Title: Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs
1Design 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
2Calixarenes
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
3Synthesis of Calix4 and 8 Derivatives
Calix8
Calix4
4NMR of Calix8 Derivative
Derivative
Calix8
14 Carbons are present in C-13 NMR Of derivative
5Calix4 derivative NMR and IR
Calix4 derivative
Calix4
6Calix8 derivative a hydrogen bond acceptor
Structure and space filling model for calix8
derivative.
7Crystal 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.
812
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
10Cu(NH3 ) 4 2 and
Cu(Arg)Cl2 As guests for Calix8
derivative Using Spartan-pro software
11Future 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.
121
Calix4arene derivatives
2
13Calix8arene derivatives
5
4
3
7
8
6
14b-cyclodextrin derivatives
Figure 3.1. Reaction shim for making
compounds 9-11
151. NaH / THF
2. Ph-CH2Br
11
12
16Spartan-pro side view of compound 12
17Side view, space filling