Synthesis of a Bile Acid-Based Click-Macrocycle and Its Application in Selective Recognition of Chloride Ion

Abstract

A novel method for the synthesis of a bile acid-based macrocycle has been developed using click chemistry. The 1,2,3-triazolium derivative of the macrocycle shows remarkable selectivity in binding of chloride ion.

Dual Role of the 1,2,3‐Triazolium Ring as a Hydrogen‐Bond Donor and Anion–π Receptor in Anion‐Recognition Processes

“…[8] Theb inding ability of C(5)ÀH···A À (A = Anion) is strongly enhanced by converting the 1,2,3-triazole unit into a1 ,2,3-triazolium cation;t he latter is expected to be an even-more-efficient anion captor,a nd uses anion-p interactions as an alternative binding mechanism. [9,10] It is well known that anion-p interactions participate in the formation of robust recognition motifs and it was expected that these complexes would exhibit very large binding energies due to the strong electrostatic effects that dominate the interaction. [11] Thec helating abilityo f1 ,2,3-triazoliuml igands to dianions canb ee asilyt uned by transforming thel igands into tridentate structures or creating multivalentm acrocycles.…”

Nitrogen-Containing Macrocycles Having a Carbohydrate Scaffold

“…The most useful variant involves a controlled 1,3-dipolar cycloaddition of azides and acetylenes (Huisgen reaction 151,152 ) catalyzed by Cu(I) species, which regioselectively provides 1,4-substituted 1,2,3-triazoles. [155][156][157] We had previously described an application of the 1,2,3-triazole chemistry in the syntheses of carbohydrate-containing macrocycles (Schemes 19,20,40,44,and 49). [155][156][157] We had previously described an application of the 1,2,3-triazole chemistry in the syntheses of carbohydrate-containing macrocycles (Schemes 19,20,40,44,and 49).…”

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

“…Later, two modern synthetic approaches based on metal-catalyzed reactions were applied for the modification of bile acids – cross-coupling [28–29] (Scheme 1) and Cu(I)-catalyzed cycloaddition of azides to alkynes (Fig. 1) [11,16,30–32]. …”