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The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption
The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption
- Source :
- ACS Sustainable Chemistry & Engineering, ACS Sustainable Chemistry & Engineering, American Chemical Society, 2016, 4 (6), pp.3504-3517. ⟨10.1021/acssuschemeng.6b00554⟩
- Publication Year :
- 2016
- Publisher :
- HAL CCSD, 2016.
-
Abstract
- International audience; Two π-conjugated thienoisoindigo-based organic small molecules have been designed to be synthetically accessible through sustainable direct heteroarylation or Sonogashira C–C bond forming cross-coupling reactions utilizing a heterogeneous palladium catalyst. To access these materials, one molecule, TII-ThNaph2, contains a thiophene π-bridge to facilitate direct heteroarylation protocols, whereas the other, TII-AcNaph2, contains an acetylene π-bridge required for Sonogashira couplings. The synthetic route to both final materials was optimized to investigate the reactivity of thienoisoindigo, which to this point has not been significantly explored in comparison to other popular organic dyes such as diketopyrrolopyrrole and isoindigo. Considering the reported interest of thienoisoindigo-based materials in organic solar cells and field-effect transistors, both final materials have been characterized for their optical, electrochemical and thermal properties offering a comparison of the structure–property relationships that manifest as a result of the two different π-bridging units.
- Subjects :
- Organic solar cell
General Chemical Engineering
Sonogashira coupling
chemistry.chemical_element
02 engineering and technology
Conjugated system
010402 general chemistry
Photochemistry
01 natural sciences
Coupling reaction
Heterogeneous catalyst
chemistry.chemical_compound
C−H Bond activation
Thiophene
Environmental Chemistry
Molecule
[CHIM]Chemical Sciences
Organic electronics
Renewable Energy, Sustainability and the Environment
General Chemistry
021001 nanoscience & nanotechnology
Thienoisoindigo
0104 chemical sciences
Direct heteroarylation
chemistry
near-ir absorption
Sustainable synthesis
0210 nano-technology
Palladium
Subjects
Details
- Language :
- English
- ISSN :
- 21680485
- Database :
- OpenAIRE
- Journal :
- ACS Sustainable Chemistry & Engineering, ACS Sustainable Chemistry & Engineering, American Chemical Society, 2016, 4 (6), pp.3504-3517. ⟨10.1021/acssuschemeng.6b00554⟩
- Accession number :
- edsair.doi.dedup.....47ceb92ed8a6b2dc74e7ec083f2709bc
- Full Text :
- https://doi.org/10.1021/acssuschemeng.6b00554⟩