Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly

1
Synthesis of Oxadiazole Derivatives for Use in
Supramolecular Assembly

• Matthew B. Weiss
• 2006

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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

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Goal

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

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Oxadiazole Molecules
2,5-di(thiophen-2-yl)-1,3,4-oxadiazole dithiophen oxadiazole
2,5-diphenyl-1,3,4-oxadiazole diphenyl oxadiazole
2-(furan-2-yl)-5-(thiophen-2-yl)-1,3,4-oxadiazole thiophen/furan oxadiazole
2-phenyl-5-(pyridine-3-yl)-1,3,4-oxadiazole pyridyl/phenyl oxadiazole
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Oxadiazole Molecules
2,5-di(thiophen-2-yl)-1,3,4-oxadiazole dithiophen oxadiazole
2,5-diphenyl-1,3,4-oxadiazole diphenyl oxadiazole
2-(furan-2-yl)-5-(thiophen-2-yl)-1,3,4-oxadiazole thiophen/furan oxadiazole
2-phenyl-5-(pyridine-3-yl)-1,3,4-oxadiazole pyridyl/phenyl oxadiazole
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Oxadiazole Molecules
2,5-di(thiophen-2-yl)-1,3,4-oxadiazole dithiophen oxadiazole
2,5-diphenyl-1,3,4-oxadiazole diphenyl oxadiazole
2-(furan-2-yl)-5-(thiophen-2-yl)-1,3,4-oxadiazole thiophen/furan oxadiazole
2-phenyl-5-(pyridine-3-yl)-1,3,4-oxadiazole pyridyl/phenyl oxadiazole
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Oxadiazole Molecules
2,5-di(thiophen-2-yl)-1,3,4-oxadiazole dithiophen oxadiazole
2,5-diphenyl-1,3,4-oxadiazole diphenyl oxadiazole
2-(furan-2-yl)-5-(thiophen-2-yl)-1,3,4-oxadiazole thiophen/furan oxadiazole
2-phenyl-5-(pyridine-3-yl)-1,3,4-oxadiazole pyridyl/phenyl oxadiazole
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Acylation Reaction
Diisopropylethylamine
0 C
Acetonitrile
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Purification

• Vacuum filtration

http//www.dartmouth.edu/chemlab/techniques/vfilt
ration.html
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Purification

• Vacuum filtration
• Vacuum desiccation

http//www.crscientific.com/vacuumdesiccators.html
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Cycloaromatization
82 C Acetonitrile
H
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Purification

• Qualitative transfer with ether

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Purification

• Qualitative transfer with ether
• Rotary evaporation

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Analysis

• Proton Nuclear Magnetic Resonance (1HNMR)

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Analysis

• Proton Nuclear Magnetic Resonance (1HNMR)
• Electron Impact Mass Spectroscopy (EI-MS)

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www.specs.com
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Dithiophen Oxadiazole
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Dithiophen Oxadiazole
EI-MS 234 g/mol
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Diphenyl Oxadiazole
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Diphenyl Oxadiazole
EI-MS 222 g/mol
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Thiophen/furan Oxadiazole
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Thiophen/furan Oxadiazole
EI-MS 218 g/mol
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Pyridyl/phenyl Oxadiazole
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Pyridyl/phenyl Oxadiazole
EI-MS 223 g/mol
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Conclusion

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

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Future Work

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

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Acknowledgments

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

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Synthesis of Oxadiazole Derivatives for Use in
Supramolecular Assembly

• Matthew B. Weiss
• 2006