Synthesis, structure, and anion binding of functional oxacalix[4]arenes

Abstract

Oxacalix[4]arenes obtained from the highly efficient, one-pot SNAr reaction were post-macrocyclization functionalized through the reduction of nitro groups and hydrolysis of the ester groups to obtain several derivatives of desired solubility and anion binding property.

Shape-Persistent Oxa- and Aza-calix[4]arene Hybrid Molecular Cage and Naked Eye Sensing of Fluoride

“…Previously we reported synthesis and structure of a nitro and ester functionalized oxacalix [4]arene 1. 13 As most reported oxacalix [4]arene skeletons, it adopts a distorted 1,3-alternate V-shaped conformation, in which two aromatic rings bearing nitro groups diverge with a large dihedral angle, while a smaller dihedral angle exists between the aromatic rings bearing ester groups. We envisioned that if we reduce the nitro groups into amino groups and the electronic properties on the four aromatic rings will change, the conformation of the oxacalix [4]arene skeleton might change: the aromatic rings with more electron withdrawing ester groups might diverge while the other two with electron donating aminos might eclipse?…”

“…Previously we reported synthesis and structure of a nitro and ester functionalized oxacalix[4]­arene 1 . As most reported oxacalix[4]­arene skeletons, it adopts a distorted 1,3-alternate V-shaped conformation, in which two aromatic rings bearing nitro groups diverge with a large dihedral angle, while a smaller dihedral angle exists between the aromatic rings bearing ester groups.…”