Calix[4]arene-Based Receptors with Hydrogen-Bonding Groups Immersed into a Large Cavity

Abstract

A one-pot procedure, which combines the Ritter and Friedel-Crafts reactions, produced the first members of a new type of calix[4]arene-based receptors. The cavity in these receptors is formed by a calix[4]arene framework fixed in the cone conformation and bulky adamantyl or (and) phenylacetylene moieties. Amido and amino groups were used as potential hygrogen bond donors. Preliminary studies revealed interesting complexation properties, in particular, the tetrahedral recognition of water molecules performed by one of the receptors.

Water‐Soluble Molecular Capsules: Self‐Assembly and Binding Properties

“…Tetracarboxycalix [4]arene 3 was obtained in a Br-Li exchange reaction on the precursor tetrabromo derivative [22] with tBuLi in THF at À78 8C followed by quenching with CO 2 . Compounds 1 a and 1 b were synthesized from calix [4] Figure 1) for the protons of the propyl amidinium chains of 2.…”

25,26,27,28-Tetrapropoxycalix[4]arene-5,17-dicarbonitrile

“…Calix[4]arene in 1,3 alternate conformation bearing two nitrile groups was prepared from appropriate bromo derivative (Sýkora et al, 2005) by heating with CuCN in N-methylpyrrolidone (Casnati et al, 1996). Such molecules can be used as a starting material for preparation of ligands for recognition of neutral molecules (Pinkhassik et al, 1998) or neutral molecules and silver cation (Pinkhassik et al, 1997).…”

“…For calix [4]arene derivatives and their uses as supramolecular building blocks, see: Gutsche (2008); Rao & Dey (2004). For applications of the title compound, see: Pinkhassik et al (1997;1998). For details of the synthesis, see: Sý kora et al 2005; Casnati et al (1996).…”

Two structural types of 1,3-alternate tetrapropoxycalix[4]arene derivatives in the solid state

“…After evaporation, the residue was purified using column chromatography on silica gel (petroleum ether-chloroform 4 : 1) to yield 0.14 g (36%) of derivative 9. 5,11,17,23-Tetrabromo-25,26,27,28-tetrapropoxycalix [4]arene (1,3-alternate) 12 30 . A mixture of derivative 11 (2.0 g, 3.37 mmol) and N-bromosuccinimide (6.0 g, 33.7 mmol, 10 equiv.)…”