A general and efficient method to form self-assembled cucurbit[n]uril monolayers on gold surfaces

An, Qi; Li, Guangtao; Tao, Cheng‐an; Li, Yan; Wu, Yiguang; Zhang, Weixia

doi:10.1039/b719927a

Cited by 126 publications

(78 citation statements)

References 27 publications

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“…Complete mixing is achieved during the first channel corner (Figure S1, Supporting Information). Once the CB[5] and the AuNPs are mixed, the CB[5] binds the AuNPs together through interactions between the Au surface and the carbonyl groups of the CB portals . The CB[5]:AuNP concentration ratio places the assembly in a diffusion‐limited assembly regime (Figure S2, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Monitoring Early‐Stage Nanoparticle Assembly in Microdroplets by Optical Spectroscopy and SERS

Salmon

Esteban

Taylor

et al. 2016

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Microfluidic microdroplets have increasingly found application in biomolecular sensing as well as nanomaterials growth. More recently the synthesis of plasmonic nanostructures in microdroplets has led to surface-enhanced Raman spectroscopy (SERS)-based sensing applications. However, the study of nanoassembly in microdroplets has previously been hindered by the lack of on-chip characterization tools, particularly at early timescales. Enabled by a refractive index matching microdroplet formulation, dark-field spectroscopy is exploited to directly track the formation of nanometer-spaced gold nanoparticle assemblies in microdroplets. Measurements in flow provide millisecond time resolution through the assembly process, allowing identification of a regime where dimer formation dominates the dark-field scattering and SERS. Furthermore, it is shown that small numbers of nanoparticles can be isolated in microdroplets, paving the way for simple high-yield assembly, isolation, and sorting of few nanoparticle structures.

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Section: Resultsmentioning

confidence: 99%

Monitoring Early‐Stage Nanoparticle Assembly in Microdroplets by Optical Spectroscopy and SERS

Salmon

Esteban

Taylor

et al. 2016

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“…[68] Li and coworkers made noncovalent CB[n] SAMs by spontaneously adsorbing of CB[n] cavities on gold surfaces utilizing the multivalent interactions between the lone-pairs of the carbonyls and the gold surface ( Figure 5b). [64] Surface-attached CB[n] molecules were found uniform in orientation and hold their carbonyls perpendicular with respect to the gold surface and their cavities open to the outer atmosphere or solution [64] This arrangement maintains the recognition properties of CB[n] and facilitates guest molecules to approach the cavities. However no binding affinities have been reported.…”

Section: Cb[n]-mediated Host-guest Chemistry On Surfacesmentioning

confidence: 99%

“…[58][59][60][61] In general, anchoring of CB[n] to surfaces has been achieved in different ways as depicted in Figure 5. [11,57,[62][63][64][65][66] When able to covalently functionalize the CB [7] macrocycle via covalent modification of CB[n] in a strongly oxidative environment to generate reactive perallyloxy sidegroups Kim and coworkers set out to employ these functional groups to covalently anchor CB [6] and CB [7] onto surfaces. Perallyloxy-CB [6] could be anchored via the thiol-ene reaction with thiol-functionalized glass slides to form a thioether bond between surface and macrocycle ( Figure 5a).…”

Section: Cb[n]-mediated Host-guest Chemistry On Surfacesmentioning

confidence: 99%

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Wiemann

Jonkheijm

2017

Israel Journal of Chemistry

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Supramolecular functional surfaces are at the heart of many materials and medical applications. Increasing interest can be seen for devising new supramolecular functionalization strategies of surfaces. In this review we place particular emphasis on the use of cucurbit[n]urilmediated host-guest complexation as surface functionalization strategy. The state of the art of cucurbit[n]uril-mediated host-guest complexes on surfaces is reviewed. Cucurbit [n] urils (CB[n]) are able to form strong host-guest complexes with affinities that span several orders of magnitudes up to the regime of the biotin-streptavidin pair and that can be modulated by applying remote stimuli provided suitably sensitive guests were selected. Strategies to fabricate stimuliresponsive surfaces creates versatile supramolecular systems and several applications of these types of surfaces are outlined.

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“…[21] To define the nature of the interactions responsible for the formation of the nanostructured Pd@CB-PN, we studied Pd@CB-PN by FTIR and XPS analysis. [17b] The XPS data showed a red shift of the oxygen (1s) peak at 531.5 eV and a new sulfur (2p) peak at 162.8 eV in Pd@CB-PN ( Figure S3), which can be assigned to the carbonyl oxygen interacting with Pd NPs [22] and sulfur in the Pd À S bond, [23] respectively. This, however, does not rule out the possible interaction between the carbonyl portal of the CB[6] units and the NPs since it has been reported that CB[6]-passivated Pd NPs also show no shifts in the C=O stretching vibration.…”

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confidence: 99%

Highly Stable, Water‐Dispersible Metal‐Nanoparticle‐Decorated Polymer Nanocapsules and Their Catalytic Applications

et al. 2014

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A facile synthesis of highly stable, water-dispersible metal-nanoparticle-decorated polymer nanocapsules (M@CB-PNs: M = Pd, Au, and Pt) was achieved by a simple two-step process employing a polymer nanocapsule (CB-PN) made of cucurbit [6]uril (CB[6]) and metal salts. The CB-PN serves as a versatile platform where various metal nanoparticles with a controlled size can be introduced on the surface and stabilized to prepare new water-dispersible nanostructures useful for many applications. The Pd nanoparticles on CB-PN exhibit high stability and dispersibility in water as well as excellent catalytic activity and recyclability in carbon-carbon and carbon-nitrogen bond-forming reactions in aqueous medium suggesting potential applications as a green catalyst.Metal nanoparticles (NPs) have attracted great attention because their unique properties such as high surface to volume ratio, quantum confinement, and surface plasmon effect can contribute to diverse applications in catalysis, nanoelectronics, molecular imaging, biosensors, and nanomedicine. [1] Many of these intriguing properties strongly depend on the size [2] and surface area [3] of the NPs. In addition, support materials (or stabilizers) [4] such as poly-mers, [5] dendrimers, [6] silica, [7] and metal oxides, [8] which are required for some applications (e.g. heterogeneous catalysis), also affect the properties of NPs. Although NPs on solid supports have been successfully employed in catalysis, most systems suffer from shortcomings such as passivation of the NP surface, [9] lack of long-term stability, [10] low dispersibility, [11] deactivation or constant leaching, [12] and low recyclability which limit their capacity and applications. [13] For example, NPs supported on mesoporous/modified silica are unstable, which leads to a rapid decay of the catalytic activity under the reaction conditions. [12] Furthermore, the catalytic activity and stability of NPs in environmentally benign media such as water has important environmental, economical, and safety implications, which are crucial in green chemistry. [14] However, to date, catalysis using NPs on solid supports has seldom been explored in water. [15] Cucurbit[n]uril (CB[n]: n = 5-8, 10) exhibits remarkable recognition abilities with high affinity and selectivity towards organic and inorganic species [16] and stabilizes NPs by forming a passive layer or acting as a protecting agent. [17] We recently reported hollow polymer nanocapsules (CB-PNs) with a thin shell composed of covalently linked cucurbit[6]uril (CB[6]) units, [18] which can be readily synthesized from commercially available allyloxyCB[6] and dithiol (3,6-dioxa-1,8-octanedithiol) in a one-pot reaction. Unique features of CB-PNs include facile tailoring of their surface to prepare new functional materials for various applications such as targeted drug delivery, diagnosis, and imaging. [18c,d] Moreover, CB-PNs synthesized in the presence of excess dithiol have "disulfide loops" protruding from the surface, [18a,b, 19] which can be used as an ...

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A general and efficient method to form self-assembled cucurbit[n]uril monolayers on gold surfaces

Abstract: A general protocol based on spontaneous adsorption of cucurbit[n]uril (CB[n]) molecules through a strong multivalence interaction between CB[n] and gold is described, by which the formation of self-assembled CB[n] monolayers on gold surfaces can be efficiently achieved.

Cited by 126 publications

References 27 publications

Monitoring Early‐Stage Nanoparticle Assembly in Microdroplets by Optical Spectroscopy and SERS

Monitoring Early‐Stage Nanoparticle Assembly in Microdroplets by Optical Spectroscopy and SERS

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Highly Stable, Water‐Dispersible Metal‐Nanoparticle‐Decorated Polymer Nanocapsules and Their Catalytic Applications

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