研究目的
To develop a novel, reliable, and scalable five-step synthesis of the Hagfeldt donor for dye-sensitized solar cells.
研究成果
A robust, scalable, and high-yielding synthetic route to the Hagfeldt donor is presented, circumventing the selectivity challenges of previous routes. The use of a masked halide group (TMS) allowed for the introduction of functionality at desired positions from the start of the synthesis. This route is reliable for accessing an important building block for dye-sensitized systems.
研究不足
The synthesis requires careful handling and interpretation of NMR spectra due to unusual behavior of intermediate compounds, particularly diarylamine 5, which shows poorly resolved signals when highly pure.
1：Experimental Design and Method Selection:
A five-step synthesis route was designed to avoid the selectivity challenges faced in previously reported routes. The key transformation involves the conversion of an aryl trimethylsilane (TMS) group into an aryl iodide.
2：Sample Selection and Data Sources:
The synthesis begins with the alkylation of 4-bromoresorcinol (1) with 1-bromo-2-ethylhexane on > 10 g scale.
3：List of Experimental Equipment and Materials:
Includes 4-bromoresorcinol, 1-bromo-2-ethylhexane, nBuLi, trimethoxyborate, bis(4-bromophenyl)amine, 1-bromo(4-trimethysilyl)benzene, iodine monochloride, and various solvents.
4：Experimental Procedures and Operational Workflow:
Detailed steps include alkylation, lithium–halogen exchange, Suzuki coupling, Buchwald–Hartwig reaction, and iodination.
5：Data Analysis Methods:
1H NMR spectroscopy was used to characterize the compounds, with variable temperature NMR and dilution experiments to resolve broad signals.
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