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INORGANICA CHIMICA ACTA · 2021 · IF 2.545

A recyclable cucurbit[6]uril-supported silicotungstic acid catalyst used in the esterification reaction

Wen Xia,Yu-Mei Nie,Na Lei,Zhu Tao,Qiang-Jiang Zhu,Yun-Qian Zhang

The esterification reaction used to prepare butyl paraben (BP) and propyl gallate (PG) catalyzed using a cucurbit[6]uril-supported Keggin-type silicotungstic acid (Q[6]-STA) catalyst has been investigated. The Q[6]-STA catalyst has been characterized using FTIR spectroscopy, XRD, SEM, EDS, thermal analysis, and surface area studies. Q[6]-STA was easy to prepare in high yield and exhibited some advantageous properties, such as high catalytic activity and its convenient recovery. Moreover, a reusability study showed that the Q[6]-STA catalyst was stable and active.

研究领域: 化学工程 · 材料科学
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JOURNAL OF MEMBRANE SCIENCE · 2024 · IF 8.4

Cucurbit[6]uril builds a water channel for improving the water/salt selectivity of polybenzimidazole

Chenchen Zhang,Si Chen,Yi Zhao,Jianqiang Meng

Polybenzimidazole (PBI) has garnered significant interest in desalination due to its exceptional chemical stability and mechanical strength , but suffers from poor water permeability. In this work, different contents of hydroxylated Cucurbit [6]uril (CB [6] were added to PBI to build a “water transport channel”. The effects of CB [6] addition on the chemical structure and surface morphology were analyzed by FTIR, SEM, and Zeta potential , respectively. Based on the solution-diffusion model, the effect of CB [6] on the water/salt transport properties of PBI membranes was thoroughly investigated. The results show that appropriate CB [6] doping can enhance water sorption of PBI through the special “outer hydrophilic and inner hydrophobic cavity” structure, and boost water diffusion with the channeling effect of the hydrophobic CB [6] cavity. While the complexation between the carbonyl group in CB [6] and Na + ions slightly increased salt sorption, the specific cavity structure of CB [6] can significantly decrease salt diffusion by blocking salt ions and increasing transport path tortuosity. The cavity effect of CB [6] was further confirmed by hybridizing CB [6] with biphenylsulfonyl-substituted PBI when the cavity can be occupied. Therefore, the introduction of CB [6] improves the water/salt diffusion selectivity and then the permeability selectivity of PBI. Notably, the PBI@CB [6] membrane with a 0.25 wt% CB [6] loading exhibited a 40-fold increase in water permeability coefficient compared to pure PBI, while experiencing only a slight decrease in salt permeability coefficient, water/salt selectivity almost exceeding the empirical upper bound line of polymers. This work provides a theoretical foundation for the development of high-performance desalination membranes based on macrocyclic molecules such as CB [6].

研究领域: 材料科学 · 环境工程
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY · 2015 ·Vol. 2015 ·期 31 ·6806-6810 · IF 3.065

A Fluorescent 1,5-Naphthalenedisulfonate Anion-Linked Cucurbit[6]uril Framework

Li Liu,Yuhang Yao,Xuefang Zhang,Ce Hao

Graphical A highly ordered 3D framework from 1,5-naphthalenedisulfonate (1,5-NDS) and cucurbit[6]uril (CB[6]) is synthesized, wherein the 1,5-NDS anions act as linkers to connect the CB[6] units together through C–H ··· O H-bonds. The fluorescence wavelength of the assembly structure is blueshifted relative to that of 1,5-NDS and the fluorescence intensity is decreased, which are ascribed to the formed H-bonds. A highly ordered 3D framework from 1,5-naphthalenedisulfonate (1,5-NDS) and cucurbit[6]uril was synthesized and structurally determined by single-crystal X-ray diffraction analysis. The crystal structure demonstrates that the 1,5-NDS anions act as linkers to connect the cucurbit[6]uril units together through C–H ··· O hydrogen bonds between the 1,5-NDS anions and cucurbit[6]uril. Furthermore, with 1,5-NDS as the fluorophore, the fluorescence properties of the corresponding assembly structure were investigated in the solid state. Relative to that observed for 1,5-NDS, the assembly exhibited a blueshift in the fluorescence wavelength from λ = 406 to 340 nm along with decreased fluorescence intensity. Theoretical calculations were in good agreement with the experimental results and disclosed that the fluorescence mechanism of the assembly structure could be ascribed to the hydrogen bonds formed between the 1,5-NDS anion and cucurbit[6]uril.

CAS / MDL: 81-04-9
研究领域: 化学 · 材料科学
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Journal of Water Process Engineering · 2025 · IF 6.7

Cucurbit[6]uril-heteropoly acids self-assemblies for adsorption and photocatalytic synergistic removal of diquat and paraquat in water

Liling Zeng,Xianyan Ao,Manli Xu,Yunqian Zhang,Zhu Tao

The synergistic removal of organic pollutants by adsorption and photocatalysis can be achieved by adsorption of enriched pollutants, followed by photocatalytic degradation to decompose the pollutants into non-toxic substances. In this work, a category of adsorption-photocatalytic bifunctional composite materials Q[6]-HPAs have been developed through the self-assembly of cucurbit[6]uril (Q[6]) and heteropoly acids (HPAs) like phosphomolybdic acid (PMA), phosphotungstic acid (PTA) and silicotungstic acid (STA). These composites exhibit enhanced surface area, structural stability, and extended light absorption into the visible range. Notably, Q[6]-HPAs have surface charge properties that attract cations and an energy band structure suitable for the generation of reactive oxygen species, thus possessing the potential for efficient adsorption and photodegradation of cationic pesticides. Among which, Q[6]-PMA and Q[6]-PTA removed over 95 % of diquat and paraquat through sequential adsorption and photodegradation. Electrostatic attraction drives the adsorption process, and ·O 2 − and ·OH radicals detected via Electron Spin Resonance (ESR) are the key to photodegradation. Ultimately, Liquid Chromatography-Mass Spectrometer (LC-MS) analysis revealed potential degradation intermediates and products, and toxicity analysis was performed.

CAS / MDL: 1910-42-5 12501-23-4
研究领域: 环境科学 · 材料科学
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JOURNAL OF SEPARATION SCIENCE · 2015 ·Vol. 38 ·期 7 ·1082-1089 · IF 2.737

Cucurbit(6)uril immobilized on silica: A novel high-performance liquid chromatographic stationary phase

Liyun Ma,Simin Liu,Qing Wang,Lin Yao,Li Xu

In the present study, one of the new generation of host molecules, cucurbit(6)uril (CB(6)), was immobilized onto silica (CB(6)/SiO 2 ) by a sol–gel approach. CB(6)/SiO 2 was characterized by NMR spectroscopy, Fourier transform infrared spectroscopy, thermogravimetric analysis, and elemental analysis. It was used as a high-performance liquid chromatographic stationary phase and its chromatographic performance was systematically investigated with different types of analytes as probes. The results revealed that the CB(6)/SiO 2 stationary phase exhibited weak hydrophobic and strong hydrophilic properties. Hence, the variables for hydrophilic interaction liquid chromatography, including components and pH of the mobile phase, were further investigated to explore the retention mechanism of this CB(6)/SiO 2 stationary phase. For less polar analytes, both hydrophobic and hydrophilic interactions could contribute to the retention, while for polar analytes, hydrophilic interaction may be predominant. Compared to the tetraethoxylsilane-coated SiO 2 stationary phases, the CB(6)/SiO 2 stationary phase exhibited a different retention behavior toward basic analytes with excellent stability. It is a novel promising hydrophilic interaction liquid chromatography stationary phase.

研究领域: 分析化学 · 材料科学
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PHYSICAL CHEMISTRY CHEMICAL PHYSICS · 2022 ·Vol. 24 ·期 22 ·13773-13783 · IF 3.945

Improved electrochemical properties of polypyrrole with cucurbit[6]uril via supramolecular interactions

Xian-Yi Jin,Xin Dai,Jie Zhao,Qingmei Ge,Mao Liu,Zhu Tao,Hang Cong

A supramolecular polymer was developed through the encapsulation of polypyrrole by cucurbit[6]uril (PPy@Q[6]), which was employed as the electrode material to improve the capacitor ability of conductive polypyrrole. In the optimized ratio of 2 : 1 (CPPy : CQ[6]), the capacitor properties of the supramolecular material were evaluated, and a high specific capacitance of 414 F g−1 at 10 mV s−1 was obtained, which was 3.1 times higher than that of pure polypyrrole (132 F g−1). A comprehensive analysis suggested that the capacitance performances should be relevant to the component, surface area, and pore volume of the materials. The addition of 0.4 M Fe2(SO4)3 into the electrolyte provided a surprising specific capacitance of 3530 F g−1 on the cucurbituril-encapsulated polypyrrole electrode material, with a high energy density of 707 W h kg−1 at a power density of 32 000 W kg−1 and a current density of 8 A g−1. The 81.6% capacitance retention maintained after 1000 cycles revealed the acceptable cycling capacity of the proposed supramolecular supercapacitor system, which demonstrated good performance even at a low temperature of −20 °C.

CAS / MDL: 30525-89-4 57-09-0
研究领域: 材料科学 · 电化学
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INORGANIC CHEMISTRY COMMUNICATIONS · 2022 · IF 3.428

Cucurbit[6]uril-based supramolecular frameworks formed through outer surface interactions and application for iodine adsorption

Jian-Hang Hu,Ran Cen,Ming Liu,Pei-Hui Shan,Timothy J. Prior,Carl Redshaw,Ying Huang,Zhu Tao,Xin Xiao

The interaction between the outer surface of cucurbit[6]uril (Q[6]) and methyl triphenyl phosphorus iodide (MTPI) has been studied in the presence of [CdCl 4 ] 2- . The MTPI is connected to four neighboring Q[6]s through weak interactions such as C-H···π and C-H···O, whilst the [CdCl 4 ] 2- is connected with the portal carbonyl oxygen, glycoside urea methylene and a bridging methylene of a Q[6] molecule via ion–dipole interactions. These interactions were evident from a single crystal X-ray diffraction study of Q[6]-MTPI-[CdCl 4 ] 2- . Furthermore, this complex exhibits a porous structure, which can be described as a Q[6]-based supramolecular framework (QSF), and its ability to adsorb iodine was also investigated.

研究领域: 化学 · 材料科学
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CRYSTAL GROWTH & DESIGN · 2021 · IF 4.076

Controllable Synthesis of Dodecamethylcucurbit[6]uril and Its Application in Separating Phenylenediamine Isomers

Long Cao,Yun-Qian Zhang,Rui-Lian Lin,Jing-Xin Liu,Zhu Tao

By using the method of building blocks, the dodecamethycucurbit[6]uril Me12Q[6] was synthesized and its structure was characterized by multiple techniques. The binding interactions between Me12Q[6] and phenylenediamine (PDA) isomers were also investigated both in the solid state and in aqueous solution. Importantly, the Me12Q[6]/[ZnCl4]2–-based supramolecular framework can selectively accommodate o-PDA rather than its isomers. The present study suggests the practical application of Me12Q[6] in separating PDA isomers and the potential utility of Me12Q[6] in isolating other organic molecules.

研究领域: 化学 · 材料科学
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Small · 2020 ·Vol. 16 ·期 39 ·2002718 · IF 11.459

Cucurbit[6]uril-Derived Sub-4 nm Pores-Dominated Hierarchical Porous Carbon for Supercapacitors: Operating Voltage Expansion and Pore Size Matching

Daping Qiu,Min Li,Cuihua Kang,Jinying Wei,Feng Wang,Ru Yang

The intrinsic properties of carbon-based material and the voltage window of electrolyte are the two key barriers to restrict the energy density of carbon-based supercapacitors (SCs). Herein, a cucurbit[6]uril-derived nitrogen-doped hierarchical porous carbon (CBC x ) with unique pore structure characteristics is synthesized and successfully applied to construct SCs based on different electrolyte systems. Owing to narrow pore size distribution (0.5–4 nm), colossal ion-accessible pore volume, prominent supermesopore volume, and reasonable heteroatom configuration, the CBC x -based SCs demonstrate excellent electrochemical performances with high operating voltages in two distinct systems. The optimal SCs can output a maximum energy/power density of 18 Wh kg −1 (11.1 Wh L −1 )/20 kW kg −1 (12.3 kW L −1 ) with an operating voltage of 1.2 V in potassium hydroxide aqueous electrolyte, as well as an ultralong cycle life of up to 50 000 cycles (0.046% decay per 100 cycles). Furthermore, the optimal SCs deliver an exceptionally high energy/power density of 95 Wh kg −1 (58.4 Wh L −1 )/70 kW kg −1 (43 kW L −1 ) with an ultrahigh operating voltage of 3.5 V in 1-ethyl-3-methylimidazolium tetrafluoroborate electrolyte. This work opens up a new application field for cucurbit[6]uril and provides an alternative avenue for optimizing the performances of carbon-based materials for SCs.

研究领域: 材料科学 · 能源存储技术
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DYES AND PIGMENTS · 2025 · IF 4.2

Alkyl-substituted cucurbit[6]uril–based fluorescent probes for glutamic acid and lysine sensing

Xin Lin,Fang-Fang Shen,Ren-Jie Song

In this study, two novel fluorescent probes, H 1 /G and H 2 /G, were constructed using two alkyl-substituted cucurbit[6]urils (CB[6]s), H 1 and H 2 , and a cationic dye guest, G. The G molecules were encapsulated within the cavities of CB[6] hosts, forming 1:1 host–guest complexes. While free G molecules exhibited negligible fluorescence in solution, the inclusion complexes demonstrated a strong fluorescence signal (618 nm). The detection limits for glutamic acid (Glu) recognition by the two probes were as low as 2.98 × 10 −7  M and 4.20 × 10 −7  M, respectively. Notably, although the two modified CB[6]s differed by only a single substituent, their resulting probes demonstrated different degrees of amino acid recognition ability. The H 2 /G probe was capable of recognizing both Glu and lysine (Lys), while the H 1 /G probe detected only Glu. By employing structurally modified CB[6]s as hosts and constructing CB[6]-based fluorescent probes capable of selectively recognizing non-aromatic amino acids, this study paves the way for the biological applications of CB[6]-based supramolecular host–guest systems.

CAS / MDL: 7647-14-5 9048-46-8
研究领域: 超分子化学 · 分析化学 · 生物有机化学 · 荧光传感
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CHEMICAL PHYSICS LETTERS · 2021 · IF 2.328

Host-guest interaction between cucurbit[6]uril and chain amino acids

Chenrui Jiang,Zhaorui Song,Meriem Fizir,Ping Yang,Meiru Liu,Pierre Dramou,Hua He

The interaction between cucurbit[6]uril and chain amino acids was studied via fluorescence probe method, molecular simulation, Fourier transform infrared spectroscopy, and nuclear magnetic resonance spectroscopy. The experimental results of this work show that the cucurbit[6]uril host possesses a strong binding force with the chain amino acids leucine and methionine, and can form a host–guest inclusion complex. At the same time, the side chain alkyl moieties of the guests leucine, methionine and valine are contained in the hydrophobic cavity of cucurbit[6]uril, but the host–guest interaction between cucurbit[6]uril and valine molecule is weak.

研究领域: 化学 · 生物化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2019 · IF 5.107

Design of cucurbit[6]uril-based hypercrosslinked polymers for efficient capture of albendazole

Dongze Wang,Xuemei Li,Xiangqun Jin,Qiong Jia

In the present study, cucurbit[6]uril-based hypercrosslinked polymers (HCPs) were successfully synthesized and employed for the capture of albendazole, a broad-spectrum anthelmintic drug. Fourier-transform infrared spectroscopy, elemental analysis, powder X-ray diffraction, scanning electron microscopy, thermogravimetric analysis, and N 2 adsorption-desorption measurements were used to prove the successful preparation of the desired HCPs. Thanks to the encapsulation of cucurbit[6]uril toward albendazole and the high surface area of HCPs, remarkable adsorption capacity of albendazole was achieved. The adsorption behavior followed Langmuir adsorption isotherm with a negative value of Gibbs free energy change, suggesting a spontaneous adsorption process. In addition, the kinetics of albendazole adsorption was investigated, which could be described with the pseudo-second-order kinetics model.

研究领域: 材料科学 · 药物化学
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