Simple thiol-ene click chemistry modification of SBA-15 silica pores with carboxylic acids

Bordoni, Andrea; Lombardo, M. Verónica; Regazzoni, Alberto E.; Soler-Illia, Galo J. A. A.; Wolosiuk, Alejandro

doi:10.1016/j.jcis.2015.03.030

Cited by 23 publications

(26 citation statements)

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…compares the FTIR spectra of bare SiO2 nanoparticles, PRTEA MSA photografted SiO2 nanoparticles (PhG-SiO2), post-grafted of a PRTEA MSA silane precursor (PG-SiO2) and the derivatization reaction of amine modified SiO2 NP with succinic anhydride (SA-SiO2). When a COOH is present, we observe the C=O stretching vibration at 1725 cm -1 , in agreement with previous reports from our group[17,18,31]. All the samples show the typical broad band originated in the OH stretching of hydrogen bonded water molecules to the surface silanol and anchored carboxylic groups between 3800 -3200 cm -1 (Figure ESI 3) and the band at 1630 cm -1 due to the scissor bending vibration of the OH groups.…”

supporting

confidence: 91%

“…[12,13] More recently, Feinle et al reported the use of PtO2 as catalyst for the hydrosilylation of carbenoic acids with trialkoxysilanes [14,15]. On the other hand, we have shown a simple approach for the synthesis of a series of organosilanes bearing deprotected carboxylic acids for a versatile functionalization of SiO2 mesoporous particles and thin films using the click-based photochemical radical thiol-ene addition (PRTEA) [15][16][17][18].This reaction involves the addition of a radical thiol, RS  to an alkene molecule (hydrothiolation) and usually requires a photoinitiator (e.g. benzophenone) for an efficient RS  production, as schematized in Scheme 1.…”

Section: Introductionmentioning

confidence: 93%

“…We have shown in previous works that the immobilized COOH groups within porous SiO2 frameworks are chemically accessible for acid-base reactions and metal and lanthanide adsorption [17,18,31]. In this context, we tested the anchoring of a fluorescent dye as fluorescein with surface complementary dangling group amino fluorescein using a carbodiimide approach.…”

Section: Chemical Post-functionalization Of Cooh-modified Sio2 Np: Flmentioning

confidence: 99%

See 2 more Smart Citations

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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

supporting

confidence: 91%

Section: Introductionmentioning

confidence: 93%

Section: Chemical Post-functionalization Of Cooh-modified Sio2 Np: Flmentioning

confidence: 99%

See 1 more Smart Citation

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

Self Cite

View full text Add to dashboard Cite

show abstract

“…Alternatively, the mesocellular foams (MCF) have also been the compelling representative mesoporous silica due to the handily achievable large spherical cell sizes (Schmidt-Winkel et al 1999;Dana and Sayari 2011). The addition of organic groups by grafting organosiloxane precursors onto the surface of the pores of mesoporous silicas results in functional mesoporous hybrid materials (Antoschuk and Jaroniec 2002;Bibby and Mercier 2002;Hossain and Mercier 2002;Walkarius et al 2002;Yoshitake et al 2002;Yee et al 2003;Messina et al 2006;Li et al 2008Li et al , 2013Li et al , 2015Idris 2015;Bordoni et al 2015;Yu et al 2015;Zhang et al 2007;Wu et al 2010;Maretto et al 2015;Coll et al 2009;Sun et al 2015;Kandula and Jeevanandam 2015). These organic-inorganic hybrid materials have been reported to exhibit improved sorption properties toward heavy metal ions.…”

Section: Introductionmentioning

confidence: 99%

Aminopropyl-grafted various silica mesostructures for adsorption of molybdenum ions from Re-containing effluent

et al. 2016

View full text Add to dashboard Cite

Four different silica mesostructures, SBA-15 with mesopore size (8.5 nm), SBA-15 with mesopore size (10.3 nm), mesocellular foam (MCF) with uniform cell size (33.2 nm), and MCF with bimodal mesoporosity, were grafted with aminopropyl groups and used for selective recovery of Mo(VI) from Re(VII)-containing effluent. Adsorption isotherms and mechanism of Mo(VI) adsorption on these materials were studied. The adsorbed complexes of Mo(VI) could be formed by ion exchange process or/and by chelation reaction. This study shows a new approach for fractional recovery and separation of Mo(VI) from Re(VII) by using amino-modified SBA-15-type mesoporous silica.

show abstract

“…It was transferred to an autoclave and subjected to 90 °C for 24 h. Then, it was filtered, washed with water and alcohol and let dry at 60 ºC all night. The obtained preparation was air dried and calcined at 500 ° C for 6 h. Finally, the obtained SBA-15 was functionalized by exposing it to reflux treatment for 2 h in 80 mL of toluene and 1 mL of 3-aminopropyltrimethoxylane[32].…”

mentioning

confidence: 99%

Paper based analytical device modified with nanoporous material for the fluorescent sensing of gliadin content in different food samples

Marín-Barroso

Moreira

Messina

et al. 2018

Microchemical Journal

Self Cite

View full text Add to dashboard Cite

A novel fluorescent paper based immunosensor for the quantification of gliadin content in different food samples was constructed. The device consists of a paper platform modified with amino functionalized mesoporous material. The nanoporous structure and the aminofunctionality increased the anti-gliadin antibodies immobilization capacity of the sensing surface, conferring high sensitivity to the system. The detection limit reached by the described system allowed us to address the control of gluten free foods, which is extremely important to maintain the food safe consumption by patients with celiac disease, wheat allergy measured by immunoglobulin E, non-celiac gluten intolerance and Dermatitis herpetiformis or Duhring disease. The gliadin determination was performed by applying a noncompetitive immunoassay format, where gliadin present in food samples was recognized by anti-gliadin antibodies immobilized on the mesoporous material and quantified by the addition of anti-gliadin antibody labelled with peroxidase, its substrate: hydrogen peroxide and a mediator: 10-acetyl-3,7-dihydrofenoxacin. This mediator by the action of the enzyme generates resorufin, which was excited by a light emitting diode at 550 nm and emitted a signal at 580nm. The calibration curve obtained for gliadin exhibited a linear range between 0-160 µg Kg-1 and a method detection limit of 0.025 mg Kg-1. The obtained values for relative recovery varied between 98.65% and 102.33% for samples enriched with gliadin. Also, the results suggested that the developed fluorescent paper based immunosensor showed good reproducibility and stability, indicating its applicability for high-sensitive gluten free food control analysis.

show abstract

Simple thiol-ene click chemistry modification of SBA-15 silica pores with carboxylic acids

Cited by 23 publications

References 65 publications

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

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

Aminopropyl-grafted various silica mesostructures for adsorption of molybdenum ions from Re-containing effluent

Paper based analytical device modified with nanoporous material for the fluorescent sensing of gliadin content in different food samples

Contact Info

Product

Resources

About