckyballs show up in Green Mars by Kim Stanley Robinson as a result of the fall of the first space elevator onto the surface of Mars.

In the Walt Disney film, Flubber, the formula and molecular structure of the Flubber was modeled after buckminsterfullerene.

In the Global television series ReGenesis, buckyballs are the primary component of a HazMat suit produced by government contractor, Shining Armor.

• I think this can be put back into the main article... It's been years & nothing's been added to the "In Fiction" list. Rayne 27 February 2008 (UTC) —Preceding unsigned comment added by 206.208.93.60 (talk)

[edit] Mathematics of Fullerenes

This section previously implied that Fullerene was also a mathematical term for a polyhedron consistign of hexagons and pentagons. I belive this is incorrect, the term refers only to carbon molecues which have this structure, not to abstract polyhedra. I have made the needed changes. I have also cited the specific Euler formula F - E + V = 2, as Euler formula is a highly ambigious term. DES ^(talk) 02:09, 5 November 2005 (UTC)

I edited this section to remove the term "rapid" from describing the growth with increasing n. There are many different types of structures that grow much more rapidly than fullerenes. Sdaug 07:56, 24 February 2006 (UTC)

[edit] Toxicity questions

Hi,

I just wanted to comment on the "Possible Dangers" section. It is unfortunate that the only mention of toxicity data is the recent work of Oeberdorster and Colvin. The articles they have published are largely considered irrelevant and misleading by fullerene scientists. They are problematic for several reasons, including:

The assertion that C₆₀ forms "Nano-C₆₀" spontaneously in water is false. The procedure to make a water/C₆₀ colloidal solution such as used in the Colvin studies has been known for years, and requires several solvent replacements and precipitation, and typically would take about a week to carry out. C₆₀ is absolutely insoluble in water, and if placed in water, does nothing more than what ordinary soot or carbon black would do, which is settle or float as a solid.

The "Nano-C₆₀" process used by Colvin et al uses tetrahydrafuran (THF). Russian scientists (experienced with making the colloid for years, and in fact measuring no toxicity on the colloid) have written that THF can, present as solvent inclusions in the C₆₀ precipitate, cause exactly the same toxicity results reported by Colvin and co-workers.

C₆₀ and C₆₀ derivatives have been widely studied for 10 years or more before Colvin and co-workers began their work. In fact, the only real negative toxicity result was reported by Tour around 1996 on the same colloid that Colvin studied. Many fullerene derivatives have been studied for toxicity, including one that Colvin studied. C3, a C₆₀ derivative invented by Wilson and co-workers has been studied since the mid 90's, in vitro and in rats with no adverse toxicity. In fact, this molecule was licensed by Merck & Co. in 2003 for pre-clinical trials in Parkinson's disease.

In the 15 years of researchers using C₆₀ and C₆₀ derivatives, there are no reported anecodotal evidence of any adverse health effects.

It is unfortunate that Colvin et al have not respected the work of literally thousands of researchers, do not cite key review articles on pharmaceutical use such as Da Ros & Prato, Wilson, and others, and mislead the general public on the real science of fullerenes. In fact, the very same molecules that Colvin uses to take credit for having discovered that derivatization can make C₆₀ "safe" were shown to have no toxicity years ago. And, to compare a 50 nm particle (the nano-C₆₀) with a soluble C₆₀ derivative is comparing apples and oranges. In fact, Oberdorster's father has work showing that particles in that size range show toxicity regardless of the chemical makeup.

The radicals that are mentioned in the Wikipedia article are a garbled explanation of the singlet oxygen generation through light absorption by C60. This has also been known for years, and this has not shown to make fullerenes toxic.

For those of you who have written this, and read it, it could be interesting for you to know that in fact one of the most promising uses of fullerenes is as drugs, and at present, both major companies and respected resarch labs around the workd are now pursuing fullerenes for this use. One of the most promising aspects being the almost total absence of adverse toxicity results.

In short, the work that is mentioned in this Wikipedia article is not respected by real chemists, pharmaceutical chemists, and fullerene scientists. Colvin is a professor of nanotechnology, and is trained neither in chemistry or toxicology. Though not having been successful in impressing her fellow scientists with her work, she has been very successful at trying to gather publicity around the "nano-toxicity" scare, which is allowing her to gain a small degree of fame, and more importantly for her, resarch dollars.

As a fullerene scientist with roots going back to their discovery, I would suggest that the section of "Possible Dangers" be deleted until someone versed in the real scientific literature could address the subject in a more serious and considered manner. As it stands, it is scientifically reckless and irresponsible. Wikipedia has recently been in the National news because of other irresponsible use, and if this is not modified, I will address the situation to those responsible at Wikipedia, since misinformation of this sort is damaging to the truth, and disregards the work of thousands of good scientists.

I have removed some unsourced and other ultra-POV comments in the article that implied it wat proven that C₆₀ is toxic. Polonium 21:17, 1 March 2006 (UTC)

Below is a link to Eva Oberdörster's paper, should anyone wish to investigate this matter. The full paper is available free of charge.

• Oberdörster, Eva (2004). Manufactured Nanomaterials (Fullerenes, C₆₀) Induce Oxidative Stress in the Brain of Juvenile Largemouth Bass. Environ Health Perspect 112 (10), 1058-1062.
• Corresponding PubMed listing: PMID:15238277

—Ryanrs 04:33, 17 March 2006 (UTC)

I don't know that either of these studies quoted in this section particularly belong in a discussion of safety: the impact on human or other life at current or even anticipated environmental levels still appears to be negligible. Moreover, what is defined as a "health risk" or "environmental risk" could become something beneficial: for example, being an agent that binds ssDNA, perhaps fullerenes will make good chemotherapy candidates. I am in complete agreement with the first person to comment on this particular section that the inclusion of this information remains controversial in the scientific community, and this section is unreliable as currently written.Tomteboda 02:25, 3 October 2006 (UTC)

[edit] Merge from popular culture

There is no good reason for a short orphan article on Fullerenes in popular culture to exist. It would hardly overwhelm this page to add it. Rmhermen 17:26, 2 February 2006 (UTC)

• I agree. —Keenan Pepper 22:21, 2 February 2006 (UTC)
• Yep, merge 'em. Shadow demon 05:26, 17 February 2006 (UTC)

[edit] Possible Dangers: "our compounds"

On 15 December 2005, User:216.217.201.187 (contrib) added text that reads, in part:

indicates that our compounds are likely to have little (if any) toxicity (diff)

The phrase our compounds is highly suspicious. It suggests either copyright violation, or worse, subtle spam/astroturfing. —Ryanrs 05:18, 17 March 2006 (UTC)

The phrase "recently discovered" could be replaced with the date the buckyballs were discovered. "Recently" really doesn't tell us anything, even though I;m sure it made sense to the author when it was originally written--24.15.4.45 06:27, 4 April 2006 (UTC)

[edit] Merge from Buckminster Fullerene

Merge. These are exactly the same subject. On the other hand, articles on individual fullerene molecules, such as (C₆₀-I_h)[5,6]fullerene (the most common one) might be a good idea. —Keenan Pepper 10:59, 13 April 2006 (UTC)

• Slight agree - They are not the same thing: buckminsterfullerene is to the fullerenes as methane is to the alkanes; it is simply a single member of a family group. However, having said that, I do still think they should be merged as it will be a while till buckyballs are risen to the profile of methane. At this current point in time, having two seperate articles is a touch trivial. mastodon 21:09, 14 April 2006 (UTC)

Did you read the article Buckminster Fullerene? It's not about any specific molecule. If it were, I would suggest it be moved to the IUPAC name, for example (C60-Ih)(5,6)fullerene ((C₆₀-I_h)[5,6]fullerene formatted as an article title). —Keenan Pepper 02:47, 15 April 2006 (UTC)

I see your point, I had not read it. Having now read it I change my answer to a full agree. Could you explain the systematic name please? Although most molecules have a systematic name, the historic name is often prefered, eg. methyl benzene vs toluene. I think that buckyball will prevail as its official name as it is by far the easiest to pronounce, so maybe the article should be moved to that? I've reformatted fullerene, what do you think? mastodon 03:18, 15 April 2006 (UTC)

See http://www.chem.qmul.ac.uk/iupac/fullerene/ for the details. Fullerene and buckyball are both general names for this class of compounds. The trivial name of (C₆₀-I_h)[5,6]fullerene is [60-I_h]fullerene and the trivial name of (C₇₉-D_5h(6))[5,6]fullerene is [70-D_5h]fullerene. —Keenan Pepper 05:21, 15 April 2006 (UTC)

• Strongly agree - They are basically describing the same thing. We never, or almost never, keep two different Wikipedia articles on the same thing from the same perspective (chemical, political, medical, etc.) -User:Nightvid

I'll go ahead and merge them then, since there are no objections. —Keenan Pepper 02:12, 16 April 2006 (UTC)

[edit] Category Chemical Elements

Why is this article listed in the category "Chemical Elements"? Fullerenes are molecules, as the article says. -- 85.180.152.67 17:56, 18 July 2006 (UTC)

But they are elemental molecules, as they contain only carbon atoms.128.6.30.196 22:28, 7 November 2006 (UTC)

[edit] References #2 and #3 are dead links

3: The link is dead and the directing website seems to only keep articles in that catergory ("Nano Debate") for the present year.Lizz612 01:16, 27 July 2006 (UTC)

2: The reference for the buckyball being Texas' state molecule is dead, and I could not trace it down on the new website. --Sailor Coruscant 02:48, 12 October 2006 (UTC)

[edit] Maximum Length of Carbon Nanotubes

The main article on Carbon Nanotubes says they can be up to a few mm long; this article says they can be a full meter. Could somebody who knows which is right please correct the other? —The preceding unsigned comment was added by 72.61.73.16 (talk • contribs) .

I can't find anyone who claims to have made meter-long nanotubes, although I can find a lot of things that could be misinterpreted as saying that. I'll change it to agree with Carbon nanotube for now. —Keenan Pepper 02:18, 6 August 2006 (UTC)

[edit] non-planar? what gives?!

From what I gather the fullerenes can be embedded in either a sphere or a cylinder. This makes them embeddable in the plane. And certainly neither a cycle of 5 nor of 7 prevent a planar embedding. I'd be inclined to change this, but will wait to be corrected, please. MotherFunctor 21:58, 30 August 2006 (UTC)

This is confused by the fact that later in the article, it describes "the term fullerene refers to any 3-regular, planar graph with all faces of size 5 or 6 (including the external face)". Seanahan 04:26 19 October 2006 (UTC)

[edit] Buckyeggs

Fresh from Slashdot:

Improbable "Buckyegg" Hatched

A buckyegg breaks pentagon rules

Abstract of: "Tb3N@C84: An Improbable, Egg-Shaped Endohedral Fullerene that Violates the Isolated Pentagon Rule" (Volume 128, Issue, Pages 11352-11353, September 6, 2006)

Basically, an egg-shaped fullerene which contains touching pentagon formations. Cites above for anyone interested (and inclined) in fullerene chemestry or nanomaterials. ~Kylu (u|t) 21:35, 30 September 2006 (UTC)

[edit] R.W. Henson

Is there any place for an acknowledgement of his contribution in this article? R.W. Henson's website DavidFarmbrough 10:36, 8 December 2006 (UTC)

[edit] Buckyball and soccerball

In the first paragraph, it says that C₆₀ molecules are sometimes called "buckyballs" because they look like a soccerball. However, it is called that because Buckminster Fuller, an architect, created geodesic domes resembling C-60. It may be called a ball because it is, but the "bucky-" part has nothing to do with it. Should not this sentence be reworded/removed? —The preceding unsigned comment was added by 204.152.152.23 (talk) 18:53, 2 March 2007 (UTC).

3D structure of nano-Bytes —Preceding unsigned comment added by 24.74.114.191 (talk) 18:46, 9 March 2008 (UTC)

[edit] Shungites

"Recently, Buckminsterfullerenes were found in a family of minerals known as Shungites in Karelia, Russia." Is the statement wrong. Can someone read the paper (do not have access) http://geology.geoscienceworld.org/cgi/content/abstract/31/3/255 and reply http://geology.geoscienceworld.org/cgi/content/extract/31/6/e33 As I understood the first article is incorrect. Can you, please, clarify it. Alexander Mayorov (talk) 19:36, 18 March 2008 (UTC)