Synthesis and Anion Binding Affinities of Novel Molecular Tweezers Based on Chenodeoxycholic Acid Bearing Different Lengths of Arm

Bulletin of the Korean chemical society

Ki Soo Kim¹  Hong-Seok Kim¹  Hyun-Seok Jang¹ 

关键词: Anion recognition;    Molecular tweezer;    Chenodeoxycholic acid;    Fluoride ion;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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.

【 授权许可】

Unknown