3,4-Ethylenedioxythiophene

Source: Wikipedia, the free encyclopedia.
3,4-Ethylenedioxythiophene
Names
Preferred IUPAC name
2,3-Dihydrothieno[3,4-b][1,4]dioxine
Identifiers
3D model (
JSmol
)
7126466
ChemSpider
ECHA InfoCard
 100.122.178 Edit this at Wikidata
EC Number
  • 603-128-0
UNII
  • InChI=1S/C6H6O2S/c1-2-8-6-4-9-3-5(6)7-1/h3-4H,1-2H2
    Key: GKWLILHTTGWKLQ-UHFFFAOYSA-N
  • C1COC2=CSC=C2O1
Properties
C6H6O2S
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]
2.1 g/L[1]
Viscosity 11 mPa·s[1]
Hazards
GHS labelling:[2]
GHS06: ToxicGHS07: Exclamation mark
Danger
H302, H311, H312, H319, H412
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]
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).

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]

EDOT is the precursor to the polymer

photovoltaics, electroluminescent displays, printed wiring, and sensors.[4][5]

Synthesis and polymerization

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

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

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

  1. ^
    ISBN 978-1-4200-6912-9
    .
  2. ^ "2,3-Dihydrothieno[3,4-b][1,4]dioxine". pubchem.ncbi.nlm.nih.gov.
  3. doi:10.1016/0379-6779(91)91506-6
    .
  4. doi:10.1002/(SICI)1521-4095(200004)12:7<481::AID-ADMA481>3.0.CO;2-C
    .
  5. ^
    doi:10.1039/b417803n
    .
  6. doi:10.3987/COM-13-S(S)8 (inactive 2024-02-17).{{cite journal}}: CS1 maint: DOI inactive as of February 2024 (link
    )
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