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Suzuki Coupling: Aqueous and Anhydrous Synthesis of Ferrocene-Capped Thiophene Bill Mitchell 2003-04
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Polythiophene Introduction Polythiophene –p-type semiconducting organic polymer –Tuneable electronic properties
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Introduction Applications –Photovoltaics (solar cells) Cheaper Higher voltage Activated by visible light Tuning will improve efficiency –Transistors, light emitting diodes Cheaper More efficient Smaller
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Introduction Problem –No cyclic voltammetry Polymerization Ferrocene –End-cap for thiophene –Electrochemically active Ferrocene
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Introduction Short chain vs. long chain –Solubility –Yield –Accuracy n= 1, 2, 3 Short chain n= 3, 4 Long chain
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Procedure 1: Aqueous 2,5-Diferrocenyl-Thiophene Suzuki Coupling –Aqueous Highly contaminated Low yield
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Side Reaction
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Anhydrous Coupling Organic soluble –Boronic ester –Less contamination –Higher yield 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-ferrocene
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Procedure 2: 1-(4,4,5,5-Tetramethyl-1,3,2-Dioxabolan-2-yl)-Ferrocene (Boronic Ester)
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Procedure 3: Anhydrous 2,5-Diferrocenyl- Thiophene In dioxane Reflux 96-120 hr.
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Results
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Results: Aqueous 2,5-Diferrocenyl-Thiophene 1 H NMR spectrum 250 MHz
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Conclusion Synthesize Ferrocene-Capped Thiophene –Aqueous method –Chromatography eluent less polar 50:50 hexane:dichloromethane 70:30 hexane:dichloromethane
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Further Research Make Derivatives –Electron donating and withdrawing –Electrochemical characterization Variable temperature
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Applications Photovoltaics Transistors
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Suzuki Coupling: Aqueous and Anhydrous Synthesis of Ferrocene-Capped Thiophene Bill Mitchell 2003-04
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Chemical Shift
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