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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

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Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly

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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

  • Understanding of metal-ligand interactions in supramolecular assemblies


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


Goal

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


Oxadiazole Molecules


Oxadiazole Molecules


Oxadiazole Molecules


Oxadiazole Molecules


Acylation Reaction

Diisopropylethylamine

0 °C

Acetonitrile


Purification

  • Vacuum filtration

http://www.dartmouth.edu/~chemlab/techniques/vfiltration.html


Purification

  • Vacuum filtration

  • Vacuum desiccation

http://www.crscientific.com/vacuumdesiccators.html


Cycloaromatization

82 °C Acetonitrile

H


Purification

  • Qualitative transfer with ether


Purification

  • Qualitative transfer with ether

  • Rotary evaporation


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


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


Dithiophen Oxadiazole


Dithiophen Oxadiazole

EI-MS = 234 g/mol


Diphenyl Oxadiazole


Diphenyl Oxadiazole

EI-MS = 222 g/mol


Thiophen/furan Oxadiazole


Thiophen/furan Oxadiazole

EI-MS = 218 g/mol


Pyridyl/phenyl Oxadiazole


Pyridyl/phenyl Oxadiazole

EI-MS = 223 g/mol


Conclusion

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


Future Work

  • Examine self-assembling properties of pyridine/phenyl oxadiazole molecule

  • Synthesize oxadiazole molecules without vacuum filtration and vacuum desiccation


Acknowledgments

  • Dr. Brisbois

  • Macalester College

  • Ms. Fruen

  • Ms. Richter

  • Team Research


Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly

Matthew B. Weiss

2006


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