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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 9
BKCSDE 27(9)
September 20, 2006 

Synthesis and Anion Binding Affinities of Novel Molecular Tweezers Based on Chenodeoxycholic Acid Bearing Different Lengths of Arm
Ki Soo Kim, Hyun-Seok Jang, Hong-Seok Kim*
Anion recognition, Molecular tweezer, Chenodeoxycholic acid, Fluoride ion
Molecular tweezers based on chenodeoxycholic acid bearing different lengths of arm were synthesized and their anion binding affinities were evaluated by 1H NMR, isothermal calorimetric titration, and ESI mass spectrometry. Molecular tweezer 6 showed a high selectivity toward H2PO4- over Cl-, Br-, I-, and CH3CO2- by 1H NMR titration, whereas the association constant for F- revealed the largest value as determined by ITC. The selectivity of 6 towards F- was about 103 times higher than that of Cl-, H2PO4-, and CH3CO2-. ITC experiment of 6 with F- in a DMSO showed two binding modes; two sequential association constants K1 = 2.77 × 105 M-1 and K2 = 8.68 × 106 M-1 were found. These sequential bindings were confirmed by ESI mass spectrometry. 1 : 1 and 1 : 2 complexes of 6 and F- were found at m/z 868.08 and 884.04.
1445 - 1449
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