Efficient Synthesis of Ditopic Polyamide Receptors for Cooperative Ion Pair Recognition in Solution and Solid States

Abstract

Following a late-stage functionalization strategy, a series of heteroditopic cryptand receptors were prepared in three steps only from 1,4-dioxane. As evidenced by H NMR spectroscopic and solid state analyses, these polyamide-crown ether conjugates present general ion pair binding capacity towards salts of monovalent cations and linear triatomic anions.

Combined reversible switching of ECD and quenching of CPL with chiral fluorescent macrocycles

“…Presumably, the amide bonds rotate and the resulting inward orientation of the C O bonds helps complex the cations. 26 As a consequence, the aromatic rings part from each other, elongating the distance between the chromophores ( Fig. 2 ).…”

From reactive carbenes to chiral polyether macrocycles in two steps – synthesis and applications made easy?

“…In fact, treatment of precursors 1c with dicarbonyl dichloride reagents afforded macrocycles 7 in moderate to good yields (35-60%, Scheme 1). 26 Binding properties of this new class of cryptands towards monovalent alkali cations, common anions and combined salts were studied in solution by 1 H NMR spectroscopy and by X-ray diffraction analysis for solid state structures. Compounds 7 were found to be cooperative heteroditopic receptors for salts as the presence of both cations and anions is needed for favorable interactions.…”

Stereoselective deconjugation of macrocyclic α,β-unsaturated esters by sequential amidation and olefin transposition: application to enantioselective phase-transfer catalysis

“…This reaction tolerates a large variety of aromatic amines. [4][5][6][7][8]11 However, despite major efforts by the group, it was never possible to achieve the analogous 1 → 3 transformation with aliphatic amines instead of anilines. Of the two consecutive steps, it was clearly the first one that was problematic under the previous conditions.…”

“…Various applications have been developed for compounds 2. In fact, such bis(aromatic) derivatives have been used as pH-independent nanosensors, 5 heteroditopic receptors for salts, 6 ratiometric luminescent or reversible chiroptical switches 7 and circularly-polarized electrochemiluminescent emitters. 8 Herein, the stereoselective synthesis of macrocycles of type 3 bearing two aliphatic amide functional groups is reported (Scheme 1B, right).…”