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Convergent Dendrimer Synthesis

Convergent Dendrimer Synthesis . March 5, 2014. Dendrimers. Definitions. Dendrimer A highly-ordered, symmetrical macromolecule synthesized from branched monomers Components Core Branch Periphery Generation A monomer which has been branched one or more times

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Convergent Dendrimer Synthesis

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  1. Convergent Dendrimer Synthesis March 5, 2014

  2. Dendrimers

  3. Definitions • Dendrimer • A highly-ordered, symmetrical macromolecule synthesized from branched monomers • Components • Core • Branch • Periphery • Generation • A monomer which has been branched one or more times • One branch= first generation

  4. A core can have numerous branching points core core

  5. Methods & Approaches • Two types: • Convergent • Divergent

  6. Methods & Approaches • Two types: • Convergent • Divergent

  7. Methods & Approaches • Two types: • Convergent • Divergent

  8. Methods & Approaches • Two types: • Convergent • Divergent

  9. Methods & Approaches • Two types: • Convergent • Divergent

  10. Methods & Approaches • Two types: • Convergent • Divergent

  11. Methods & Approaches • Two types: • Convergent • Divergent

  12. Why a Convergent Synthesis?

  13. More Control

  14. Applications • Drug Delivery • Gene Delivery • Sensors • Nano Particles

  15. Applications • Drug Delivery • Gene Delivery • Sensors • Nano Particles Why are we doing it?

  16. Applications • Drug Delivery • Gene Delivery • Sensors • Nano Particles Energy!!!

  17. Starting Molecule

  18. Synthetic Pathway • Esterification of Carboxylic Groups • Dimethyl-5-hydroxyisophthalate • Alkylation of alcohol with 3-Halide-1-propanol • Dimethyl-5-oxy-propanol-isophthalate • Saponification • 5-propanol-hydroxyisophthalate • Esterification of Alcohol • 5-acetoxypropoxy-isophthalate • Curtius Rearrangement

  19. Molecular Changes

  20. Esterification 85.6% Recovery

  21. Alkylation Special Considerations 68% Recovery (Br) 73% Recovery (Cl)

  22. Special Considerations: K2CO3 + X(CH2)3OH  Salt + Product

  23. Saponification 73% Recovery

  24. Esterification Special Considerations

  25. Special Considerations: Pyridine is very basic

  26. Special Considerations: Pyridine is very basic Hit solution hard with HCl

  27. Special Considerations: Pyridine is very basic Hit solution hard with HCl pH dependence: At pH of 4= 17.5% recovery At pH of 2= 85.3% recovery

  28. Synthesis Shortcut!? • Fahad recently discovered:

  29. Future Work: Curtius Rearrangement

  30. References • Tetrahedron Letters 39(1998) 8005-8008, Richard Taylor • Puapaiboon, “A Convergent Approach to Polyurethane Dendrimers” pgs 56-73 • Lu, “Polymeric Reagents in Solid-Phase Synthesis of Small Molecules and Dendrimers” pg 72

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