New Cleft-like Molecules and Macrocycles from Phosphonate Substituted Spirobisindanol

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.

Pyrene-Based Asymmetric Supramolecule: Kinetically Controlled Polymorphic Superstructures by Molecular Self-Assembly

“…Among various physical interactions, inter- and intramolecular H-bonds often serve as useful tools to construct the designed superstructures due to mild physical bonding energy, good selectivity, directionality and reversibility. − Additionally, the self-assembled superstructures can be finely tuned with the help of nanophase separations and intermolecular interactions. The well-defined hierarchical superstructures have been applied in organic sensors, optical devices, and microreactors. − …”

A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix

“…Non covalent interactions are used in order to assemble designed building blocks. These assemblies have various applications such as microreactors [ 2 , 3 ], organic or anionic species sensors [ 4 , 5 ], and materials for optical and electroluminescent devices [ 6 , 7 , 8 ].…”