593:
697:
640:
437:
25:
37:
404:
771:
655:
17:
745:
48:
425:. Although only poorly processable, "the expected high temperature stability and potentially very high electrical conductivity of PT films (if made) still make it a highly desirable material." Nonetheless, intense interest has focused on soluble polythiophenes, which usually translates to polymers derived from 3-alkylthiophenes, which give the so-called polyalkylthiophenes (PATs).
675:
with approximately 94% H–T content. Precipitation of ferric chloride in situ (in order to maximize the surface area of the catalyst) produced significantly higher yields and monomer conversions than adding monomer directly to crystalline catalyst. Higher molecular weights were reported when dry air was bubbled through the reaction mixture during polymerization. Exhaustive
475:
strong thermochromic effects, the absorbance spectra of the regioirregular polymers did not change significantly at elevated temperatures. Finally, Fluorescence absorption and emission maxima of poly(3-hexylthiophene)s occur at increasingly lower wavelengths (higher energy) with increasing HH dyad content. The difference between absorption and emission maxima, the
762:
accepted for electrochemical polymerization was more likely. Given the difficulties of studying a system with a heterogeneous, strongly oxidizing catalyst that produces difficult to characterize rigid-rod polymers, the mechanism of oxidative polymerization is by no means decided. The radical cation mechanism is generally accepted.
155:
oxidant is used to convert PTs (and other conducting polymers) into the optimally conductive state. Thus about one of every five rings is oxidized. Many different oxidants are used. Because of the redox reaction, the conductive form of polythiophene is a salt. An idealized stoichiometry is shown using the oxidant PF
674:
This method has proven to be extremely popular; antistatic coatings are prepared on a commercial scale using ferric chloride. In addition to ferric chloride, other oxidizing agents have been reported. Slow addition of ferric chloride to the monomer solution produced poly(3-(4-octylphenyl)thiophene)s
631:
Chemical synthesis offers two advantages compared with electrochemical synthesis of PTs: a greater selection of monomers, and, using the proper catalysts, the ability to synthesize perfectly regioregular substituted PTs. PTs were chemically synthesized by accident more than a century ago. Chemical
474:
formed "crystalline, flexible, and bronze-colored films with a metallic luster". On the other hand, the corresponding regiorandom polymers produced "amorphous and orange-colored films". Comparison of the thermochromic properties of the Rieke PATs showed that, while the regioregular polymers showed
154:
PT is an ordinary organic polymer, being a red solid that is poorly soluble in most solvents. Upon treatment with oxidizing agents (electron-acceptors) however, the material takes on a dark color and becomes electrically conductive. Oxidation is referred to as "doping". Around 0.2 equivalent of
761:
studied the oligomerization of 3-(alkylsulfanyl)thiophenes, and concluded from their quantum mechanical calculations, and considerations of the enhanced stability of the radical cation when delocalized over a planar conjugated oligomer, that a radical cation mechanism analogous to that generally
2696:
Zhu, Lishan; Wehmeyer, Richard M.; Rieke, Reuben D. (1991). "The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, α,β-unsaturated ketones, and allylic, aryl, and vinyl halides".
374:
Shifts in PT absorption bands due to changes in temperature result from a conformational transition from a coplanar, rodlike structure at lower temperatures to a nonplanar, coiled structure at elevated temperatures. For example, poly(3-(octyloxy)-4-methylthiophene) undergoes a color change from
469:
Regioregularity affects the properties of PTs. A regiorandom copolymer of 3-methylthiophene and 3-butylthiophene possessed a conductivity of 50 S/cm, whereas a more regioregular copolymer with a 2:1 ratio of HT to HH couplings had a higher conductivity of 140 S/cm. Films of regioregular
679:
after polymerization with polar solvents was found to effectively fractionate the polymer and remove residual catalyst before NMR spectroscopy. Using a lower ratio of catalyst to monomer (2:1, rather than 4:1) may increase the regioregularity of poly(3-dodecylthiophene)s. Andreani
383:
PTs exhibit an isosbestic point: highly regioregular poly(3-alkylthiophene)s (PATs) show a continuous blue-shift with increasing temperature if the side chains are short enough so that they do not melt and interconvert between crystalline and disordered phases at low temperatures.
346:
estimated that the effective conjugation extended over 11 repeat units, while later studies increased this estimate to 20 units. Using the absorbance and emission profile of discrete conjugated oligo(3-hexylthiophene)s prepared through polymerization and separation, Lawrence
858:
of the materials, combined with their processing and material properties common to polymeric materials. Dynamic applications utilize changes in the conductive and optical properties, resulting either from application of electric potentials or from environmental stimuli.
688:
rather than chloroform, which they attributed to the stability of the radical species in carbon tetrachloride. Higher-quality catalyst, added at a slower rate and at reduced temperature, was shown to produce high molecular weight PATs with no insoluble polymer residue.
564:. Electrochemical polymerization is convenient, since the polymer does not need to be isolated and purified, but it can produce polymers with undesirable alpha-beta linkages and varying degrees of regioregularity. The stoichiometry of the electropolymerization is:
299:
The extended π-systems of conjugated PTs produce some of the most interesting properties of these materials—their optical properties. As an approximation, the conjugated backbone can be considered as a real-world example of the "electron-in-a-box" solution to the
607:
Electron-donating substituents lower the oxidation potential, whereas electron-withdrawing groups increase the oxidation potential. Thus, 3-methylthiophene polymerizes in acetonitrile and tetrabutylammonium tetrafluoroborate at a potential of about 1.5 V vs.
110:
along the polymer backbone. Conductivity however is not the only interesting property resulting from electron delocalization. The optical properties of these materials respond to environmental stimuli, with dramatic color shifts in response to changes in
1208:
McCullough, Richard D.; Tristram-Nagle, Stephanie; Williams, Shawn P.; Lowe, Renae D.; Jayaraman, Manikandan (1993). "Self-orienting head-to-tail poly(3-alkylthiophenes): new insights on structure-property relationships in conducting polymers".
1950:
Elsenbaumer, R. L.; Jen, K.-Y.; Miller, G. G.; Eckhardt, H.; Shacklette, L. W.; Jow, R. "Poly (alkylthiophenes) and Poly (substituted heteroaromatic vinylenes): Versatile, Highly
Conductive, Processible Polymers with Tunable Properties". In
2724:
Chen, Tian An; Rieke, Reuben D. (1992). "The first regioregular head-to-tail poly(3-hexylthiophene-2,5-diyl) and a regiorandom isopolymer: nickel versus palladium catalysis of 2(5)-bromo-5(2)-(bromozincio)-3-hexylthiophene polymerization".
1605:
Izumi, Tsuyoshi; Kobashi, Seiji; Takimiya, Kazuo; Aso, Yoshio; Otsubo, Tetsuo (2003). "Synthesis and
Spectroscopic Properties of a Series of β-Blocked Long Oligothiophenes up to the 96-mer: Revaluation of Effective Conjugation Length".
2300:
Li, L.; Counts, K. E.; Kurosawa, S.; Teja, A. S.; Collard, D. M. (2004). "Tuning the
Electronic Structure and Solubility of Conjugated Polymers with Perfluoroalkyl Substituents: Poly(3-perfluorooctylthiophene), the First Supercritical
933:
Arosio, Paolo; Moreno, Margherita; Famulari, Antonino; Raos, Guido; Catellani, Marinella; Valdo Meille, Stefano (2009). "Ordered
Stacking of Regioregular Head-to-Tail Polyalkylthiophenes: Insights from the Crystal Structure of Form I′
806:
PEDOT also has been proposed for dynamic applications where a potential is applied to a polymer film. PEDOT-coated windows and mirrors become opaque or reflective upon the application of an electric potential, a manifestation of its
335:; or temporary, resulting from changes in the environment or binding. This twist in the backbone reduces the conjugation length, and the separation between energy levels is increased. This results in a shorter absorption wavelength.
2807:
Fraleoni-Morgera, Alessandro; Della-Casa, Carlo; Lanzi, Massimiliano; Costa-Bizzarri, Paolo (2003). "Investigation on
Different Procedures in the Oxidative Copolymerization of a Dye-Functionalized Thiophene with 3-Hexylthiophene".
1534:
Lawrence, Jimmy; Goto, Eisuke; Ren, Jing M.; McDearmon, Brenden; Kim, Dong Sub; Ochiai, Yuto; Clark, Paul G.; Laitar, David; Higashihara, Tomoya (2017-10-04). "A Versatile and
Efficient Strategy to Discrete Conjugated Oligomers".
3014:
Barbarella, Giovanna; Zambianchi, Massimo; Di Toro, Rosanna; Colonna, Martino; Iarossi, Dario; Goldoni, Francesca; Bongini, Alessandro (1996). "Regioselective
Oligomerization of 3-(Alkylsulfanyl)thiophenes with Ferric Chloride".
2105:
Englebienne, Patrick; Weiland, Mich le (1996). "Synthesis of water-soluble carboxylic and acetic acid-substituted poly(thiophenes) and the application of their photochemical properties in homogeneous competitive immunoassays".
1880:
Barbarella, Giovanna; Bongini, Alessandro; Zambianchi, Massimo (1994). "Regiochemistry and
Conformation of Poly(3-hexylthiophene) via the Synthesis and the Spectroscopic Characterization of the Model Configurational Triads".
416:
Polythiophene and its oxidized derivatives have poor processing properties. They are insoluble in ordinary solvents and do not melt readily. For example, doped unsubstituted PTs are only soluble in exotic solvents such as
351:
determined the effective conjugation length of poly(3-hexylthiophene) to be 14 units. The effective conjugation length of polythiophene derivatives depend on the chemical structure of side chains, and thiophene backbones.
3299:
2870:
Andreani, F.; Salatelli, E.; Lanzi, M. (February 1996). "Novel poly(3,3" – and 3',4'-dialkyl- 2,2':5',2" – terthiophene)s by chemical oxidative synthesis: evidence for a new step towards the optimization of this process".
2348:
Murphy, Amanda R.; Fréchet, Jean M. J.; Chang, Paul; Lee, Josephine; Subramanian, Vivek (2004). "Organic Thin Film
Transistors from a Soluble Oligothiophene Derivative Containing Thermally Removable Solubilizing Groups".
218:
is formed. The bipolaron moves as a unit along the polymer chain and is responsible for the macroscopically observed conductivity of the material. Conductivity can approach 1000 S/cm. In comparison, the conductivity of
2183:
Jung, S.; Hwang, D.-H.; Zyung, T.; Kim, W. H.; Chittibabu, K. G.; Tripathy, S. K. (1998). "Temperature dependent photoluminescence and electroluminescence properties of polythiophene with hydrogen bonding side chain".
651:. This method produces approximately 100% HT–HT couplings, according to NMR spectroscopy analysis of the diads. 2,5-Dibromo-3-alkylthiophene when treated with highly reactive "Rieke zinc" is an alternative method.
123:, and binding to other molecules. Changes in both color and conductivity are induced by the same mechanism, twisting of the polymer backbone and disrupting conjugation, making conjugated polymers attractive as
2775:
Costa
Bizzarri, P.; Andreani, Franco; Della Casa, Carlo; Lanzi, Massimiliano; Salatelli, Elisabetta (1995). "Ester-functionalized poly(3-alkylthienylene)s: substituent effects on the polymerization with
1977:
Andersson, M. R.; Selse, D.; Berggren, M.; Jaervinen, H.; Hjertberg, T.; Inganaes, O.; Wennerstroem, O.; Oesterholm, J.-E. (1994). "Regioselective polymerization of 3-(4-octylphenyl)thiophene with FeCl
798:
properties. The thin layer of PEDOT:PSS is virtually transparent and colorless, prevents electrostatic discharges during film rewinding, and reduces dust buildup on the negatives after processing.
1402:
Abdou, M.S.A.; Holdcroft, Steven (1993). "Oxidation of π-conjugated polymers with gold trichloride: enhanced stability of the electronically conducting state and electroless deposition of Au".
732:), and speculated that the polymerization may occur at the surface of solid ferric chloride. However, this is challenged by the fact that the reaction also proceeds in acetonitrile, which FeCl
320:
1429:
Rudge, Andy; Raistrick, Ian; Gottesfeld, Shimshon; Ferraris, John P. (1994). "A study of the electrochemical properties of conducting polymers for application in electrochemical capacitors".
667:
In contrast to methods that require brominated monomers, the oxidative polymerization of thiophenes using ferric chloride proceeds at room temperature. The approach was reported by Sugimoto
207:
2522:
Roncali, J.; Garreau, R.; Yassar, A.; Marque, P.; Garnier, F.; Lemaire, M. (1987). "Effects of steric factors on the electrosynthesis and properties of conducting poly(3-alkylthiophenes)".
433:
Soluble polymers are derivable from 3-substituted thiophenes where the 3-substituent is butyl or longer. Copolymers also are soluble, e.g., poly(3-methylthiophene-'co'-3'-octylthiophene).
753:
Polymerization of thiophene can be effected by a solution of ferric chloride in acetonitrile. The kinetics of thiophene polymerization also seemed to contradict the predictions of the
2016:
Chen, Tian-An; Wu, Xiaoming; Rieke, Reuben D. (1995). "Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rieke Zinc: Their Characterization and Solid-State Properties".
878:
470:
poly(3-(4-octylphenyl)thiophene) (POPT) with greater than 94% HT content possessed conductivities of 4 S/cm, compared with 0.4 S/cm for regioirregular POPT. PATs prepared using Rieke
3133:
Martina, V; Ionescu, K.; Pigani, L; Terzi, F; Ulrici, A.; Zanardi, C.; Seeber, R (March 2007). "Development of an electronic tongue based on a PEDOT-modified voltammetric sensor".
740:
also point to a radical mechanism. The mechanism can also be inferred from the regiochemistry of the dimerization of 3-methylthiophene since C2 in has the highest spin density.
392:
The optical properties of PTs can be sensitive to many factors. PTs exhibit absorption shifts due to application of electric potentials (electrochromism), or to introduction of
223:
is approximately 5×10 S/cm. Generally, the conductivity of PTs is lower than 1000 S/cm, but high conductivity is not necessary for many applications, e.g. as an antistatic film.
379:(a point where the absorbance curves at all temperatures overlap) indicates coexistence between two phases, which may exist on the same chain or on different chains. Not all
338:
Determining the maximum effective conjugation length requires the synthesis of regioregular PTs of defined length. The absorption band in the visible region is increasingly
1333:
604:
and quality of the resulting polymer depends upon the electrode material, current density, temperature, solvent, electrolyte, presence of water, and monomer concentration.
2898:
Gallazzi, M.; Bertarelli, C.; Montoneri, E. (2002). "Critical parameters for product quality and yield in the polymerisation of 3,3"-didodecyl-2,2′:5′,2"-terthiophene".
1736:
Marsella, Michael J.; Swager, Timothy M. (1993). "Designing conducting polymer-based sensors: selective ionochromic response in crown ether-containing polythiophenes".
2434:
Groenendaal, L. B.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J. R. (2000). "Poly(3,4-Ethylenedioxythiophene) and Its Derivatives: Past, Present, and Future".
342:
as the conjugation length increases, and the maximum effective conjugation length is calculated as the saturation point of the red-shift. Early studies by ten Hoeve
1247:
Loponen, M.; Taka, T.; Laakso, J.; Vakiparta, K.; Suuronen, K.; Valkeinen, P.; Osterholm, J. (1991). "Doping and dedoping processes in poly (3-alkylthiophenes)".
1578:
Nakanishi, Hidetaka; Sumi, Naoto; Aso, Yoshio; Otsubo, Tetsuo (1998). "Synthesis and Properties of the Longest Oligothiophenes: the Icosamer and Heptacosamer".
512:
Oligothiophenes capped at both ends with thermally-labile alkyl esters were cast as films from solution, and then heated to remove the solublizing end groups.
270:(MALDI-MS) studies have shown that poly(3-hexylthiophene)s are also partially halogenated by the residual oxidizing agent. Poly(3-octylthiophene) dissolved in
1151:
Kobayashi, M.; Chen, J.; Chung, T.-C.; Moraes, F.; Heeger, A.J.; Wudl, F. (January 1984). "Synthesis and properties of chemically coupled poly(thiophene)".
693:
indicate that the catalyst/monomer ratio correlated with increased yield of poly(3-octylthiophene). Longer polymerization time also increased the yield.
331:, and the longer the absorption wavelength. Deviation from coplanarity may be permanent, resulting from mislinkages during synthesis or especially bulky
2843:
Qiao, X.; Wang, Xianhong; Zhao, Xiaojiang; Liu, Jian; Mo, Zhishen (2000). "Poly(3-dodecylthiophenes) polymerized with different amounts of catalyst".
1706:
H. W. Heuer; R. Wehrmann; S. Kirchmeyer (2002). "Electrochromic Window Based on Conducting Poly(3,4-ethylenedioxythiophene)-Poly(styrene sulfonate)".
505:
substituents at the 3 position have been polymerized. Such chiral PTs in principle could be employed for detection or separation of chiral analytes.
1916:
Diaz-Quijada, G. A.; et al. (1996). "Regiochemical Analysis of Water Soluble Conductive Polymers: Sodium Poly(ω-(3-thienyl)alkanesulfonates)".
2585:
Yamamoto, Takakazu; Sanechika, Kenichi; Yamamoto, Akio (January 1980). "Preparation of thermostable and electric-conducting poly(2,5-thienylene)".
1641:
De Souza, J.; Pereira, Ernesto C. (2001). "Luminescence of poly(3-thiopheneacetic acid) in alcohols and aqueous solutions of poly(vinyl alcohol)".
2558:
2661:
Chen, Tian An; O'Brien, Richard A.; Rieke, Reuben D. (1993). "Use of highly reactive zinc leads to a new, facile synthesis for polyarylenes".
1178:
Mastragostino, M.; Soddu, L. (1990). "Electrochemical characterization of "n" doped polyheterocyclic conducting polymers—I. Polybithiophene".
2129:
Kim; Chen, Li; Gong; Osada, Yoshihito (1999). "Titration Behavior and Spectral Transitions of Water-Soluble Polythiophene Carboxylic Acids".
327:
The number of coplanar rings determines the conjugation length—the longer the conjugation length, the lower the separation between adjacent
264:
2455:
1108:
Mehmood, Umer; Al-Ahmed, Amir; Hussein, Ibnelwaleed A. (2016). "Review on recent advances in polythiophene based photovoltaic devices".
708:
reported that polymerization was only observed in solvents where the catalyst was either partially or completely insoluble (chloroform,
487:
Water-soluble PT's are represented by sodium poly(3-thiophenealkanesulfonate)s. In addition to conferring water solubility, the pendant
2164:
Andersson, M.; Ekeblad, P. O.; Hjertberg, T.; Wennerström, O.; Inganäs, O. (1991). "Polythiophene with a free amino-acid side-chain".
1855:
479:, also increases with HH dyad content, which they attributed to greater relief from conformational strain in the first excited state.
3176:
Bäuerle, Peter; Scheib, Stefan (1993). "Molecular recognition of alkali-ions by crown-ether-functionalized poly(alkylthiophenes)".
993:Österholm, J.-E.; Passiniemi, P.; Isotalo, H.; Stubb, H. (February 1987). "Synthesis and properties of FeCl4-doped polythiophene".
886:
463:
103:
3071:
2952:
Niemi, V. M.; Knuuttila, P.; Österholm, J. E.; Korvola, J. (1992). "Polymerization of 3-alkylthiophenes with ferric chloride".
854:. In general, two categories of applications are proposed for conducting polymers. Static applications rely upon the intrinsic
1719:
3396:
2486:
255:
produce PTs with lower conductivities than iodine, but with higher environmental stabilities. Oxidative polymerization with
28:
Polythiophenes demonstrate interesting optical properties resulting from their conjugated backbone, as demonstrated by the
639:
1507:
Meier, H.; Stalmach, U.; Kolshorn, H (September 1997). "Effective conjugation length and UV/vis spectra of oligomers".
704:
In terms of mechanism, the oxidative polymerization using ferric chloride, a radical pathway has been proposed. Niemi
444:
One undesirable feature of 3-alkylthiophenes is the variable regioregularity of the polymer. Focusing on the polymer
312:
spectra of well-defined oligo(thiophene) systems is ongoing. Conjugation relies upon overlap of the π-orbitals of the
3294:
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3272:
3121:
3101:
2754:"Preparation of soluble polythiophene derivatives utilizing transition metal halides as catalysts and their property"
1960:
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130:
The development of polythiophenes and related conductive organic polymers was recognized by the awarding of the 2000
786:
has been extensively used as an antistatic coating (as packaging materials for electronic components, for example).
750:
A carbocation mechanism is inferred from the structure of 3-(4-octylphenyl)thiophene prepared from ferric chloride.
95:
substituents at the 3- or 4-position(s). They are also colored solids, but tend to be soluble in organic solvents.
2925:
Laakso, J.; Jarvinen, H.; Skagerberg, B. (1993). "Recent developments in the polymerization of 3-alkylthiophenes".
2394:"Fluorine Substituted Conjugated Polymer of Medium Band Gap Yields 7% Efficiency in Polymer−Fullerene Solar Cells"
2249:
Desimone, J. M.; Guan, Z.; Elsbernd, C. S. (1992). "Synthesis of Fluoropolymers in Supercritical Carbon Dioxide".
3435:
3415:
1763:
Rughooputh, S. D. D. V.; Hotta, S.; Heeger, A. J.; Wudl, F. (May 1987). "Chromism of soluble polythienylenes".
1065:
McQuade, D. Tyler; Pullen, Anthony E.; Swager, Timothy M. (2000). "Conjugated Polymer-Based Chemical Sensors".
1020:
Nielsen, Christian B.; McCulloch, Iain (2013). "Recent advances in transistor performance of polythiophenes".
283:
3440:
509:
1477:
609:
592:
966:
Tourillon, G.; Garnier, F. (April 1982). "New electrochemically generated organic conducting polymers".
278:, and can be cast into films with conductivities reaching 1 S/cm. Other, less common p-dopants include
1668:
Roux, Claudine; Leclerc, Mario (1992). "Rod-to-coil transition in alkoxy-substituted polythiophenes".
367:
7 to 415 nm at pH 4. This is attributed to formation of a compact coil structure, which can form
3425:
3329:
Roncali, Jean (1992). "Conjugated poly(thiophenes): synthesis, functionalization, and applications".
2043:
Xu, Bai; Holdcroft, Steven (1993). "Molecular control of luminescence from poly(3-hexylthiophenes)".
309:
2508:
3050:
Rosseinsky, D. R.; Mortimer, R. J. (2001). "Electrochromic Systems and the Prospects for Devices".
823:
696:
601:
491:
groups act as counterions, producing self-doped conducting polymers. Substituted PTs with tethered
131:
2078:
Patil, A. O.; Ikenoue, Y.; Wudl, Fred; Heeger, A. J. (1987). "Water soluble conducting polymers".
239:
produce highly conductive materials, which are unstable owing to slow evaporation of the halogen.
3350:
Roncali, Jean (1997). "Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems".
905:
Strictly speaking, "polythiophene" is a misnomer, since the polymer consists of thienylene (2,5-C
855:
737:
513:
356:
305:
51:
654:
301:
940:
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resulting from branching at the α-carbon of a 3-substituted thiophene inhibits polymerization.
528:
462:
These three diads can be combined into four distinct triads. The triads are distinguishable by
203:
In principle, PT can be n-doped using reducing agents, but this approach is rarely practiced.
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535:. Regiochemistry is not an issue in since this monomer is symmetrical. PEDOT is found in
244:
107:
1334:"MALDI-MS Evaluation of Poly(3-hexylthiophene) Synthesized by Chemical Oxidation with FeCl
8:
3420:
3267:(Eds: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), Marcel Dekker, New York, 1998.
827:
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40:
3213:"Polythiophenes Inhibit Prion Propagation by Stabilizing Prion Protein (PrP) Aggregates"
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Heffner, G.; Pearson, D. (1991). "Solution processing of a doped conducting polymer".
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Street, G. B.; Clarke, T. C. (1981). "Conducting Polymers: A Review of Recent Work".
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Price, Samuel C.; Stuart, Andrew C.; Yang, Liqiang; Zhou, Huaxing; You, Wei (2011).
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functionalities exhibit properties that vary with the alkali metal. and main-chain.
91:. The rings are linked through the 2- and 5-positions. Poly(alkylthiophene)s have
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Kane-Maguire, Leon A. P.; Wallace, Gordon G. (2010). "Chiral conducting polymers".
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at the dyad level, 3-substituted thiophenes can couple to give any of three dyads:
376:
143:
1107:
647:
Regioregular PTs have been prepared by lithiation 2-bromo-3-alkylthiophenes using
396:(ionochromism). Soluble PATs exhibit both thermochromism and solvatochromism (see
36:
2983:
Olinga, T.; François, B. (1995). "Kinetics of polymerization of thiophene by FeCl
2270:
808:
648:
633:
536:
492:
139:
1784:
1520:
700:
Proposed mechanisms for ferric chloride oxidative polymerizations of thiophenes.
519:
Fluorinated polythiophene yield 7% efficiency in polymer-fullerene solar cells.
124:
2646:
2621:
2606:
1129:
867:
812:
613:
445:
248:
135:
3146:
2571:
1478:"Substituted .. – undecithiophenes, the longest characterized oligothiophenes"
1287:
516:(AFM) images showed a significant increase in long-range order after heating.
3409:
3197:
2806:
1834:
McCullough, Richard D. (1998). "The Chemistry of Conducting Polythiophenes".
1556:
721:
556:
In an electrochemical polymerization, a solution containing thiophene and an
440:
The four possible triads resulting from coupling of 3-substituted thiophenes.
403:
380:
368:
319:
55:
3388:
3229:
866:, PTs can also be functionalized with receptors for detecting metal ions or
623:, which then couple with another monomer to produce a radical cation dimer.
16:
3371:
3248:
3154:
3036:
2549:
2456:
10.1002/(SICI)1521-4095(200004)12:7<481::AID-ADMA481>3.0.CO;2-C
2417:
2370:
2326:
2278:
2235:
1627:
1564:
1086:
1042:
787:
540:
476:
328:
275:
240:
206:
29:
2213:
1332:
McCarley, Tracy Donovan; Noble; Dubois, C. J.; McCarley, Robin L. (2001).
770:
671:
in 1986. The stoichiometry is analogous to that of electropolymerization.
3092:
Garnier, F. "Field-Effect Transistors Based on Conjugated Materials". In
2115:
1856:
10.1002/(SICI)1521-4095(199801)10:2<93::AID-ADMA93>3.0.CO;2-F
1548:
871:
835:
729:
620:
557:
313:
210:
Removal of two electrons (p-doping) from a PT chain produces a bipolaron.
116:
3342:
3321:
2738:
2710:
2682:
2535:
2091:
2064:
2029:
2002:
1937:
1902:
1811:
1749:
1689:
1493:
1222:
2478:
968:
Journal of Electroanalytical Chemistry and Interfacial Electrochemistry
831:
795:
332:
3363:
3211:
Margalith, Ilan; Suter, Carlo; Ballmer, Boris; Schwarz, Petra (2012).
3072:
10.1002/1521-4095(200106)13:11<783::AID-ADMA783>3.0.CO;2-D
3028:
2829:
2409:
2362:
2150:
1619:
1591:
1361:
1078:
952:
877:
274:
can be doped by solutions of ferric chloride hexahydrate dissolved in
2774:
2227:
1720:
10.1002/1616-3028(20020201)12:2<89::AID-ADFM89>3.0.CO;2-1
779:
619:
In terms of mechanism, oxidation of the thiophene monomer produces a
496:
488:
260:
215:
69:
2553:
1459:; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998,
1207:
1019:
780:
poly(3,4-ethylenedioxythiophene)-poly(styrene sulfonate) (PEDOT-PSS)
1955:(Eds: Kuzmany, H.; Mehring, M.; Roth, S.), Springer, Berlin, 1987,
1705:
304:; however, the development of refined models to accurately predict
3013:
1476:
Ten Hoeve, W.; Wynberg, H.; Havinga, E. E.; Meijer, E. W. (1991).
1274:
Bartuš, Ján (1991). "Electrically Conducting Thiophene Polymers".
596:
Proposed initial steps in the electropolymerization of thiophenes.
783:
713:
709:
323:
Conjugated π-orbitals of a coplanar and a twisted substituted PT.
271:
236:
112:
79:. The parent PT is an insoluble colored solid with the formula (C
66:
1428:
913:
S) repeat units. Similarly, thiophene is not a monomer as such.
684:
reported higher yields of soluble poly(dialkylterthiophene)s in
612:, whereas unsubstituted thiophene requires an additional 0.2 V.
407:
Ionoselective PTs reported by Bäuerle (left) and Swager (right).
3383:. Advances in Polymer Science. Vol. 145. pp. 57–122.
1976:
992:
863:
851:
725:
717:
502:
393:
316:, which, in turn, requires the thiophene rings to be coplanar.
232:
220:
73:
2951:
2473:. Advances in Polymer Science. Vol. 129. pp. 1–166.
371:
with PVA upon partial deprotonation of the acetic acid group.
127:
that can provide a range of optical and electronic responses.
1475:
847:
561:
532:
92:
32:
of a substituted polythiophene solution under UV irradiation.
3210:
543:, electroluminescent displays, printed wiring, and sensors.
146:"for the discovery and development of conductive polymers".
47:
2897:
1879:
1731:
1729:
1331:
471:
375:
red–violet at 25 °C to pale yellow at 150 °C. An
3116:(Eds: Müllen, K.; Wegner, G.), Wiley-VCH, Weinheim, 1998,
3112:
Harrison, M. G.; Friend, R. H. "Optical Applications". In
3096:(Eds: Müllen, K.; Wegner, G.), Wiley-VCH, Weinheim, 1998,
2521:
1246:
3132:
2584:
1798:
Frommer, Jane E. (1986). "Conducting polymer solutions".
1762:
2924:
2752:
Sugimoto, R.; Taketa, S.; Gu, H. B.; Yoshino, K (1986).
2462:
2429:
2427:
1726:
1533:
1150:
932:
862:
PTs have been touted as sensor elements. In addition to
2751:
1875:
1873:
1604:
1301:
Qiao, X.; Wang, Xianhong; Mo, Zhishen (2001). "The FeCl
1203:
1201:
364:
149:
20:
The monomer repeat unit of unsubstituted polythiophene.
2869:
2077:
1972:
1970:
1968:
1577:
54:
image of poly(3-decylthiophene-2,5-diyl) on hexagonal
2556:[On the companion of benzene in stone coal].
2554:"Ueber den Begleiter des Benzols im Steinkohlentheer"
2424:
2347:
1506:
662:
397:
43:
of poly(3-butylthiophene) from the crystal structure.
2660:
2299:
2248:
1870:
1242:
1240:
1198:
2978:
2976:
2620:Lin, John W-P.; Dudek, Lesley P. (September 1980).
2587:
Journal of Polymer Science: Polymer Letters Edition
2391:
2157:
1965:
1915:
1064:
289:
3049:
2745:
2622:"Synthesis and properties of poly(2,5-thienylene)"
2104:
1701:
1699:
1177:
885:Polythiophenes show potential in the treatment of
231:A variety of reagents have been used to dope PTs.
3378:
2182:
1237:
508:Poly(3-(perfluorooctyl)thiophene)s is soluble in
400:) in chloroform and 2,5-dimethyltetrahydrofuran.
3407:
3279:Polythiophenes: Electrically Conductive Polymers
2973:
2695:
2128:
1305:-doped poly(3-alkyithiophenes) in solid state".
965:
2842:
2471:Polythiophenes—Electrically Conducting Polymers
1696:
1640:
1598:
3381:Molecular Engineering of p-Conjugated Polymers
2982:
2559:Berichte der deutschen chemischen Gesellschaft
1735:
1401:
1374:
3175:
2468:
411:
3307:
1953:Electronic Properties of Conjugated Polymers
551:
3114:Electronic Materials: The Oligomer Approach
3094:Electronic Materials: The Oligomer Approach
2042:
2015:
1667:
1457:Electronic Materials: The Oligomer Approach
265:matrix-assisted laser desorption/ionization
3379:Reddinger, J. L.; Reynolds, J. R. (1999).
1833:
1300:
1110:Renewable & Sustainable Energy Reviews
881:Chiral PT synthesized by Yashima and Goto.
3238:
3228:
2723:
2645:
1276:Journal of Macromolecular Science, Part A
1041:
2727:Journal of the American Chemical Society
2619:
2398:Journal of the American Chemical Society
2351:Journal of the American Chemical Society
2209:
2207:
2080:Journal of the American Chemical Society
2018:Journal of the American Chemical Society
1829:
1827:
1825:
1823:
1821:
1738:Journal of the American Chemical Society
1608:Journal of the American Chemical Society
1537:Journal of the American Chemical Society
1482:Journal of the American Chemical Society
1455:Bässler, H. "Electronic Excitation". In
1211:Journal of the American Chemical Society
876:
801:
769:
695:
632:syntheses from 2,5-dibromothiophene use
591:
435:
402:
318:
205:
46:
35:
23:
15:
3349:
3328:
1797:
815:windows promise significant savings in
794:per year with PEDOT:PSS because of its
778:As an example of a static application,
626:
531:(EDOT) is the precursor to the polymer
527:The 3,4-disubstituted thiophene called
482:
214:Upon "p-doping", charged unit called a
3408:
3135:Analytical and Bioanalytical Chemistry
1273:
822:Another potential application include
2548:
2204:
1818:
560:produces a conductive PT film on the
294:
428:
150:Mechanism of conductivity and doping
3217:The Journal of Biological Chemistry
495:also exhibit water solubility. and
13:
3258:
2987:in choloroform and acetonitrile".
1034:10.1016/j.progpolymsci.2013.05.003
663:Routes employing chemical oxidants
653:
638:
387:
14:
3452:
2524:The Journal of Physical Chemistry
458:5,5', or tail–tail (TT), coupling
455:2,2', or head–head (HH), coupling
452:2,5', or head–tail (HT), coupling
363:(PVA) shifts from 480 nm at
259:can result in doping by residual
3017:The Journal of Organic Chemistry
2699:The Journal of Organic Chemistry
2469:Schopf, G.; Koßmehl, G. (1997).
1580:The Journal of Organic Chemistry
743:
290:Structure and optical properties
3265:Handbook of Conducting Polymers
3204:
3169:
3126:
3106:
3086:
3043:
3007:
2945:
2918:
2891:
2863:
2836:
2800:
2768:
2717:
2689:
2654:
2613:
2578:
2542:
2515:
2385:
2341:
2293:
2242:
2176:
2122:
2098:
2071:
2036:
2009:
1944:
1909:
1791:
1756:
1661:
1634:
1571:
1527:
1500:
1469:
1449:
1422:
1395:
1368:
1325:
1294:
1267:
765:
738:Quantum mechanical calculations
2305:-soluble Conjugated Polymer".
1171:
1144:
1101:
1058:
1013:
986:
959:
926:
899:
1:
2912:10.1016/S0379-6779(01)00665-8
2857:10.1016/S0379-6779(00)00233-2
2198:10.1016/S0379-6779(98)00161-1
1800:Accounts of Chemical Research
1708:Advanced Functional Materials
1655:10.1016/S0379-6779(00)00453-7
1319:10.1016/S0379-6779(00)00587-7
920:
355:The absorption band of poly (
284:trifluoromethanesulfonic acid
3001:10.1016/0379-6779(94)02457-A
2966:10.1016/0032-3861(92)90138-M
2939:10.1016/0379-6779(93)90225-L
2885:10.1016/0032-3861(96)83153-3
2794:10.1016/0379-6779(95)03401-5
2626:Journal of Polymer Science A
2271:10.1126/science.257.5072.945
1765:Journal of Polymer Science B
1443:10.1016/0013-4686(94)80063-4
1416:10.1016/0379-6779(93)91226-R
1389:10.1016/0379-6779(91)91821-Q
1261:10.1016/0379-6779(91)91111-M
1192:10.1016/0013-4686(90)87029-2
1165:10.1016/0379-6779(84)90044-4
1007:10.1016/0379-6779(87)90881-2
980:10.1016/0022-0728(82)90015-8
643:Kumada coupling route to PT.
546:
510:supercritical carbon dioxide
7:
1785:10.1002/polb.1987.090250508
1521:10.1002/actp.1997.010480905
1022:Progress in Polymer Science
782:product ("Clevios P") from
226:
108:delocalization of electrons
10:
3457:
3281:, Springer, Berlin, 1997,
2647:10.1002/pol.1980.170180910
2607:10.1002/pol.1980.130180103
1130:10.1016/j.rser.2015.12.177
870:as well. PTs with pendant
828:electroluminescent devices
412:Substituted polythiophenes
359:) in aqueous solutions of
3304:(journal). ISSN 0379-6779
3147:10.1007/s00216-006-1102-1
2572:10.1002/cber.188301601324
1288:10.1080/00222339108054069
811:. Widespread adoption of
809:electrochromic properties
552:Electrochemical synthesis
3198:10.1002/adma.19930051113
2216:Chemical Society Reviews
892:
824:field-effect transistors
712:, carbon tetrachloride,
602:degree of polymerization
522:
132:Nobel Prize in Chemistry
3389:10.1007/3-540-70733-6_2
3277:G. Schopf, G. Koßmehl,
3230:10.1074/jbc.M112.355958
2108:Chemical Communications
840:nonlinear optic devices
537:electrochromic displays
514:Atomic force microscopy
357:3-thiophene acetic acid
104:electrical conductivity
3436:Organic semiconductors
2327:10.1002/adma.200305333
882:
864:biosensor applications
790:coats 200 m × 10 m of
775:
757:mechanism. Barbarella
755:radical polymerization
701:
659:
644:
636:and related reactions
597:
529:ethylenedioxythiophene
441:
408:
324:
211:
59:
44:
33:
21:
3416:Molecular electronics
2552:(January–June 1883).
880:
836:photochemical resists
802:Proposed applications
773:
699:
691:Factorial experiments
657:
649:Kumada cross-coupling
642:
595:
439:
423:arsenic pentafluoride
406:
322:
209:
50:
39:
27:
19:
2116:10.1039/cc9960001651
1549:10.1021/jacs.7b05299
686:carbon tetrachloride
658:Rieke method for PT.
627:From bromothiophenes
483:Special substituents
302:Schrödinger equation
245:trifluoroacetic acid
102:when oxidized. The
3441:Conductive polymers
3343:10.1021/cr00012a009
3322:10.1147/rd.251.0051
3190:1993AdM.....5..848B
3064:2001AdM....13..783R
2822:2003MaMol..36.8617F
2739:10.1021/ja00051a066
2711:10.1021/jo00004a021
2683:10.1021/ma00065a036
2675:1993MaMol..26.3462C
2638:1980JPoSA..18.2869L
2599:1980JPoSL..18....9Y
2536:10.1021/j100311a030
2448:2000AdM....12..481G
2319:2004AdM....16..180L
2263:1992Sci...257..945D
2143:1999MaMol..32.3964K
2092:10.1021/ja00240a044
2065:10.1021/ma00069a009
2057:1993MaMol..26.4457X
2030:10.1021/ja00106a027
2003:10.1021/ma00100a039
1995:1994MaMol..27.6503A
1930:1996MaMol..29.5416D
1903:10.1021/ma00089a022
1895:1994MaMol..27.3039B
1848:1998AdM....10...93M
1812:10.1021/ar00121a001
1777:1987JPoSB..25.1071R
1750:10.1021/ja00078a090
1690:10.1021/ma00034a012
1682:1992MaMol..25.2141R
1543:(39): 13735–13739.
1494:10.1021/ja00015a067
1431:Electrochimica Acta
1354:2001MaMol..34.7999M
1223:10.1021/ja00064a070
1180:Electrochimica Acta
1122:2016RSERv..57..550M
938:-butylthiophene)".
419:arsenic trifluoride
361:poly(vinyl alcohol)
41:Space-filling model
3178:Advanced Materials
3052:Advanced Materials
2479:10.1007/BFb0008700
2307:Advanced Materials
1836:Advanced Materials
883:
776:
702:
677:Soxhlet extraction
660:
645:
598:
442:
409:
325:
295:Conjugation length
212:
60:
58:(top-right inset).
45:
34:
22:
3398:978-3-540-65210-6
3364:10.1021/cr950257t
3029:10.1021/jo960982j
3023:(23): 8285–8292.
2830:10.1021/ma0348730
2758:Chemistry Express
2488:978-3-540-61857-7
2410:10.1021/ja1112595
2404:(12): 4625–4631.
2363:10.1021/ja039529x
2151:10.1021/ma981848z
1938:10.1021/ma960126+
1620:10.1021/ja034333i
1592:10.1021/jo981541y
1362:10.1021/ma002140z
1079:10.1021/cr9801014
1028:(12): 2053–2069.
953:10.1021/cm802168e
792:photographic film
429:3-Alkylthiophenes
268:mass spectrometry
121:applied potential
106:results from the
3448:
3426:Organic polymers
3402:
3375:
3352:Chemical Reviews
3346:
3331:Chemical Reviews
3325:
3301:Synthetic Metals
3253:
3252:
3242:
3232:
3223:(23): 18872–87.
3208:
3202:
3201:
3173:
3167:
3166:
3141:(6): 2101–2110.
3130:
3124:
3110:
3104:
3090:
3084:
3083:
3047:
3041:
3040:
3011:
3005:
3004:
2995:(1–3): 297–298.
2989:Synthetic Metals
2980:
2971:
2969:
2960:(7): 1559–1562.
2949:
2943:
2942:
2927:Synthetic Metals
2922:
2916:
2915:
2900:Synthetic Metals
2895:
2889:
2888:
2867:
2861:
2860:
2845:Synthetic Metals
2840:
2834:
2833:
2804:
2798:
2797:
2782:Synthetic Metals
2772:
2766:
2765:
2749:
2743:
2742:
2721:
2715:
2714:
2693:
2687:
2686:
2658:
2652:
2651:
2649:
2632:(9): 2869–2873.
2617:
2611:
2610:
2582:
2576:
2575:
2566:(1): 1465–1478.
2546:
2540:
2539:
2519:
2513:
2512:
2506:
2502:
2500:
2492:
2466:
2460:
2459:
2431:
2422:
2421:
2389:
2383:
2382:
2345:
2339:
2338:
2297:
2291:
2290:
2246:
2240:
2239:
2228:10.1039/b908001p
2222:(7): 2545–2576.
2211:
2202:
2201:
2186:Synthetic Metals
2180:
2174:
2173:
2161:
2155:
2154:
2126:
2120:
2119:
2102:
2096:
2095:
2075:
2069:
2068:
2040:
2034:
2033:
2013:
2007:
2006:
1974:
1963:
1948:
1942:
1941:
1913:
1907:
1906:
1877:
1868:
1867:
1831:
1816:
1815:
1795:
1789:
1788:
1771:(5): 1071–1078.
1760:
1754:
1753:
1733:
1724:
1723:
1703:
1694:
1693:
1665:
1659:
1658:
1649:(1–3): 167–170.
1643:Synthetic Metals
1638:
1632:
1631:
1602:
1596:
1595:
1575:
1569:
1568:
1531:
1525:
1524:
1504:
1498:
1497:
1473:
1467:
1453:
1447:
1446:
1426:
1420:
1419:
1404:Synthetic Metals
1399:
1393:
1392:
1377:Synthetic Metals
1372:
1366:
1365:
1329:
1323:
1322:
1307:Synthetic Metals
1298:
1292:
1291:
1271:
1265:
1264:
1255:(1–2): 479–484.
1249:Synthetic Metals
1244:
1235:
1234:
1205:
1196:
1195:
1175:
1169:
1168:
1153:Synthetic Metals
1148:
1142:
1141:
1105:
1099:
1098:
1067:Chemical Reviews
1062:
1056:
1055:
1045:
1017:
1011:
1010:
1001:(1–3): 213–218.
995:Synthetic Metals
990:
984:
983:
963:
957:
956:
930:
914:
903:
868:chiral molecules
817:air conditioning
747:
614:Steric hindrance
588:+ 2n H + 2n e
501:Thiophenes with
493:carboxylic acids
464:NMR spectroscopy
377:isosbestic point
280:gold trichloride
144:Hideki Shirakawa
3456:
3455:
3451:
3450:
3449:
3447:
3446:
3445:
3406:
3405:
3399:
3310:IBM J. Res. Dev
3261:
3259:Further reading
3256:
3209:
3205:
3174:
3170:
3131:
3127:
3111:
3107:
3091:
3087:
3048:
3044:
3012:
3008:
2986:
2981:
2974:
2950:
2946:
2923:
2919:
2896:
2892:
2868:
2864:
2841:
2837:
2805:
2801:
2779:
2773:
2769:
2750:
2746:
2722:
2718:
2694:
2690:
2659:
2655:
2618:
2614:
2583:
2579:
2547:
2543:
2520:
2516:
2504:
2503:
2494:
2493:
2489:
2467:
2463:
2432:
2425:
2390:
2386:
2346:
2342:
2304:
2298:
2294:
2257:(5072): 945–7.
2247:
2243:
2212:
2205:
2181:
2177:
2162:
2158:
2127:
2123:
2103:
2099:
2076:
2072:
2041:
2037:
2014:
2010:
1980:
1975:
1966:
1949:
1945:
1914:
1910:
1878:
1871:
1832:
1819:
1796:
1792:
1761:
1757:
1734:
1727:
1704:
1697:
1666:
1662:
1639:
1635:
1603:
1599:
1576:
1572:
1532:
1528:
1509:Acta Polymerica
1505:
1501:
1474:
1470:
1454:
1450:
1427:
1423:
1400:
1396:
1373:
1369:
1337:
1330:
1326:
1304:
1299:
1295:
1272:
1268:
1245:
1238:
1206:
1199:
1176:
1172:
1149:
1145:
1106:
1102:
1063:
1059:
1018:
1014:
991:
987:
964:
960:
931:
927:
923:
918:
917:
912:
908:
904:
900:
895:
850:, and chemical
804:
768:
736:is soluble in.
735:
665:
634:Kumada coupling
629:
587:
583:
579:
575:
571:
554:
549:
525:
485:
431:
414:
390:
388:Optical effects
297:
292:
257:ferric chloride
229:
198:
194:
190:
186:
182:
178:
174:
170:
166:
158:
152:
140:Alan MacDiarmid
90:
86:
82:
12:
11:
5:
3454:
3444:
3443:
3438:
3433:
3428:
3423:
3418:
3404:
3403:
3397:
3376:
3358:(1): 173–206.
3347:
3337:(4): 711–738.
3326:
3305:
3297:
3275:
3260:
3257:
3255:
3254:
3203:
3168:
3125:
3105:
3085:
3042:
3006:
2984:
2972:
2944:
2917:
2890:
2879:(4): 661–665.
2862:
2835:
2810:Macromolecules
2799:
2777:
2767:
2764:(11): 635–638.
2744:
2716:
2688:
2663:Macromolecules
2653:
2612:
2577:
2541:
2514:
2505:|journal=
2487:
2461:
2442:(7): 481–494.
2423:
2384:
2340:
2302:
2292:
2241:
2203:
2175:
2156:
2131:Macromolecules
2121:
2097:
2070:
2045:Macromolecules
2035:
2024:(1): 233–244.
2008:
1983:Macromolecules
1978:
1964:
1943:
1918:Macromolecules
1908:
1883:Macromolecules
1869:
1817:
1790:
1755:
1725:
1695:
1670:Macromolecules
1660:
1633:
1614:(18): 5286–7.
1597:
1570:
1526:
1515:(9): 379–384.
1499:
1468:
1448:
1421:
1394:
1367:
1342:Macromolecules
1335:
1324:
1302:
1293:
1282:(9): 917–924.
1266:
1236:
1197:
1170:
1143:
1100:
1073:(7): 2537–74.
1057:
1012:
985:
974:(1): 173–178.
958:
924:
922:
919:
916:
915:
910:
906:
897:
896:
894:
891:
887:prion diseases
813:electrochromic
803:
800:
767:
764:
733:
728:, acetone, or
664:
661:
628:
625:
621:radical cation
590:
589:
585:
581:
577:
573:
569:
553:
550:
548:
545:
524:
521:
484:
481:
460:
459:
456:
453:
446:microstructure
430:
427:
413:
410:
389:
386:
369:hydrogen bonds
314:aromatic rings
296:
293:
291:
288:
253:sulfonic acids
249:propionic acid
228:
225:
201:
200:
196:
192:
188:
184:
180:
176:
172:
168:
164:
156:
151:
148:
136:Alan J. Heeger
88:
84:
80:
63:Polythiophenes
9:
6:
4:
3:
2:
3453:
3442:
3439:
3437:
3434:
3432:
3429:
3427:
3424:
3422:
3419:
3417:
3414:
3413:
3411:
3400:
3394:
3390:
3386:
3382:
3377:
3373:
3369:
3365:
3361:
3357:
3353:
3348:
3344:
3340:
3336:
3332:
3327:
3323:
3319:
3315:
3311:
3306:
3303:
3302:
3298:
3296:
3295:0-387-61483-4
3292:
3288:
3287:3-540-61483-4
3284:
3280:
3276:
3274:
3273:0-8247-0050-3
3270:
3266:
3263:
3262:
3250:
3246:
3241:
3236:
3231:
3226:
3222:
3218:
3214:
3207:
3199:
3195:
3191:
3187:
3183:
3179:
3172:
3164:
3160:
3156:
3152:
3148:
3144:
3140:
3136:
3129:
3123:
3122:3-527-29438-4
3119:
3115:
3109:
3103:
3102:3-527-29438-4
3099:
3095:
3089:
3081:
3077:
3073:
3069:
3065:
3061:
3057:
3053:
3046:
3038:
3034:
3030:
3026:
3022:
3018:
3010:
3002:
2998:
2994:
2990:
2979:
2977:
2967:
2963:
2959:
2955:
2948:
2940:
2936:
2933:(2–3): 1204.
2932:
2928:
2921:
2913:
2909:
2905:
2901:
2894:
2886:
2882:
2878:
2874:
2866:
2858:
2854:
2850:
2846:
2839:
2831:
2827:
2823:
2819:
2815:
2811:
2803:
2795:
2791:
2787:
2783:
2771:
2763:
2759:
2755:
2748:
2740:
2736:
2733:(25): 10087.
2732:
2728:
2720:
2712:
2708:
2704:
2700:
2692:
2684:
2680:
2676:
2672:
2668:
2664:
2657:
2648:
2643:
2639:
2635:
2631:
2627:
2623:
2616:
2608:
2604:
2600:
2596:
2592:
2588:
2581:
2573:
2569:
2565:
2562:(in German).
2561:
2560:
2555:
2551:
2550:Meyer, Victor
2545:
2537:
2533:
2529:
2525:
2518:
2510:
2498:
2490:
2484:
2480:
2476:
2472:
2465:
2457:
2453:
2449:
2445:
2441:
2437:
2430:
2428:
2419:
2415:
2411:
2407:
2403:
2399:
2395:
2388:
2380:
2376:
2372:
2368:
2364:
2360:
2357:(6): 1596–7.
2356:
2352:
2344:
2336:
2332:
2328:
2324:
2320:
2316:
2312:
2308:
2296:
2288:
2284:
2280:
2276:
2272:
2268:
2264:
2260:
2256:
2252:
2245:
2237:
2233:
2229:
2225:
2221:
2217:
2210:
2208:
2199:
2195:
2191:
2187:
2179:
2171:
2167:
2166:Polym. Commun
2160:
2152:
2148:
2144:
2140:
2136:
2132:
2125:
2117:
2113:
2109:
2101:
2093:
2089:
2085:
2081:
2074:
2066:
2062:
2058:
2054:
2050:
2046:
2039:
2031:
2027:
2023:
2019:
2012:
2004:
2000:
1996:
1992:
1988:
1984:
1973:
1971:
1969:
1962:
1961:0-387-18582-8
1958:
1954:
1947:
1939:
1935:
1931:
1927:
1923:
1919:
1912:
1904:
1900:
1896:
1892:
1888:
1884:
1876:
1874:
1865:
1861:
1857:
1853:
1849:
1845:
1842:(2): 93–116.
1841:
1837:
1830:
1828:
1826:
1824:
1822:
1813:
1809:
1805:
1801:
1794:
1786:
1782:
1778:
1774:
1770:
1766:
1759:
1751:
1747:
1744:(25): 12214.
1743:
1739:
1732:
1730:
1721:
1717:
1713:
1709:
1702:
1700:
1691:
1687:
1683:
1679:
1675:
1671:
1664:
1656:
1652:
1648:
1644:
1637:
1629:
1625:
1621:
1617:
1613:
1609:
1601:
1593:
1589:
1585:
1581:
1574:
1566:
1562:
1558:
1554:
1550:
1546:
1542:
1538:
1530:
1522:
1518:
1514:
1510:
1503:
1495:
1491:
1487:
1483:
1479:
1472:
1466:
1465:3-527-29438-4
1462:
1458:
1452:
1444:
1440:
1436:
1432:
1425:
1417:
1413:
1409:
1405:
1398:
1390:
1386:
1382:
1378:
1371:
1363:
1359:
1355:
1351:
1347:
1343:
1339:
1328:
1320:
1316:
1312:
1308:
1297:
1289:
1285:
1281:
1277:
1270:
1262:
1258:
1254:
1250:
1243:
1241:
1232:
1228:
1224:
1220:
1216:
1212:
1204:
1202:
1193:
1189:
1185:
1181:
1174:
1166:
1162:
1158:
1154:
1147:
1139:
1135:
1131:
1127:
1123:
1119:
1115:
1111:
1104:
1096:
1092:
1088:
1084:
1080:
1076:
1072:
1068:
1061:
1053:
1049:
1044:
1043:10044/1/14442
1039:
1035:
1031:
1027:
1023:
1016:
1008:
1004:
1000:
996:
989:
981:
977:
973:
969:
962:
954:
950:
946:
943:
942:
937:
929:
925:
902:
898:
890:
888:
879:
875:
873:
869:
865:
860:
857:
853:
849:
845:
841:
837:
833:
829:
825:
820:
818:
814:
810:
799:
797:
793:
789:
785:
781:
772:
763:
760:
756:
751:
748:
746:
741:
739:
731:
727:
723:
722:diethyl ether
719:
715:
711:
707:
698:
694:
692:
687:
683:
678:
672:
670:
656:
652:
650:
641:
637:
635:
624:
622:
617:
615:
611:
605:
603:
594:
567:
566:
565:
563:
559:
544:
542:
541:photovoltaics
538:
534:
530:
520:
517:
515:
511:
506:
504:
499:
498:
494:
490:
480:
478:
473:
467:
465:
457:
454:
451:
450:
449:
447:
438:
434:
426:
424:
420:
405:
401:
399:
395:
385:
382:
381:thermochromic
378:
372:
370:
366:
362:
358:
353:
350:
345:
341:
336:
334:
330:
329:energy levels
321:
317:
315:
311:
307:
303:
287:
285:
281:
277:
273:
269:
266:
262:
258:
254:
250:
246:
242:
241:Organic acids
238:
234:
224:
222:
217:
208:
204:
162:
161:
160:
147:
145:
141:
137:
133:
128:
126:
122:
118:
114:
109:
105:
101:
96:
94:
78:
75:
71:
68:
64:
57:
56:boron nitride
53:
49:
42:
38:
31:
26:
18:
3380:
3355:
3351:
3334:
3330:
3316:(1): 51–57.
3313:
3309:
3300:
3278:
3264:
3220:
3216:
3206:
3181:
3177:
3171:
3138:
3134:
3128:
3113:
3108:
3093:
3088:
3055:
3051:
3045:
3020:
3016:
3009:
2992:
2988:
2957:
2953:
2947:
2930:
2926:
2920:
2906:(1): 91–95.
2903:
2899:
2893:
2876:
2872:
2865:
2848:
2844:
2838:
2816:(23): 8617.
2813:
2809:
2802:
2785:
2781:
2770:
2761:
2757:
2747:
2730:
2726:
2719:
2702:
2698:
2691:
2669:(13): 3462.
2666:
2662:
2656:
2629:
2625:
2615:
2590:
2586:
2580:
2563:
2557:
2544:
2530:(27): 6706.
2527:
2523:
2517:
2470:
2464:
2439:
2435:
2401:
2397:
2387:
2354:
2350:
2343:
2310:
2306:
2295:
2254:
2250:
2244:
2219:
2215:
2189:
2185:
2178:
2169:
2165:
2159:
2137:(12): 3964.
2134:
2130:
2124:
2110:(14): 1651.
2107:
2100:
2083:
2079:
2073:
2051:(17): 4457.
2048:
2044:
2038:
2021:
2017:
2011:
1989:(22): 6503.
1986:
1982:
1952:
1946:
1924:(16): 5416.
1921:
1917:
1911:
1889:(11): 3039.
1886:
1882:
1839:
1835:
1803:
1799:
1793:
1768:
1764:
1758:
1741:
1737:
1711:
1707:
1673:
1669:
1663:
1646:
1642:
1636:
1611:
1607:
1600:
1586:(24): 8632.
1583:
1579:
1573:
1540:
1536:
1529:
1512:
1508:
1502:
1488:(15): 5887.
1485:
1481:
1471:
1456:
1451:
1434:
1430:
1424:
1407:
1403:
1397:
1380:
1376:
1370:
1348:(23): 7999.
1345:
1341:
1327:
1310:
1306:
1296:
1279:
1275:
1269:
1252:
1248:
1217:(11): 4910.
1214:
1210:
1183:
1179:
1173:
1159:(1): 77–86.
1156:
1152:
1146:
1113:
1109:
1103:
1070:
1066:
1060:
1025:
1021:
1015:
998:
994:
988:
971:
967:
961:
947:(1): 78–87.
944:
941:Chem. Mater.
939:
935:
928:
901:
884:
861:
856:conductivity
821:
805:
777:
766:Applications
758:
752:
749:
742:
705:
703:
681:
673:
668:
666:
646:
630:
618:
606:
599:
555:
526:
518:
507:
500:
486:
477:Stokes shift
468:
461:
443:
432:
415:
391:
373:
354:
348:
343:
337:
326:
310:fluorescence
298:
276:acetonitrile
243:, including
230:
213:
202:
153:
129:
97:
62:
61:
30:fluorescence
3184:(11): 848.
3058:(11): 783.
2705:(4): 1445.
2593:(1): 9–12.
2086:(6): 1858.
1676:(8): 2141.
1116:: 550–561.
872:crown ether
832:solar cells
730:formic acid
558:electrolyte
394:alkali ions
340:red-shifted
333:side chains
263:, although
117:temperature
98:PTs become
77:heterocycle
67:polymerized
3421:Thiophenes
3410:Categories
2851:(3): 261.
2788:(2): 141.
2436:Adv. Mater
2313:(2): 180.
2192:(2): 107.
2172:: 546–548.
1806:(1): 2–9.
1437:(2): 273.
1383:(3): 341.
1313:(2): 449.
1186:(2): 463.
921:References
796:antistatic
774:PEDOT-PSS.
720:, and not
306:absorption
100:conductive
70:thiophenes
65:(PTs) are
3080:137731242
2507:ignored (
2497:cite book
1714:(2): 89.
1557:0002-7863
1410:(2): 93.
1138:101640805
1052:136757919
844:batteries
576:S → (C
547:Synthesis
497:urethanes
489:sulfonate
216:bipolaron
199:+ 1/5 nA
175:+ 1/5n PF
3431:Plastics
3372:11848868
3249:22493452
3163:12701566
3155:17235499
3037:11667817
2418:21375339
2379:33756974
2371:14871066
2335:97859155
2287:35348519
2279:17789638
2236:20567781
1628:12720435
1565:28872865
1231:15848137
1087:11749295
261:catalyst
227:Oxidants
3240:3365923
3186:Bibcode
3060:Bibcode
2954:Polymer
2873:Polymer
2818:Bibcode
2671:Bibcode
2634:Bibcode
2595:Bibcode
2444:Bibcode
2315:Bibcode
2259:Bibcode
2251:Science
2139:Bibcode
2053:Bibcode
1991:Bibcode
1926:Bibcode
1891:Bibcode
1864:7147581
1844:Bibcode
1773:Bibcode
1678:Bibcode
1350:Bibcode
1118:Bibcode
1095:4936796
934:Poly(3-
852:sensors
819:costs.
784:Heraeus
714:pentane
710:toluene
272:toluene
237:bromine
125:sensors
113:solvent
3395:
3370:
3293:
3285:
3271:
3247:
3237:
3161:
3153:
3120:
3100:
3078:
3035:
2485:
2416:
2377:
2369:
2333:
2285:
2277:
2234:
1959:
1862:
1626:
1563:
1555:
1463:
1229:
1136:
1093:
1085:
1050:
848:diodes
759:et al.
726:xylene
718:hexane
716:, and
706:et al.
682:et al.
669:et al.
503:chiral
349:et al.
344:et al.
251:, and
233:Iodine
221:copper
179:→ (C
142:, and
74:sulfur
3159:S2CID
3076:S2CID
2375:S2CID
2331:S2CID
2283:S2CID
1860:S2CID
1227:S2CID
1134:S2CID
1091:S2CID
1048:S2CID
893:Notes
562:anode
533:PEDOT
523:PEDOT
398:above
93:alkyl
3393:ISBN
3368:PMID
3291:ISBN
3283:ISBN
3269:ISBN
3245:PMID
3151:PMID
3118:ISBN
3098:ISBN
3033:PMID
2776:FeCl
2509:help
2483:ISBN
2414:PMID
2367:PMID
2275:PMID
2232:PMID
1957:ISBN
1624:PMID
1561:PMID
1553:ISSN
1461:ISBN
1083:PMID
788:AGFA
600:The
472:zinc
421:and
308:and
282:and
235:and
197:0.2n
72:, a
3385:doi
3360:doi
3339:doi
3318:doi
3235:PMC
3225:doi
3221:287
3194:doi
3143:doi
3139:387
3068:doi
3025:doi
2997:doi
2962:doi
2935:doi
2908:doi
2904:128
2881:doi
2853:doi
2849:114
2826:doi
2790:doi
2780:".
2735:doi
2731:114
2707:doi
2679:doi
2642:doi
2603:doi
2568:doi
2532:doi
2475:doi
2452:doi
2406:doi
2402:133
2359:doi
2355:126
2323:doi
2267:doi
2255:257
2224:doi
2194:doi
2147:doi
2112:doi
2088:doi
2084:109
2061:doi
2026:doi
2022:117
1999:doi
1981:".
1934:doi
1899:doi
1852:doi
1808:doi
1781:doi
1746:doi
1742:115
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