Supramolecular assemblies of cucurbit[n]urils and 4-aminopyridine controlled by cucurbit[n]uril size (n = 5, 6, 7 and 8)

Lü, Yun; Yu, Zhi-Chao; Yang, Xinan; Dai, Jingjing; Shan, Pei‐Hui; Feng, Xian-Hao; Tao, Zhu; Redshaw, Carl; Xiao, Xin

doi:10.1016/j.cclet.2022.108040

Cited by 10 publications

(4 citation statements)

References 35 publications

(82 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[43,44] Moreover, the host-guest inclusion constant is much higher than other similar macrocyclic host molecules. [45] Therefore, Q[n]s are particularly suitable as assembly units to construct stable Q[n]-based supramolecular self-assembly QSFs, [46,47] which can then be used in gas separation, [48][49][50][51] drug delivery, [52][53][54] chemical sensors, [55][56][57] catalyst carriers, [58][59][60] environmental pollution control [61,62] and other fields. It has been demonstrated that the positively charged outer surface of Q[n] can interact with anionic and electron-rich species, [46] providing binding sites for polyiodide anions.…”

Section: Introductionmentioning

confidence: 99%

A Cucurbit[8]uril‐Based Supramolecular Framework Material for Reversible Iodine Capture in the Vapor Phase and Solution

Lu,

Yu,

Zhang

et al. 2023

Small

Self Cite

View full text Add to dashboard Cite

The safe and efficient management of hazardous radioactive iodine is significant for nuclear waste reprocessing and environmental industries. A novel supramolecular framework compound based on cucurbit[8]uril (Q[8]) and 4‐aminopyridine (4‐AP) is reported in this paper. In the single crystal structure of Q[8]‐(4‐AP), two 4‐AP molecules interact with the outer surface of Q[8] and the two other 4‐AP molecules are encapsulated into the Q[8] cavity to form the self‐assembly Q[8]‐(4‐AP). Iodine adsorption experiments show that the as‐prepared Q[8]‐(4‐AP) not only has a high adsorption capacity (1.74 g· g−1) for iodine vapor but also can remove the iodine in the organic solvent and the aqueous solution with the removal efficiencies of 95% and 91%, respectively. The presence of a large number of hydrogen bonds between the iodine molecule and the absorbent, as seen in the single crystal structure of iodine‐loaded Q[8]‐(4‐AP) (I2@Q[8]‐(4‐AP)), is thought to be responsible for the exceptional iodine adsorption capacity of the material. In addition, the adsorption‐desorption tests reveal that the self‐assembly material has no significant loss of iodine capture capacity after five cycles, indicating that it has sufficient reusability.

show abstract

Section: Introductionmentioning

confidence: 99%

A Cucurbit[8]uril‐Based Supramolecular Framework Material for Reversible Iodine Capture in the Vapor Phase and Solution

Lu,

Yu,

Zhang

et al. 2023

Small

Self Cite

View full text Add to dashboard Cite

show abstract

“…Cucurbiturils cannot conform to the shape of guests, and therefore it is expected that complexation occurs with exceptional specificity and with high association constants [ 19 ]. This unique structure makes CB[n] a prime component in a wide range of applications, such as sensing, catalysis, biomolecular recognition, drug delivery, polymer material, molecular machines [ 20 , 21 ], separation of organic molecules [ 22 ] and in supramolecular assemblies [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Interaction of Benzo(a)Pyrene and Fluoranthene with Cucurbit[n]urils (n = 6–8): Experimental and Molecular Dynamic Study

et al. 2023

View full text Add to dashboard Cite

The inclusion complexes of cucurbit[n]uril, CB[n] (n = 6–8), with poly aromatic hydrocarbon (PAH) Benzo(a)Pyrene (BaP), and fluoranthene (FLT) were investigated carefully in aqueous media. Fluorescence and 1H NMR spectroscopy were used to characterize and investigate the inclusion complexes that were prepared in the aqueous media. The most predominant complexes of both guests with hosts were the 1:1 guest: host complexes. Stability constants of 2322 ± 547 M−1, 7281 ± 689 M−1, 3566 ± 473 M−1 were obtained for the complexes of BaP with CB[6], CB[7], and CB[8], respectively. On the other hand, stability constants of 5900.270 ± 326 M−1, 726.87 ± 78 M−1, 3327.059 ± 153 M−1 were obtained for the complexes of FLT with CB[6], CB[7], and CB[8], respectively. Molecular dynamic (MD) simulations were used to study the mode and mechanism of the inclusion process and to monitor the stability of these complexes in aqueous media at an atomistic level. Analysis of MD trajectories has shown that both BaP and FLT form stable inclusion complexes with CB[7] and CB[8] in aqueous media throughout the simulation time, subsequently corroborating the experimental results. Nevertheless, the small size of CB[6] prohibited the encapsulation of the two PAHs inside the cavity, but stable exclusion complex was observed between them. The main driving forces for the stability of these complexes are the hydrophobic forces, van der Waals interactions, electrostatic effect, the π····π and C‒H···π interaction. These results suggest that BaP and FLT can form stable complexes with CB[n] (n = 6–8) in solution.

show abstract

“…Their structure is characterized by a hydrophobic inner cavity and a hydrophilic port, and they possess strong structural rigidity. Q[n]s can selectively accommodate guest molecules of suitable size and shape, and thus exhibit extensive host-guest chemistry [12][13][14][15][16]. Electrostatic calculations have shown that the port of the cucurbit[n]uril is negative, and the outer surface is more positive, indicating that the outer surface of the cucurbit[n]uril is capable of interacting with anions and electron-rich substances, which would potentially provide sites for binding of iodide ions [17][18].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Self-assembly Formed from Cucurbit[8]uril and p-Hydroxybenzoic Acid

Wang,

Yu,

Bai

et al. 2023

Chem. Res. Chin. Univ.

View full text Add to dashboard Cite

The binding behavior of cucurbit [8]uril (Q[8]) and p-hydroxybenzoic acid (p-HBA) has been investigated using 1 H NMR titration experiments, UV/vis absorption, isothermal titration calorimetry (ITC), and X-ray crystallography. Results revealed that, in solution, the Q[8] can accommodate two p-HBA molecules to form a 1:2 host-guest inclusion complex, namely (p-HBA)2@Q[8]. From a poorly scattering crystal, we were able to identify two symmetry unique Q[8] rings, but with different p-HBA fillings. The structure can be represented as Q[8] + 1.5 p-HBA which gives Q[8]@(p-HBA)2.Q[8]@p-HBA as the structural formula. This supramolecular structure was screened for its ability to iodine capture. The experimental results showed that the adsorption efficiency of the supramolecular organic framework materials for iodine capture was 43.8%, with an equilibrium adsorption capacity of 223.3 mg/g.

show abstract

Supramolecular assemblies of cucurbit[n]urils and 4-aminopyridine controlled by cucurbit[n]uril size (n = 5, 6, 7 and 8)

Cited by 10 publications

References 35 publications

A Cucurbit[8]uril‐Based Supramolecular Framework Material for Reversible Iodine Capture in the Vapor Phase and Solution

A Cucurbit[8]uril‐Based Supramolecular Framework Material for Reversible Iodine Capture in the Vapor Phase and Solution

Investigation of the Interaction of Benzo(a)Pyrene and Fluoranthene with Cucurbit[n]urils (n = 6–8): Experimental and Molecular Dynamic Study

Supramolecular Self-assembly Formed from Cucurbit[8]uril and p-Hydroxybenzoic Acid

Contact Info

Product

Resources

About

Supramolecular assemblies of cucurbit[n]urils and 4-aminopyridine controlled by cucurbit[n]uril size (n = 5, 6, 7 and 8)

Cited by 10 publications

References 35 publications

A Cucurbit[8]uril‐Based Supramolecular Framework Material for Reversible Iodine Capture in the Vapor Phase and Solution

A Cucurbit[8]uril‐Based Supramolecular Framework Material for Reversible Iodine Capture in the Vapor Phase and Solution

Investigation of the Interaction of Benzo(a)Pyrene and Fluoranthene with Cucurbit[n]urils (n = 6–8): Experimental and Molecular Dynamic Study

Supramolecular Self-assembly Formed from Cucurbit[8]uril and p-Hydroxybenzoic Acid

Contact Info

Product

Resources

About

Supramolecular assemblies of cucurbit[n]urils and 4-aminopyridine controlled by cucurbit[n]uril size (n = 5, 6, 7 and 8)