We have synthetized medium-sized cyclophanes and macrocycles containing phosphonic 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 for complexing lanthanides, as luminescent sensors and for diagnostic bioassays in medicine. Furthermore, because it would be of great interest for biochemistry as well as for pharmacological studies to dispose of preorganized rigid chiral hosts for biorelevant molecules we designed inter alia, some new chiral macrocycles capable of a triple binding mode and we used them for constructing macrocycles that could also be of interest for chiral recognition and chiral separations. Thus, in this paper we shall review the salient aspects of some macrocycles synthetized in our laboratory, all possessing the phosphonate moiety and a spirobisindanol scaffold and able to act as complexing agents for cations and organic substrates. In particular, we shall describe their NMR characterization, their stereochemistry in solution and in the solid state, and their use as chiral receptors for biorelevant molecules. Chiral HPLC resolution of some of them is also reported.

We have synthetized medium-sized cyclophanes and macrocycles containing phosphonic 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 for complexing lanthanides, as luminescent sensors and for diagnostic bioassays in medicine. Furthermore, because it would be of great interest for biochemistry as well as for pharmacological studies to dispose of preorganized rigid chiral hosts for biorelevant molecules we designed inter alia, some new chiral macrocycles capable of a triple binding mode and we used them for constructing macrocycles that could also be of interest for chiral recognition and chiral separations. Thus, in this paper we shall review the salient aspects of some macrocycles synthetized in our laboratory, all possessing the phosphonate moiety and a spirobisindanol scaffold and able to act as complexing agents for cations and organic substrates. In particular, we shall describe their NMR characterization, their stereochemistry in solution and in the solid state, and their use as chiral receptors for biorelevant molecules. Chiral HPLC resolution of some of them is also reported.

New cleft-like molecules and macrocycles from phosphonate substituted spirobisindanol

CONSIGLIO, GIUSEPPE;FAILLA, Salvatore;
2008

Abstract

We have synthetized medium-sized cyclophanes and macrocycles containing phosphonic 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 for complexing lanthanides, as luminescent sensors and for diagnostic bioassays in medicine. Furthermore, because it would be of great interest for biochemistry as well as for pharmacological studies to dispose of preorganized rigid chiral hosts for biorelevant molecules we designed inter alia, some new chiral macrocycles capable of a triple binding mode and we used them for constructing macrocycles that could also be of interest for chiral recognition and chiral separations. Thus, in this paper we shall review the salient aspects of some macrocycles synthetized in our laboratory, all possessing the phosphonate moiety and a spirobisindanol scaffold and able to act as complexing agents for cations and organic substrates. In particular, we shall describe their NMR characterization, their stereochemistry in solution and in the solid state, and their use as chiral receptors for biorelevant molecules. Chiral HPLC resolution of some of them is also reported.
We have synthetized medium-sized cyclophanes and macrocycles containing phosphonic 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 for complexing lanthanides, as luminescent sensors and for diagnostic bioassays in medicine. Furthermore, because it would be of great interest for biochemistry as well as for pharmacological studies to dispose of preorganized rigid chiral hosts for biorelevant molecules we designed inter alia, some new chiral macrocycles capable of a triple binding mode and we used them for constructing macrocycles that could also be of interest for chiral recognition and chiral separations. Thus, in this paper we shall review the salient aspects of some macrocycles synthetized in our laboratory, all possessing the phosphonate moiety and a spirobisindanol scaffold and able to act as complexing agents for cations and organic substrates. In particular, we shall describe their NMR characterization, their stereochemistry in solution and in the solid state, and their use as chiral receptors for biorelevant molecules. Chiral HPLC resolution of some of them is also reported.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/10346
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 4
  • ???jsp.display-item.citation.isi??? 4
social impact