A cationic water-soluble pillar[5]arene: synthesis and host–guest complexation with sodium 1-octanesulfonate

Abstract

By the introduction of trimethylammonium groups at both upper and lower rims, a cationic water-soluble pillar[5]arene was prepared, which forms a stable 1 : 1 host-guest complex with sodium 1-octanesulfonate in water.

Water-Soluble Pillar[5]arenes: Synthesis and Characterization of the Inclusion Complexes with p-Toluenesulfonic Acid

“…Initial 1,4-dimethoxypillar [5]arene 1 was obtained from commercially available 1,4-dimethoxybenzene by literary method. [6] Further removal of methoxyl protections led to pillar [5]arene 2.…”

“…Initial 1,4-dimethoxypillar [5]arene 1 was obtained from commercially available 1,4-dimethoxybenzene by literary method. [6] Further removal of methoxyl protections led to pillar [5]arene 2. [7] Pillar [5]arene with ethoxycarbonyl fragments 3 was obtained by the reaction of compound 2 with ethyl bromoacetate.…”

“…[4] However, the greatest interest is in using water as a solvent. [5] The solvent properties of water are vital in biology because many biochemical reactions take place only in aqueous solutions. In addition, water is used to transport of biological molecules.…”

Pillararene-based fluorescent indicator displacement assay for the selective recognition of ATP

“…In particular, water-soluble pillararenes are of significance as prosperous hosts for various guests of biological importance [23][24][25][26][27][28]. With their ease of synthetic manipulation, completely different host-guest systems can be realized through the pillararene scaffold [29,30].…”

Supramolecular FRET modulation by pseudorotaxane formation of a ditopic stilbazolium dye and carboxylato-pillar[5]arene

“…Especially, the discovery of water soluble derivatives (WPns) have further extended their applications in various biological systems. Mostly ionic (carboxylato [28][29][30], ammonium [31,32], imidazolium [33]) pillararenes, in particular carboxylato-Pns have been used in binding studies performed in aqueous medium. Carboxylato-pillar [5]arene (WP5), first synthesized by Ogoshi in 2010 [28] is an ideal host for ammonium-containing and electron-deficient guests [34][35][36].…”