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Suzuki Coupling:

Suzuki Coupling:. Aqueous and Anhydrous Synthesis of Ferrocene-Capped Thiophene. Bill Mitchell 2003-04. Introduction. Polythiophene p-type semiconducting organic polymer Tuneable electronic properties . Polythiophene. Introduction. Applications Photovoltaics (solar cells) Cheaper

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Suzuki Coupling:

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  1. Suzuki Coupling: Aqueous and Anhydrous Synthesis of Ferrocene-Capped Thiophene Bill Mitchell 2003-04

  2. Introduction • Polythiophene • p-type semiconducting organic polymer • Tuneable electronic properties Polythiophene

  3. Introduction • Applications • Photovoltaics (solar cells) • Cheaper • Higher voltage • Activated by visible light • Tuning will improve efficiency • Transistors, light emitting diodes • Cheaper • More efficient • Smaller

  4. Introduction • Problem • No cyclic voltammetry • Polymerization • Ferrocene • End-cap for thiophene • Electrochemically active Ferrocene

  5. Introduction • Short chain vs. long chain • Solubility • Yield • Accuracy n= 1, 2, 3 Short chain n= 3, 4 Long chain

  6. Procedure 1:Aqueous 2,5-Diferrocenyl-Thiophene • Suzuki Coupling • Aqueous • Highly contaminated • Low yield

  7. Side Reaction

  8. Anhydrous Coupling Organic soluble • Boronic ester • Less contamination • Higher yield 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-ferrocene

  9. Procedure 2:1-(4,4,5,5-Tetramethyl-1,3,2-Dioxabolan-2-yl)-Ferrocene(Boronic Ester)

  10. Procedure 3:Anhydrous 2,5-Diferrocenyl-Thiophene In dioxane Reflux 96-120 hr.

  11. Results

  12. Results:Aqueous 2,5-Diferrocenyl-Thiophene 1H NMR spectrum 250 MHz

  13. Conclusion • Synthesize Ferrocene-Capped Thiophene • Aqueous method • Chromatography eluent less polar • 50:50 hexane:dichloromethane • 70:30 hexane:dichloromethane

  14. Further Research • Make Derivatives • Electron donating and withdrawing • Electrochemical characterization • Variable temperature

  15. Applications • Photovoltaics • Transistors

  16. Suzuki Coupling: Aqueous and Anhydrous Synthesis of Ferrocene-Capped Thiophene Bill Mitchell 2003-04

  17. Chemical Shift

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