Click-chemistry for surface modification of monodisperse-macroporous particles

Bayraktar, Aslıhan; Saraçoğlu, Berna; Gölgelioğlu, Çiğdem; Tuncel, Alï

doi:10.1016/j.jcis.2011.08.071

Cited by 13 publications

(10 citation statements)

References 14 publications

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“…A variety of functional materials including fluorescent dyes, proteins, polyelectrolyte, and inorganic materials have been introduced for further surface functionalization of polymer particles. In order to functionalize solid substrates including polymer particles, various surface modification techniques such as layer‐by‐layer self‐assembly, click chemistry, grafting‐to, and grafting‐from polymerization have been energetically developed. Recently, click chemistry, especially azide‐alkyne cycloaddition (Huisgen cycloaddition), has been attracting much attention because of its high selectivity, chemical orthogonality, adaptability in aqueous media.…”

Section: Introductionmentioning

confidence: 99%

Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Kasuya

Taniguchi

Motokawa

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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We developed a novel fluorescence labeling technique for quantification of surface densities of atom transfer radical polymerization (ATRP) initiators on polymer particles. The cationic P(St-CPEM-C 4 DMAEMA) and anionic P(St-CPEM) polymer latex particles carrying ATRP-initiating chlorine groups were prepared by emulsifier-free emulsion polymerization of styrene (St), 2-(2-chloropropionyloxy)ethyl methacrylate (CPEM), and N-n-butyl-N,N-dimethyl-N-(2-methacryloyloxy)ethylammonium bromide (C 4 DMAEMA). ATRP initiators on the surface of polymer particles were converted into azide groups by sodium azide, followed by fluorescent labeling with 5-(N,Ndimethylamino)-N 0 -(prop-2-yn-1-yl)naphthalene-1-sulfonamide (Dansyl-alkyne) by copper-catalyzed azide-alkyne cycloaddition (CuAAC). The reaction time required for both azidation of ATRP-initiating groups and successive fluorescence labeling of azide groups with Dansyl-alkyne by CuAAC were investigated in detail by FTIR and fluorescence spectral measurement, respectively. The ATRP initiator densities on the cationic P(St-CPEM-C 4 DMAEMA) and anionic P(St-CPEM) particle surfaces were estimated to be 0.21 and 0.15 molecules nm 22 , respectively, which gave close agreement with values previously determined by a conductometric titration method. The fluorescence labeling through click chemistry proposed herein is a versatile technique to quantify the surface ATRP initiator density both on anionic and cationic polymer particles.

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Section: Introductionmentioning

confidence: 99%

Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Kasuya

Taniguchi

Motokawa

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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“…Due to its stability and easy functionalization with both azide and alkyne groups, horseradish peroxidase (HRP) is the most-used enzyme. The tagged enzyme immobilization can be performed at room temperature on various conductive materials while maintaining its bioactivity [80]. The electrochemical detection can be performed indirectly through redox probes, or directly by means of the electron transfer (ET) between the enzyme active center and the electrode surface…”

Section: Electrochemical Biosensors Prepared Using Cuaacmentioning

confidence: 99%

Copper(I)-Catalyzed Click Chemistry as a Tool for the Functionalization of Nanomaterials and the Preparation of Electrochemical (Bio)Sensors

Yáñez‐Sedeño

González‐Cortés

Campuzano

et al. 2019

Sensors

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Proper functionalization of electrode surfaces and/or nanomaterials plays a crucial role in the preparation of electrochemical (bio)sensors and their resulting performance. In this context, copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) has been demonstrated to be a powerful strategy due to the high yields achieved, absence of by-products and moderate conditions required both in aqueous medium and under physiological conditions. This particular chemistry offers great potential to functionalize a wide variety of electrode surfaces, nanomaterials, metallophthalocyanines (MPcs) and polymers, thus providing electrochemical platforms with improved electrocatalytic ability and allowing the stable, reproducible and functional integration of a wide range of nanomaterials and/or different biomolecules (enzymes, antibodies, nucleic acids and peptides). Considering the rapid progress in the field, and the potential of this technology, this review paper outlines the unique features imparted by this particular reaction in the development of electrochemical sensors through the discussion of representative examples of the methods mainly reported over the last five years. Special attention has been paid to electrochemical (bio)sensors prepared using nanomaterials and applied to the determination of relevant analytes at different molecular levels. Current challenges and future directions in this field are also briefly pointed out.

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“…End-capping treatment of the synthesized silica hybrid material was determined to be crucial for effective and selective separation due to shielding residual silanol groups [36]. In other important study, Bayraktar et al used to click chemistry to develop the surface hydrophilicity of uniform porous particles in micron-size range [37]. Surface modified column packing materials were prepared by the covalent attachment of appropriate molecular brushes onto the surfaces of particles.…”

Section: Separation Properties Of Prepared Column Packing Materialsmentioning

confidence: 99%

Synthesis of the Coumarin-Containing Porous Silica as Column Packing Material

Kazmaz

Karataş

Köytepe

et al. 2015

J Inorg Organomet Polym

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For the synthesis of the coumarin based column packing materials, amino functionalized porous silica was prepared from the modification of silica with 3-aminopropyl triethoxysilane. This amino functional silica was reacted with 4-chloromethyl-7,8-dihydroxycoumarin. The produced silica based column packing material was characterized by spectral techniques, scanning electron microscope, X-ray diffraction analysis (X-ray), N 2 adsorption isotherms and thermal analysis techniques. The effect of coumarin group on the silica structure and separation properties as well as the thermal stability of materials was investigated. Average particle diameters, pore size and surface areas of the coumarin based silica particles were 2680 ± 750 lm, *33 nm and 118 ± 6 m 2 /g, respectively. 240 mm 9 4.6 mm high performance liquid chromatography column was packed with coumarin functionalized porous silica. Then, this column was applied to the separation of similar structure aromatic compounds such as benzene, toluene and xylene. Column performance was investigated by measuring time of continuous use peak asymmetry, resolution, and selectivity. Chromatographic resolutions of coumarin-modified packing material were in the range of 2.28-2.35. According to these data, for the separation of aromatic compounds, while pure silica does not provide effective separation, coumarin based column packing material has showed good separation and selectivity.

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Click-chemistry for surface modification of monodisperse-macroporous particles

Cited by 13 publications

References 14 publications

Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Quantification of ATRP initiator density on polymer latex particles by fluorescence labeling technique using copper-catalyzed azide-alkyne cycloaddition

Copper(I)-Catalyzed Click Chemistry as a Tool for the Functionalization of Nanomaterials and the Preparation of Electrochemical (Bio)Sensors

Synthesis of the Coumarin-Containing Porous Silica as Column Packing Material

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