研究目的
To synthesize novel 4-alkyl-3-aryl-2,6-dicyanoanilines using tris(hydroxymethyl)aminomethane (THAM) as a catalyst under microwave irradiation or conventional heating and study their photophysical properties.
研究成果
The study successfully developed a one-pot synthesis method for novel 4-alkyl-3-aryl-2,6-dicyanoanilines using THAM catalyst under microwave or conventional heating. The compounds exhibited good quantum yields (up to 0.52) and Stokes' shifts (41-105 nm), with potential applications in biological imaging and photophysics. Future work will focus on exploring these applications further.
研究不足
The reaction yields were moderate (45-66%), and some byproducts were formed, requiring purification. The quantum yield of one compound with a nitro group was low (0.04), indicating sensitivity to electron-withdrawing substituents. The methods may not be scalable or applicable to all aldehydes without optimization.
1：Experimental Design and Method Selection:
The study involved a multi-component one-step reaction using THAM as a catalyst under microwave irradiation or conventional heating to synthesize 4-alkyl-3-aryl-2,6-dicyanoanilines. The optimized conditions were determined through systematic variation of catalyst equivalents, power, time, and temperature.
2：Sample Selection and Data Sources:
Aromatic aldehydes (e.g., 1-pyrenecarbaldehyde, 4-biphenylcarbaldehyde) and aliphatic aldehydes (nonanal, hexanal) were procured from Sigma-Aldrich, and malononitrile, THAM, and solvents from Spectrochem. Samples were synthesized and characterized.
3：List of Experimental Equipment and Materials:
Microwave oven (Raga’s scientific), TLC plates (Merck HPTLC silica gel 60 F254), NMR spectrometer (Bruker-AV 200 MHz), FT-IR spectrophotometer (Thermo Fisher in ATR mode), HR-MS instrument (Thermo Scientific Q-Exactive), UV-Vis spectrophotometer (Analytik Jena Specord Plus), spectrofluorometer (JASCO FP-8300). Materials included dimethylformamide, ethyl acetate, petroleum ether, silica gel for column chromatography.
4：0). Materials included dimethylformamide, ethyl acetate, petroleum ether, silica gel for column chromatography.
Experimental Procedures and Operational Workflow:
4. Experimental Procedures and Operational Workflow: For microwave method, a mixture of reactants and catalyst in DMF was irradiated at specified power and time, then extracted and purified. For conventional heating, the mixture was heated at 80°C for 8 hours, then processed similarly. Products were characterized using NMR, IR, HR-MS, and photophysical measurements.
5：Data Analysis Methods:
Quantum yields were calculated using a standard equation with quinine sulphate as reference. Spectral data were analyzed for absorption and emission maxima, Stokes' shifts, and quantum yields.
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