Synthesis, X-ray Structure, and Anion-Binding Properties of a Cryptand-Like Hybrid Calixpyrrole

Abstract

The novel cryptand in/out-3, containing two tripyrrolemethane units bridged by three 1,3- diisopropylidenbenzene arms, was readily synthesized by a convergent three-step synthesis. It binds fluoride by inclusion with excellent selectivity with respect to a number of other tested anions. The structure of the free receptor and that of its fluoride complex were investigated in solution by NMR spectroscopy. The solid-state X-ray structure of the free cryptand 3 was also determined.

Anion receptor chemistry: highlights from 2010

“…Proton NMR titrations of a new tripyrrole-methane based cryptand 87 reveal a preferred binding of F À over Cl À , NO 3 À , HSO 4 À , CH 3 COO À and H 2 PO 4 À , added as their tetrabutylammonium salts. 62 Complex formation is kinetically slow in CD 2 Cl 2 . However, the integration of the resonances of free and complexed cryptand results in a calculated stability constant of 1562 M À1 in a 1 : 1 binding mode.…”

Selective recognition and discrimination of H2PO4− and F− based on a cleft-shaped anion receptor incorporating bisamide and bispyrrole groups

“…The formation of a 1:1 complex of 1 with H 2 PO 4 2 was further confirmed through the observation of a main peak (m/z ¼ 597.1) in the negative ion ESI-MS (see Figure 4) (43)(44)(45). No mass peaks assigned to the complexes with other stoichiometries were seen, showing the exclusive formation of a 1:1 complex between 1 and H 2 PO 4 2 .…”

Self assembled macrobicycle and tricycle cages containing pyrrole rings by dynamic covalent chemistry method

“…Such cage molecules have been reported to recognize several analytes such as carbohydrate [9,10], hydrocarbons [11] and anions [12][13][14][15][16][17][18][19][20], and have also been demonstrated for applications such as gas sorption [21][22][23][24], separation [25,26] and sensing [27,28]. It therefore becomes necessary to find a convenient synthetic method for them which facilitates further development of this field.…”