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Synthesis of Supramolecular Self-assembling Macromolecular Structures. Matthew B. Weiss 2006. Chemistry Department Macalester College. Goals. Goals. Improve yields. Goals. Improve yields Develop a purification protocol. Goals. Improve yields Develop a purification protocol
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Synthesis of Supramolecular Self-assembling Macromolecular Structures Matthew B. Weiss 2006
Goals • Improve yields
Goals • Improve yields • Develop a purification protocol
Goals • Improve yields • Develop a purification protocol • Show successful self-assembly
Background Information Balsells (2005) Loye (2003)
Identified Variables • Problems with protocol • Low Yield
Acylation Reaction dichloromethane
Acylation Reaction 0 °C Diisopropylethylamine dichloromethane
Acylation Reaction 0 °C Diisopropylethylamine dichloromethane
Cycloaromatization 82 °C Acetonitrile H
Cycloaromatization 82 °C Acetonitrile H
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
Self-assembly Procedure • Dissolved palladium(II) chloride in acetonitrile at 78 °C
Self-assembly Procedure • Dissolved palladium(II) chloride in acetonitrile at 78 °C • Dissolved oxadiazole molecule in acetonitrile at 0 °C
Problems Encountered • Extracting self-assembled macromolecules using deuterated solvents.
Future Work • Utilize other components for ligation, such as PtCl2 or ReCl2.
Future Work • Utilize other components for ligation, such as PtCl2 or ReCl2. • Assess the fluorescence of modified tetramers.
Acknowledgments • Dr. Ronald Brisbois • Macalester College • Minnesota Academy of Science • Ms. Lois Fruen • Breck Team Science Research
Synthesis of Oxadiazole Derivatives for Use in Supramolecular Assembly Matthew B. Weiss 2006
Analysis • Electron Impact Mass Spectroscopy (EI-MS) http://www.svsu.edu/emplibrary/set_chem_facilities_ftir.jpg
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.