New cleft-like molecules and macrocycles from phosphonate substituted spirobisindanol.
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.
Consiglio
Giuseppe A
GA
Dipartimento di Metodologie Fisiche e Chimiche per l'Ingegneria, Università di Catania, Viale A. Doria, 6-95125-Catania Italy.
Failla
Salvatore
S
Finocchiaro
Paolo
P
D007189:Indans / Q000737:chemistry*; D028581:Lanthanoid Series Elements / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D007189:Indans; D028581:Lanthanoid Series Elements; D047028:Macrocyclic Compounds; D063065:Organophosphonates; D013141:Spiro Compounds