In the present work, we have designed and synthesized a triphenylamine modified cyanophenylenevinylene derivative (TPCI), which can self-assembly with cucurbit[6]uril (CB[6]) and cucurbit[8]uril (CB[8]) through host-guest interactions to form supramolecular complexes (TPCI-CB[6]) and supramolecular polymers (TPCI-CB[8]) in the aqueous solution. The supramolecular assemblies of TPCI-CB[6] and TPCI-CB[8] not only exhibited high singlet oxygen (¹O₂) production efficiency as photosensitizers, but also realized the application in the construction of artificial light-harvesting systems due to the excellent fluorescence properties in the aqueous solution. The production efficiency of ¹O₂ has been effectively improved after the addition of CB[6] and CB[8] for TPCI, which were applied as efficient photosensitizers in the photooxidation reactions of thioanisole and its derivatives with the highest yield of 98% in the aqueous solution. The excellent fluorescence properties of TPCI-CB[6] and TPCI-CB[8] can be used as energy donors in artificial light-harvesting systems with energy acceptors sulforhodamine 101 (SR101) and cyanine dye 5 (Cy5), in which one-step energy transfer processes of TPCI-CB[6]+SR101 and TPCI-CB[8]+Cy5, and a two-step sequential energy transfer process of TPCI-CB[6]+SR101+Cy5 were constructed to simulate the natural photosynthesis system.

01 May 2023·Microchimica Acta

Cucurbit[8]uril-mediated SERS plasmonic nanostructures with sub-nanometer gap for the identification and determination of estrogens

Article

Author: Xu, Pei ; Teng, Yuanjie ; Li, Xin ; Pan, Zaifa ; Shao, Kang ; Chen, Yingxin ; Sun, Nan

The SERS intensity of analytes is primarily influenced by the density and distribution of hotspots, which are often difficult to manipulate or regulate. In this study, cucurbit[8]uril (CB[8]), a kind of rigid macrocyclic molecule, was introduced to achieve ~ 1-nm nanogap between gold nanoparticles to increase the density of SERS hotspots. Three kinds of estrogens (estrone (E1), bisphenol A (BPA), and hexestrol (DES)) which are molecules with weak SERS signals were targeted in the hotspots by CB[8] to further improve the sensitivity and selectivity of SERS. It was demonstrated that CB[8] can link gold nanoparticles together through carbonyl groups. In addition, the host-guest interaction of CB[8] and estrogens was proved from the nuclear magnetic resonance hydrogen and infrared spectra. In the presence of CB[8], the SERS intensities of E1, BPA, and DES were increased to 19-fold, 74-fold, and 4-fold, respectively, and the LOD is 3.75 µM, 1.19 µM, and 8.26 µM, respectively. Furthermore, the proposed SERS method was applied to actual milk sample analysis with recoveries of E1 (85.0 ~ 112.8%), BPA (83.0 ~ 103.7%), and DES (62.6 ~ 132.0%). It is expected that the proposed signal enlarging strategy can be applied to other analytes after further development.

01 Jan 2023·Chemosphere

Construction of self-healing polyethersulfone ultrafiltration membrane by cucurbit[8]uril hydrogel via RTIPS method and host-guest chemistry

Article

Author: Liu, Shenghui ; Jiang, Haotian

In this work, the self-healing polyethersulfone ultrafiltration membrane constructed by host-guest chemistry between cucurbit [8]uril (CB [8] is a family of macrocyclic compounds comprising 8 glycoluril units) and two guest molecules based on reverse thermally induced phase separation (RTIPS) method was developed, which had excellent self-healing performance, better mechanical properties, and high permeation flux and BSA rejection rate. The membrane autonomously restored it BSA rejection rate up to about 89% from rejection rate levels as low as 21% after damage. The observed self-healing performance were attributed to the swelling of pore-filled CB [8] hydrogel into the damage position, the molecular interdiffusion of the hydrogel chains, the strong hydrogen bond of the hydrogel chains and the host-guest interaction between CB [8] and two guest molecules (HEC-Np and PVA-MV). SEM morphologies illustrated that the prepared pore-filled membrane via the RTIPS method had homogeneous and porous skin surface and sponge-like cross-section, which imparted the prepared membranes with improved permeability and better mechanical properties. Properties of MR-CB [8] membranes, which varied with increased content of CB [8], were evaluated by permeability, water contact angle, thermogravimetric analysis (TGA), mechanical properties, FRR, scanning electron microscope (SEM) and atomic force microscopy (AFM). The contact angle water showed that CB [8] hydrogel enhanced the surface hydrophilicity of the prepared membrane. TGA illustrated that the thermal stability improved with the increased content of CB [8]. The optimal pore-filled CB [8] hydrogel membrane (MR-CB [8]₂) exhibited that the pure water flux reached 2100.5 L/m² h, while the BSA rejection rate remained at 86.0%. The results of this work suggested pore-filled CB [8] hydrogel membrane was a more promising way to develop polyethersulfone ultrafiltration membranes with self-healing performance.

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Indication	Highest Phase	Country/Location	Organization	Date
Hemorrhage	Preclinical	-	Canopus Holding SA	-
Hemorrhage	Preclinical	US	Canopus Biopharma, Inc.	-
Hemorrhagic Fever, Ebola	Preclinical	US	-	-
Hemorrhagic Fever, Ebola	Preclinical	-	Canopus Holding SA	-

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