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

A chiral ditopic polyammonium receptor featuring two [9]aneN(3) 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.

[1]  S. Shimizu,et al.  Design of a novel inherently chiral calix[4]arene for chiral molecular recognition. , 2007, Organic letters.

[2]  Angelo Taglietti,et al.  Linear recognition of dicarboxylates by ditopic macrocyclic complexes , 2007 .

[3]  Dario Pasini,et al.  A ‘clicked’ macrocyclic probe incorporating Binol as the signalling unit for the chiroptical sensing of anions , 2012 .

[4]  L. Pu,et al.  Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching. , 2002, Journal of the American Chemical Society.

[5]  Dong-Mi Li,et al.  Highly sensitive determination of enantiomeric composition of chiral acids based on aggregation-induced emission. , 2012, Chemical communications.

[6]  Jianzhang Zhao,et al.  Enhanced Enantioselective Recognition with Diastereoisomeric BINOL Based Chiral Fluorescent Boronic Acid Sensors , 2011, Journal of Fluorescence.

[7]  Alfonso,et al.  Optically active dioxatetraazamacrocycles: chemoenzymatic syntheses and applications in chiral anion recognition , 2000, Chemistry.

[8]  Changwei Hu,et al.  Imidazolium-functionalized BINOL as a multifunctional receptor for chromogenic and chiral anion recognition. , 2009, Organic letters.

[9]  M. Formica,et al.  Polynuclear metal complexes of ligands containing phenolic units , 2008 .

[10]  T. Gunnlaugsson,et al.  Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors , 2006 .

[11]  Lei Zhu,et al.  Facile quantification of enantiomeric excess and concentration with indicator-displacement assays: an example in the analyses of alpha-hydroxyacids. , 2004, Journal of the American Chemical Society.

[12]  R. Vilar,et al.  Anions as templates in coordination and supramolecular chemistry , 2006 .

[13]  Jianzhang Zhao,et al.  Chiral mono boronic acid as fluorescent enantioselective sensor for mono alpha-hydroxyl carboxylic acids. , 2008, The Journal of organic chemistry.

[14]  L. Pu,et al.  A cyclohexyl-1,2-diamine-derived bis(binaphthyl) macrocycle: enhanced sensitivity and enantioselectivity in the fluorescent recognition of mandelic acid. , 2005, Angewandte Chemie.

[15]  Lin Pu,et al.  Fluorescence of organic molecules in chiral recognition. , 2004, Chemical reviews.

[16]  A. Garau,et al.  Selective binding and fluorescence sensing of diphosphate in H2O via Zn(2+)-induced allosteric regulation of the receptor structure. , 2012, Chemical communications.

[17]  L. Pu.  Enantioselective fluorescent sensors: a tale of BINOL. , 2012, Accounts of chemical research.

[18]  Md. Alamgir Hossain,et al.  Influence of dimensionality and charge on anion binding in amide-based macrocyclic receptors , 2006 .

[19]  C. Giorgi,et al.  Exploring the binding ability of polyammonium hosts for anionic substrates: selective size-dependent recognition of different phosphate anions by bis-macrocyclic receptors. , 2011, Inorganic chemistry.

[20]  R. Delgado,et al.  Recognition of anions by polyammonium macrocyclic and cryptand receptors: Influence of the dimensionality on the binding behavior , 2010 .

[21]  Jianzhang Zhao,et al.  Chiral donor photoinduced-electron-transfer (d-PET) boronic acid chemosensors for the selective recognition of tartaric acids, disaccharides, and ginsenosides. , 2011, Chemistry.

[22]  C. Morton,et al.  Excited-state deprotonation of 2-naphthol by anions , 1991 .

[23]  Keli Han,et al.  Rational design of d-PeT phenylethynylated-carbazole monoboronic acid fluorescent sensors for the selective detection of alpha-hydroxyl carboxylic acids and monosaccharides. , 2009, Journal of the American Chemical Society.

[24]  Angelo Taglietti,et al.  Some guidelines for the design of anion receptors , 2006 .

[25]  J. Sessler,et al.  Novel Deep Cavity Calix[4]pyrroles Derived from Steroidal Ketones , 2002 .

[26]  P. Beer,et al.  Strategic anion templation , 2006 .

[27]  Jianzhang Zhao,et al.  Chiral binol-bisboronic acid as fluorescence sensor for sugar acids. , 2004, Angewandte Chemie.

[28]  Jianzhang Zhao,et al.  Enhanced fluorescence and chiral discrimination for tartaric acid in a dual fluorophore boronic acid receptor. , 2005, Chemical communications.

[29]  A. Bianchi,et al.  The Use of Calculated Species Distribution Diagrams to Analyze Thermodynamic Selectivity , 1999 .

[30]  A. Bianchi,et al.  Anion coordination chemistry in aqueous solution of polyammonium receptors , 2006 .