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Molecules 2008, 13(3), 678-700; doi:10.3390/molecules13030678
Review

New Cleft-like Molecules and Macrocycles from Phosphonate Substituted Spirobisindanol

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Received: 25 February 2008; in revised form: 14 March 2008 / Accepted: 16 March 2008 / Published: 20 March 2008
(This article belongs to the Special Issue Spiro Compounds)
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Abstract: We have synthetized medium-sized cyclophanes and macrocycles containingphosphonic groups, directly linked to the aromatic rings of the phanes or as pendant arms,for use as specific receptors for the selective complexation of neutral guests or forcomplexing lanthanides, as luminescent sensors and for diagnostic bioassays in medicine.Furthermore, because it would be of great interest for biochemistry as well as forpharmacological studies to dispose of preorganized rigid chiral hosts for biorelevantmolecules we designed inter alia, some new chiral macrocycles capable of a triple bindingmode and we used them for constructing macrocycles that could also be of interest forchiral recognition and chiral separations. Thus, in this paper we shall review the salientaspects of some macrocycles synthetized in our laboratory, all possessing the phosphonatemoiety and a spirobisindanol scaffold and able to act as complexing agents for cations andorganic substrates. In particular, we shall describe their NMR characterization, theirstereochemistry in solution and in the solid state, and their use as chiral receptors forbiorelevant molecules. Chiral HPLC resolution of some of them is also reported.
Keywords: Stereochemistry; NMR; FAB; X-ray-structures; Hosts for biomolecules; Chiral HPLC resolutions; Hamburger Macrobicycles. Stereochemistry; NMR; FAB; X-ray-structures; Hosts for biomolecules; Chiral HPLC resolutions; Hamburger Macrobicycles.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Consiglio, G.A.; Failla, S.; Finocchiaro, P. New Cleft-like Molecules and Macrocycles from Phosphonate Substituted Spirobisindanol. Molecules 2008, 13, 678-700.

AMA Style

Consiglio GA, Failla S, Finocchiaro P. New Cleft-like Molecules and Macrocycles from Phosphonate Substituted Spirobisindanol. Molecules. 2008; 13(3):678-700.

Chicago/Turabian Style

Consiglio, Giuseppe A.; Failla, Salvatore; Finocchiaro, Paolo. 2008. "New Cleft-like Molecules and Macrocycles from Phosphonate Substituted Spirobisindanol." Molecules 13, no. 3: 678-700.


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