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Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs

Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs. Farzad Fani-Pakdel and Jason R. Telford Department of Chemistry, University of Iowa Iowa City, IA. Calixarenes:. Calixarenes are macrocycles that are made from phenol or P-tert-butylphenol .

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Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs

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  1. Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs Farzad Fani-Pakdel and Jason R. Telford Department of Chemistry, University of Iowa Iowa City, IA

  2. Calixarenes: Calixarenes are macrocycles that are made from phenol or P-tert-butylphenol Calixarenes and its derivatives can be used to complex a range of cations, anions and neutral molecules. Calix[4]arene Calix[6]arene Calix[8]arene

  3. Synthesis of Calix[4] and [8] Derivatives: Calix[8] Calix[4]

  4. NMR of Calix[8] Derivative Derivative Calix[8] 14 Carbons are present in C-13 NMR Of derivative

  5. Calix[4] derivative: NMR and IR Calix[4] derivative Calix[4]

  6. Calix[8] derivative a hydrogen bond acceptor Structure and space filling model for calix[8] derivative.

  7. Crystal Structure for Calix[4] Derivative • Hydrogen atoms are not shown. • There is a cavity that can be both hydrogen bond donor and acceptor • It can also bind metals through O / N in a Td cavity.

  8. 1:2 1:1 Comparing 1:1 with 1:2 complex of calix[4]derivative: fluoride. Using Hyper NMR

  9.  Acknowledgements:  • Department of Chemistry, University of Iowa • Carver Scientific Research Initiative • Dr D. J. Burton • Dale Swenson • Telford Research Group

  10. Cu(NH3 ) 4 2+ and Cu(Arg)Cl2 As guests for Calix[8] derivative Using Spartan-pro software

  11. Future Work Now that we have made some supramolecular hosts we are systematically testing organic ligands that match our super-molecule in size, hydrogen bonding and other intermolecular interactions. We will also investigate the metal complexes of such compounds in order to evaluate outer sphere metal-complex recognition. In order to study these interactions, NMR, UV-Vis, fluorescence, mass spectroscopy and finally crystal structures will be used.

  12. 1 Calix[4]arene derivatives 2

  13. Calix[8]arene derivatives 5 3 4 7 6 8

  14. 1. NaH / THF TBDMSCl Pyridine 9 2. MeI P(Ph)3 , Br2 11 DMF 10 b-cyclodextrinderivatives Figure 3.1. Reaction shim for making compounds 9-11

  15. 1. NaH / THF 2. Ph-CH2Br 11 12

  16. Spartan-pro side view of compound 12

  17. Side view, space filling

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