Simin Liu

From Packed “Sandwich” to “Russian Doll”: Assembly by Charge‐Transfer Interactions in Cucurbit[10]uril

As the host possessing the largest cavity in the cucurbit[n]uril (CB[n]) family, CB[10] has previously displayed unusual recognition and assembly properties with guests but much remains to be explored. Herein, we present the recognition properties of CB[10] toward a series of bipyridinium guests including the tetracationic cyclophane known as blue box along with electron-rich guests and detail the influence of encapsulation on the charge-transfer interactions between guests. For the mono-bipyridinium guest (methylviologen, MV2+ ), CB[10] not only forms 1:1 and 1:2 inclusion complexes, but also enhances the charge-transfer interactions between methylviologen and dihydroxynaphthalene (HN) by mainly forming the 1:2:1 packed sandwich complex (CB[10]⋅2u2009MV2+ ⋅HN). For guest 1 with two bipyridinium units, an interesting conformational switching from linear to U shape is observed by adding catechol to the solution of CB[10] and the guest. For the tetracationic cyclophane-blue box, CB[10] forms a stable 1:1 inclusion complex; the two bipyridinium units tilt inside the cavity of CB[10] according to the X-ray crystal structure. Finally, a supramolecular Russian doll was built up by threading a guest through the cavities of both blue box and CB[10].

Inhibition and Stabilization: Cucurbituril Induced Distinct Effects on the Schiff Base Reaction

The different effects of cucurbit[7]uril (CB[7]) on the Schiff base reactions in aqueous solution were explored by 1H NMR spectroscopy and single X-ray crystallography. With CB[7], the condensation reaction of aldehyde and primary amine is dramatically inhibited. In contrast, the presence of CB[7] does tremendously stabilize iminium cation in water through ion-dipole interactions. A single crystal structure of the complex of iminium ion 7 with CB[7] grown in water is reported.

Probing guest compounds enabling the facile isolation of cucurbit[10]uril

A large set of commercially available amino compounds were assessed toward binding with cucurbit[10]uril (CB[10] ), with the purpose of facilitating the isolation of pure CB[10]. We found that the addition of a specific guest into a relevant mixture of CB[n] allowed the displacement of CB[5] from CB[10]·CB[5]. Subsequent washing of the resulting precipitate-CB[10]·Gn (G=guest) with dimethyl sulfoxide (DMSO), enabled to get pure CB[10] in a facile and highly efficient way.

Facile synthesis of 1.3 nm monodispersed Ag nanoclusters in an aqueous solution and their antibacterial activities for E. coli

A facile one-pot strategy was developed to prepare ultrastable monodispersed Ag nanoclusters (NCs) in aqueous solution by using ISOBAM-104, as a stabilizing agent. The as-prepared Ag NCs with an average size of 1.3 nm, which can be preserved in water solution for more than one year under ambient conditions without obvious agglomeration, exhibited excellent antibacterial activities for E. coli (DH5α), compared to most of the previously reported results.

A Highly Selective and Strong Anti-Interference Host-Guest Complex as Fluorescent Probe for Detection of Amantadine by Indicator Displacement Assay

Amantadine (AMA) and its derivatives are illicit veterinary drugs that are hard to detect at very low concentrations. Developing a fast, simple and highly sensitive method for the detection of AMA is highly in demand. Here, we designed an anthracyclic compound (ABAM) that binds to a cucurbit[7]uril (CB[7]) host with a high association constant of up to 8.7 × 108 M−1. The host-guest complex was then used as a fluorescent probe for the detection of AMA. Competition by AMA for occupying the cavity of CB[7] allows ABAM to release from the CB[7]-ABAM complex, causing significant fluorescence quenching of ABAM (indicator displacement assay, IDA). The linear range of the method is from 0.000188 to 0.375 μg/mL, and the detection limit can be as low as 6.5 × 10−5 μg/mL (0.35 nM). Most importantly, due to the high binding affinity between CB[7] and ABAM, this fluorescence host-guest system shows great anti-interference capacity. Thus, we are able to accurately determine the concentration of AMA in various samples, including pharmaceutical formulations.

CCDC 1477092: Experimental Crystal Structure Determination

Related Article: Wanjun Gong, Jun Ma, Zhiyong Zhao, Fang Gao, Feng Liang, Haijun Zhang, Simin Liu|2017|J.Org.Chem.|82|3298|doi:10.1021/acs.joc.6b02971