Chirality is a property of matter that plays a key role in several branches of science, from optics to medicine.1 Many biological processes involve chiral molecules in order to achieve highly specific and selective interactions. The separation of chiral isomers is an appealing burgeoning field that captures the interest of many researchers.2 An interesting approach for harnessing the full potential of molecular receptors consists of their arrangement in monolayers hosted on an inorganic surface.3 A chiral organic–inorganic hybrid material, based on a porous silicon surface functionalized with a chiral cavitand, was designed and synthesized.4 The affinity of this device in water toward a bromine-marked alkyl-ammonium salt has been evaluated using XPS detection. UV and CD measurements highlight the enantioselective extraction from a racemic mixture in water of the S-enantiomer of the selected guest.5[1] G. H. Wagniere, On Chirality and the Universal Asymmetry, Wiley-VCH, Zurich, Weinheim, 2007[2] (a) G. A. Hembury, V. V. Borovkov and Y. Inoue, Chem. Rev., 2008, 108, 1; (b) Y. Liu, W. Xuan and Y. Cui, Adv. Mater., 2010, 22, 4112.[3] (a) Y. L. Bunimovich, Y. S. Shin, W.-S. Yeo, M. Amori, G. Kwong and J. R. Heath, J. Am. Chem. Soc., 2006, 128, 16323; (b) A. Motta, C. Tudisco and G. G. Condorelli, Sci. Adv. Mater., 2011, 3, 362.[4] (a) C. Tudisco, G. Trusso Sfrazzetto, A. Pappalardo, A. Motta, G. A. Tomaselli, I. L. Fragalà, F. P. Ballistreri and G. G. Condorelli, Eur. J. Inorg. Chem., 2011, 2124.[5] A. D’Urso, C. Tudisco, F. P. Ballistreri, G. G. Condorelli, R. Randazzo, G. A. Tomaselli, R. M. Toscano, G. Trusso Sfrazzetto, A. Pappalardo Chem. Commun., 2014, 50, 4993-4996.

Enantioselective extraction mediated by a chiral silicon surface

D'URSO, ALESSANDRO;BALLISTRERI, Francesco Paolo;CONDORELLI, Guglielmo Guido;RANDAZZO, ROSALBA;TOMASELLI, Gaetano;TOSCANO, Rosa Maria;TRUSSO SFRAZZETTO, GIUSEPPE;PAPPALARDO, ANDREA
2014-01-01

Abstract

Chirality is a property of matter that plays a key role in several branches of science, from optics to medicine.1 Many biological processes involve chiral molecules in order to achieve highly specific and selective interactions. The separation of chiral isomers is an appealing burgeoning field that captures the interest of many researchers.2 An interesting approach for harnessing the full potential of molecular receptors consists of their arrangement in monolayers hosted on an inorganic surface.3 A chiral organic–inorganic hybrid material, based on a porous silicon surface functionalized with a chiral cavitand, was designed and synthesized.4 The affinity of this device in water toward a bromine-marked alkyl-ammonium salt has been evaluated using XPS detection. UV and CD measurements highlight the enantioselective extraction from a racemic mixture in water of the S-enantiomer of the selected guest.5[1] G. H. Wagniere, On Chirality and the Universal Asymmetry, Wiley-VCH, Zurich, Weinheim, 2007[2] (a) G. A. Hembury, V. V. Borovkov and Y. Inoue, Chem. Rev., 2008, 108, 1; (b) Y. Liu, W. Xuan and Y. Cui, Adv. Mater., 2010, 22, 4112.[3] (a) Y. L. Bunimovich, Y. S. Shin, W.-S. Yeo, M. Amori, G. Kwong and J. R. Heath, J. Am. Chem. Soc., 2006, 128, 16323; (b) A. Motta, C. Tudisco and G. G. Condorelli, Sci. Adv. Mater., 2011, 3, 362.[4] (a) C. Tudisco, G. Trusso Sfrazzetto, A. Pappalardo, A. Motta, G. A. Tomaselli, I. L. Fragalà, F. P. Ballistreri and G. G. Condorelli, Eur. J. Inorg. Chem., 2011, 2124.[5] A. D’Urso, C. Tudisco, F. P. Ballistreri, G. G. Condorelli, R. Randazzo, G. A. Tomaselli, R. M. Toscano, G. Trusso Sfrazzetto, A. Pappalardo Chem. Commun., 2014, 50, 4993-4996.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/244885
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