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Efficient synthesis of 2,5-dicarbonyl derivatives of 3,4-ethylenedithiothiophene (EDTT) via addition-elimination reaction
- Source :
- Tetrahedron. 73:5847-5852
- Publication Year :
- 2017
- Publisher :
- Elsevier BV, 2017.
-
Abstract
- Derivatives of 3,4-ethylenedithiothiophene (EDTT) are reported starting from tetrabromothiophene. Selective 2,5-dilithiation followed by reaction with a range of aldehydes gives diols as mixtures of diastereomers. Only the 2 and 5 positions in thiophene react leaving the 3,4-bromides for further elaboration. The diols are oxidised to their corresponding diketones using activated MnO2. Reaction with 1,2-ethanedithiol, by addition-elimination, provides access to novel monomers for the preparation of conjugated copolymers of 3,4-ethylenedithiothiophene (EDTT). A range of these monomers can be attained by applying the synthesis of a series of ketones applicable to further synthesis of ?-extended thiophene-based organic semiconductors. Finally, this new route was compared to 3,4-ethylenedioxythiophene (EDOT) dialdehyde derivatives synthesised by an alternative to literature chemistry.
- Subjects :
- Addition elimination
Organic Chemistry
Diastereomer
02 engineering and technology
Conjugated system
010402 general chemistry
021001 nanoscience & nanotechnology
01 natural sciences
Biochemistry
0104 chemical sciences
Organic semiconductor
chemistry.chemical_compound
Monomer
chemistry
Addition-elimination reaction
3,4-Ethylenedithiothiophene
Organic semiconductors
Drug Discovery
Thiophene
Copolymer
Organic chemistry
1,2-Ethanedithiol
EDTT
0210 nano-technology
Subjects
Details
- ISSN :
- 00404020
- Volume :
- 73
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi.dedup.....90cb8d639bceed916634001d82e31eb1