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

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

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 1 H 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