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

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Synthesis of oxadiazole derivatives for use in supramolecular assembly l.jpg

Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly

Matthew B. Weiss

2006


Potential applications l.jpg
Potential Applications Supramolecular Assembly

  • Modeling natural self-assemblies (i.e. mitochondria or cell wall formation)

  • Formation of nanoscale structures

  • Understanding of metal-ligand interactions in supramolecular assemblies


Background l.jpg
Background Supramolecular Assembly

Supramolecular self assembly:

  • Involves metal-ligand interactions

  • Utilizes metal-ligand bonding to stabilize structure

  • Occurs when bond-angles are optimal optimal for assembling interactions


Slide4 l.jpg
Goal Supramolecular Assembly

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


Oxadiazole molecules l.jpg
Oxadiazole Molecules Supramolecular Assembly


Oxadiazole molecules6 l.jpg
Oxadiazole Molecules Supramolecular Assembly


Oxadiazole molecules7 l.jpg
Oxadiazole Molecules Supramolecular Assembly


Oxadiazole molecules8 l.jpg
Oxadiazole Molecules Supramolecular Assembly


Acylation reaction l.jpg

Acylation Reaction Supramolecular Assembly

Diisopropylethylamine

0 °C

Acetonitrile


Purification l.jpg
Purification Supramolecular Assembly

  • Vacuum filtration

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


Purification11 l.jpg
Purification Supramolecular Assembly

  • Vacuum filtration

  • Vacuum desiccation

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


Cycloaromatization l.jpg
Cycloaromatization Supramolecular Assembly

82 °C Acetonitrile

H


Purification13 l.jpg
Purification Supramolecular Assembly

  • Qualitative transfer with ether


Purification14 l.jpg
Purification Supramolecular Assembly

  • Qualitative transfer with ether

  • Rotary evaporation


Analysis l.jpg
Analysis Supramolecular Assembly

  • 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


Analysis16 l.jpg
Analysis Supramolecular Assembly

  • 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 l.jpg
Dithiophen Oxadiazole Supramolecular Assembly


Dithiophen oxadiazole18 l.jpg
Dithiophen Oxadiazole Supramolecular Assembly

EI-MS = 234 g/mol


Diphenyl oxadiazole l.jpg
Diphenyl Oxadiazole Supramolecular Assembly


Diphenyl oxadiazole20 l.jpg
Diphenyl Oxadiazole Supramolecular Assembly

EI-MS = 222 g/mol


Thiophen furan oxadiazole l.jpg
Thiophen/furan Oxadiazole Supramolecular Assembly


Thiophen furan oxadiazole22 l.jpg
Thiophen/furan Oxadiazole Supramolecular Assembly

EI-MS = 218 g/mol


Pyridyl phenyl oxadiazole l.jpg
Pyridyl/phenyl Oxadiazole Supramolecular Assembly


Pyridyl phenyl oxadiazole24 l.jpg
Pyridyl/phenyl Oxadiazole Supramolecular Assembly

EI-MS = 223 g/mol


Conclusion l.jpg
Conclusion Supramolecular Assembly

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


Future work l.jpg
Future Work Supramolecular Assembly

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

  • Synthesize oxadiazole molecules without vacuum filtration and vacuum desiccation


Acknowledgments l.jpg
Acknowledgments Supramolecular Assembly

  • Dr. Brisbois

  • Macalester College

  • Ms. Fruen

  • Ms. Richter

  • Team Research


Synthesis of oxadiazole derivatives for use in supramolecular assembly28 l.jpg

Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly

Matthew B. Weiss

2006


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