Talk:Polyacetylene

message: The "Synthesis" paragraph says:
   "[...] solid phase polymerization, conducted at −296 °C produces trans-polyacetylene.[6]"
I don't know the subject, but there can't obviously be a synthesis performed 23 K below absolute-zero.
Maybe "−196 °C " was meant, but the correction should be done by someone who knows this and not by me guessing it.
Thanks for the very good article!  — Preceding unsigned comment added by 192.0.182.71 (talk) 14:25, 17 April 2014 (UTC)
thread_title: Please correct a wrong temperature shown

message: How easy is it to get acetylene to polymerize?
- Now a days poly(acetylene) is generally not made by polymerizing acetylene, which is a highly flammable gas that spontaneously oligomerizes upon concentration. The most common synthesis now is using special metathesis catalysts deveopled by Professor Grubs at Cal Tech (which are known as Grub's catalysts) on molecules like cyclooctatetraene. Acetylene itself polymerizes in a similar fashion to ethylene; anionic, cationic, and radical polymerizations will all work. I'm not sure what you mean by "how easy" it is to polymerize it... Either it polymerizes or it doesn't; there is really no difficulty associated with it. Fearofcarpet 20:03, 18 Mar 2005 (UTC)
thread_title: How easy to polymerize

message: I think a structural formula for the cis configuration would be appropriate. —Preceding unsigned comment added by 88.111.138.155 (talk) 15:41, 27 May 2007 (UTC)
thread_title:  Cis 

message: I am suspicious of the use of 'acetylene black' as a synonym for 'polyacetylene'. I've been looking into carbon black for battery manufacture. Acetylene black is a form of carbon black as discussed in the quote below:
Carbon black is a powdered form of elemental carbon manufactured by the vapour-phase pyrolysis of hydrocarbon mixtures, such as heavy petroleum distillates and residual oils, coal-tar products, natural gas and acetylene. ... Carbon blacks are categorized as acetylene black, channel black, furnace black, lampblack or thermal black, according to the process by which they are manufactured. 
Carbon Black (IARC Summary & Evaluation, Vol 65, 1996)
Elsewhere (no reference) it was noted that the conductivity of various manufactures of carbon black depend on the residual hydrogen content, etc. I suspect that polyacetylene can be an impurity in acetylene black due to incomplete pyrolysis. Especially since this claim was unreferenced, I thought it prudent to remove it. Perhaps someone can substantiate it and reinsert the statement.
Tendermecies (talk) 15:52, 18 May 2008 (UTC)
replies: text: Five and a half year later, still no mentioning of the redirected term acetylene black in the article itself. That is somewhat frustrating, but thank you for the reference, Tendermecies. Thyl Engelhardt213.70.217.172 (talk) 12:59, 5 February 2014 (UTC)
thread_title:  'Acetylene black' as a synonym for 'polyacetylene' 

message: Rather reluctantly,  I get involved in an editing dispute.  Anyway, the references provided are good and hardly "obscure".  Nor is the issue.  That conductive polyacetylenes were discovered in the 1960's (not 1970's) is well-known in electrochemistry and is even the subject of a chapter in a major contemporary text-book on conductive polymers.   I would suggest that this cite gets posted here too. 
What is the problem,  to induce such gaming and POV-pushing,  not to mention gross WP:civility violations ?  If I read the cases right,  the sort of thing that gets people desysoped or banned.   Personally,  I would not have been as obliging as nucleophilic.  And yes,  polyacetylene is the parent compound to polypyrrole, etc.  The only difference electronically is that polyacetylene has more long-range order and so is more "metallic". Clipjoint (talk) 21:13, 11 February 2011 (UTC)
replies: text: There is more relevant discussion of this issue evolving on Talk:Nobel Prize. Nucleophilic (talk) 21:16, 24 February 2011 (UTC)
replies: text: Reverted another attempt to remove cites,  etc. on prior history.  Clear POV-pushing in the face of so many good review articles, etc.. While smokefoot is a valuable member of the wikipedia community,  this does not empower him any more than any other editor. Nucleophilic (talk) 14:06, 19 May 2012 (UTC)
replies: text: Editors are associated with developing articles on [[John McGinness[[ and Peter Proctor and others apparently embittered by not being recognized by the Nobel Prize for conducting organic materials should desist from editing this and related articles owing to a conflict of interest.  The articles and the work that they suggest are not mentioned in the Nobel Prize citation but intended to prop up the POV by these apparently embittered individuals.  The Nobelists reviews also do not mention these articles in their reviews. --Smokefoot (talk) 14:49, 19 May 2012 (UTC)
thread_title:  Discussion continued 

message: Ichthyothereol is cited at the bottom of the article as an example of naturally-occurring polyacetylene.  However, the molecule clearly has carbon-carbon triple bonds, as opposed to the carbon-carbon double bonds featured in the rest of the article.  Surely this would make ichthyothereol a polyyne and not a polyacetylene?  A Google search for <ichthyothereol polyyne> appears to indicate such. 192.197.178.2 (talk) 15:40, 8 June 2012 (UTC)
replies: text: The literature is not consistent. The cited refs highlight many "polyynes" (per that technical definition) and specifically and only identify them as "polyacetylenes". One meaning is from the polymer world--the polymerization of triple-bonded monomers gives consecutive double-bonded units in the polymer--and it the meaning used in this article. But the other meaning appears to be just "poly" meaning "many". I agree it's confusing when there are two meanings of the term, and I agree that the "multiple alkynes" meaning does seem synonymous with the "polyyne" meaning. So I have moved its content there. However, we cannot ignore the reality that this meaning is associated with the article here as well, so I also added a note here to help readers disambiguate the ideas. DMacks (talk) 20:03, 12 November 2012 (UTC)
thread_title:  Isn't ichthyothereol a Polyyne? 

message: ===Polyacetylene Peer Review 1===
:Overall the content regarding poly acetylene has been vastly improved over the previous version of the polyacetylene page.  The page contains a large amount of high quality and relevant information without the information being technically overwhelming.  There are a few adjustments that could be made that would improve the quality of the page.
====Content====
:Overall the content section contains a lot of new information that elucidates the history, synthesis, and properties of polyacetylene.  Each section contains appropriate length, and  the vast majority of the information here is accessible to a non expert reader. There are a few things that could be improved though.
:In the introduction section of the polyacetylene article the final sentence  of the introduction introduces the idea that there are some limitations of polyacetylene preventing their widespread use and production, however this point even though it addressed, the limits and applications could be its own paragraph in and of itself with a figure showing how the oxidation of the fibers happens and the production of the carbonyl, epoxy, or alcohol group.
:The thoroughness of the synthetic methods could be improved.  In synthesizing polyacetylene via the ROMP method there are some advantages versus synthesiszing polyacetylene from acetylene such as, avoiding the violent polymerization process from pure polyacetylene. 
:The doping and properties section seem pretty good with a lot of good and relevant information there, however when you discuss the differences in conductivity between cis and trans type poly acetylene why is there a 4 order of magnitude difference, and does this carry over to once the various polyacetylene molecules are doped? In addition how prevalent is the cross-linking in the polyacetylene fibers?  Does the cross-linking depend on the structural isomer?
:The history section has a vast array of information attached to it, this entire section should be relocated to the top of the paragraph as the paragraph introduces many of the ideas discussed in the article.  In additions some figures would improve this section of the article, such as cuprene?  In addition this section discusses that shirikawa worked on ways to further improve the conductivity, could you elaborate in the history section one or two of the methods he went on to develop to improve the conductivity?  Finally the history has some limits of polyacetylene applicability, these limitations seems to be in multiple paragraph throughout the article, removing the duplicate phrasing would help the cohesiveness of the article.
====Figures====
:The figures could use some improvement. In the Durham synthesis please replace the delta with heat, as many non scientific users would most likely be confused by the delta sign for heat.  In addition the size is too small to clearly make out the identity of some of these pictures, re-sizing some of the images would help readers out. For the Grubbs synthetic route, if the various R groups that have been studdied, or even just a few different identifiable R groups would help clarify to a non-chemist reader that R could be a variety of groups.  For the cis and trans isomers could you re-do these images in a 3-D model program such as, avagadro, to allow for some image variety.  Please ensure that the chemdraw images are all aligned and centered relative to one another.
:In addition a cuprene image would improve your history section as that was the first iteration of polyacetylene.
====Refereces====
:There are at least 10 novel references present, however a vast majority of the references are technical journals, some non jornal sources would help.  In addition a lot of resources present come from the Heeger, Shiriakawa, MacDiarmid group.
====Overall Presentation====
:Overall the article represents a good start.  The major concepts are all linked to their respective wikipedia page.  The content provides a thoughtful background to polyacetylene and a sufficient introduction to its synthesis and properties.  In addition the figures support the structure and synthetic scheme of polyacetylene very well.  Some areas for improvement include reorganizing the page so that the introduction leads into the history, which can then lead into the structure and properties of polyacetylene, as the current organization is a bit confusing. Some of the figures present in the article are rather confusing and could use additional clarification, such as identifying the R groups in the Durham synthetic scheme, and replacing the delta with "heat" in order to keep the figures accessible to everyone. In addition possibly incorporating the applications and limitations of polyacetylene such as its stability into its own section would be a good transition doped properties from  Finally a chem draw representation of cuprene, or some image of a heavily cross-linked polyacetylene would add a lot to visualizing early polyacetylene. In addition read through the content to remove duplicate phrasing such as the limits of polyacetylene being in both the history, properties, and doping.  A significant amount of your references are from Shirakawa, and Heeger who won the Nobel prize, diversifying your references to include additional authors wouldnt be a bad idea.  Finally check the language and grammar to ensure the article meets wikipedia's standards.Asimov1951 (talk) 00:06, 28 February 2014 (UTC)
thread_title: Peer review and responses during the educational assignment in March 2014

message: :Overall the content regarding poly acetylene has been vastly improved over the previous version of the polyacetylene page.  The page contains a large amount of high quality and relevant information without the information being technically overwhelming.  There are a few adjustments that could be made that would improve the quality of the page.
====Content====
:Overall the content section contains a lot of new information that elucidates the history, synthesis, and properties of polyacetylene.  Each section contains appropriate length, and  the vast majority of the information here is accessible to a non expert reader. There are a few things that could be improved though.
:In the introduction section of the polyacetylene article the final sentence  of the introduction introduces the idea that there are some limitations of polyacetylene preventing their widespread use and production, however this point even though it addressed, the limits and applications could be its own paragraph in and of itself with a figure showing how the oxidation of the fibers happens and the production of the carbonyl, epoxy, or alcohol group.
:The thoroughness of the synthetic methods could be improved.  In synthesizing polyacetylene via the ROMP method there are some advantages versus synthesiszing polyacetylene from acetylene such as, avoiding the violent polymerization process from pure polyacetylene. 
:The doping and properties section seem pretty good with a lot of good and relevant information there, however when you discuss the differences in conductivity between cis and trans type poly acetylene why is there a 4 order of magnitude difference, and does this carry over to once the various polyacetylene molecules are doped? In addition how prevalent is the cross-linking in the polyacetylene fibers?  Does the cross-linking depend on the structural isomer?
:The history section has a vast array of information attached to it, this entire section should be relocated to the top of the paragraph as the paragraph introduces many of the ideas discussed in the article.  In additions some figures would improve this section of the article, such as cuprene?  In addition this section discusses that shirikawa worked on ways to further improve the conductivity, could you elaborate in the history section one or two of the methods he went on to develop to improve the conductivity?  Finally the history has some limits of polyacetylene applicability, these limitations seems to be in multiple paragraph throughout the article, removing the duplicate phrasing would help the cohesiveness of the article.
====Figures====
:The figures could use some improvement. In the Durham synthesis please replace the delta with heat, as many non scientific users would most likely be confused by the delta sign for heat.  In addition the size is too small to clearly make out the identity of some of these pictures, re-sizing some of the images would help readers out. For the Grubbs synthetic route, if the various R groups that have been studdied, or even just a few different identifiable R groups would help clarify to a non-chemist reader that R could be a variety of groups.  For the cis and trans isomers could you re-do these images in a 3-D model program such as, avagadro, to allow for some image variety.  Please ensure that the chemdraw images are all aligned and centered relative to one another.
:In addition a cuprene image would improve your history section as that was the first iteration of polyacetylene.
====Refereces====
:There are at least 10 novel references present, however a vast majority of the references are technical journals, some non jornal sources would help.  In addition a lot of resources present come from the Heeger, Shiriakawa, MacDiarmid group.
====Overall Presentation====
:Overall the article represents a good start.  The major concepts are all linked to their respective wikipedia page.  The content provides a thoughtful background to polyacetylene and a sufficient introduction to its synthesis and properties.  In addition the figures support the structure and synthetic scheme of polyacetylene very well.  Some areas for improvement include reorganizing the page so that the introduction leads into the history, which can then lead into the structure and properties of polyacetylene, as the current organization is a bit confusing. Some of the figures present in the article are rather confusing and could use additional clarification, such as identifying the R groups in the Durham synthetic scheme, and replacing the delta with "heat" in order to keep the figures accessible to everyone. In addition possibly incorporating the applications and limitations of polyacetylene such as its stability into its own section would be a good transition doped properties from  Finally a chem draw representation of cuprene, or some image of a heavily cross-linked polyacetylene would add a lot to visualizing early polyacetylene. In addition read through the content to remove duplicate phrasing such as the limits of polyacetylene being in both the history, properties, and doping.  A significant amount of your references are from Shirakawa, and Heeger who won the Nobel prize, diversifying your references to include additional authors wouldnt be a bad idea.  Finally check the language and grammar to ensure the article meets wikipedia's standards.Asimov1951 (talk) 00:06, 28 February 2014 (UTC)
thread_title: Polyacetylene Peer Review 1

message: :Overall the article represents a good start.  The major concepts are all linked to their respective wikipedia page.  The content provides a thoughtful background to polyacetylene and a sufficient introduction to its synthesis and properties.  In addition the figures support the structure and synthetic scheme of polyacetylene very well.  Some areas for improvement include reorganizing the page so that the introduction leads into the history, which can then lead into the structure and properties of polyacetylene, as the current organization is a bit confusing. Some of the figures present in the article are rather confusing and could use additional clarification, such as identifying the R groups in the Durham synthetic scheme, and replacing the delta with "heat" in order to keep the figures accessible to everyone. In addition possibly incorporating the applications and limitations of polyacetylene such as its stability into its own section would be a good transition doped properties from  Finally a chem draw representation of cuprene, or some image of a heavily cross-linked polyacetylene would add a lot to visualizing early polyacetylene. In addition read through the content to remove duplicate phrasing such as the limits of polyacetylene being in both the history, properties, and doping.  A significant amount of your references are from Shirakawa, and Heeger who won the Nobel prize, diversifying your references to include additional authors wouldnt be a bad idea.  Finally check the language and grammar to ensure the article meets wikipedia's standards.Asimov1951 (talk) 00:06, 28 February 2014 (UTC)
thread_title: Overall Presentation

message: Overall, I really liked the page. 
====Content==== 
The sections are comprehensive and of good length. The chemistry is accurate as far as I can tell. The pages and items that need linked are generally done. It would be good to add a link to cis/trans as it is used often and also, is a fairly important concept for the article. The examples are very nice and well discussed. They supplement the material very well to aid in understanding. I poked around a bit on Wikipedia and the material seems to be specific to the page and the only stuff that does appear elsewhere is necessary to be in multiple places. 
* Introduction- The introduction is very thorough, but too dense for an introduction. It would be best to break up the content into another section with the introduction only being about 6 sentences. A lot of the material in the first paragraph relates to doping so maybe move that material to Doping subsection. The second paragraph, though informative, could be trimmed down in the Introduction and the rest moved elsewhere. 
* Synthesis- Outlining the various synthetic routes was good, but I also think it would be useful to more clearly state why some of the methods are more advantageous than others. I do see that you did it for the ROMP section, but adding a sentence or two to the other two sections would make it more clear why there have been multiple methods developed.
* Properties- This was a really interesting section. I'm not sure if all of these properties and their origin have been thoroughly investigated, but some additional chemistry would be good. Maybe what sort of reactions are occurring when the PA is exposed to air.
* History- I thought this was thorough and interesting. The flow is a bit odd, mainly due to were paragraph breaks occurred. Just give it another read before publishing the site. 
 
====Figures====
There are many new figures added that are informative and support the ideals presented in the text. They are easy to read once clicking the link. I would suggest making some of the items as centered and larger instead of thumbnails. Here is the general format to center and enlarge your pictures: ["[File: **File name from wikicommons** |thumb|center| upright=2.5|**Description**]"] (take out the "'s and replace the info in the *'s to use it on your Wikisite) you can change the 2.5 to get the size you want. Also some of the figures span two sections. You can fix this by pasting picture links at the end of a paragraph instead of at the end of the section. It might be nice if the Doping section and History had a small picture to break up the text. The “Durham precursor polymer” picture is a bit odd. It would be best to try and put the bonds in back as broken up instead of the bonds in front. Also, the original page had a pretty nice picture that could definitely be used again.
====References====
The references were originally pretty weak, but the editors doubled the number with some really good resources. It would be nice if a few more non-journal resources were available for the general public to access.  I actually found this link through a bit of digging on google (http://www.ch.ic.ac.uk/local/organic/tutorial/steinke/4yrPolyConduct2003.pdf) and thought it was pretty useful. It is written at a pretty low chemistry level such that it might be work linking somewhere, especially because it is free and accessible to all. 
 
====Overall Presentation==== 
Overall, I actually enjoyed reading the page, which in itself says something about the quality. I thought the material was well presented and also at a level that was appropriate for anyone coming to this page (people with at least basic chemistry knowledge). The page was well linked for any non-science people making it a great Wikipedia resource. I also learned quite a bit about PA and was entertained throughout (History was one of my favorite sections and I liked the properties and learning that the different structures actually are visually different). The content is great. A few changes should be made to really polish up the page. There were a few awkward phrasings that were ultimately okay, but could be improved by reading through it again before putting the site live. Adding a few more references that the general public can easily access would also be really helpful and make the page more impactful. A little rearranging needs to be done with both the pictures and content to make the page flow better and more visually appealing to draw in a person just browsing the page. In general, the page was greatly improved and really interesting.
5402013SD (talk) 02:51, 28 February 2014 (UTC)
thread_title: Peer Review 2

message: Overall, I actually enjoyed reading the page, which in itself says something about the quality. I thought the material was well presented and also at a level that was appropriate for anyone coming to this page (people with at least basic chemistry knowledge). The page was well linked for any non-science people making it a great Wikipedia resource. I also learned quite a bit about PA and was entertained throughout (History was one of my favorite sections and I liked the properties and learning that the different structures actually are visually different). The content is great. A few changes should be made to really polish up the page. There were a few awkward phrasings that were ultimately okay, but could be improved by reading through it again before putting the site live. Adding a few more references that the general public can easily access would also be really helpful and make the page more impactful. A little rearranging needs to be done with both the pictures and content to make the page flow better and more visually appealing to draw in a person just browsing the page. In general, the page was greatly improved and really interesting.
5402013SD (talk) 02:51, 28 February 2014 (UTC)
thread_title: Overall Presentation

message: The peer reviewers did a good job overall. I agree that the intro is too dense and too long and that the figures need to be larger, and consistently placed in the text. I agree with most, if not all, of the peer reviewers comments. I look forward to seeing the revised site!
UMChemProfessor (talk) 22:11, 1 March 2014 (UTC)
thread_title: Instructor Comments

message: Nice additions to the article. A few suggestions here. 
* I agree that the History section should be moved to the first or second section in the article. 
* Sources cited could be more diverse. E.g. When Nobel prize is mentioned, citing the Nobel prize site may be better than just citing an article. 
* To re-arrange the pictures under the synthesis section, please see Wikipedia:Picture tutorial for different location and size changes you can make.
ChemLibrarian (talk) 15:28, 3 March 2014 (UTC)
thread_title:  Suggestions from ChemLibrarian