研究目的
To synthesize a series of new 1,2,3-triazole-coumarin hybrid derivatives using a green click chemistry approach and to investigate the effect of substituents at the para position through DFT computational studies.
研究成果
The research successfully developed a green, one-pot synthesis method for coumarin-based triazoles with good yields. DFT studies revealed that electron-withdrawing and electron-donating groups at the para position affect orbital distributions and excitation energies. The method is simple, efficient, and applicable to a wide range of aryl alkynes, offering potential for further development in drug discovery and materials science.
研究不足
The study is limited to the synthesis and computational analysis of specific coumarin-triazole hybrids; biological or material applications are not explored. The green synthesis approach may have constraints in scalability or with certain substituents, as yields vary (63-92%). DFT calculations are theoretical and may not fully capture experimental nuances.
1：Experimental Design and Method Selection:
The study employs a green synthesis approach using copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction. The methodology includes optimization of reaction conditions (catalyst, solvent, temperature, time) and DFT calculations for theoretical support.
2：Sample Selection and Data Sources:
Starting materials include 3-azidocoumarin and various aromatic terminal alkyne derivatives (12 examples). Samples are selected based on the presence of electron-rich and electron-deficient substituents.
3：List of Experimental Equipment and Materials:
Equipment includes Kofler hot stage apparatus for melting points, Bruker FT-500 NMR spectrometer, Nicolet Magna FTIR 550 spectrophotometer, Agilent Technology mass spectrometer, Varian Cary 100 UV-VIS spectrophotometer, and Elemental Analysen system GmbH VarioEL CHNS mode for elemental analysis. Materials include chemicals from Merck and Aldrich, CuSO4·5H2O, sodium ascorbate, solvents like DMF, t-BuOH, water, etc.
4：Experimental Procedures and Operational Workflow:
Synthesis involves preparation of terminal alkyne derivatives from hydroxy-substituted benzaldehydes, benzonitrile, and acetophenone with propargyl bromide using K2CO3 in DMF. Click reaction is performed with 3-azidocoumarin, alkynes, CuSO4·5H2O/NaAsc in water at 50°C, monitored by TLC. Products are filtered, washed, and purified if necessary. Characterization is done using IR, NMR, UV-VIS, mass spectrometry, and elemental analysis. DFT calculations are performed using Gaussian 09 with B3LYP/6-31G(d) basis set.
5：Data Analysis Methods:
Data from spectroscopy and spectrometry are analyzed for structural confirmation. DFT calculations are used to predict spectroscopic properties, HOMO-LUMO gaps, and electron density distributions.
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