Synthesis and caesium complexing properties of water-soluble cavitands

Facile, high-yielding synthesis of deepened cavitands: a synthetic and theoretical study

“…[5,18] or by hydrolysis of the tetra(acetoxymethyl)cavitand. [19] Here, we propose NaOH hydrolysis of 3 that affords 4 in excellent yield (81%). Tetrol 4 was employed to synthesize 10 using the easily available benzyl bromide derivative (see Experimental Section, Method B.…”

Impedance interrogated affinity biosensors for medical applications: novel targets and mechanistic studies

“…The binding properties of the host, it must be noted, are solvent-dependent. Although a range of hosts synthesised based on tetrol, tetra(carboxymethyl) and tetra-(diethanolaminomethyl) structures that bind caesium and its radioisotopes have the advantage of being water-soluble (Pellet-Rostaing et al , 1999), a number are predominantly hydrophobic and need prior organic or ionic liquid dispersions before use in aqueous interface systems. Dicyclohexano-18-crown-6 (DC18C6 for Sr 2+ binding) ) is a hydrophobic example and needs either apolar solvents or an ionic liquid dispersion.…”

Anion Complexation by Glycocluster Thioureamethyl Cavitands: Novel ESI‐MS‐Based Methods for the Determination of Ka Values

“…Tetrakis(1-glucosylthioureidomethyl)tetramethyl cavitand (11) 1, 138.8, 125.9, 120.0, 99.2, 84.3, 81.0, 78.2, 73.0, 70.2, 31.2, 21.9 Tetrakis(1-tetraacetylglucosylthiomethyl)tetramethyl cavitand (15): A solution of 2,3,4,6-tetra-O-acetyl-b-glucopyranosylthiol [32] (530 mg, 1.45 mmol) in CH 2 Cl 2 (5 mL) was added to a suspension of K 2 CO 3 (0.95 g, 2.9 mmol) in a solution of tetrakis(bromomethyl)tetramethyl cavitand (1, 289 mg, 0.29 mmol) in CH 2 Cl 2 (15 mL). The reaction mixture was stirred at room temperature for 75 h, whereupon the salts were filtered off.…”

“…Several groups have reported the synthesis of cavitands with an enhanced solubility in water. This requires the introduction of either charged moieties, such as quaternary ammonium, [8] amidinium, [9] pyridinium, [10] carboxylate, [11] phosphoric acid salt, [12] phenoxide, [13] etc., or neutral substituents, such as peptides, [14] diethanolamine, [15] dendritic wedges, [16] Pd-organometallic centers. [17] Saccharides have been used as water-solubilizing moieties in the cases of calix [4]arenes [18] and resorcinols, [19] and there is one example of a cavitand.…”