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{{Short description|Chemical compound}} |
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| verifiedrevid = 421523135 |
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| verifiedrevid = 424439824 |
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| ImageFile = PEDOT-TMA.png |
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| ImageFile = PEDOT-TMA.png |
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| OtherNames = Oligotron; Pedot tetramethacrylate; Poly(3,4-ethylenedioxythiophene), tetramethacrylate end-capped, PEDOT-TM, Meth-Pedot, Pedot-Meth |
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|Section1 = {{Chembox Identifiers |
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| OtherNames = Oligotron; Pedot tetramethacrylate; Poly(3,4-ethylenedioxythiophene), tetramethacrylate end-capped |
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| Formula = |
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| MolarMass = ~6000 g/mol |
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| MolarMass = ~6000 g/mol |
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| Bulk Conductivity = 0.1-.5 S/cm |
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| Sheet Resistance = 1-10 M Ω/sq |
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| Methacrylate Equiv Wt = 1360-1600 g/mol}} |
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'''Poly(3,4-ethylenedioxythiophene)-tetramethacrylate''' or '''PEDOT-TMA''' is a p-type ] based on ] or the EDOT ]. It is a modification of the ] structure. Advantages of this polymer relative to PEDOT (or ]) are that it is dispersible in organic solvents, and it is non-corrosive. PEDOT-TMA was developed under a contract with the ], and it was first announced publicly on April 12, 2004 {{Ref|1}}. The trade name for PEDOT-TMA is Oligotron. PEDOT-TMA was featured in an article entitled "Next Stretch for Plastic Electronics" that appeared in ] in 2004 {{Ref|2}}. It was also featured in an article entitled "Light, and magic" in the ] section of ] {{Ref|3}}. |
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'''Poly(3,4-ethylenedioxythiophene)-tetramethacrylate''' or '''PEDOT-TMA''' is a p-type ] based on ] or the EDOT ]. It is a modification of the ] structure. Advantages of this polymer relative to PEDOT (or ]) are that it is dispersible in organic solvents, and it is non-corrosive. PEDOT-TMA was developed under a contract with the ], and it was first announced publicly on April 12, 2004.<ref>{{cite web |url= https://www.nsf.gov/news/news_summ.jsp?cntn_id=100360 |title= New Molecule Heralds Breakthrough in Electronic Plastics |first= J. |last= Chamot |date=April 12, 2004 |access-date=October 3, 2012}}</ref> The trade name for PEDOT-TMA is Oligotron. PEDOT-TMA was featured in an article entitled "Next Stretch for Plastic Electronics" that appeared in ] in 2004.<ref>{{cite journal |last= Collins |first= Graham P. |date=August 1, 2004 |title= Next Stretch for Plastic Electronics |journal= Scientific American |volume= 291 |issue= 2 |pages= 75–81|doi= 10.1038/scientificamerican0804-74 |pmid= 15298122 |bibcode= 2004SciAm.291b..74C }}</ref><ref>{{cite news |date=2004-05-22 |title=Light and Magic |newspaper=The Economist |page=74|access-date=October 3, 2012 |url= http://www.economist.com/node/2685725}}</ref> |
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The U.S. Patent office issued a patent protecting PEDOT-TMA on April 22, 2008 {{Ref|4}}. |
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The U.S. Patent office issued a patent protecting PEDOT-TMA on April 22, 2008.<ref>{{ cite patent |
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| country = US |
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| number = 7361728 |
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| status = patent |
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| title = Electrically conducting materials from branched end-capping intermediates |
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| pubdate = 2008-04-22 |
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| inventor = Elliott; Brian J. |
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| invent1 = Ellis; William W. |
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| invent2 = Luebben; Silvia D. |
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| invent3 = Sapp; Shawn A. |
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| invent4 = Chieh-Hui Chang, Raechelle A. D'Sa |
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| assign1 = TDA Research, Inc. |
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}}</ref> |
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PEDOT-TMA differs from the parent polymer PEDOT in that it is capped on both ends of the polymer. This limits the chain-length of the polymer, making it more soluble in organic solvents than PEDOT. The methacrylate groups on the two end-caps allow further chemistry to occur such as cross-linking to other polymers or materials. |
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PEDOT-TMA differs from the parent polymer PEDOT in that it is capped on both ends of the polymer. This limits the chain-length of the polymer, making it more soluble in organic solvents than PEDOT. The methacrylate groups on the two end-caps allow further chemistry to occur such as cross-linking to other polymers or materials. |
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== Physical properties == |
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==Application Overview== |
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The bulk conductivity of PEDOT-TMA is 0.1-.5 S/cm, the sheet resistance 1-10 M Ω/sq, and the methacrylate equivalent weight 1360-1600 g/mol. The chemical composition of a film of PEDOT-TMA was measured by energy-dispersive x-ray spectroscopy (EDS). The relative C, O, and S weight percentages were 51.28%, 35.37%, and 10.43%. There was also 2.92% Fe present in the film.<ref>{{cite journal |last= He |first= Jiarong |author2=Jing Su |author3=Jinglun Wang |author4=Lingzhi Zhang |year= 2018 |title= Synthesis of water-free PEDOT with polyvinylpyrrolidone stabilizer in organic dispersant system |journal= Organic Electronics |volume=53 |pages=117–126 |doi=10.1016/j.orgel.2017.11.035}}</ref> |
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==Applications== |
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Several devices and materials have been described in both journals and the patent literature that use PEDOT-TMA as a critical component. In this section, a brief overview of these inventions is given. |
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Several devices and materials have been described in both journals and the patent literature that use PEDOT-TMA as a critical component. In this section, a brief overview of these inventions is given. |
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* Patternable OLEDs: In a study<ref>{{cite journal |last= Liu |first= J. |author2=L. N. Lewis |author3=A. R. Dugal |year= 2007 |title= Photoactivated and patternable charge transport materials and their use in organic light-emitting devices |journal= Appl. Phys. Lett. |volume=90 |issue= 23 |page= 233503 |doi= 10.1063/1.2746404 |bibcode= 2007ApPhL..90w3503L }}</ref> by researchers at ], PEDOT-TMA was used in the hole injection layer in a series of ] devices. They have also filed a patent application to protect this invention.<ref>{{cite book |last1= Liu |first1= Jie |author2=Larry Neil Lewis |author3=Anil Raj Duggal |author4=Rubinsztajn Slawomir |title= US Patent Application US 2007/0077452, Organic light emitting devices having latent activated layers and methods of fabricating the same |date=2005-10-04}}</ref> |
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* Quantum dot modified OLEDs: In an international patent application, PEDOT-TMA surfaces were modified with quantum dots such as CdSe, CdS, and ZnS.<ref>{{cite book |last1= Vitukhnovskii |first1= Alexey |author2=Andrey Vashenko |author3=Denis Bychkovskii |title= WO Patent Application 2014/209154A1, Organic light-emitting element with the radiating layer containing quantum dots with modified surface |date=2014-12-31}}</ref> |
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* Ion selective membranes: PEDOT-TMA was used as a key ingredient in ]s<ref>{{cite journal |last= Rzewuska |first= Anna |author2=Marcin Wojciechowski |author3=Ewa Bulska |author4=Elizabeth A. H. Hall |author5=Krzysztof Maksymiuk |author6=Agata Michalska |year= 2008 |title= Composite Polyacrylate-Poly(3,4- ethylenedioxythiophene) Membranes for Improved All-Solid-State Ion-Selective Sensors |journal= Anal. Chem. |volume=80 |issue=1 |pages=321–327|doi=10.1021/ac070866o |pmid=18062675}}</ref> and in particular in calcium-selective electrodes.<ref>{{cite journal |last= Ocana Tejada |first= Cristina |author2=Natalia Abramova |author3=Andrey Bratov |author4=Tom Lindfors |author5=Johan Bobacka |year= 2018 |title= Calcium-selective electrodes based on photo-cured polyurethane-acrylate membranes covalently attached to methacrylate functionalized poly(3,4-ethylenedioxythiophene) as a solid-contact |journal= Talanta |volume=186 |pages=279–285|doi=10.1016/j.talanta.2018.04.056|pmid= 29784361 |s2cid= 29167779 |url= http://urn.fi/URN:NBN:fi-fe2020100883135 }}</ref> The performance of PEDOT-TMA films in solid contact ion selective electrodes compared to other commercially available conducting polymers has also been reported.<ref>{{cite journal |last= Ocana |first= C. |author2=M. Munoz-Correas |author3=N. Abramova |author4=A. Bratov |year= 2020 |title= Comparison of Different Commercial Conducting Materials as Ion-to-Electron Transducer Layers in Low-Cost Selective Solid-Contact Electrodes |journal= Sensors |volume=20 |issue= 5 |pages=1348–1360|doi=10.3390/s20051348 |pmid= 32121463 |pmc=7085546|bibcode= 2020Senso..20.1348O |doi-access= free }}</ref> |
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* Dye sensitized solar cell: PEDOT-TMA was used in the construction of effective ]s.<ref>{{cite journal |last= Kim |first= Kyung Ho |author2=Takashi Okubo |author3=Naoyo Tanaka |author4=Naoto Mimura |author5=Masahiko Maekawa |author6=Takayoshi Kuroda-Sowa |year= 2010 |title= Dye-sensitized Solar Cells with Halide-bridged Mixed-valence Cu(I)-Cu(II) Coordination Polymers with Hexamethylenedithiocarbamate Ligand |journal= Chem. Lett. |volume=39 |issue=7 |pages=792–793 |doi= 10.1246/cl.2010.792 }}</ref><ref>{{cite journal |last= Okubo |first= Takashi |author2=Naoyo Tanaka |author3=Haruho Anma Kyung |author4=Ho Kim |author5=Masahiko Maekawa |author6=Takayoshi Kuroda-Sowa |year=2012 |title= Dye-sensitized Solar Cells with New One-Dimensional Halide-Bridged Cu(I)–Ni(II) Heterometal Coordination Polymers Containing Hexamethylene Dithiocarbamate Ligand |journal=Polymers |volume=4 |issue= 3 |pages=1613–1626 | doi= 10.3390/polym4031613 |doi-access=free }}</ref> The PEDOT-TMA was spun-coat to give a 15 nm thick layer which was used as the counter-electrode in a series of ]s. Efficiencies as high as 7.85% were obtained.<ref>{{cite journal |last= Kim |first= Kyung Ho |author2=Kazuomi Utashiro |author3=Zhuguang Jin |author4=Yoshio Abe |author5=Midori Kawamura |year=2013 |title= Dye-Sensitized Solar Cells with Sol-Gel Solution Processed Ga-Doped ZnO Passivation Layer |journal= Int. J. Electrochem. Sci. |volume=8 |issue= 4 |pages=5183–5190 |doi= 10.1016/S1452-3981(23)14672-4 |s2cid= 225060588 |doi-access=free }}</ref><ref>{{cite journal |last= Kim |first= Kyung Ho |author2=Kazuomi Utashiro |author3=Yoshio Abe |author4=Midori Kawamura |year=2014 |title= Structural Properties of Zinc Oxide Nanorods Grown on Al-Doped Zinc Oxide Seed Layer and Their Applications in Dye-Sensitized Solar Cells |journal= Materials |volume=7 |issue= 4 |pages=2522–2533 |doi= 10.3390/ma7042522 |pmid= 28788581 |pmc=5453348 |bibcode= 2014Mate....7.2522K |doi-access= free }}</ref><ref>{{cite journal |last= Yoshimura |first= Nobutaka |author2=Atsushi Kobayashi |author3=Wataru Genno |author4=Takashi Okubo |author5=Masaki Yoshida |author6=Masako Kato |year=2020 |title= Photosensitizing Ruthenium(II)-Dye Multilayers: Photoinduced Charge Separation and Back Electron Transfer Suppression |journal= Sustainable Energy & Fuels |volume=4 |issue= 7 |pages=3450–3457 |doi= 10.1039/D0SE00151A|s2cid= 218997972 }}</ref> |
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* Flexible touch screens: PEDOT-TMA was used in the construction of electrodes for flexible touch screens as described in a patent application by the Honeywell Corporation.<ref>{{cite book |last1= Edwards |first1= Lewin |author2=Patricia McCrimmon |author3=Richard Thomas Watson |title= US Patent Application 2010/0182245, Tactile-Feedback Touch Screen |date=2010-07-22}}</ref> |
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* Energy storage and conversion devices: Synkera Technologies, Inc. filed a patent application detailing a variety of energy storage and conversion devices that use PEDOT-TMA in their construction.<ref>{{cite book |last1= Routkevitch |first1= Dmitri |author2=Rikard A. Wind |title= US Patent Application 2010/0304204, Energy Conversion and Energy Storage Devices and Methods for Making Same |date=2010-12-02}}</ref> |
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* Glucose sensor: A glucose sensor was prepared by Gymama Slaughter of Virginia State University.<ref>{{cite journal |last= Slaughter |first= Gymama |year=2010 |title= Fabrication of Nanoindented Electrodes for Glucose Detection |journal= J. Diabetes Sci. Technol. |volume=4 |issue=2 |pages=320–327 |doi=10.1177/193229681000400212|pmid= 20307392 |pmc=2864167}}</ref> |
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* Carbon nanotube composites: Researchers from ] used PEDOT-TMA to prepare composites with carbon nanotubes. These composites form highly aligned arrays of the nanotubes, and exhibit high conductivity at room temperature (25.0 S/cm).<ref>{{cite journal |last= Peng |first= Huisheng |author2=Xuemei Sun | year= 2009 |title= Highly Aligned Carbon Nanotube/Polymer Composites with Much Improved Electrical Conductivities |journal= Chemical Physics Letters |volume=471 |issue=1–3 |pages=103–105 |doi= 10.1016/j.cplett.2009.02.008 |bibcode= 2009CPL...471..103P |s2cid= 98836276 }}</ref> |
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* Metal wire-based photovoltaic device: Researchers from The Institute of Advanced Energy at ] used PEDOT-TMA to fabricate organic photovoltaic devices.<ref>{{cite journal |last= Chuangchote |first= Surawut |author2=Takashi Sagawaa |author3=Susumu Yoshikawa |year=2011 |title= Design of metal wires-based organic photovoltaic cells |journal= Energy Procedia |volume= 9 |pages=553–558 |doi= 10.1016/j.egypro.2011.09.064|url= https://repository.kulib.kyoto-u.ac.jp/dspace/bitstream/2433/235662/1/j.egypro.2011.09.064.pdf |doi-access= free |bibcode= 2011EnPro...9..553C }}</ref> |
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* Embedded capacitors: Researchers from The Polymer Composite Laboratory at ] prepared composites of ] with PEDOT-TMA and ]. They extensively studied the properties of these materials as a function of Graphene oxide composition. The materials were characterized by UV-Vis spectroscopy, FT-IR and FT-Raman spectroscopy, X-Ray diffraction, thermogravimetric analysis, atomic force microscopy and scanning electron microscopy. Finally, the dielectric properties of the materials were evaluated, and the potential application of the composites in constructing embedded capacitors was discussed.<ref>{{cite journal |last= Deshmukh |first= Kalim |author2=Girish M. Joshi |year=2015 |title= Embedded capacitor applications of grapheme oxide reinforced poly(3,4-ethylenedioxythiophene)-tetramethacrylate (PEDOT-TMA) composites |journal= Journal of Materials Science: Materials in Electronics |volume= 26 |issue= 8 |doi= 10.1007/s10854-015-3159-0 |pages=5896–5909|s2cid= 137234524 }}</ref> This research group has also developed thermistors made from Graphene Oxide/PEDOT-TMA composites.<ref>{{cite journal |last= Joshi |first= Girish |author2=Kalim Deshmukh |year=2015 |title= Conjugated Polymer/Graphene oxide Nanocomposite As Thermistor |journal= AIP Conference Proceedings |volume= 1665 |issue= 1 |pages= 050017 |doi= 10.1063/1.4917658|bibcode= 2015AIPC.1665e0017J }}</ref> |
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* Titanium dioxide nanocomposites: A research group led by A.A.M. Farag has prepared and characterized nanocomposites of {{chem|TiO|2}}<ref>{{cite journal |last= Ashery |first= A. |author2=G. Said |author3=W.A. Arafa |author4=A.E.H. Gaballah |author5=A.A.M. Farag |year=2016 |title= Morphological and crystalline structural characteristics of PEDOT/{{chem|TiO|2}} nanocomposites for applications towards technology in electronic devices |journal= Journal of Alloys and Compounds |volume=671 |pages=291–298 |doi=10.1016/j.jallcom.2016.02.088}}</ref> and {{chem|ZnO|}}<ref>{{cite journal |last= Ashery |first= A. |author2=A.A.M. Farag |author3=A.E.H. Gaballah |author4=G. Said |author5=W.A. Arafa |year=2017 |title= Nanostructural, optical and heterojunction characteristics of PEDOT/{{chem|ZnO|}} nanocomposite thin films |journal= Journal of Alloys and Compounds |volume=723 |
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|pages=276–287 |doi=10.1016/j.jallcom.2017.06.260}}</ref> with PEDOT-TMA. This group has also prepared and characterized heterojunction diodes using this nanocomposite.<ref>{{cite journal |last= Ashery |first= A. |author2=G. Said |author3=W.A. Arafa |author4=A.E.H. Gaballah |author5=A.A.M. Farag |year=2016 |title= Structural and optical characteristics of PEDOT/n-Si heterojunction diode |journal= Synthetic Metals |volume=214 |pages=92–99 |doi=10.1016/j.synthmet.2016.01.008}}</ref> |
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* Ultrathin Fiber-Mesh Polymer Thermistors: Ultrathin fibers were prepared that show a 10^3 increase in resistance over a narrow temperature range suitable for on-skin and implantable sensors. These thermistors prevent overheating in devices that use thermal protection circuits.<ref>{{cite journal |last= Okutani |first= Chihiro |author2=Tomoyuki Yokota |author3=Takeo Someya |year=2022 |title= Ultrathin Fiber-Mesh Polymer Thermistors |journal= Advanced Science |volume= 9 |issue= 30 |pages=e2202312 |doi=10.1002/advs.202202312|pmid= 36057993 |pmc= 9596841 |s2cid= 252070381 }}</ref> |
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==References== |
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*'''Patternable OLED's:''' In a study {{Ref|5}} by researchers at ], PEDOT-TMA was used in the hole injection layer in a series of ] devices. They have also filed a patent application to protect this invention {{Ref|6}}. |
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{{Reflist}} |
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*'''Ion Selective Membranes:''' PEDOT-TMA was used as a key ingredient in ]s {{Ref|7}}. |
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*'''Dye Sensitized Solar Cell:''' PEDOT-TMA was used in the construction of an effective ] {{Ref|8}}. |
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*'''Flexible Touch Screens:''' PEDOT-TMA was used in the construction of electrodes for flexible touch screens as described in a patent application by the Honeywell Corporation {{Ref|9}}. |
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*'''Energy Storage and Conversion Devices:''' Synkera Technologies, Inc. filed a patent application detailing a variety of energy storage and conversion devices that use PEDOT-TMA in their construction {{Ref|10}}. |
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*'''Glucose Sensor:''' A glucose sensor was prepared by Gymama Slaughter of Virginia State University {{Ref|11}}. |
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*'''Carbon Nanotube Composites:''' Researchers from ] used PEDOT-TMA to prepare composites with carbon nanotubes. These composites form highly aligned arrays of the nanotubes, and exhibit high conductivity at room temperature (25.0 S/cm){{Ref|12}}. |
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== References== |
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* {{Note|1}}J. Chamot. "New Molecule Heralds Breakthrough in Electronic Plastics," 4/12/2004. http://www.nsf.gov/news/news_summ.jsp?cntn_id=100360 |
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* {{Note|2}}G. P. Collins. "Next Stretch for Plastic Electronics." ], July 2004, p. 75-81. |
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* {{Note|3}} ], May 22, 2004; p. 74. |
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* {{Note|4}}Elliott; Brian J., Ellis; William W., Luebben; Silvia D., Sapp; Shawn A., Chang; Chieh-Hui, D'Sa; Raechelle A. "Electrically conducting materials from branched end-capping intermediates," United States Patent 7,361,728. |
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* {{Note|5}}J. Liu, L. N. Lewis and A. R. Dugal. "Photoactivated and patternable charge transport materials and their use in organic light-emitting devices." Appl. Phys. Lett. 90, 233503 (2007) http://dx.doi.org/10.1063/1.2746404 |
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* {{Note|6}}Jie Liu, Larry Neil Lewis, Anil Raj Duggal, Rubinsztajn Slawomir. "Organic light emitting devices having latent activated layers and methods of fabricating the same." US 2007/0077452 A1, Oct 4, 2005. |
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* {{Note|7}}Anna Rzewuska, Marcin Wojciechowski, Ewa Bulska, Elizabeth A. H. Hall, Krzysztof Maksymiuk, and Agata Michalska. "Composite Polyacrylate-Poly(3,4- ethylenedioxythiophene) Membranes for Improved All-Solid-State Ion-Selective Sensors." Anal. Chem., 80 (1), 321 -327, 2008. |
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* {{Note|8}}Kyung Ho Kim, Takashi Okubo, Naoyo Tanaka, Naoto Mimura, Masahiko Maekawa and Takayoshi, Kuroda-Sowa. "Dye-sensitized Solar Cells with Halide-bridged Mixed-valence Cu(I)-Cu(II) Coordination Polymers with Hexamethylenedithiocarbamate Ligand." Chem. Lett., 39 (7), 792-793, 2010. |
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* {{Note|9}}Lewin Edwards, Patricia McCrimmon, and Richard Thomas Watson. "Tactile-Feedback Touch Screen." US 2010/0182245 A1, Jul. 22, 2010. |
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* {{Note|10}}Dmitri Routkevitch, and Rikard A. Wind. "Energy Conversion and Energy Storage Devices and Methods for Making Same." US 2010/0304204 A1, Dec. 2, 2010. |
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* {{Note|11}} Gymama Slaughter. "Fabrication of Nanoindented Electrodes for Glucose Detection." J Diabetes Sci Technol. 2010 March; 4(2): 320–327. |
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* {{Note|11}} Huisheng Peng and Xuemei Sun. "Highly Aligned Carbon Nanotube/Polymer Composites with Much Improved Electrical Conductivities." Chemical Physics Letters 471 (2009), 103-5. |
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