Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen
Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs Farzad Fani-Pakdel and Jason R. Telford Department of Chemistry, University of Iowa City, IA
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
![Synthesis of Calix[4] and [8] Derivatives: Calix[8] Calix[4]](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-3.jpg "Synthesis of Calix[4] and [8] Derivatives: Calix[8] Calix[4]")
Synthesis of Calix[4] and [8] Derivatives: Calix[8] Calix[4]
![NMR of Calix[8] Derivative Calix[8] 14 Carbons are present in C-13 NMR Of derivative](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-4.jpg "NMR of Calix[8] Derivative Calix[8] 14 Carbons are present in C-13 NMR Of derivative")
NMR of Calix[8] Derivative Calix[8] 14 Carbons are present in C-13 NMR Of derivative Derivative
![Calix[4] derivative: NMR and IR Calix[4] derivative Calix[4]](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-5.jpg "Calix[4] derivative: NMR and IR Calix[4] derivative Calix[4]")
Calix[4] derivative: NMR and IR Calix[4] derivative Calix[4]
![Calix[8] derivative a hydrogen bond acceptor Structure and space filling model for calix[8] derivative.](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-6.jpg "Calix[8] derivative a hydrogen bond acceptor Structure and space filling model for calix[8] derivative.")
Calix[8] derivative a hydrogen bond acceptor Structure and space filling model for calix[8] derivative.
![Crystal Structure for Calix[4] Derivative §Hydrogen atoms are not shown. §There is a cavity](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-7.jpg "Crystal Structure for Calix[4] Derivative §Hydrogen atoms are not shown. §There is a cavity")
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.
![1: 1 1: 2 Comparing 1: 1 with 1: 2 complex of calix[4]derivative: fluoride.](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-8.jpg "1: 1 1: 2 Comparing 1: 1 with 1: 2 complex of calix[4]derivative: fluoride.")
1: 1 1: 2 Comparing 1: 1 with 1: 2 complex of calix[4]derivative: fluoride. Using Hyper NMR
Acknowledgements: § Department of Chemistry, University of Iowa § Carver Scientific Research Initiative § Dr D. J. Burton § Dale Swenson § Telford Research Group
![Cu(NH 3 ) 4 2+ and Cu(Arg)Cl 2 As guests for Calix[8] derivative Using](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-10.jpg "Cu(NH 3 ) 4 2+ and Cu(Arg)Cl 2 As guests for Calix[8] derivative Using")
Cu(NH 3 ) 4 2+ and Cu(Arg)Cl 2 As guests for Calix[8] derivative Using Spartan-pro software
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.
![1 Calix[4]arene derivatives 2](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-12.jpg "1 Calix[4]arene derivatives 2")
1 Calix[4]arene derivatives 2
![Calix[8]arene derivatives 3 6 4 7 5 8](http://slidetodoc.com/presentation_image/561c35322b2f31e12aa7aace8b28792a/image-13.jpg "Calix[8]arene derivatives 3 6 4 7 5 8")
Calix[8]arene derivatives 3 6 4 7 5 8
b-cyclodextrin derivatives 1. Na. H / THF TBDMSCl Pyridine 9 P(Ph)3 , Br 2 11 DMF 10 2. Me. I
1. Na. H / THF 2. Ph-CH 2 Br 11 12
Spartan-pro side view of compound 12
Side view, space filling
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