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Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs Farzad Fani-Pakdel and...
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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 Iowa City, IA
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Transcript of Design and Synthesis of Calixarene Scaffolds Bearing Hydrogen Bond Motifs Farzad Fani-Pakdel and...
Design and Synthesis of Calixarene Scaffolds Bearing
Hydrogen Bond Motifs
Farzad Fani-Pakdel and Jason R. TelfordDepartment of Chemistry, University of Iowa
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[8]areneCalix[6]arene
Synthesis of Calix[4] and [8] Derivatives:
t-But
OH
CH2
t-But
O
CH2
BrCH2CONH2
t-But
OH
CH2
NH2
O4
Cs2CO3 / acetone
Excess
7 days, 50 degree
2
O O
NO2NO2
OH OH
NO2
Br
Cs2CO3 / Acetone
7days, 50 degree44
ExcessCalix[8]
Calix[4]
NMR of Calix[8] Derivative
DerivativeCalix[8]
14 Carbons are present in C-13 NMROf derivative
O O
NO2NO2
4
16
18
20
22
24
26
28
30
32
34
36
38
40
42
44
46
%T
1000 2000 3000
Wavenumbers (cm-1)
36
38
40
42
44
46
48
50
52
54
%T
1000 2000 3000
Wavenumbers (cm-1)
Calix[4] derivative: NMR and IR
Calix[4]
Calix[4] derivative
t-Bu
t-Bu
t-Bu
NO2
NO2
NO2
NO2
t-Bu
t-But-Bu
t-Bu
NO2
NO2NO2
NO2
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 that can be both hydrogen bond donor and
acceptor
It can also bind metals through
O / N in a Td cavity.
Comparing 1:1 with 1:2 complex of calix[4]derivative: fluoride.Using Hyper NMR
1:1 1:2
Acknowledgements: Department of Chemistry, University of Iowa
Carver Scientific Research Initiative
Dr D. J. Burton
Dale Swenson
Telford Research Group
Cu(NH3 ) 4 2+ and Cu(Arg)Cl2
As guests for Calix[8] derivativeUsing 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.
O
CH2
O
CH2
2
t-But t-But
O
CH2
OH
CH2
NH2
O
2
t-But t-But
1
2
Calix[4]arene
derivatives
O
CH2
8
t-But
CN 8
O
CH2
8
t-But
NO2
O
CH2
8
t-But
CN
O
CH2
8
t-But
O
CH2
8
t-But
NH2
O
76
543
O
CH2
8
t-But
Calix[8]arene derivatives
TBDMSCl
Pyridine
P(Ph)3 , Br2
1. NaH / THF
2. MeI
DMF
9
11 10
n
OO
OO
O
7
Si Me
t-Bu
Me
OO
OO
O
7
Si Me
t-Bu
Me
MeMe
OBr
OO
O
7
Me
Me
-cyclodextrin derivatives
OO
OO
O
7
Si Me
t-Bu
Me
OO
OO
O
7
Si Me
t-Bu
Me
1. NaH / THF
2. Ph-CH2Br
1211
Spartan-pro side view of compound 12
Side view, space filling
