研究目的
To investigate the effect of alkyl chain length on the photochromic properties of diarylethene derivatives, specifically focusing on synthesis, photochromism, and fatigue resistance.
研究成果
The synthesis of diarylethene derivatives with varying alkyl chain lengths demonstrated that alkyl substituents significantly affect photochromic properties, including absorption maxima, molar absorption coefficients, quantum yields, and fatigue resistance. Longer alkyl chains generally decreased photoconversion ratios and absorption coefficients, with ethyl chains showing optimal cyclization quantum yields. These findings enhance understanding of structure-property relationships in photochromic materials and aid in designing tunable diarylethenes for optical applications.
研究不足
The study is limited to specific diarylethene derivatives with pyrrole and thiophene units; other heterocyclic moieties were not explored. The alkyl chain lengths tested were only up to butyl; longer chains may show different effects. Fatigue resistance degradation was observed, indicating potential side reactions and limited durability for practical applications.
1:Experimental Design and Method Selection:
The study involved synthesizing diarylethene derivatives with varying alkyl chain lengths and characterizing their photochromic properties using UV/Vis spectroscopy, HPLC, and X-ray crystallography. Theoretical models for photoisomerization were implied based on previous literature.
2:Sample Selection and Data Sources:
Four diarylethene compounds (1o-4o) were synthesized with methyl, ethyl, propyl, and butyl chains at the 2-position of thiophene rings. Samples were prepared in acetonitrile solution (2.0 × 10^-5 mol L^-1) and PMMA films (10% w/w).
3:0 × 10^-5 mol L^-1) and PMMA films (10% w/w). List of Experimental Equipment and Materials:
3. List of Experimental Equipment and Materials: Equipment included Bruker AV400 NMR spectrometer, Bruker AmaZon SL Ion Trap Mass spectrometer, Bruker Vertex-70 IR spectrometer, PE CHN 2400 analyzer, WRS-1B melting point apparatus, Agilent 8453 UV/Vis spectrophotometer, SHG-200 UV lamp, CX-21 ultraviolet fluorescence analysis cabinet, BMH-250 visible lamp, Agilent 1260 HPLC, and Bruker Smart-Apex II CCD diffractometer. Materials included chemical reagents like THF, n-BuLi, dichloromethane, Na2SO4, petroleum ether, ethyl acetate, p-toluenesulfonic acid, acetone, pyridine, diethyl ether, acetonitrile, and PMMA.
4:Experimental Procedures and Operational Workflow:
Synthesis involved lithiation and condensation reactions followed by acid-catalyzed dehydration. Photochromic properties were measured by irradiating samples with UV (297 nm) and visible light (λ > 500 nm), recording absorption spectra, and analyzing photoconversion ratios and quantum yields. Fatigue resistance was tested by repeated irradiation cycles. X-ray crystallography was performed for structural analysis.
5:Data Analysis Methods:
Data were analyzed using UV/Vis spectrophotometry for absorption coefficients and wavelengths, HPLC for photoconversion ratios, and crystallographic software (SHELXS-2014 and SHELXL-2014) for structural parameters. Quantum yields were determined using a reference compound.
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NMR Spectrometer
AV400
Bruker
Used for recording NMR spectra of synthesized compounds.
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Mass Spectrometer
AmaZon SL Ion Trap
Bruker
Used for recording mass spectra of the compounds.
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IR Spectrometer
Vertex-70
Bruker
Used for recording IR spectra of the compounds.
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Elemental Analyzer
CHN 2400
PE
Used for elemental analysis of the compounds.
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UV/Vis Spectrophotometer
8453
Agilent
Used for measuring absorption spectra of the compounds.
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HPLC System
1260
Agilent
Used for analyzing photoconversion ratios of the compounds.
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X-ray Diffractometer
Smart-Apex II CCD
Bruker
Used for X-ray crystallographic analysis of the compounds.
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Melting Point Apparatus
WRS-1B
Used for testing melting points of the compounds.
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UV Lamp
SHG-200
Used for photo-irradiation with UV light.
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Ultraviolet Fluorescence Analysis Cabinet
CX-21
Used for photo-irradiation.
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Visible Lamp
BMH-250
Used for photo-irradiation with visible light.
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