Photo-responsive reversible assembly of gold nanoparticles coated with pillar[5]arenes

Zhou, Qizhong; Zhang, Bin; Han, Deman; Chen, Rener; Qiu, Fangli; Wu, Jiashou; Jiang, Hujiang

doi:10.1039/c4cc09778e

Cited by 32 publications

(15 citation statements)

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“…In the same year, a switchable nanosystem containing AuNPs immobilized by sulfhydryl‐functionalized pillar[5]arene (SH‐P5) was constructed in organic solvents by Zhou et al., in which the assembly activity of the coated nanoparticles was efficiently regulated by the host−guest complexation and anthracene photodimerization of the guest (Figure 4D). [ 50 ] Based on the reversible properties of the thermo‐ and photo‐responsive switches on the AuNPs, the hybrid material SH‐P5‐AuNPs was testified as a promising reusable and separable catalyst in organic phases.…”

Section: Supramolecular Switches Based On Pillar[n]arene Derivatives mentioning

confidence: 99%

Pillar[n]arene‐Based Supramolecular Switches in Solution and on Surfaces

2020

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response to specific physical or chemical stimuli including, but not limited to, pH, light, redox, competitive agents, and tem perature. In particular, pseudorotaxanes, comprising of a rod component without bulky end groups encircled by a wheel entity via noncovalent bonds, can be employed as a superior class of candidates for supramolecular switches. [3] There fore, the study of macrocyclic receptors as the wheel entity of pseudorotaxanes has become one of the research hotspots in the field and received great attention. [4] Following the advance of macrocyclic chemistry based on crown ethers, cyclo dextrins, calixarenes, and cucurbit[n]urils, pillar[n]arenes (n = 5-15), first reported by Ogoshi et al. in 2008, have emerged as a rising star among synthesized macro cycles. [5] Pillar[n]arenes, composed of n hydroquinone units linked by methylene bridges at the 2 and 5positions, pos sess rigid pillarlike molecular structures and πelectron rich hydrophobic cavities that are favorable for the binding of electrondeficient guests. [6] Owing to the highly modi fiable rims of pillar[n]arenes, numerous pillar[n]arene derivatives with diverse functionalities can be facilely obtained either via the cyclization of pretailored 1,4dialkoxybenzene monomers or by postsynthetic modification. [7] The versatile functionalization of pillar[n]arenes beneficially affords their pos sible usages in both organic and aqueous phases, making the host−guest interactions with a large variety of ionic or neutral guests possible. [8] Thus far, pillar[n]arenes and their deriva tives have served as a prominent family of building blocks for the rational creation of supramolecular switches on the basis of the formation of various pseudorotaxanes upon their respon sive complexation with guest entities. [3] Although the dynamic activities of supramolecular switches are generally and fundamentally investigated in solution, growing interest has been focused on the transfer of supra molecular switches from solution phase to more condensed phases, that is, solid surfaces and interfaces. Through the incor poration on rigid solid supports of metal or other inorganic surfaces, the installed switches are able to produce amplified collective switching motions, concurrently modulating the sur face properties and endowing the inherent substrates with valid responses to specific triggers. [2a,9] Hence, the shifting of supra molecular switches from solution to solid surfaces denotes a significant step toward the realization of artificial nanosystems with operationally controllable properties, stimuliresponsive features, and multifunctionalities. The design and synthesis of new synthetic macrocycles has driven the rapid development of supramolecular chemistry and materials. Pillar[n]arenes, as a new type of macrocyclic compounds, are used as a promising type of building blocks for switchable supramolecular systems due to their versatile functionalization and the ability of binding toward various guest molecules. A number of guests can form inclusion complexes with...

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Section: Supramolecular Switches Based On Pillar[n]arene Derivatives mentioning

confidence: 99%

Pillar[n]arene‐Based Supramolecular Switches in Solution and on Surfaces

2020

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“…36 Zhou and co-workers constructed the photoactivated reversible assembly of Au NPs modified by pillar [5]arene with one thiol substituent 5 [5] by introducing a guest molecule with a dynamic covalent bond, i.e., reversible photocycloaddition of anthracene, and a guest part of the quaternary ammonium group ( Figure 4G). 34 The assembly and disassembly processes of the Au NPs were realized by reversible host-guest interactions and photodimerization of terminated anthracene group through activation by temperature or photoirradiation.…”

Section: Solid Nanosurfacesmentioning

confidence: 99%

“…(G) Photoactivated reversible assembly of Au NPs modified by 5[5]. Reproduced from Zhou et al,34 with permission of the Royal Society of Chemistry. (H) Pillar[5]arene-functional polymers used for synthesizing hybrid Au NPs.…”

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confidence: 99%

Molecular-Scale Porous Materials Based on Pillar[n]arenes

Song

Kakuta

Yamagishi

et al. 2018

Chem

270

122

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We begin this review with an introduction to pillar[n]arenes by showing the research history of macrocyclic compounds and the shape, chemical structure, host-guest properties, synthesis, and functionalization of pillar[n]arenes. We then present the modification of pillar[n]arenes on surfaces such as solid and porous surfaces for the creation of molecular-scale porous materials. We also highlight pillar[n]arene assemblies such as one-dimensional channels, twodimensional sheets, and three-dimensional vesicles, as well as the application of porous and soft-porous pillar[n]arene crystals for gas and organic vapor sorption materials. Finally, we discuss the advantages of using pillar[n]arenes for the synthesis of molecular-scale porous materials over other applications of pillar[n]arenes, as well as future perspectives in this exciting field.

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“…Supramolecular structures can respond to external triggers including pH change [41][42][43], light [44][45][46][47][48][49][50], electrochemical stimuli [51,52], and temperature [53,54]. Of particular interest is the responsivity to light due to its non-invasiveness, which can be achieved with molecules that undergo photodimerization [55][56][57], photocleavage [58,59], and cis-trans photoisomerization [60][61][62][63][64][65]. While it had been well-established to access oligomer formation and gelation, a light-switchable particle size has remained a challenge until realized through the mentioned electrostatic self-assembly combining a polyelectrolyte and an ionic azo dye [4].…”

Section: Introductionmentioning

confidence: 99%

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

Zika

Gröhn

2021

Beilstein J. Org. Chem.

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Light- and pH-responsive nano-assemblies with switchable size and structure are formed by the association of a photoacid, anthocyanidin, and a linear polyelectrolyte in aqueous solution. Specifically, anionic disulfonated naphthol derivatives, neutral hydroxyflavylium, and cationic poly(allylamine) are used as building blocks for the ternary electrostatic self-assembly, forming well-defined supramolecular assemblies with tunable sizes of 50 to 500 nm. Due to the network of possible chemical reactions for the anthocyanidin and the excited-state dissociation of the photoacid upon irradiation, different ways to alter the ternary system through external triggering are accessible. The structure and trigger effects can be controlled through the component ratios of the samples. Dynamic and static light scattering (DLS, SLS) and ζ-potential measurements were applied to study the size and the stability of the particles, and information on the molecular structure was gained by UV–vis spectroscopy. Isothermal titration calorimetry (ITC) provided information on the thermodynamics and interaction forces in the supramolecular assembly formation.

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Photo-responsive reversible assembly of gold nanoparticles coated with pillar[5]arenes

Abstract: Organic solvent soluble gold nanoparticles based on pillar[5]arenes were prepared for the first time. They can reversibly aggregate and disassemble based on photo[4+4] cycloaddition of anthracene and can be used as recyclable catalysts.

Cited by 32 publications

References 50 publications

Pillar[n]arene‐Based Supramolecular Switches in Solution and on Surfaces

Pillar[n]arene‐Based Supramolecular Switches in Solution and on Surfaces

Molecular-Scale Porous Materials Based on Pillar[n]arenes

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

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