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One-pot three-component synthesis and photophysical properties of highly fluorescent novel 4-alkyl-3-aryl-2,6-dicyanoanilines by using tris(hydroxymethyl)aminomethane as a catalyst
摘要： Novel 4-alkyl-3-aryl-2,6-dicyanoanilines were synthesized by a multi-component one-step reaction of aromatic aldehyde, malononitrile and aliphatic aldehyde using tris(hydroxymethyl)aminomethane (THAM) as a catalyst under microwave (MW) irradiation or conventional heating. The optimized reaction condition involved use of 2.5 equivalents of THAM under MW irradiation at 140 W using 20 % MW power for 5 min or conventional heating at 80 °C for 8 h in dimethylformamide. The photophysical properties including λmax, quantum yield and Stokes’ shifts of newly synthesized molecules were studied. All compounds exhibited quantum yield in the range of 0.04 to 0.52 with respect to standard quinine sulphate having quantum yield 0.54. The Stokes’ shifts of all compounds were found in the range of 41-105 nm. The current strategy provides operationally simple protocol using THAM as a catalyst to synthesize 4-alkyl-3-aryl-2,6-dicyanoanilines with diverse structural features to make them available for exploration of their photophysical as well as biological applications.
关键词： Fluorescent,Quantum Yield,Tris(hydroxymethyl)aminomethane,Microwave,Malononitrile,Dicyanoanilnes
更新于2025-09-23 15:23:52
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Thermal, spectroscopic, electrochemical, and electroluminescent characterization of malononitrile derivatives with triphenylamine structure
摘要： Three push-pull molecules with linear, quadrupolar and tripodal arrangements, consisting of triphenylamine (electro-donor) substituted with malononitrile groups (electro-acceptor), were synthesized with high yield by a simple procedure. Impact of the number of malononitrile substituents on optoelectronic properties was investigated with cyclic voltammetry, absorption and emission spectroscopy, as well as density functional theory calculation. The derivatives formed amorphous materials and exhibited low energy band gaps ranging from 2.06 to 2.49 eV. UV–Vis absorption and photoluminescence emission spectra were investigated in solutions (CHCl3, NMP) and in solid-state as thin films and two kinds of blends (with PMMA and PVK:PBD). Quantum yield of photoluminescence was dependent on the molecule structure, solvent, and solid-state layer formulation. The compounds exhibited high photoluminescence quantum yield in the range of 15–42% and 12–59% in solid-state as film and blend with PMMA (1 wt%), respectively, being promising for applications in light emitting diodes. The diodes with active layer consisting of neat derivatives and compounds molecularly dispersed in PVK:PBD (50:50 wt%) matrix showed orange and green electroluminescence.
关键词： Triphenylamine,Photoluminescence,Electrochemistry,Malononitrile,Electroluminescence
更新于2025-09-23 15:21:21