Enhanced enantioselective recognition with diastereoisomeric BINOL based chiral fluorescent boronic acid sensors

Journal of Fluorescence

Volumn 21, Issue 6, 2011, Pages 2077-2084

  Li, Qiuting ^a   Guo, Huimin ^a   Wu, Yubo ^a   Zhang, Xin ^a   Liu, Yifan ^a   Zhao, Jianzhang ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

BINOL; Boronic acid; Chiral fluorescent chemosensors

Indexed keywords

ALCOHOLS; ENANTIOSELECTIVITY; FLUORESCENCE;

BINOL; BORONIC ACID; CHIRAL ANALYTES; CHIRAL FLUORESCENT CHEMOSENSORS; DIASTEREOISOMERS; EMISSION INTENSITY; ENANTIOSELECTIVE RECOGNITION; MOLECULAR PROBES;

PROBES;

EID: 84856251959     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-011-0906-3     Document Type: Article

References (16)

1. Farina V, Reeves JT, Senanayake CH, Song J (2006) Asymmetric synthesis of active pharmaceutical ingredients. Chem Rev 106:2734-2793 (Pubitemid 44207755)
2. Stibor I, Zlatuíková P (2005) Chiral recognition of anions. Top Curr Chem 255:31-63
3. Pu L (1998) 1,1'-Bimaphthyl dimers, oligomers, and polymers: Molecular recognition, asymmetric catalysis, and new materials. Chem Rev 98:2405-2494
4. Pu L (2004) Fluorescence of organic molecules in chiral recognition. Chem Rev 104:1687-1716
5. Gunnlaugsson T, Glynn M, Tocci GM, Kruger PE, Pfeffer FM (2006) Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors. Coord Chem Rev 250:3094-3117
6. Willener Y, Joly KM, Moody CJ, Tucker JHR (2008) An exploration of ferrocenyl ureas as enantioselective electrochemical sensors for chiral carboxylate anions. J Org Chem 73:1225-1233 (Pubitemid 351263634)
7. Leung D, Folmer-Andersen JF, Lynch VM, Anslyn EV (2008) Using enantioselective indicator displacement assays to determine the enantiomeric excess of r-Amino acids. J Am Chem Soc 130:12318-12327
8. Liu H, Qian P, Wu Y, Chen D, Hou X, Sabat M, Pu L (2010) Highly enantioselective recognition of structurally diverse a- Hydroxycarboxylic acids by a fluorescent sensor. Angew Chem Int Ed 49:602-606
9. Oshovsky GV, Reinhoudt DN, Verboom W (2007) Supramolecular chemistry in water. Angew Chem Int Ed 46:2366-2393 (Pubitemid 46973576)
10. Wiskur SL, Ait-Haddou H, Lavigne JJ, Anslyn EV (2001) Teaching old indicators new tricks. Acc Chem Res 34:963-972
11. Ni W, Fang H, Springsteen G (2004) The design of boronic acid spectroscopic reporter compounds by taking advantage of the pKa-lowering effect of diol binding: Nitrophenol-based color reporters for diols. J Org Chem 69:1999-2007 (Pubitemid 38366665)
12. James TD, Shinkai S (2002) Artificial receptors as chemosensors for carbohydrates. Top Curr Chem 218:159-200
13. Di Cesare N, Adhikari DP, Heynekamp JJ, Heagy MD, Lakowicz JR (2002) Spectroscopic and photophysical characterization of fluorescent chemosensors for monosaccharides based on NPhenylboronic acid derivatives of 1,8-Naphthalimide. J Fluoresc 12:147-154
14. James TD (2007) Saccharide-selective boronic acid based Photoinduced Electron Transfer (PET) fluorescent sensors. Top Curr Chem 277:107-152
15. Liang X, James TD, Zhao J (2008) 6, 6c'-Bis-substituted BINOL boronic acids as enantiosele- ctive and chemselective fluorescent chemosensors for D-sorbitol. Tetrahedron 64:1309-1315
16. Han F, Chi L, Liang X, Ji S, Liu S, Zhou F, Wu Y, Han K, Zhao J, James TD (2009) 3, 6-Disubstituted Carbazole-Based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid. J Org Chem 74:1333-1336