Glycerol as Reaction Medium for Sonogashira Couplings: A Green Approach for the Synthesis of New Triarylamine-Based Materials with Potential Application in Optoelectronics.
Chemistry
; : e202402901, 2024 Aug 22.
Article
em En
| MEDLINE
| ID: mdl-39172104
ABSTRACT
This study focuses on the design, eco-friendly synthesis, and characterization of several novel three-legged triphenylamine derivatives. By performing Sonogashira couplings of functionalized aryl iodides with tris(4-ethynylphenyl)amine in glycerol, a readily available bio-derived solvent, we achieved the synthesis of target products in short times and high yields, up to 94%, with consistently lower E-factors and reduced costs compared to standard conditions using toluene as the reaction medium. The target molecules possess a D-(π-A)3 or D-(π-D)3 structure, where an electron-donating core connects to three electron-donating (D) or electron-accepting (A) peripheral aromatic subunits through an acetylene spacer. Their main optical and electronic properties have been determined experimentally and by DFT simulations and suggest a possible implementation in energy conversion technologies such as luminescent solar concentrators (LSCs) and perovskite solar cells (PSCs).
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Chemistry
Ano de publicação:
2024
Tipo de documento:
Article