A Cucurbituril-Based Gyroscane: A New Supramolecular Form This research was supported by the Australian Research Council and the University of New South Wales. G.R.L. acknowledges the award of a Royal Society Fellowship tenable in Australia.

Day, Anthony I.; Blanch, Rodney J.; Arnold, Alan P.; Lorenzo, Susan; Lewis, Gareth R.; Dance, Ian G.

doi:10.1002/1521-3773(20020118)41:2<275::aid-anie275>3.0.co;2-m

Cited by 502 publications

(52 citation statements)

References 28 publications

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“…Complexes composed of two or multiple rings interlocked or held together by noncovalent interactions have intrigued supramolecular chemists for decades not only for their unique and fascinating structures, but also for their potential applications in catalysis and molecular machines . In the systems comprising two rings, [2]catenanes featuring interlocked rings (Figure a) have been well explored, whereas the ring‐in‐ring complexes, in which one macrocycle threads through another with their mean planes roughly orthogonal to each other (Figure b), or two different‐sized macrocycles are essentially parallel/coplanar or adopt other orientations forming Russian dolls, a gyroscane, or a ring‐in‐ring rotaxane, remain challenging goals in noncovalent synthesis . Ring‐in‐ring complexes are also key intermediates for the preparation of molecular Borromean rings .…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Induced Cluster‐to‐Cluster Transformation of Homoleptic Gold(I) Thiolates between Catenane and Ring‐in‐Ring Structures

Chang

et al. 2019

Angew Chem Int Ed

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Supramolecular ensembles adopting ring-in-ring structures are less developed compared with catenanes featuring interlocked rings.W hile catenanes with inter-ring closedshell metallophilic interactions,s uch as d 10 -d 10 Au I -Au I interactions,h ave been well-documented, the ring-in-ring complexes featuring such metallophilic interactions remain underdeveloped. Herein is described an unprecedented ring-inring structure of aA u I -thiolate Au 12 cluster formed by recrystallization of aA u I -thiolate Au 10 [2]catenane from alkane solvents such as hexane,w ith use of ab ulky dibutylfluorene-2-thiolate ligand. The ring-in-ring Au I -thiolate Au 12 cluster features inter-ring Au I -Au I interactions and underwent cluster core change to form the thermodynamically more stable Au 10 [2]catenane structure upon dissolving in, or recrystallization from, other solvents such as CH 2 Cl 2 ,CHCl 3 ,and CH 2 Cl 2 / MeCN.T he cluster-to-cluster transformation process was monitored by 1 HNMR and ESI-MS measurements.D ensity functional theory (DFT) calculations were performed to providei nsight into the mechanism of the "ring-in-ringÐ [2]catenane" interconversions.

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Section: Introductionmentioning

confidence: 99%

Solvent‐Induced Cluster‐to‐Cluster Transformation of Homoleptic Gold(I) Thiolates between Catenane and Ring‐in‐Ring Structures

Chang

et al. 2019

Angew Chem Int Ed

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Section: Cucurbituril (Cb)mentioning

confidence: 99%

“…The macrocycle was named cucurbituril, owing to its similarity to a pumpkin (cucurbitaceae family). The cucurbituril is often abbreviated as CB[n], highlighting the n glycoluril building blocks in the macrocycle [79,80] Even though the calix [4]pyrrole offers an excellent scaffold that can be tailored for the development of potent antioxidants, it has been understudied in this regard. However, the complex of Au and calix [4]pyrrole has been studied for the antioxidant and radical scavenging efficiencies.…”

Section: Cucurbituril (Cb)mentioning

confidence: 99%

Macrocycles and Supramolecules as Antioxidants: Excellent Scaffolds for Development of Potential Therapeutic Agents

et al. 2020

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Oxidative stress due to the high levels of reactive oxygen species (ROS) that damage biomolecules (lipids, proteins, DNA) results in acute inflammation. However, without proper intervention, acute inflammation progresses to chronic inflammation and then to several chronic diseases, including cancer, myocardial infarction, cardiovascular diseases, chronic inflammation, atherosclerosis, and more. There has been extensive research on the antioxidants of natural origin. However, there are myriad possibilities for the development of synthetic antioxidants for pharmacological applications. There is an increasing interest in the identification of novel synthetic antioxidants for the modulation of biochemical processes related to ROS. In this regard, derivatives of supramolecules, such as calix[n]arene, resorcinarene, calixtyrosol, calixpyrrole, cucurbit[n]uril, porphyrin etc. are gaining attention for their abilities to scavenge the free radicals. Supramolecular chemistry offers excellent scaffolds for the development of novel antioxidants that can be used to modulate free radical reactions and to improve the disorders related to oxidative stress. This review focuses on the interdisciplinary approach for the design and development of novel synthetic antioxidants based on supramolecular scaffolds, with potentially protective effects against oxidative stress.

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“…Cucurbit[ n ]urils (Q[ n ]), which are pumpkin-shaped macrocyclic host molecules, have garnered substantial awareness since they can tightly bind to different biological molecules in the solid state and aqueous solution (Kim et al, 2000 ; Day et al, 2002 ; Li et al, 2016 ; Chen et al, 2017a ; Gao et al, 2017a , b ; Wang et al, 2017 ). Several examples of supramolecular assemblies of Q[ n ] and certain BAs have been reported (Masson et al, 2009 ; Chen et al, 2017b ).…”

Section: Introductionmentioning

confidence: 99%

Study on the Binding Interaction of the α,α′,δ,δ′-Tetramethylcucurbit[6]uril With Biogenic Amines in Solution and the Solid State

et al. 2018

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1H NMR spectroscopy and MALDI-TOF mass spectrometry were utilized to examine the binding interaction of α,α′,δ,δ′-tetramethylcucurbit[6]uril (TMeQ[6]) and six biogenic amines (spermine, spermidine, 2-phenethylamine, tyramine, histamine, and tryptamine). Their 1H NMR spectra both at pD = 7 and pD = 3 revealed that four biogenic amines (spermine, spermidine, 2-phenethylamine, and histamine) can fit in the TMeQ[6] cavity, respectively, and other biogenic amines were located outside of the TMeQ[6] portal. In addition, a solid-state evaluation with single-crystal X-ray diffraction analysis showed the binding interaction of spermine, spermidine, 2-phenethylamine, and tyramine with TMeQ[6].

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A Cucurbituril-Based Gyroscane: A New Supramolecular Form This research was supported by the Australian Research Council and the University of New South Wales. G.R.L. acknowledges the award of a Royal Society Fellowship tenable in Australia.

Cited by 502 publications

References 28 publications

Solvent‐Induced Cluster‐to‐Cluster Transformation of Homoleptic Gold(I) Thiolates between Catenane and Ring‐in‐Ring Structures

Solvent‐Induced Cluster‐to‐Cluster Transformation of Homoleptic Gold(I) Thiolates between Catenane and Ring‐in‐Ring Structures

Macrocycles and Supramolecules as Antioxidants: Excellent Scaffolds for Development of Potential Therapeutic Agents

Study on the Binding Interaction of the α,α′,δ,δ′-Tetramethylcucurbit[6]uril With Biogenic Amines in Solution and the Solid State

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