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759791

Sigma-Aldrich

2,5-Dibromo-3,4-ethylenedioxythiophene

97%

Synonym(s):

5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine

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About This Item

Empirical Formula (Hill Notation):
C6H4Br2O2S
CAS Number:
Molecular Weight:
299.97
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

assay

97%

form

solid

mp

95-100 °C

storage temp.

−20°C

SMILES string

Brc1sc(Br)c2OCCOc12

InChI

1S/C6H4Br2O2S/c7-5-3-4(6(8)11-5)10-2-1-9-3/h1-2H2

InChI key

FHMRWRBNAIDRAP-UHFFFAOYSA-N

General description

2,5-Dibromo-3,4-ethylenedioxythiophene (DBEDOT) is a monomer which is used in the synthesis of highly conducting poly(3,4-ethylenedioxythiophene) (PEDOT) polymer. This polymer is formed by solid-state polymerisation of DBEDOT and is used widely in organic-light emitting diodes and polymer field effect transistors. DBEDOT is a well-ordered crystalline monomer and produces PEDOT polymer which has a high degree of order. [1]

Application

Used as a monomer in the synthesis of poly(3,4-ethylenedioxythiophene) (PEDOT) polymer which are used in electrochromic devices.[2]

Features and Benefits

Polymerisation of DBEDOT can take place under very gentle conditions in the absence of external agents or catalysts.[1]

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Synthesis and characterization of thiophene functionalized polystyrene copolymers and their electrochemical properties
Sahin, E., Camurlu, P., Toppare, L., Mercore, V. M., Cianga, I., & Yagci, Y.
Polymer International, 54(12), 1599-1605 (2005)
Hong Meng et al.
Journal of the American Chemical Society, 125(49), 15151-15162 (2003-12-05)
Prolonged storage ( approximately 2 years) or gentle heating (50-80 degrees C) of crystalline 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) affords a highly conducting, bromine-doped poly(3,4-ethylenedioxythiophene) (PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR spectroscopies. The novel solid-state polymerization (SSP) does not
Minami Kato et al.
ChemSusChem, 13(9), 2379-2385 (2020-02-11)
Many types of batteries have been proposed as next-generation energy-storage systems. One candidate is a rocking-chair-type "molecular ion battery" in which a molecular ion, instead of Li+ , works as a charge carrier. Previously, we reported a viologen-type derivative as

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