3,4-Ethylenedioxythiophene (EDOT) is an organosulfur compound with the formula C2H4O2C4H2S. The molecule consists of thiophene, substituted at the 3 and 4 positions with an ethylene glycolyl unit. It is a colorless viscous liquid.[3]
The original synthesis proceeded via the diester of 3,4-dihydroxythiophene-2,5-dicarboxylate.
One synthesis of EDOT
EDOT is often prepared from C4 precursors such as butanediol and butadiene via routes that produce the thiophene and dioxane rings in separate steps. Representative is the reaction of 2,3-butanedione, trimethyl orthoformate, and ethylene glycol to form the dioxane. Sulfidization with elemental sulfur gives the bicyclic target.[6]
EDOT is converted into the conducting polymerPEDOT by oxidation. The mechanism for this conversion begins with production of the radical cation [EDOT]+, which attacks a neutral EDOT molecule followed by deprotonation. Further similar steps result in the dehydropolymerization. The idealized conversion using peroxydisulfate is shown
n C2H4O2C4H2S + n (OSO3)22− → [C2H4O2C4S]n + 2n HOSO3−
For commercial purposes, the polymerization is conducted in the presence of polystyrenesulfonate.[5]
Referencesedit
^ abcdefgElschner, Andreas; Kirchmeyer, Stephan; Lovenich, Wilfried (2010). PEDOT: Principles and Applications of an Intrinsically Conductive Polymer. CRC Press. p. 51. ISBN978-1-4200-6912-9.
^Jonas, F.; Schrader, L. (1991). "Conductive Modifications of Polymers with Polypyrroles and Polythiophenes". Synthetic Metals. 41 (3): 831–836. doi:10.1016/0379-6779(91)91506-6.
^Groenendaal, L. B.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J. R. (2000). "Poly(3,4-Ethylenedioxythiophene) and Its Derivatives: Past, Present, and Future". Adv. Mater. 12 (7): 481–494. doi:10.1002/(SICI)1521-4095(200004)12:7<481::AID-ADMA481>3.0.CO;2-C.
^ abKirchmeyer, S.; Reuter, K. (2005). "Scientific Importance, Properties and Growing Applications of Poly(3,4-Ethylenedioxythiophene)". J. Mater. Chem. 15 (21): 2077–2088. doi:10.1039/b417803n.
^Hachiya, I.; Yamamoto, T.; Inagaki, T.; et al. (2014). "Two-Step Synthesis of 3,4-Ethylenedioxythiophene (EDOT) from 2,3-Butanedione". Heterocycles. 88: 607–612. doi:10.3987/COM-13-S(S)8 (inactive 2024-02-17).{{cite journal}}: CS1 maint: DOI inactive as of February 2024 (link)
January 01, 1970
ethylenedioxythiophene, edot, organosulfur, compound, with, formula, c2h4o2c4h2s, molecule, consists, thiophene, substituted, positions, with, ethylene, glycolyl, unit, colorless, viscous, liquid, names, preferred, iupac, name, dihydrothieno, dioxine, identifi. 3 4 Ethylenedioxythiophene EDOT is an organosulfur compound with the formula C2H4O2C4H2S The molecule consists of thiophene substituted at the 3 and 4 positions with an ethylene glycolyl unit It is a colorless viscous liquid 3 3 4 Ethylenedioxythiophene Names Preferred IUPAC name 2 3 Dihydrothieno 3 4 b 1 4 dioxine Identifiers CAS Number 126213 50 1 3D model JSmol Interactive image Beilstein Reference 7126466 ChemSpider 3622202 ECHA InfoCard 100 122 178 EC Number 603 128 0 PubChem CID 4421864 UNII 8SEC7Q2K7G Y CompTox Dashboard EPA DTXSID301047399 DTXSID40888925 DTXSID301047399 InChI InChI 1S C6H6O2S c1 2 8 6 4 9 3 5 6 7 1 h3 4H 1 2H2Key GKWLILHTTGWKLQ UHFFFAOYSA N SMILES C1COC2 CSC C2O1 Properties Chemical formula C 6H 6O 2S Molar mass 142 17 g mol 1 Appearance colorless liquid Density 1 34 g cm3 1 Melting point 10 5 C 50 9 F 283 6 K 1 Boiling point 225 C 437 F 498 K 1 Solubility in water 2 1 g L 1 Viscosity 11 mPa s 1 Hazards GHS labelling 2 Pictograms Signal word Danger Hazard statements H302 H311 H312 H319 H412 Precautionary statements P262 P264 P264 P265 P270 P273 P280 P301 P317 P302 P352 P305 P351 P338 P316 P317 P321 P330 P337 P317 P361 P364 P362 P364 P405 P501 Flash point 104 C 219 F 377 K 1 Autoignitiontemperature 360 C 680 F 633 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references EDOT is the precursor to the polymer PEDOT which is found in electrochromic displays photovoltaics electroluminescent displays printed wiring and sensors 4 5 Synthesis and polymerization editThe original synthesis proceeded via the diester of 3 4 dihydroxythiophene 2 5 dicarboxylate nbsp One synthesis of EDOT EDOT is often prepared from C4 precursors such as butanediol and butadiene via routes that produce the thiophene and dioxane rings in separate steps Representative is the reaction of 2 3 butanedione trimethyl orthoformate and ethylene glycol to form the dioxane Sulfidization with elemental sulfur gives the bicyclic target 6 EDOT is converted into the conducting polymer PEDOT by oxidation The mechanism for this conversion begins with production of the radical cation EDOT which attacks a neutral EDOT molecule followed by deprotonation Further similar steps result in the dehydropolymerization The idealized conversion using peroxydisulfate is shown n C2H4O2C4H2S n OSO3 22 C2H4O2C4S n 2n HOSO3 For commercial purposes the polymerization is conducted in the presence of polystyrenesulfonate 5 References edit a b c d e f g Elschner Andreas Kirchmeyer Stephan Lovenich Wilfried 2010 PEDOT Principles and Applications of an Intrinsically Conductive Polymer CRC Press p 51 ISBN 978 1 4200 6912 9 2 3 Dihydrothieno 3 4 b 1 4 dioxine pubchem ncbi nlm nih gov Jonas F Schrader L 1991 Conductive Modifications of Polymers with Polypyrroles and Polythiophenes Synthetic Metals 41 3 831 836 doi 10 1016 0379 6779 91 91506 6 Groenendaal L B Jonas F Freitag D Pielartzik H Reynolds J R 2000 Poly 3 4 Ethylenedioxythiophene and Its Derivatives Past Present and Future Adv Mater 12 7 481 494 doi 10 1002 SICI 1521 4095 200004 12 7 lt 481 AID ADMA481 gt 3 0 CO 2 C a b Kirchmeyer S Reuter K 2005 Scientific Importance Properties and Growing Applications of Poly 3 4 Ethylenedioxythiophene J Mater Chem 15 21 2077 2088 doi 10 1039 b417803n Hachiya I Yamamoto T Inagaki T et al 2014 Two Step Synthesis of 3 4 Ethylenedioxythiophene EDOT from 2 3 Butanedione Heterocycles 88 607 612 doi 10 3987 COM 13 S S 8 inactive 2024 02 17 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint DOI inactive as of February 2024 link Retrieved from https en wikipedia org w index php title 3 4 Ethylenedioxythiophene amp oldid 1214820016, wikipedia, wiki, book, books, library,
