Triamide macrocyclic chloride receptors via a one-pot tandem reduction–condensation–cyclization reaction

Abstract

A pyridine containing triamide macrocycle and its substituted analog have been synthesized in one pot from the corresponding monomer without the use of coupling reagents. The macrocycle can selectively bind chloride ions. The ease of synthesis and chloride-binding properties of the macrocycle make it a highly attractive scaffold for ion-encapsulation, ion-transport and water purification.

Anion-Selective Cholesterol Decorated Macrocyclic Transmembrane Ion Carriers

“…However, in the case of the other ions the order of selectivity is the reverse of the Hofmeister series. The unfunctionalized macrocycle was found to bind with Cl – . A downfield shift as well as sharpening of the amide proton for macrocycle 4 was also observed upon addition of TBACl (Figure b).…”

“…Synthesis of the macrocycles was highly modular wherein desirable pendant groups could be readily appended onto the macrocycle scaffold 5 as shown in Scheme . Macrocycle 5 was easily accessed in one-pot using a method previously developed in our group . Hydrogenolysis of the benzyl groups, followed by treatment with the appropriate R-tosyl group, afforded the requisite functionalized macrocycles 1 – 4 .…”

“…Macrocycle 5 was easily accessed in one-pot using a method previously developed in our group. 44 Hydrogenolysis of the benzyl groups, followed by treatment with the appropriate R-tosyl group, afforded the requisite functionalized macrocycles 1−4.…”

Cyclic vs. acyclic alkyne towards Hg2+ ion detection: combined experimental and theoretical studies

“…S15, ESI †), where, Io and I are the fluorescence intensities of the free probe and that at any concentration of quencher, K is the binding constant and [Q] is the quencher concentration. The association constants for both probes 3 (6.36 Â 10 5 M À1 ) and 4 (1.05 Â 10 5 M À1 ) were also obtained by using the free online software Bindfit, where the fluorescence titration data was fitted in 1 : 2 (non-cooperative) 59 and 1 : 1 binding models, respectively (Fig. S16, ESI †).…”

Macrocyclic Transmembrane Anion Transporters via a One-Pot Condensation Reaction

“…The computed electrostatic potential surface of macrocycle 1 (Figure S7) shows that the aromatic units being electron-deficient substituents can participate in anion−π interactions. The structures of macrocycles 1 and 2 bound with chloride ions (Figure S8) show that the amide NH bonds in the macrocycle can selectively bind with chloride ions via hydrogen bonding, similar to 2,6-diamidopyridyl-derived anion receptors. − The chloride selectivity can also be explained by the trend of Cl¯ > Br¯ > I¯ seen for anion−π interactions . Two types of pores are proposed on the basis of the Hill coefficient (Figure c).…”