研究目的
To synthesize and characterize dipolar thiazole derivatives with nitro and amino substituents to study their optical properties, particularly for nonlinear optics (NLO) applications.
研究成果
Compound 2, with its red-shifted UV-vis absorption and good thermal stability, shows high potential as an organic NLO material due to effective π-conjugation from its specific substituent arrangement.
研究不足
The study is limited to two specific compounds; broader applicability and performance in actual NLO devices were not tested. Synthesis yields were moderate (33% for compound 1, 60% for compound 2), and thermal stability varied between compounds.
1:Experimental Design and Method Selection:
The study involved synthesizing two thiazole derivatives using nucleophilic substitution and Sonogashira coupling-aminovinylation methods, followed by characterization using various spectroscopic and thermal analysis techniques to evaluate optical and thermal properties.
2:Sample Selection and Data Sources:
Compounds were synthesized from purchased chemicals; samples were prepared in acetonitrile for UV-vis analysis and in deuterated CDCl3 for NMR.
3:List of Experimental Equipment and Materials:
Equipment includes Agilent Technologies Cary 630 FTIR, Shimadzu UV-vis 1601 spectrophotometer, Delta JEOL USA NMR spectrometer, STA 8000 thermal analyzer, Agilent 6520 Accurate-Mass Q-TOF LCMS. Materials include 2-bromo-5-nitrothiazole, triethylamine, diethylamine, 2-bromo-4-nitroacetophenone, phenylacetylene, copper(I) iodide, bis(triphenylphosphine)palladium(II) dichloride, ammonium thiocyanate, p-toluidine, acetone, THF, methanol, dichloromethane, acetonitrile, CDCl
4:Experimental Procedures and Operational Workflow:
Synthesis of compound 1 involved refluxing ammonium thiocyanate and 2-bromo-4-nitroacetophenone in acetone, followed by addition of p-toluidine, precipitation, and purification. Synthesis of compound 2 involved Sonogashira coupling of phenylacetylene with 2-bromo-5-nitrothiazole using catalysts, followed by addition of diethylamine, reflux, evaporation, and chromatography. Characterization included IR, UV-vis, NMR, thermal analysis, and mass spectrometry.
5:Data Analysis Methods:
Data were analyzed using standard spectroscopic and thermal analysis techniques; chemical shifts and absorption wavelengths were interpreted, and thermal stability was assessed based on decomposition temperatures.
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FTIR Spectrometer
Cary 630
Agilent Technologies
Recorded IR spectra of synthesized compounds
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UV-vis Spectrophotometer
UV-1601
Shimadzu
Collected UV-vis spectra in wavelength range of 200-700 nm
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NMR Spectrometer
Delta
JEOL USA
Obtained 1H and 13C NMR spectra
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LCMS
6520 Accurate-Mass Q-TOF
Agilent
Analyzed samples with dual electrospray ionization
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Thermal Analyzer
STA 8000
Not specified in paper
Characterized thermal stability with temperature range from 40°C to 1000°C
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TLC Plates
Silica Gel 60 f254
Merck
Used for thin-layer chromatography to monitor reactions
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Aluminium Oxide
90 active basic
Not specified in paper
Used for chromatography purification
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