Supramolecular assemblies through host–guest complexation between cucurbiturils and an amphiphilic guest molecule

Assaf, Khaleel I.; Alnajjar, Mohammad A.; Nau, Werner M.

doi:10.1039/c7cc09519h

Cited by 36 publications

(21 citation statements)

References 40 publications

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“…The ability of CB8 to encapsulate the perylene‐core and the phenyl/tolyl group in case of PMI1 and PMI3 explains the observed assembly formation at high concentration. Figure S22 shows a proposed binding mode for CB8• PMI1 and CB8• PMI3 that is expected in the extended polymeric structure …”

Section: Resultsmentioning

confidence: 89%

Structural Effects on Guest Binding in Cucurbit[8]uril‐Perylenemonoimide Host‐Guest Complexes

et al. 2018

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A series of water‐soluble fluorescent perylene dyes (perylenemonoimides PMI1, PMI2, and PMI3) with two aromatic binding units (a perylene‐core and a phenyl group) as guest molecules for binding with cucurbit[8]uril (CB8) were synthesized. The guest structure was varied by modifying the phenyl group and the spacer between the two binding units. Differences in binding, self‐assembly, and optical properties of the corresponding host‐guest complexes were observed. At low micromolar concentrations, a highly emissive 1:1 CB8•PMI1 complex with high binding affinity (Ka=1.5 x 107 M–1) was formed in water. Interestingly, at higher concentrations of the CB8•PMI1 complex (e. g., >10–4 M), non‐emissive self‐assembled nanowires were formed. In comparison, the binding affinity of CB8•PMI2 and CB8•PMI3 was determined to be only 5.0 x 105 M–1 and 1.7 x 104 M–1, respectively. The host‐guest complexes with various binding affinities could serve as fluorescent displacement probes for the detection of a range of CB8‐binding guest analytes.

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Section: Resultsmentioning

confidence: 89%

Structural Effects on Guest Binding in Cucurbit[8]uril‐Perylenemonoimide Host‐Guest Complexes

et al. 2018

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“…6) and the precipitate, the bound peaks of G2 were found to fully disappear in 60 min, while a singlet peak at 3.1 ppm appeared and remained, and the yellow precipitate contained no CB [8] and was soluble in DMSO and CDCl 3 . First, we suspected that the precipitate was anthraquinone, because anthracene derivatives can easily be oxidized, 45,46 despite the photoreaction being conducted under N 2 atmosphere. However, the NMR signals for the precipitate did not match those of anthraquinone.…”

Section: Complexation Of G2 With Cb[n] and Photoreactions Of Complexesmentioning

confidence: 99%

Expected and unexpected photoreactions of 9-(10-)substituted anthracene derivatives in cucurbit[n]uril hosts

Liu

Zhang

et al. 2020

Chem. Sci.

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“…Molecular recognition in water is the basis for many vital processes [ 12 , 13 ]. A significant number of macrocyclic compounds which are able to bind guest molecules in water (cyclodextrins [ 14 ], cucurbiturils [ 15 ], calixarenes [ 16 ] and thiacalixarenes [ 17 , 18 , 19 ]) have been synthesized. Pillararenes are new type of synthetic hosts with an excellent ability to molecular recognition [ 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

Nazarova

Shurpik

Padnya

et al. 2020

IJMS

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Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (S-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and 1H NMR spectroscopy. This work demonstrates the first case of using S-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of S-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.

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Supramolecular assemblies through host–guest complexation between cucurbiturils and an amphiphilic guest molecule

Cited by 36 publications

References 40 publications

Structural Effects on Guest Binding in Cucurbit[8]uril‐Perylenemonoimide Host‐Guest Complexes

Structural Effects on Guest Binding in Cucurbit[8]uril‐Perylenemonoimide Host‐Guest Complexes

Expected and unexpected photoreactions of 9-(10-)substituted anthracene derivatives in cucurbit[n]uril hosts

Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

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