Enantioselective molecular sensing of aromatic amines using tetra-(S)-di-2-naphthylprolinol calix[4]arene

被引:38
作者
Jennings, K [1 ]
Diamond, D [1 ]
机构
[1] Dublin City Univ, Sch Chem Sci, Natl Ctr Sensor Res, Dublin 9, Ireland
关键词
D O I
10.1039/b100378j
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
This paper presents new analytical data, and evidence of the fluorescence quenching mechanism involved in enantioselective signals obtained with the chiral host tetra-(S)-di-2-naphthylprolinol calix[4]arene. Excellent selectivity is obtained with phenylglycinol and norephidrine in methanol, and samples of unknown enantiomeric composition have been determined with an average error of 1.08 and 0.62%, respectively (n = 6), on the basis of a single fluorescence measurement. The absence of any quenching observed with the related amines of phenylalaninol is attributed to a methylene spacer which inhibits efficient interaction between the aryl group of the guest and the naphthyl group of the host. The importance of the phenyl group of the guest in the quenching mechanism is confirmed by the complete absence of any quenching effect with cyclohexylethylamine.
引用
收藏
页码:1063 / 1067
页数:5
相关论文
共 21 条
[1]  
BECKETT H, 1991, BIOCHEM SOC T, P19
[2]   Infrared discrimination of enantiomerically enriched and racemic samples of methamphetamine salts [J].
Chappell, JS .
ANALYST, 1997, 122 (08) :755-760
[3]  
CRAM TC, 1992, FORENSIC SCI INT, V55, P131
[4]  
DAGLIESH CE, 1952, J CHEM SOC, P3940
[5]   Calixarenes: Designer ligands for chemical sensors. [J].
Diamond, D ;
Nolan, K .
ANALYTICAL CHEMISTRY, 2001, 73 (01) :22A-29A
[6]  
DORSEY JG, 1996, ANAL CHEM, V68, P291
[7]  
FABBRIZZI L, 1995, CHEM SOC REV, P197
[8]  
Fischer E., 1894, Chem. Gesellschaft, V27, P2985, DOI DOI 10.1002/CBER.18940270364
[9]   The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy [J].
Fleischhauer, J ;
Harmata, M ;
Kahraman, M ;
Koslowski, A ;
Welch, CJ .
TETRAHEDRON LETTERS, 1997, 38 (50) :8655-8658
[10]   Determination of the enantiomeric composition of chiral amines based on the quenching of the fluorescence of a chiral calixarene [J].
Grady, T ;
Harris, SJ ;
Smyth, MR ;
Diamond, D ;
Hailey, P .
ANALYTICAL CHEMISTRY, 1996, 68 (21) :3775-3782