A BINOL-based chiral polyammonium receptor for highly enantioselective recognition and fluorescence sensing of (S,S)-tartaric acid in aqueous solution.

作者: Andrea Bencini , Carmine Coluccini , Alessandra Garau , Claudia Giorgi , Vito Lippolis

DOI: 10.1039/C2CC35383K

关键词: Tartaric acidFluorescenceCatalysisStereoisomerismLinkerEnantioselective synthesisChemistryMoleculeAqueous solutionStereochemistry

摘要: A chiral ditopic polyammonium receptor featuring two [9]aneN3 moieties separated by a (S)-BINOL linker is able to selectively bind and sense in water (S,S)-tartaric acid over its (R,R)/meso forms.

参考文章(30)
Ning-Ning Liu, Song Song, Dong-Mi Li, Yan-Song Zheng, Highly sensitive determination of enantiomeric composition of chiral acids based on aggregation-induced emission Chemical Communications. ,vol. 48, pp. 4908- 4910 ,(2012) , 10.1039/C2CC30448A
Qiao-Sen Lu, Liang Dong, Ji Zhang, Jing Li, Lu Jiang, Yu Huang, Song Qin, Chang-Wei Hu, Xiao-Qi Yu, None, Imidazolium-Functionalized BINOL as a Multifunctional Receptor for Chromogenic and Chiral Anion Recognition Organic Letters. ,vol. 11, pp. 669- 672 ,(2009) , 10.1021/OL8027303
Ignacio Alfonso, Francisca Rebolledo, Vicente Gotor, Optically Active Dioxatetraazamacrocycles: Chemoenzymatic Syntheses and Applications in Chiral Anion Recognition Chemistry - A European Journal. ,vol. 6, pp. 3331- 3338 ,(2000) , 10.1002/1521-3765(20000915)6:18<3331::AID-CHEM3331>3.0.CO;2-8
Michael D. Lankshear, Paul D. Beer, Strategic anion templation Coordination Chemistry Reviews. ,vol. 250, pp. 3142- 3160 ,(2006) , 10.1016/J.CCR.2006.04.018
Pedro Mateus, Nicolas Bernier, Rita Delgado, Recognition of anions by polyammonium macrocyclic and cryptand receptors: Influence of the dimensionality on the binding behavior Coordination Chemistry Reviews. ,vol. 254, pp. 1726- 1747 ,(2010) , 10.1016/J.CCR.2009.11.005
Maria Lawrence, Charles J. Marzzacco, Craig Morton, Catherine Schwab, Arthur M. Halpern, Excited-state deprotonation of 2-naphthol by anions The Journal of Physical Chemistry. ,vol. 95, pp. 10294- 10299 ,(1991) , 10.1021/J100178A012
Mykhaylo Dukh, Pavel Drašar, Ivan Černý, VladimÍr Pouzar, James A. Shriver, VladimÍr Král, Jonathan L. Sessler, Novel Deep Cavity Calix[4]pyrroles Derived from Steroidal Ketones Supramolecular Chemistry. ,vol. 14, pp. 237- 244 ,(2002) , 10.1080/10610270290026149
Nélida Gimeno, Ramón Vilar, Anions as templates in coordination and supramolecular chemistry Coordination Chemistry Reviews. ,vol. 250, pp. 3161- 3189 ,(2006) , 10.1016/J.CCR.2006.05.016
Ming-Hua Xu, Jing Lin, Qiao-Sheng Hu, Lin Pu, Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching. Journal of the American Chemical Society. ,vol. 124, pp. 14239- 14246 ,(2002) , 10.1021/JA020989K
Antonio Bianchi, Enrique Garcia-España, The Use of Calculated Species Distribution Diagrams to Analyze Thermodynamic Selectivity Journal of Chemical Education. ,vol. 76, pp. 1727- 1734 ,(1999) , 10.1021/ED076P1727