Bromine and iodine–cucurbit[6]uril complexes: preparation and applications in synthetic organic chemistry

Reddy, K. Rosi; Cavallini, T. S.; Demets, Grégoire Jean-François; Silva, Luís F.

doi:10.1039/c4nj00284a

Cited by 19 publications

(19 citation statements)

References 19 publications

(29 reference statements)

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“…CB[ n ]s are also not toxic, cheap and resistant to microorganisms, which makes them excellent candidates to replace cyclodextrins for most applications. Our own contribution to this field includes the stabilization of reactive species and drug carriers, and the use of CB[ n ] as structural elements in hybrid composites, as templates for nanoparticle synthesis, or to develop special catalysts and coatings, sensors and specialty polymers . Their ability to host a wide range of substrates is mainly due to the hydrophobicity of the inner cavity lacking hydrogen bond donor/acceptor moieties.…”

Section: Soluble Supramolecular Assembliesmentioning

confidence: 99%

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Correia

Chowdhury

Ramos

et al. 2018

Polymer International

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This review article focuses on supramolecular assemblies involving cucurbit[n]uril‐based containers and viologen guests as key building elements. Cucurbit[n]urils (CB[n], n = 5–8,10) are fascinating hosts forming a wide range of inclusion complexes (caviplexes) with 4,4′‐bipyridinium salts, known as viologens, either as discrete 1:1 inclusion compounds with CB[7] or as ternary inclusion compounds involving two hosts or two guests (2:1 with CB[7] and 1:2 or 1:1:1 with CB[8]). This property is currently being actively exploited to design and prepare self‐assembled dynamic stimuli‐responsive supramolecular polymers including gels, vesicles, films and organized arrays of polymeric microspheres or nanoparticles. This review highlights the main benefits of such polymers and gives an overview of the achievements and progress made in this field over the past decades. © 2018 Society of Chemical Industry

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Section: Soluble Supramolecular Assembliesmentioning

confidence: 99%

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Correia

Chowdhury

Ramos

et al. 2018

Polymer International

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“…Inspired by nature, chemists have attempted to mimic enzyme reactive sites through the host–guest chemistry of bowl‐shaped macrocyclic structures . One class of macrocyclic host molecules, cucurbit[ n ]urils (CB[ n ], where n= 5–8), has been utilized in the catalysis of oxidation, solvolysis, photochemical and metal‐ion assisted reactions …”

Section: Figurementioning

confidence: 99%

Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions

Palma

Artelsmair

et al. 2017

Angewandte Chemie

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The ability to mimic the activity of natural enzymes using supramolecular constructs (artificial enzymes) is a vibrant scientific research field. Herein, we demonstrate that cucurbit[7]uril (CB[7]) can catalyse Diels–Alder reactions for a number of substituted and unreactive N‐allyl‐2‐furfurylamines under biomimetic conditions, without the need for protecting groups, yielding powerful synthons in previously unreported mild conditions. CB[7] rearranges the substrate in a highly reactive conformation and shields it from the aqueous environment, thereby mimicking the mode of action of a natural Diels–Alderase. These findings can be directly applied to the phenomenon of product inhibition observed in natural Diels–Alderase enzymes, and pave the way toward the development of novel, supramolecular‐based green catalysts.

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“…[4][5][6][7][8][9][10] One class of macrocyclic host molecules,c ucurbit[n]urils (CB[n], where n = 5-8), has been utilized in the catalysis of oxidation, solvolysis,p hotochemical and metal-ion assisted reactions. [11][12][13][14][15][16][17][18][19][20] CB[n]s consist of n glycoluril units (where n is typically between 5a nd 8) that are bound via methylene bridges in aring-like arrangement (Figure 1a). [21] Thenumber of repeat units defines the portal size and cavity volume.T he dipolar nature of the carbonyl-fringed portals of CB[n]imparts ahigh cation binding affinity arising from an ion-dipole effect, whereas the inner cavity of CB[n]isremarkably hydrophobic.…”

mentioning

confidence: 99%

Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions

et al. 2017

View full text Add to dashboard Cite

The ability to mimic the activity of natural enzymes using supramolecular constructs (artificial enzymes) is a vibrant scientific research field. Herein, we demonstrate that cucurbit[7]uril (CB[7]) can catalyse Diels-Alder reactions for a number of substituted and unreactive N-allyl-2-furfurylamines under biomimetic conditions, without the need for protecting groups, yielding powerful synthons in previously unreported mild conditions. CB[7] rearranges the substrate in a highly reactive conformation and shields it from the aqueous environment, thereby mimicking the mode of action of a natural Diels-Alderase. These findings can be directly applied to the phenomenon of product inhibition observed in natural Diels-Alderase enzymes, and pave the way toward the development of novel, supramolecular-based green catalysts.

show abstract

Bromine and iodine–cucurbit[6]uril complexes: preparation and applications in synthetic organic chemistry

Cited by 19 publications

References 19 publications

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Dynamic supramolecular polymers built from cucurbit[n]urils and viologens

Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions

Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions

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