A Self‐Assembled Cage for Wide‐Scope Chiral Recognition in Water

Abstract

Herein, we report the self-assembly of an anionic homochiral octahedral cage by condensing six Ga 3+ cations and four trisacylhydrazone ligands.T he robust nature of the hydrazone bond renders the cage stable in water,where it can take advantage of the hydrophobic effect for host-guest recognition. In addition to the internal binding site,n amely, the inner cavity,the octahedral cage possesses four "windows", each of which represents an external binding site allowing peripheral complexation. These internal and external binding sites endowthe cage with the capability to bind abroad range of guests whose sizes could either be smaller than or exceed the volume of the cage'si nner cavity.U pon accommodation of ac hiral guest, one of the two cage enantiomers becomes more favored than the other,p roducing circular-dichroism (CD) signals.T he CD signal intensity of the cage is observed to be proportional to the ee value of the chiral guest, allowing aquantitative determination of the latter.

Supramolecular cuboctahedra with aggregation-induced emission enhancement and external binding ability

“…S19, ESI † ). 50 Three sets of signals belong to free S2 (black), one porphyrin adduct S2⊃G (green), and two porphyrin adducts S2⊃G 2 (yellow), respectively, with continuous charge states from 11+ to 21+, in Fig. 8b , consistent with the TWIM-MS spectrum ( Fig.…”

Circular Dichroism Based Chirality Sensing with Supramolecular Host–Guest Chemistry

“…Although calibration curves have been constructed for several hosts with a variety of chiral analytes, [25,28,54,55,66] they are rarely used for the determination of ee values and the absolute configuration of real samples. We have demonstrated that amide naphthotubes can be used for chirality analysis of the products from the catalytic asymmetric epoxidation of styrene and asymmetric hydrogenation of acetophenone.…”

“…Therefore, they can be used for chirality analysis. Li and co‐workers [28] reported an anionic homochiral octahedral cage ( 9 , Figure 6a) self‐assembled from six Ga 3+ cations and four trisacylhydrazone ligands in water. The cage is a racemic mixture consisting of two homochiral enantiomers.…”

Water-Soluble Self-Assembled Cage with Triangular Metal–Metal-Bonded Units Enabling the Sequential Selective Separation of Alkanes and Isomeric Molecules

“…Since the first serendipitous isolation of a self-assembled tetrahedral coordination cage, the development of discrete three-dimensional (3D) coordination cages, − especially water-soluble molecular cages comprising accessible cavities, has attracted a great deal of research attention. − Such molecular cages adopt different geometries and include accessible hydrophobic inner spaces; indeed, these species have found widespread use in the selective encapsulation, separation, and release of a variety of guest molecules, as well as in the promotion of chemical reactions in the aqueous phase. − The design and development of new systems that can distinguish between structurally similar compounds would provide new applications for self-assembled tetrahedral coordination cages, especially in the context of the separation of isomeric molecules.…”