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Optimizing Supramolecular Self-Assembly of Oxadiazole Derivatives

This research project, conducted by Matthew B. Weiss in 2006 at Macalester College, focuses on synthesizing and purifying oxadiazole molecules with high yields. The study involves self-assembling these molecules into macromolecular structures, highlighting successful synthesis and purification techniques. Challenges faced include low yields and difficulties in extracting the self-assembled macromolecules using deuterated solvents. Future work includes exploring the fluorescence of modified tetramers and utilizing alternative ligation components. Acknowledgments include Dr. Ronald Brisbois, Macalester College, Minnesota Academy of Science, and Ms. Lois Fruen.

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Optimizing Supramolecular Self-Assembly of Oxadiazole Derivatives

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  1. Synthesis of Supramolecular Self-assembling Macromolecular Structures Matthew B. Weiss 2006

  2. Chemistry Department Macalester College

  3. Goals

  4. Goals • Improve yields

  5. Goals • Improve yields • Develop a purification protocol

  6. Goals • Improve yields • Develop a purification protocol • Show successful self-assembly

  7. Oxadiazole Molecule

  8. Background Information Balsells (2005) Loye (2003)

  9. Identified Variables • Problems with protocol • Low Yield

  10. Potential Self-assembly

  11. Acylation Reaction dichloromethane

  12. Acylation Reaction 0 °C Diisopropylethylamine dichloromethane

  13. Acylation Reaction 0 °C Diisopropylethylamine dichloromethane

  14. Cycloaromatization H

  15. Cycloaromatization 82 °C Acetonitrile H

  16. Cycloaromatization 82 °C Acetonitrile H

  17. Oxadiazole Molecules

  18. Oxadiazole Molecules

  19. Oxadiazole Molecules

  20. Oxadiazole Molecules

  21. Oxadiazole Molecules

  22. Oxadiazole Molecules

  23. 1HNMRs of Oxadiazole Derivatives

  24. 1HNMRs of Oxadiazole Derivatives

  25. 1HNMRs of Oxadiazole Derivatives

  26. 1HNMRs of Oxadiazole Derivatives

  27. Results of Synthesis • The five oxadiazole molecules were successfully synthesized and purified with high yields: • dithiophen • diphenyl • thiophen/furan • pyridyl/phenyl • pyridyl-t-butyl/phenyl

  28. Macromolecular Synthesis

  29. Self-assembled Tetramer

  30. Self-assembled Dimer

  31. Self-assembly Procedure • Dissolved palladium(II) chloride in acetonitrile at 78 °C

  32. Self-assembly Procedure • Dissolved palladium(II) chloride in acetonitrile at 78 °C • Dissolved oxadiazole molecule in acetonitrile at 0 °C

  33. Problems Encountered • Extracting self-assembled macromolecules using deuterated solvents.

  34. Analysis of Macromolecule

  35. Future Work • Utilize other components for ligation, such as PtCl2 or ReCl2.

  36. Future Work • Utilize other components for ligation, such as PtCl2 or ReCl2. • Assess the fluorescence of modified tetramers.

  37. Acknowledgments • Dr. Ronald Brisbois • Macalester College • Minnesota Academy of Science • Ms. Lois Fruen • Breck Team Science Research

  38. Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly Matthew B. Weiss 2006

  39. Analysis • Electron Impact Mass Spectroscopy (EI-MS) http://www.svsu.edu/emplibrary/set_chem_facilities_ftir.jpg

  40. Nuclear Magnetic Resonance • All particles have a property called spin. • In a magnetic field, particles spin with or against the field. • When excited with microwave energy, particles become excited and change their spin slightly.

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