Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs - PowerPoint PPT Presentation

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Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs

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Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs Farzad Fani-Pakdel and Jason R. Telford Department of Chemistry, University of Iowa – PowerPoint PPT presentation

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Title: Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs


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.
Calix4arene
Calix8arene
Calix6arene
3
Synthesis of Calix4 and 8 Derivatives
Calix8
Calix4
4
NMR of Calix8 Derivative
Derivative
Calix8
14 Carbons are present in C-13 NMR Of derivative
5
Calix4 derivative NMR and IR
Calix4 derivative
Calix4
6
Calix8 derivative a hydrogen bond acceptor
Structure and space filling model for calix8
derivative.
7
Crystal Structure for Calix4 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
12
11
Comparing 11 with 12 complex of
calix4derivative 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 Calix8
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
Calix4arene derivatives
2
13
Calix8arene derivatives
5
4
3
7
8
6
14
b-cyclodextrin derivatives
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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