“Thiol-ene” photoclick chemistry as a rapid and localizable functionalization pathway for silica capillary monolithic columns

Laaniste, Asko; Marechal, A.; El-Debs, Racha; Randon, Jérôme; Dugas, Vincent; Demesmay, Claire

doi:10.1016/j.chroma.2014.06.031

Cited by 28 publications

(20 citation statements)

References 28 publications

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“…Poly (BMA‐co‐EDMA) capillary monoliths with the permeabilities ranging between 1.5 × 10 −15 and 9 × 10 −14 m 2 were synthesized by Moravcova et al and used in capillary LC . The permeabilities ranging between 1.5 × 10 −14 and 8.5 × 10 −14 m 2 were reported for the silica‐based monoliths used in pressure‐driven liquid chromatographic separations . The permeabilities of the capillary monoliths used in electrochromatographic separations were slightly higher and typically in the range of 5 × 10 −14 –20 × 10 −14 m 2 .…”

Section: Resultsmentioning

confidence: 99%

New vinylester‐based monoliths as a new stationary phase for capillary electrochromatography

Kip

Tuncel

2015

Electrophoresis

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Vinyl ester-based monoliths are proposed as a new group of stationary phase for CEC. The capillary monolithic columns were prepared by using two vinyl ester monomers, vinyl pivalate (VPV), and vinyl decanoate (VDC) by using ethylene dimethacrylate (EDMA) as the cross-linking agent, and 2-acrylamido-2-methylpropane sulfonic acid as the charge-bearing monomer. The monoliths with different pore structures and permeabilities were obtained by varying the type and composition of the porogen mixture containing isoamyl alcohol and 1,4-butanediol. The electrochromatographic separation of alkylbenzenes was successfully performed by using an acetonitrile/aqueous buffer system as the mobile phase in a CEC system. Vinyl ester monoliths with short alkyl chain length (i.e. poly(VPV-co-EDMA) exhibited better separation performance compared with the monolith with long alkyl chain length (i.e. poly(VDC-co-EDMA). In the case of VPV-based monoliths, the theoretical plate numbers higher than 250 000 plates/m were achieved by using a porogen mixture containing 33% v/v of isoamyl alcohol. For both VDC and VPV-based monoliths, the column efficiency was almost independent of the superficial velocity in the range of 2-12 cm/min.

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Section: Resultsmentioning

confidence: 99%

New vinylester‐based monoliths as a new stationary phase for capillary electrochromatography

Kip

Tuncel

2015

Electrophoresis

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“…On the other hand, when surface bound thiols react with vinyl compounds in solution the "thiol-ene" reaction may result in an undesired surface polymerization. [36] Thus, it is apparent after observing Table 2 that the particles remain dispersed in solution after the "ene- When we analyze the functionalization by post-grafting of the carboxyl-derivatized silane, there is a slight increase in the apparent hydrodynamic radius from DLS measurements and a slight tendency towards greater polydispersity ( 2 =0.085 and − 2 =0.122). However, the degree of final monodispersion can be considered satisfactory and is also correlated with the synthesis methodology.…”

Section: Dlsmentioning

confidence: 98%

Click-based thiol-ene photografting of COOH groups to SiO2 nanoparticles: Strategies comparison

Penelas

Soler-Illia

Levi

et al. 2019

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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We present the study of the anchoring of carboxylic groups on SiO2 nanoparticles from different approximations based on the photochemical radical thiol-ene addition (PRTEA) reaction: a photografting approach between mercaptosuccinic acid (MSA) and vinyl-modified SiO2 nanoparticles and the post-grafting on the surface of silica colloids of the silane precursor 2-((2-(trimethoxysilyl)ethyl)thio)succinic acid (TMSMSA), obtained from the PRTEA. These synthetic strategies were compared with a widely common derivatization methodology based on the nucleophilic attack of surface-anchored amino groups with succinic anhydride. The successful functionalization of the colloidal silica was confirmed by infrared spectroscopy (FTIR), zeta potential at different pH and contact angle measurements. We found that although these three approaches were valid for -COOH immobilization, they had a noticeable impact on the dispersability and agglomeration of the colloidal suspension at the end of the synthesis. Scanning electron microscopy, dynamic light scattering (DLS) and fluorescence correlation spectroscopy (FCS) measurements indicated that the PRTEA photografting between MSA and vinyl-modified SiO2 resulted in highly dispersed colloidal particles. On the other hand, the presence of surface -COOH groups was highly beneficial for redispersion of the colloidal material after lyophilization or freeze-drying procedures.

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“…Svec and co‐workers synthesized porous polymer monoliths by in situ polymerization of thiol‐containing monolithic capillaries, which were then modified with lauryl methacrylate, and [2‐(methacryloyloxy)ethyl]dimethyl‐(3‐sulfopropyl) ammonium betaine using thiol‐ene click chemistry. Marechal and co‐workers initially prepared a vinyl‐functionalized silica monolith, which was then modified using 1‐octadecanethiol by thiol‐ene photoclick chemistry. Lämmerhofer and co‐workers first prepared a poly(glycidyl methacrylate‐co‐ethylene dimethacrylate) monolith, which was subsequently coated with a poly‐3‐mercaptopropyl methylsiloxane film by the thiol‐ene click reaction.…”

Section: Introductionmentioning

confidence: 99%

One‐pot preparation of an organic polymer monolith by thiol‐ene click chemistry for capillary electrochromatography

Wang

Shen

et al. 2017

J of Separation Science

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A novel organic monolith was successfully fabricated by a one-pot thiol-ene click reaction of triallyl isocyanurate with pentaerythritol tetrakis-(2-mercaptoacetate) and mercaptopropionic acid in the presence of porogens. We investigated the effects of the ratio of monomer and cross-linking agent, the type and ratio of porogen, and click reaction temperature on the permeability and morphology of the prepared poly triallyl isocyanurate-co-pentaerythritol tetrakis (2-mercaptoacetate) monoliths. The monolith was also characterized by scanning electron microscopy and Fourier transform infrared spectroscopy. The results indicated that the monoliths had continuous porous framework, good permeability, and high mechanical stability. A series of analytes with different properties such as alkylbenzenes, polycyclic aromatic hydrocarbons, anilines, and phenols were used to evaluate the electrochromatographic performance of the prepared monoliths in pressurized capillary electrochromatography. The prepared polymer monolith showed typical reversed-phase electrochromatographic behavior for hydrophobic substances. Moreover, the prepared monolith showed a mix of reversed-phase and cation exchange interaction modes for basic aniline compounds. The minimum plate height of the monolith was 8.76 μm (132 100 plates/m) for propylbenzene. These results demonstrated that one-pot thiol-ene click chemistry can provide a simple and reliable method for the preparation of organic monoliths.

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“Thiol-ene” photoclick chemistry as a rapid and localizable functionalization pathway for silica capillary monolithic columns

Cited by 28 publications

References 28 publications

New vinylester‐based monoliths as a new stationary phase for capillary electrochromatography

New vinylester‐based monoliths as a new stationary phase for capillary electrochromatography

Click-based thiol-ene photografting of COOH groups to SiO2 nanoparticles: Strategies comparison

One‐pot preparation of an organic polymer monolith by thiol‐ene click chemistry for capillary electrochromatography

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