Synthesis of Surface-Modified Nanoparticles via Cycloaddition-Reactions

Binder, Wolfgang H.; Petraru, Laura; Sachenshofer, Robert; Zirbs, Ronald

doi:10.1007/s00706-006-0483-3

Cited by 30 publications

(22 citation statements)

References 15 publications

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“…Two recent examples have demonstrated the versatility of the click reaction on nanoparticles (NPs), namely on Au NPs [95] as well as on CdSe NPs and polyhedral oligomeric silsesquioxanes (POSS). [96] The transformation of the conventional Au monolayer chemistry to those of NPs is demonstrated in Scheme 50. Thus a conventional vazido-alkyl ligand is generated on Au NPs (diameter %2.0 nm) by a nucleophilic displacement reaction (bromomethyl/azidomethyl exchange) and subsequent click reaction with acyl-activated acetylene ligands 121.…”

Section: Click Reactions On Surfaces (Including Carbon Nanotubes and mentioning

confidence: 99%

‘Click’ Chemistry in Polymer and Materials Science

Binder

Sachsenhofer

2007

Macromol. Rapid Commun.

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IntroductionThe azide/alkyne 'click' reaction [1] (also termed the Sharpless 'click' reaction) is a recent re-discovery of a reaction fulfilling many requirements for the affixation of ligands onto polymers by post-modification processes, which include a) often quantitative yields, b) a high tolerance of functional groups, c) an insensitivity of the reaction to solvents, irrespective of their protic/aprotic or polar/ non-polar character, and d) reactions at various types of interfaces, such as solid/liquid, liquid/liquid, or even solid/ solid interfaces. The present review focuses on issues related to the reaction itself as well as on the wide applications in polymer science, material, and surface science.The basic reaction, which is nowadays summed up under the name 'Sharpless-type click reaction', is a variant of the Huisgen 1,3-dipolar cycloaddition reaction [2a,2b] between C-C triple, C-N triple bonds, and alkyl-/aryl-/ sulfonyl azides (see Scheme 1).The relevant outcomes of this reaction are tetrazoles, 1,2,3-triazoles, or 1,2-oxazoles (Scheme 1a-c, respectively). Besides the 1,3-dipolar cycloaddition reaction, classical Diels-Alder-type reactions (Scheme 1d) have been used extensively for the functionalization of polymeric materials and surfaces. [3] These reactions are located within a series of reactions named click reactions, which is defined by a gain of thermodynamic enthalpy of at least 20 kcal Á mol À1 , [1] thus leading to reactions characterized by high yields, simple reaction conditions, fast reaction times, and high selectivity. Among many reactions tested, the 1,3-dipolar cycloaddition process has emerged as the method of choice to effect the requirements of ligating two ReviewThe modification of polymers after the successful achievement of a polymerization process represents an important task in macromolecular science. Cycloaddition reactions, among them the metal catalyzed azide/alkyne 'click' reaction (a variation of the Huisgen 1,3-dipolar cycloaddition reaction between terminal acetylenes and azides) represents an important contribution towards this endeavor. They combine high efficiency (usually above 95%) with a high tolerance of functional groups and solvents, as well as moderate reaction temperatures (25-70 8C). The present review assembles recent literature for applications of this reaction in the field of polymer science (linear polymers, dendrimers, gels) as well as the use of this and related reactions for surface modification on carbon nanotubes, fullerenes, and on solid substrates, and includes the authors own publications in this field. A number of references (>100) are included.

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Section: Click Reactions On Surfaces (Including Carbon Nanotubes and mentioning

confidence: 99%

‘Click’ Chemistry in Polymer and Materials Science

Binder

Sachsenhofer

2007

Macromol. Rapid Commun.

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866

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“…Likewise, TiO 2 nanoparticles with surface hydroxyl group can form a surface complex with the active NCO groups on tolylene diisocyanate (TDI) 66 . Cycloaddition and Brust-Schiffrin method are two other popular approaches to the functionalization of nanoparticle surfaces [67][68][69] .…”

Section: Surface Modification Based On Organic Reactionsmentioning

confidence: 99%

Surface Modifications and Applications of Magnetic and Selective Nonmagnetic Nanoparticles

Shen

Yang

2009

Annual Review of Nano Research

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“…Despite reviewing the literature as well as many of our own experiments (10,45,(82)(83)(84)(85)(86)(87)(88)(89)(90), it is difficult to describe the "best" catalytic system.…”

Section: Catalystsmentioning

confidence: 99%

“…This effect has been demonstrated in the azide/alkyne "click" reaction within the pocket of enzymes (ABPP) (17,42,71,278) by direct microcontact printing (72,73) or via AFM tips (74), thus opening the chance for a sufficiently complete reaction at an interface. Thus a large variety of "click" reactions on SAMs (45,89,145,237,263,264,(283)(284)(285)(286)(287)(288)(289)(290), polymeric surfaces (57,125,190,246,274,291,292), nanoclays (293), LbL layers (229,246), BCP micelles (136,137), polymersomes (247)(248)(249), and liposomes (250)(251)(252) have been reported. In the case of SAMs the use of appropriately azide- (45,109,(283)(284)(285)(286) or alkyne-functionalized …”

Section: Click Reactions On Surfaces Andmentioning

confidence: 99%

“Click” Chemistry in Macromolecular Synthesis

Binder

Zirbs

2009

Encyclopedia of Polymer Science and Technology

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The concept of self-healing polymers requires fast and efficient crosslinking processes, ideally based on catalytic reactions. Recently, we have developed a clickbased concept to enable self-healing properties in polymeric materials, with a focus on fast crosslinking processes. Basically, liquid reagents were encapsulated and thus can be activated by a catalytic system, inherently present within the polymer-matrix. As especially the combination of self-healing properties of nanocomposite-materials in aerospace industry deems valuable in terms of property-optimization, we focus on crosslinking processes under mild conditions, based on the copper(I)-catalyzed alkyne-azide "click" cycloaddition reaction (CuAAC). Thus we have immobilized copper(I) catalysts onto the surface of nanoparticles, on the one hand to increase the stability of the catalyst and to stimulate the self-healing processes, on the other hand to enhance the properties of the polymeric nanocomposites via the presence of the nanoparticles. For this purpose the surface of different types of nanoparticles has been chemically modified, in the subsequent step immobilizing the corresponding Cu(I) catalyst coordinatively onto their surfaces. The prepared immobilized Cu(I) were extensively characterized via TGA, XRD and TEM, furthermore demonstrating and optimizing the activity of the immobilized catalyst for all types of "click"-reactions.

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Synthesis of Surface-Modified Nanoparticles via Cycloaddition-Reactions

Cited by 30 publications

References 15 publications

‘Click’ Chemistry in Polymer and Materials Science

‘Click’ Chemistry in Polymer and Materials Science

Surface Modifications and Applications of Magnetic and Selective Nonmagnetic Nanoparticles

“Click” Chemistry in Macromolecular Synthesis

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