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Citation: WANG Jian, YUAN Xiao-Ya, WANG Jin-Yue, CHEN Shu-Hua. Design and Microwave Synthesis of Chiral Single-armed Molecular Tweezers Derived from α-Hyodeoxycholic Acid[J]. Chinese Journal of Applied Chemistry, ;2009, 26(5): 501-506. shu

Design and Microwave Synthesis of Chiral Single-armed Molecular Tweezers Derived from α-Hyodeoxycholic Acid

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a College of Chemistry, Sichuan University, Chengdu 610064;
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b College of Science, Chongqing Jiaotong University, Chongqing;
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c Department of Chemistry and Chemical Engineering, Yibin University, Yibin

Corresponding author: CHEN Shu-Hua,
Received Date: 12 May 2008
Available Online: 4 August 2008
Fund Project: 国家自然科学基金(20072026,20272038)资助项目 (20072026,20272038)

A novel type of molecular tweezers with different chiral center and cleft has been designed and synthesized with α-hyodeoxycholic acid as spacer and D/L-amino acid methyl ester as chiral arm attached at 3-position under microwave irradiation.Their structures were elucidated by ¹H NMR,FTIR spectra and elemental analysis.Their molecular recognition properties for D/L-amino acid methyl esters were investigated by UV-Vis spectral titration,which showed that all these molecular clefts possessed a good recognition ability for D/L-amino acid methyl esters.The supramolecular complexes formed between the tweezers and various substrates consisted of a 1:1 type of host to guest of molecules.Based on the Hildebrand-Benesi equation,plotting 1/ΔA vs 1/[G]₀ gave a straight line.From the line slopes and intercepts,the stability constants(K_a) of the complexes were calculated and thereafter the correspondent Gibbs free energies(-ΔG⁰) were also obtained.Preliminary results indicate that due to the structural micro-environmental changes,the synthesized chiral single-armed molecular tweezers exhibit different enantio-selectivity for D/L-amino acid methyl esters.
- α-hyodeoxycholic acid,
- molecular tweezers,
- synthesis,
- recognition
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