1 / 28

Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly

Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly. Matthew B. Weiss 2006. Potential Applications. Modeling natural self-assemblies (i.e. mitochondria or cell wall formation) Formation of nanoscale structures

shania
Download Presentation

Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

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

  2. Potential Applications • Modeling natural self-assemblies (i.e. mitochondria or cell wall formation) • Formation of nanoscale structures • Understanding of metal-ligand interactions in supramolecular assemblies

  3. Background Supramolecular self assembly: • Involves metal-ligand interactions • Utilizes metal-ligand bonding to stabilize structure • Occurs when bond-angles are optimal optimal for assembling interactions

  4. Goal • To synthesize and purify four oxadiazole derivatives for future use in supramolecular assembly

  5. Oxadiazole Molecules

  6. Oxadiazole Molecules

  7. Oxadiazole Molecules

  8. Oxadiazole Molecules

  9. Acylation Reaction Diisopropylethylamine 0 °C Acetonitrile

  10. Purification • Vacuum filtration http://www.dartmouth.edu/~chemlab/techniques/vfiltration.html

  11. Purification • Vacuum filtration • Vacuum desiccation http://www.crscientific.com/vacuumdesiccators.html

  12. Cycloaromatization 82 °C Acetonitrile H

  13. Purification • Qualitative transfer with ether

  14. Purification • Qualitative transfer with ether • Rotary evaporation

  15. Analysis • Proton Nuclear Magnetic Resonance (1HNMR) http://images.google.com/imgres?imgurl=http://picturethis.pnl.gov/im2/97070309-2CND0/97070309-2CND.jpg&imgrefurl=http://picturethis.pnl.gov/picturet.nsf/by%2Bid/SMAA-477QHM%3Fopendocumen&h=480&w=383&sz=65&tbnid=SDbg_KQV31kJ:&tbnh=126&tbnw=100&hl=en&start=1&prev=/images%3Fq%3DNuclear%2Bmagnetic%2Bresonance%2B%26svnum%3D10%26hl%3Den%26lr%3D%26sa%3DG

  16. Analysis • Proton Nuclear Magnetic Resonance (1HNMR) • Electron Impact Mass Spectroscopy (EI-MS) http://images.google.com/imgres?imgurl=http://picturethis.pnl.gov/im2/97070309-2CND0/97070309-2CND.jpg&imgrefurl=http://picturethis.pnl.gov/picturet.nsf/by%2Bid/SMAA-477QHM%3Fopendocumen&h=480&w=383&sz=65&tbnid=SDbg_KQV31kJ:&tbnh=126&tbnw=100&hl=en&start=1&prev=/images%3Fq%3DNuclear%2Bmagnetic%2Bresonance%2B%26svnum%3D10%26hl%3Den%26lr%3D%26sa%3DG www.specs.com

  17. Dithiophen Oxadiazole

  18. Dithiophen Oxadiazole EI-MS = 234 g/mol

  19. Diphenyl Oxadiazole

  20. Diphenyl Oxadiazole EI-MS = 222 g/mol

  21. Thiophen/furan Oxadiazole

  22. Thiophen/furan Oxadiazole EI-MS = 218 g/mol

  23. Pyridyl/phenyl Oxadiazole

  24. Pyridyl/phenyl Oxadiazole EI-MS = 223 g/mol

  25. Conclusion • The four oxadiazole molecules: dithiophen, diphenyl, thiophen/furan, pyridyl/phenyl, were successfully synthesized and purified

  26. Future Work • Examine self-assembling properties of pyridine/phenyl oxadiazole molecule • Synthesize oxadiazole molecules without vacuum filtration and vacuum desiccation

  27. Acknowledgments • Dr. Brisbois • Macalester College • Ms. Fruen • Ms. Richter • Team Research

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

More Related