Thiophene → 3,4-Ethylenedioxythiophene

HRID 1179518Notes

Reaction equation

HRID 1179518 reaction equation
[CH2:1]1[CH2:9][O:8][C:7]2[CH:6]=[CH:5][S:4][C:3]=2[O:2]1.S1C=CC=C1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>C(O)CCCC.O>[CH2:9]1[O:8][C:7]2[C:6](=[CH:5][S:4][CH:3]=2)[O:2][CH2:1]1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 62655Sodium PersulfateHCID 21871601HCID 21871601, compound2×

Product 1

HCID 44218643,4-Ethylenedioxythiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 62761-PentanolSolvent2×

Conditions

Temperature
80 °C

Procedure

Block copolymers of EDOT with poly(propylene glycol), Poly(EDOT-block-PG), were synthesized from EDOT and a low molecular weight poly(propylene glycol) (PPG) oligomer following a two-step method in Example 1. PPG (MW=1500) was reacted with 2-thiophene carbonyl chloride in the presence of pyridine to form a di-thiophene derivative macromonomer PPGdTh. This macromonomer was then copolymerized with ethylenedioxythiophene (EDOT) in the presence of an oxidizing agent and a suitable counterion. This second step was preferably conducted in diffusion-controlled conditions to avoid the homopolymerization of thiophene; for example, a solution of the PPGdTh (2×10−1 M) in 1-pentanol was mixed with a solution of sodium persulfate (2×10−1 M) and poly(para-styrenesulfonate) in water. To this mixture a diluted solution of EDOT in 1-pentanol (10−2 M) was added dropwise under strong stirring at 80° C. The product was filtered to eliminate the homopolymer and then extracted with water to eliminate unreacted monomer and byproducts.

Workup

  1. filtrationThe product was filtered
  2. extractionextracted with water

Sources & evidence

ORD record
ord-13fc1db030b9433697b242e2195fcd90
Source dataset
uspto-grants-2007_10
Patent number
US07279534B2

Reaction notes

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