Talk:Polyfluorene

How is it made?
Lets start this article by discussing how polyfluorenes are manufactured, and whether or not they exist in nature. What do the chemical reactions look like? Are they petroleum or coal derivatives? —Preceding unsigned comment added by 76.25.140.229 (talk) 03:12, 26 August 2008 (UTC)


 * I would love to chime in but I don't know enough about it. Shrampes (talk) 04:07, 29 November 2008 (UTC)


 * This source has more information that can be used in the article. Maybe I get to it sometime... Shrampes (talk) 19:19, 6 December 2008 (UTC)

Class - CHEM538W11grp2
I (Aromaticmoleculessmell (talk) 19:02, 4 February 2011 (UTC)) and user:polymersgrpmem plan on editing this page until about april 2011; We will help address some of the concerns about synthesis and discovery of fluorene and polyflourene, as well as some other important sections (we'll post an outline soon).

An outline of the proposed changes for this page can be found here User:UMChemProfessor/Chem538W11Grp2 sandbox (Aromaticmoleculessmell (talk) 04:57, 11 February 2011 (UTC))

Section 1
In regards to the peer review I previously submitted, it appears that most of my comments and concerns were addressed. Specifically, my suggestion about re-organizing the section on “Discovery of Polyfluorenes and their Interesting Properties” was addressed in that it appears to have been split into two different sections: one about discovery and one about properties. Another suggestion to include a discussion of unwanted green emission was also addressed and the topic incorporated into the site. Further, an image of the basic polyfluorene repeat unit was also added to the site, as suggested. Not addressed was a concern with respect to the references. While the references seem to be more consistent in format, many of the journal references lack doi numbers, and the majority of the references are journals. Citing more accessible sources, such as books (only one book is currently cited) and websites, would be beneficial for the public.

Section 2
The web page is definitely suitable for those readers looking to understand the topic in more detail, however the page may be less informative for those with little or no chemistry background since the information provided is more specific and less basic/general in its explanation. For this reason, it is important to link to other Wikipedia sites that can further explain certain ideas/topics (a good job was done in linking to other sites) and to provide texts and websites that can give more general background information (perhaps suggested under a “Further Reading” section).

There is a logical flow to the page, however I do have one suggestion about organization. The section on “Synthesis of Polyfluorene and Copolymers of Fluorene” incorporates a good bit of discussion on how the polymer properties are affected by the structure synthesized. Because of this, the following section on “Properties of Polyfluorenes” feels a bit out of place. It may be better positioned between “Discovery of Polyfluorenes” and “Synthesis of Polyfluorene and Copolymers of Fluorene.” Another suggestion is to re-word the section title “Problems with Polyfluorenes” to something along the lines of “Challenges Associated with Polyfluorenes” (basically, replacing the word “problems” with something a little less negative).

The length of each section seems appropriate based upon the content, and no section feels too long or too short. No one particular section feels over-emphasized or under-emphasized compared to the other sections.

The sandbox does satisfy the aims and objectives listed in the outline. One goal stated in the objectives was to provide a discussion of synthetic routes by which to obtain polyfluorenes. While the section on “Synthesis of Polyfluorene and Copolymers of Fluorene” does provide a discussion of synthetic routes, along with examples, it may be helpful to include an example reaction scheme showing reactants, products, and reaction conditions (but not a detailed mechanism).

Most of the important terms are linked to their respective Wikipedia pages. The company names (Dow Chemical Company and IBM) under “Industrial Uses of Polyfluorene” could be linked to their Wiki pages.

The images meet the quality guidelines described in the handbook, and the ChemDraw structures are chemically accurate. The polyfluorene repeat unit shown in the box at the top of the page could stand to be a bit larger. Also, the chemical formula listed for the repeat unit is (C 13 H 10 ) n – should this be (C 13 H 8 ) n ? Figure 2 should be larger for better viewing. In regards to alignment and position, Figures 3 and 4 would be better located nearer to “Synthesis of Polyfluorene and Copolymers of Fluorene” since that is the section in which they are referenced. Further, Figure 4 appears to be misaligned with the section heading and text in its current location. The last figure showing numbered positions on the fluorene molecule is missing a figure number and does not seem to be directly referenced in the text as are the other figures. This should probably be addressed to maintain consistency.

An impressive list of references is provided for the web page. Many journal articles are referenced in particular. However, it would be advantageous to cite more books and websites which the general public would have a better chance of accessing. Many of the references are cited multiple times in the references list. For example, references 28 and 48-50 are copies of each other, as are 16 and 38. There are many instances of this, so I suggest looking over the references list again. As previously mentioned, including doi and ISBN numbers where possible would also be helpful.

In general, the web page is presented well and has a good layout. A few typos were noted and some sentences would benefit from re-wording, so I suggest reading through the page carefully to correct these. For example, the paragraph starting with, “Other properties of polyfluorenes are also influenced by the synthetic route[…]” under “Synthesis of Polyfluorene and Copolymers of Fluorene” was a bit difficult to read and could do with re-structuring and re-wording some of the sentences. Another example is the sentence, “Although reports of the oxidative polymerization of fluorene (into a fully conjugated form) exist from at least 1972, it was not until after the highly publicized high conductivity of doped polyacetylene, presented in 1977 by Heeger, MacDiarmid and Shirakawa, that substantial interest in the electronic properties of conjugated polymers was aroused.” This sentence is very long, so I suggest splitting it: “Reports of the oxidative polymerization of fluorene into a fully conjugated form exist from 1972. However, it was not until after the highly-publicized high conductivity of doped polyacetylene – presented in 1977 by Heeger, MacDiarmid and Shirakawa – that substantial interest in the electronic properties of conjugated polymers was aroused.”

All of the assigned criteria for the page have been met. A minimum of three sections was required, but the group provided four new sections (not including the introduction and reference list) and one sub-section. Four new figures have been added to the site and two figures kept from the original site. Further, the group provided many more references than the eight required.

Section 3
The sandbox version of the site is a great improvement over the current site. The group has followed through with their objectives to create a very informative Wiki page for polyfluorenes. The groups provides a discussion of the discovery of polyfluorenes, followed by information on synthetic routes, properties, challenges associated with the polymers, and industrial uses of polyfluorene. The page is appropriate in length, has images to supplement the text, has links to other Wikipedia pages for further reference, and is supported by an impressive list of references.

That being said, the page would benefit from some edits. More books and web pages should be referenced, the reference list should be cleaned up to remove copies of the same citation, and the page should be read through carefully to correct typos and re-word/re-structure some sentences. Additionally, some of the figures should be readjusted for size and position, and the location of the “Properties of Polyfluorenes” section may need to be moved. Overall, however, the page looks great and is going to be a useful resource for the public. Well done!

Pharmscistudent (talk) 08:12, 25 March 2011 (UTC)

Section 1.
In rereading my previous review and reading through the new sandbox, most of the concerns had been addressed. There are a few things that could be changed that were not addressed from the previous review. One of the main things is reference suggestions, of which the page still only contains one book source with all the rest being journal sources. I had given a few articles from magazines that I thought would be more informative to the general public as well. It would be recommended that you still look for at least one more book source to include, if not as a reference, then as a suggested reading or something like that. Many reference DOI’s are still missing as well and should be added if possible. I also mentioned that more of the material defect and doping properties be mentioned, and this was more or less answered in the problems section, but not directly. One big thing that was missed was possible degradation and how that influences their commercial aptitude. Also mentioned was the fact that you could change Industrial Uses to Application of Polyfluorine, though this is just a suggestion and is ok that it was kept. Overall most suggestions were met.

Section 2.
When thinking about the suitability of both general and advanced readers of the polyfluorine topic, the advanced readers with chemistry background definitely get a good understanding as the page goes on, however, the introduction may even be too advanced for a general user, but I am not quite sure how to make it more user friendly while still saying something about the molecule. It may be beneficial to link both conjugated polymers and visible spectrum to respective pages, or at least explain briefly. The page is probably best orientated for a intermediate science reader, with some chemical background, which is a good place to be to get a general understanding of the topic. Advanced readers benefit by the sources given to the primary journal references for more information, whereas general users do not have such an advantage from those references since there are few accessible references with basic understanding.

I have also noticed that there are terms that could still be referenced to a Wikipedia page, a few of these are listed here: optoelectronic, luminescence, liquid crystal displays, aromatic, and band gap, just to name a few. There are possibly others present. Another thing to note is that you should probably link the first mention of the topic, instead of having the word mentioned multiple times before a link is present. Be sure to go through and look at any important words and check to see if they have a respective Wikipedia site. What I did was go through and just bracket a bunch of things I thought would have a site and then narrowed it down from there by eliminating red ones unless I thought that a site on the topic would be worth making.

It seems as if the page has a good logical flow, which builds upon itself by starting with the basic identity of the compound, with history, then works its way through synthesis and characteristics on to applications. The biggest thing I noticed was the fact that paragraphs are very long and contain multiple parts that could be broken up, since it is very hard to follow the text without getting lost. An example can be seen here with a paragraph break at "Another important quality of polyfluorenes is their thermotropic…" By changing the paragraph breakdown, a better flow could be formed. There are also a few repeated things, such as the R group effects. This is probably ok, but may be a little redundant. There is also some mixing of properties and synthesis in the synthesis section, which could probably be adjusted to better represent the subsection.

The group did a decent job determining how much to say about each section and each of the sections in the page seems to have been given fair ground, without an over or under-emphasis in this regard. There are a few things that seem a little wordy however, such as the industrial uses section; also the repetitiveness between properties and synthesis could probably be condensed. This section should also mention more details of the other applications besides OLED’s, such as the plastic solar cells and field effect transistors. I am a wordy writer myself so I am not the best person to give suggestions on how to fix this. There is also some emphasis bias present in the applications section as mentioned above, where the focus was given to the OLED application and the others where not discussed in detail. The general properties and synthesis were discussed well and seemed to cover all the general bases. It was also nice to include the problems section so people are not saying to themselves why aren’t they used. You could also mention the cost of synthesis and whether they degrade readily. The degradation rate if known would be a very valuable topic to discuss in the problems section. So if we get picky, the problems and applications sections may be slightly under-emphasized. Overall the page is adequate in determining section lengths, while doing justice to each sub-topic.

The images on the page appear to meet the criteria set out by the chemistry Wikipedia handbook, and seem to have been made with ACS formatting in Chemdraw. However, some images such as figure 2 and the fluorene monomer could be increased in size and quality respectively. There is a higher quality fluorene present in the Wikimedia Commons. The images are present in the general region they are discussed in the text, so alignment seems to be acceptable. The images are appropriate and give a good understanding of structure and properties of these compounds. The only one that could possibly be moved down a bit for a better fit is Figure 4, so that it is under the topic heading. The overall webpage is well organized and is presented in a good fashion. I noticed a few grammatical errors and a few spelling errors, so I would recommend reading through it, since spell check may not catch them all. I noticed one point where it was written groves instead of grooves. Another thing to note is that the text of the “Problems with Polyfuorine” section title appears to be smaller than the other sections. There is also extra space under “Synthesis of Polyfluorene and Copolymers of Fluorene” that should be corrected. The references are also somewhere that needs quite a bit of work. I have noticed that there are quite a few repeats, since the references were not formed once and then abbreviated in the coding. Here is an example that should help: >ref name=Glow /ref<, and then when you want to repeat the reference type >ref name=Glow /<. (arrows reversed) I would also suggest adding some more non-journal sources, since all of your sources except for one appear to be journal articles. I had a few suggestions of books and articles, I mentioned previously, but I am not sure how much else is out there. You definitely have an impressive number of references that shows you did your research and that the topic is a decently important one.

All of the objectives of the outline appear to have been met with greater detail than was insinuated by the initial page ideas. There were even sections added, that were not present in the outline giving better page organization and development, while giving more information to better support the initial aims of the site improvement. The group went above and beyond the requirements giving a very impressive number of references, including essentially six new sections and four new images.

Section 3.
The site starts out with a basic introduction of polyfluorine, giving its importance and its properties, such as its chromophoric properties and conjugation. The site then goes on to describe some history of how it was discovered back in the 1880’s as isolated from coal tar. Some synthetic methods are then discussed in order to form polymers and copolymers to give specific light emitting properties by tuning band gaps. The properties are then discussed in which they are the only molecules to that appear to emit over the entire visible spectrum. They then discuss the problems of these materials such as aggregation. The main applications of these materials as OLED’s, field effect transistors and plastic solar cells is then discussed.

The overall page is well thought out and gives a decent amount of detail on the subject without being too overbearing. The group did a good job of breaking up the material into the subcategories selected, as well as providing a level of language best suited for a person with intermediate chemical understanding, which helps bridge the gap between beginner and advanced. They did a good job describing the synthesis and properties of these materials, showing people why they are important. The images are illustrative of the many different forms to give insight into versatility. Some areas that could use some work are the applications section, to have more about the other major application other than OLED’s. Also the reference section could use some attention to fix the repetitions. I would also spend some time looking into grammar and spelling as well as splitting the large paragraphs into smaller sections. There are still more links that could be added in the text as well. It may also be good to look at the introduction and try to make it more user friendly to a person with general knowledge, though this is a hard thing to do. This page is by far a vast improvement on the current page and would contribute honorably to the Wipedia Encyclopedia. Good Work!

JFSK538MM (talk) 01:08, 25 March 2011 (UTC)

Polyfluorene Class Peer Review
The current site has basic information, but has some sources that could be useful. It’s explanation of the basic polymer backbone with the monomer units is simple and to the point with a good image to enforce this detail. This site however is not very detailed and I agree that it needs attention and is a worthy subject to work with. Review read: Source 17 on sandbox: J. POLYM. SCI. PART A: POLYM. CHEM 39: 2867-2873

Section 1.

 * The objectives are clear and original, since they would expand the current site and add many new ideas, with historical, synthetic and application sections. There does not appear to be any sites with duplicate information.  It would be recommended that the site contain links to the Wikipedia fluorene site, which will explain some basic properties of the monomer, although this site itself is not very thorough.  Other useful related links could be the electroluminescence page, conjugated systems page, quantum efficiency page, and the OLED page.  Many others could also be used.  The suggested length of the page is definitely feasible for a semester long project and would add more than the requirements for the assignment to the site.

Section 2.

 * The length of the work seems to be appropriate. There is not more being added to the site than can be handled by a two -person team.  I don’t think that splitting any of the sections would be useful, but some small things could be added, such as how defects/doping affect the properties.  How do different R groups on the fluorene change the properties?  Be sure to explain briefly what each of the properties mean and link to respective sites if there are any.  Since the original site is very limited, any work on the site would compliment the limited original site with its basic fluorene unit and some basic properties.  It would definitely build it into a better page, with much more background, synthetic and application information.  This section does meet the stated objectives well and should give people a clear understanding of basics of polyfluorene.  One thing that could be changed is the “Industrial Uses of Polyfluorene” to just “Applications of Polyfluorene.”  Maybe it sounds friendlier.  It may be useful to mention stability based on repeated excitation events or cyclic voltametry tests if the data exists.  How much does this affect degradation?

Images.

 * It is not clear from the structure given on the page, which part of that monomer unit is the actual polyfluorene molecule. So it could be difficult to know what they are looking at without reading through the text.  This molecules take home message seems to be that this is an example of some repeat unit, however a brief description of its specific properties may give it a stronger message.  It may just be helpful to show the polyfluorene by itself like it is on the original page.  The image looks good for the site and is a legible size, with good resolution.  From the looks of the image, the appropriate Chemdraw settings were used.  More images would definitely be useful, possibly even a picture of the fluorescence occuring or a table of repeat polymer units.

Section 3.

 * The references need to be diversified; nearly every reference is a journal article that the majority of the public would not have access. Also add DOI numbers.  Here are a few books that may be useful as sources:  “Advances in Polymer Science: Polyfluorenes” by Ullrich Scherf 2008, this book gives information about applications in OLED’s, focus on emissive defects, electroluminescence efficiency, band gap tuning, and the incorporation of charge-transfer substituents in the context of hole and electron injection.  “Organic light-emitting materials and devices” by Hong Meng  pg's 159 and 122, 2007, contains a few short sections also.  I also found an interesting short article out of Popular Science that uses polyfluorenes as sensors. (Laser Sensor Can See Explosives' Vapor Trails Even at Extremely Low Concentrations, posted 6/7/10 by: Clay Dillow.  Also check C&EN “Better blue for polyfluorene OLED’s”.  These would all be good articles with simpler understanding for the average person.  Also check out Scientific American and Popular Mechanics to see if additional lay-person articles exist.  Your list of resources is very extensive and has many good review articles.  I found the original articles out of the 1800’s quite interesting and I believe this is a very excellent way to start the historical background.

Overall.

 * I believe that you have the start of what will become a nice site. The sections you decided to mention as well as your objectives seem well within the realm of the scope of the project, and polyfluorenes seem to be relevant compounds in today’s market.  My research this semester has sort of been based on these kinds of properties.  Your images look very nice, and you have a great number of primary source materials.  I like the historical background back the 1880’s.  I would recommend adding more alternative sources such as books and magazines to your resource repertoire.  This would allow more people to access this information.  I would also recommend putting strong emphasis on these compounds have emission over the entire visible range; which is probably one of the most important properties.  Be sure to add more images and tables as mentioned above.  Good Start!

JFSK538MM (talk) 01:45, 18 February 2011 (UTC)

Section 1
The objectives described for the new polyfluorene site are clear and also appropriate for Wikipedia. No duplicated information was found during a search of other sites. The topics proposed in the objectives and outline will provide good coverage of the subject and give a much-needed update to the current site. Judging from the objectives and outline, the article will be of a feasible length for both a course project and a Wikipedia article. The following is a suggestion of sites that could be linked to from this site: fluorene, luminophore, electroluminescence, photoluminescence, and polymer light-emitting diodes.

Section 2
The topics listed in the outline seem as though they will provide a discussion that meets the goals stated in the objectives. The sections are organized well and ordered appropriately. The length seems like it will be appropriate for providing a good overview of polyfluorene/s while still being a manageable length for a course project. The proposed additions to the site will be complementary to the current site, adding important information which the current site lacks.

In terms of merging or splitting sections, I would be cautious when writing the section on “Discovery of Polyfluorenes and their Interesting Properties." It seems that a lot of information will be covered in this section, so I advise to keep it well organized to make it clear for the reader. You might even want to consider splitting the section into one about discovery and one about properties for better organization. If you decide to keep it as one section, I suggest re-phrasing the section title, perhaps to something along the lines of "Discovery and Properties" (something doesn't sound quite right with the current phrasing).

There is one concept which I did want to mention: from what I have seen in the literature, unwanted green emission has been a challenge associated with blue-emitting polyfluorene LEDs. It is unclear from the outline whether this will be discussed in the new site, but I think it is an important challenge to address. I see that your reference by Lin et al. (2010) discusses this unwanted emission. Another article you can refer to is by Romaner et al. in ''Adv. Funct. Mater. 2003, 13'', 8 (link to article). The topic of this unwanted green emission would probably work in either "Polyfluorenes as electroactive polymers" or "Industrial Uses of Polyfluorene," depending on the discussion at hand.

Images
The image included with the outline looks very nice; it is clearly drawn and of a good size. The image also appears to follow the appropriate ChemDraw settings. Further, the image makes sense on its own and has a clear caption. Since the image is a supplement to a topic explained in the text, the figure will serve to clarify the discussion by providing an example for the reader.

The site would definitely benefit from a good selection of images. I think it would be a good idea to include an image of the basic polyfluorene repeat unit like the one featured on the current site. Also, many eye-catching and colorful images could be provided for the discussion on industrial applications.

Section 3
You have chosen a great selection of articles to reference, however your reference list is not very diverse. It would be a good idea to include other sources, such as websites and/or books (especially since not everyone has ready access to journal articles). There are a few books which discuss polyfluorenes that are available for full online access via the U of M library website, such as Polyfluorenes by Ullrich Scherf and Dieter Neher (2008). Also, I noticed that your references are not formatted uniformly. You may want to change this to have the references look more consistent. After a brief literature search, I do not see any key references missing from your list.

Overall Comments
The objectives and outline for the new site look very promising. The current site desperately needs an upgrade, so I think it is great that you are taking on this project. The topics addressed in the outline will provide a good overview of polyfluorenes. The proposed sections are organized well and cover key concepts. I would definitely link to other sites from this page in order to provide supplementary information for the reader. It would also be a good idea to add some diversity to your references by including websites and books. I think you could have a lot of fun with the images you pick for the site considering your topic. Overall, this is a great start to the project, and I look forward to reading the completed product! Good luck to you!

Pharmscistudent (talk) 05:05, 18 February 2011 (UTC)

Requested move (class work integration)
User:UMChemProfessor/Chem538W11Grp2 sandbox → Polyfluorene — We have drastically updated the page and would like to have it moved to the main polyfluorene page. Aromaticmoleculessmell (talk) 13:29, 8 April 2011 (UTC)


 * Comment you're going to need a history merge, a straight rename won't work, since we'll loose the contribution history of the existing article. WP:SPLICE for history merge requests. 65.93.12.101 (talk) 19:38, 8 April 2011 (UTC)
 * Comment I suggest this talk page also be moved into archivespace of the article's talk page. 65.93.12.101 (talk) 19:39, 8 April 2011 (UTC)


 * Article and talk page were histmerged into existing pages.