80262-44-8

Usage

Uses

Used in Drug Delivery Systems:
Cucurbituril is used as a carrier molecule for drug delivery, leveraging its host-guest complex formation ability to encapsulate and protect therapeutic agents. This enhances the delivery, bioavailability, and therapeutic outcomes of drugs, particularly in targeted treatments.
Used in Molecular Switching:
In the field of molecular electronics and sensing, cucurbituril is used as a molecular switch. Its ability to selectively bind with guest molecules allows for the control of molecular interactions, which can be harnessed in the design of responsive materials and devices.
Used in Supramolecular Chemistry:
Cucurbituril serves as a fundamental building block in supramolecular chemistry, where it is used to construct complex molecular architectures and assemblies. Its high selectivity and stability contribute to the formation of well-defined supramolecular structures with potential applications in catalysis, materials science, and nanotechnology.
Used in Analytical Chemistry:
Cucurbituril is employed as a selective recognition agent in analytical chemistry, particularly in the development of sensors and assays. Its ability to form stable complexes with specific analytes makes it a valuable tool for detecting and quantifying target molecules in complex samples.
Used in Environmental Remediation:
Cucurbituril is utilized in environmental applications for the capture and removal of pollutants. Its host-guest complexation properties can be exploited to selectively bind and sequester contaminants from water and air, aiding in pollution control and environmental protection.

InChI:InChI=1/C36H36N24O12/c61-25-37-1-38-14-16-42(26(38)62)4-46-18-20-50(30(46)66)8-54-22-24-58(34(54)70)11-57-23-21-53(33(57)69)7-49-19-17-45(29(49)65)3-41(25)15-13(37)39-2-40(14)28(64)44(16)6-48(18)32(68)52(20)10-56(22)36(72)60(24)12-59(23)35(71)55(21)9-51(19)31(67)47(17)5-43(15)27(39)63/h13-24H,1-12H2/t13-,14+,15+,16-,17-,18+,19+,20-,21-,22+,23+,24-

Upstream product

• 280774-26-7 C₅H₁₃N*C₃₆H₃₆N₂₄O₁₂ 
• 50-00-0 formaldehyd 
• 496-46-8 glycouril 
• 496-46-8 glycoluril 
• 462-95-3 formaldehyde diethyl acetal 
• 950526-90-6 C₂₈H₃₀N₂₀O₁₀ 
• 950526-89-3 glycoluril tetramer 
• 848440-50-6 glycoluril dimer 
• 101241-21-8 3a,6a-diphenylglycoluril 

Relevant academic research and scientific papers

Synthesis of Disubstituted Cucurbit[6]uril and Its Rotaxane Derivative

(Matrix Presented) Synthesis of diphenyl cucurbit[6]uril (CB[6]) has been achieved via co-oligomerization of diphenyl glycoluril and unsubstituted glycoluril. The unsymmetrically substituted CB[6], Ph2CB[B], was further converted to a rotaxane incorporating bis(dinitrophenyl)spermine.

Supramolecular assembly of poly(ionic liquid) nanogel driven by host-stabilized charge transfer interaction

Poly(ionic liquid) (PIL)-based nanogels, functionalized by naphthyl (Np), are fabricated via a facile one-step ternary crosslinking copolymerization in selective solvent. The size of PIL nanogels can be conveniently regulated through the feed ratio of IL monomer to crosslinker. The presence of Np groups in PIL nanogel is confirmed by using ultraviolet–visible (UV–vis), Fourier transform infrared, and X-ray photoelectron spectroscopy measurements. Through introducing cucurbit[8]uril (CB[8]) and bisviologen compound (DEDV) as the host molecule and electron acceptor, respectively, host-stabilized charge transfer (HSCT) interaction is achieved through utilizing Np containing PIL nanogel as the building block. The studies reveal that PIL nanogels can form schistose aggregates in the scale of micrometer via HSCT interaction. The aggregates will be broken in the presence a competitive guest molecule (amantadine) and can recover by adding another host molecule (CB[7]). HSCT interaction among CB[8], DEDV and PIL nanogel is investigated by dynamic light scattering, UV–vis, and Proton nuclear magnetic resonance. Our studies thus provided an applicable strategy for constructing dynamic polymer nanoparticles through noncovalent interaction.

PROCESS FOR THE PREPARATION OF CUCURBITURIL DERIVATIVES

This invention relates to cucurbituril and/or one or more derivatives thereof with low formaldehyde content, to a process of manufacturing said cucurbituril and/or one or more derivatives thereof and to the use of said cucurbituril and/or one or more derivatives thereof, in particular in consumer and industrial products, and in industrial processes.

Synthesis and self-assembly processes of monofunctionalized Cucurbit[7]uril

We present a building-block approach toward functionalized CB[7] derivatives by the condensation of methylene-bridged glycoluril hexamer 1 and glycoluril bis(cyclic ethers) 2 and 12. The CB[7] derivatives Me 2CB[7] and CyCB[7] are highly soluble in water (264 mM and 181 mM, respectively). As a result of the high intrinsic solubility of Me 2CB[7], it is able to solubilize the insoluble benzimidazole drug albendazole. The reaction of hexamer 1 with glycoluril derivative 12, which bears a primary alkyl chloride group, gives CB[7] derivative 18 in 16% isolated yield. Compound 18 reacts with NaN3 to yield azide-substituted CB[7] 19 in 81% yield, which subsequently undergoes click reaction with propargylammonium chloride (21) to yield CB[7] derivative 20 in 95% yield, which bears a covalently attached triazolyl ammonium group along its equator. The results of NMR spectroscopy (1H, variable-temperature, and DOSY) and electrospray mass spectrometry establish that 20 undergoes self-assembly to form a cyclic tetrameric assembly (204) in aqueous solution. CB[7] derivatives bearing reactive functional groups (e.g., N3, Cl) are now available for incorporation into more complex functional systems.

Cucurbit[n]uril formation proceeds by step-growth cyclo-oligomerization

In contrast to the high yield formation of cucurbit[n]uril (CB[n]) from a 1:2 ratio of glycoluril to formaldehyde, the condensation of glycoluril with less than 2 equiv of formaldehyde delivers a reaction mixture that contains glycoluril oligomers (2-6) and CB[n] compounds that lack one or more methylene bridges known as nor-seco-cucurbit[n]urils (ns-CB[n]). In this paper we report the chromatographic purification of C-shaped glycoluril oligomers (dimer-hexamer), their characterization in solution, and their X-ray crystal structures. Quite interestingly, despite being acyclic glycoluril pentamer 5 and hexamer 6 retain the ability to bind to guests typical of CB[6] but are also able to expand their cavity to accommodate larger guests like cationic adamantane derivatives. We performed product resubmission experiments with glycoluril oligomers 2-6 and found preferences for the formation of specific ring sizes during CB[n] formation. A comprehensive mechanistic scheme is proposed that accounts for the observed formation of 2-6 and ns-CB[n]. Overall, the experiments establish that a step-growth cyclo-oligomerization process operates during CB[n] formation.

Mechanism of the conversion of inverted CB[6] to CB[6]

(Figure Presented) Inverted cucurbit[n]urils (iCB[n]) form as intermediates during the synthesis of cucurbit[n]urils from glycoluril and formaldehyde in HCl (85°C). Product resubmission experiments establish that the diastereomeric iCB[6] and iCB[7] are kinetic products that are less stable thermodynamically than CB[6] or CB[7] (>2.8 kcal mol-1). When iCB[6] or iCB[7] is heated under aqueous acidic conditions, a preference for ring contraction is noted in the formation of CB[5] and CB[6], respectively. Interestingly, under anhydrous acidic conditions ring size is preserved with iCB[6] delivering CB[6] cleanly. To establish the intramolecular nature of the iCB[6] to CB[6] conversion under anhydrous, but not aqueous, acidic conditions we performed crossover experiments involving mixtures of iCB[6] and its 13C=O labeled isotopomer 13C12-iCB[6]. An unusual diastereomeric CB[6] with a Moebius geometry (13) is proposed as a mechanistic intermediate in the conversion of iCB[6] to CB[6] under anhydrous acidic conditions. The improved mechanistic understanding provided by this study suggests improved routes to CB[n]-type compounds.

Supramolecular solid-gas complexes: A thermodynamic approach

(Table Presented) Phasing up to complex problems: A thermodynamic approach based on solution data has been proposed for the determination of the stability of gas complexes and elucidation of the selectivity of gas binding. Stability constants, reaction enthalpies, and entropies for the complexation of gaseous guests (n-alkylamines) by solid macrocyclic hosts (β-cyclodextrin, cucurbit[6]uril) were calculated by using the Born-Haber type cycle (see picture).

Controlling factors in the synthesis of cucurbituril and its homologues

The acid-catalyzed synthesis of cucurbit[n]urils from formaldehyde and glycoluril is poorly understood. In this paper, we examine a wide range of reaction conditions that include the effects of acid type, acid concentration, reactant concentrations, and temperature to both probe the mechanism and optimize the yields of isolated cucurbit[n]urils, where n = 5-10. A mechanism for the formation of these cucurbit[n]urils is presented. Individual cucurbit[n]urils were unambiguously identified in reaction mixtures using ESMS and 13C NMR.

Two mechanisms of slow host-guest complexation between cucurbit[6]uril and cyclohexylmethylamine: pH-Responsive supramolecular kinetics

20 times more rapid is the complexation of the organic ammonium ion receptor cucurbit[6]uril (CB6) with cyclohexylmethylamine than with the cyclohexylmethylammonium species (see scheme). Within the narrow pH region around the pKa-value of the amine, the complexation kinetics are accelerated but the binding constant remains essentially unaffected. In this region, the ammonium complex is formed through binding of the amine from followed by fast protonation and not through direct complexation of the ammonium form. Molecular dynamics calculations suggest that the amine form undergoes a direct inclusion into CB6 while the ingression of the ammonium form is retarded by the formation of an association complex, which reacts through a different, higher lying transition state to the inclusion complex.

Host-guest complexes of cucurbituril with 4-amino-4′-nitroazobenzene and 4,4′-diaminoazobenzene in acidic aqueous solutions

The thermodynamics and kinetics of the reaction of cucurbituril (Cuc) with 4-amino-4′-nitroazobenzene (DO3) and 4,4′-diaminoazobenzene (Diam) have been studied in aqueous HCl, and it is shown that DO3 is well suited as an indicator for uncomplexed Cuc (actual concentration of Cuc) and Diam is well suited as an indicator for the total concentration of Cuc (sequestering agent) in aqueous solutions. The formation of 1:1 guest-host complexes is observed. For proton concentrations up to 1 mol dm-3, DO3 reacts according to eqn. (a), with the values for the dissociation constant of DO3H+ log(Ka/dm3 mol-1) = CucH+ + DO3H22+ ? CucH+ + DO3H+ + H+ ? CucH+ + DO3 + 2H+ ? CucDO3H+ + 2H+ (a) -2.42, DO3H22+ log(Kb/dm3 mol-1) = 0.53, for the stability constant of CucDO3H+ log (Kc/mol dm3) = 8.05 and for the rate constant of complex formation log (kf/dm3 mol-1 s-1) = 5.25. Reaction enthalpies and activation energies have also been determined. The complexation of Cuc with Diam has been studied in 0.1-1 mol dm-3 HCl where a very strong complexation has been observed.