Synthesis and Surface Reactivity of Vinylized Macroporous Silica Monoliths: One-Pot Hybrid versus Postsynthesis Grafting Strategies

Langmuir

Volumn 31, Issue 42, 2015, Pages 11649-11658

  El Debs, Racha ^a   Cadoux, Franck ^a   Bois, Laurence ^b   Bonhommé, Anne ^a   Randon, Jérôme ^a   Dugas, Vincent ^a   Demesmay, Claire ^a  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ CLAUDE BERNARD LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FOURIER TRANSFORM INFRARED SPECTROSCOPY; GAS ADSORPTION; GRAFTING (CHEMICAL); ION CHROMATOGRAPHY; MONOLITHIC INTEGRATED CIRCUITS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PORE SIZE; SILICA; SYNTHESIS (CHEMICAL);

CHROMATOGRAPHIC APPLICATION; HYBRID SILICA MONOLITHS; MACROPOROUS MONOLITHS; MACROPOROUS SILICA MONOLITHS; METHYLTRIMETHOXYSILANE; NITROGEN ADSORPTION ISOTHERM; POSTSYNTHESIS GRAFTING; VINYLTRIMETHOXYSILANES;

HYBRID MATERIALS;

EID: 84945922185     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.5b02681     Document Type: Article

References (53)

1. Su, B.-L.; Sanchez, C.; Yang, X.-Y. Hierarchically Structured Porous Materials: From Nanoscience to Catalysis, Separation, Optics, Energy, and Life Science; Wiley-VCH: Weinheim, 2011.
2. Unger, K. K.; Tanaka, N.; Machtejevas, E. Monolithic Silicas in Separation Science; Wiley-VCH: Weinheim, 2011.
3. Unger, K. K.; Skudas, R.; Schulte, M. M. Particle packed columns and monolithic columns in high-performance liquid chromatography-comparison and critical appraisal J. Chromatogr. A 2008, 1184, 393-415 10.1016/j.chroma.2007.11.118
4. Monton, M. R. N.; Forsberg, E. M.; Brennan, J. D. Tailoring Sol-Gel-Derived Silica Materials for Optical Biosensing Chem. Mater. 2012, 24, 796-811 10.1021/cm202798e
5. Sachse, A.; Galarneau, A.; Fajula, F.; Di Renzo, F.; Creux, P.; Coq, B. Functional silica monoliths with hierarchical uniform porosity as continuous flow catalytic reactors Microporous Mesoporous Mater. 2011, 140, 58-68 10.1016/j.micromeso.2010.10.044
6. Munirathinam, R.; Huskens, J.; Verboom, W. Supported Catalysis in Continuous-Flow Microreactors Adv. Synth. Catal. 2015, 357, 1093-1123 10.1002/adsc.201401081
7. Kanamori, K.; Nakanishi, K.; Hanada, T. Spinodal decomposition in siloxane sol-gel systems in macroporous media Soft Matter 2009, 5, 3106-3113 10.1039/b903444g
8. Der Voort, P. V.; Vansant, E. F. Silylation of the Silica Surface A Review J. Liq. Chromatogr. Relat. Technol. 1996, 19, 2723-2752 10.1080/10826079608015107
9. Impens, N. R. E. N.; van der Voort, P.; Vansant, E. F. Silylation of micro-, meso- and non-porous oxides: a review Microporous Mesoporous Mater. 1999, 28, 217-232 10.1016/S1387-1811(98)00239-X
10. Hoffmann, F.; Cornelius, M.; Morell, J.; Fröba, M. Silica-Based Mesoporous Organic-Inorganic Hybrid Materials Angew. Chem., Int. Ed. 2006, 45, 3216-3251 10.1002/anie.200503075
11. Dugas, V.; Elaissari, A.; Chevalier, Y. In Recognition Receptors in Biosensors; Zourob, M., Ed.; Springer: New York, 2010.
12. Moitra, N.; Ichii, S.; Kamei, T.; Kanamori, K.; Zhu, Y.; Takeda, K.; Nakanishi, K.; Shimada, T. Surface Functionalization of Silica by Si-H Activation of Hydrosilanes J. Am. Chem. Soc. 2014, 136, 11570-11573 10.1021/ja504115d
13. Nakanishi, K. Pore Structure Control of Silica Gels Based on Phase Separation J. Porous Mater. 1997, 4, 67-112 10.1023/A:1009627216939
14. Kanamori, K.; Yonezawa, H.; Nakanishi, K.; Hirao, K.; Jinnai, H. Structural formation of hybrid siloxane-based polymer monolith in confined spaces J. Sep. Sci. 2004, 27, 874-886 10.1002/jssc.200401816
15. Dong, H.; Reidy, R. F.; Brennan, J. D. Shrinkage and Springback Behavior of Methylsilsesquioxanes Prepared by an Acid/Base Two-Step Processing Procedure Chem. Mater. 2005, 17, 6012-6017 10.1021/cm051369w
16. Hara, T.; Kobayashi, H.; Ikegami, T.; Nakanishi, K.; Tanaka, N. Performance of monolithic silica capillary columns with increased phase ratios and small-sized domains Anal. Chem. 2006, 78, 7632-7642 10.1021/ac060770e
17. Loy, D. A.; Baugher, B. M.; Baugher, C. R.; Schneider, D. A.; Rahimian, K. Substituent Effects on the Sol-Gel Chemistry of Organotrialkoxysilanes Chem. Mater. 2000, 12, 3624-3632 10.1021/cm000451i
18. Kanamori, K.; Nakanishi, K. Controlled pore formation in organotrialkoxysilane-derived hybrids: from aerogels to hierarchically porous monoliths Chem. Soc. Rev. 2011, 40, 754-770 10.1039/C0CS00068J
19. Nakanishi, K.; Kanamori, K. Organic-inorganic hybrid poly(silsesquioxane) monoliths with controlled macro- and mesopores J. Mater. Chem. 2005, 15, 3776-3786 10.1039/b508415f
20. Igarashi, N.; Hashimoto, K.; Tatsumi, T. Studies on the structural stability of mesoporous molecular sieves organically functionalized by a direct method J. Mater. Chem. 2002, 12, 3631-3636 10.1039/b207617a
21. Ma, J.; Liang, Z.; Qiao, X.; Deng, Q.; Tao, D.; Zhang, L.; Zhang, Y. Organic-Inorganic Hybrid Silica Monolith Based Immobilized Trypsin Reactor with High Enzymatic Activity Anal. Chem. 2008, 80, 2949-2956 10.1021/ac702343a
22. Chen, M.-L.; Zhang, J.; Zhang, Z.; Yuan, B.-F.; Yu, Q.-W.; Feng, Y.-Q. Facile preparation of organic-silica hybrid monolith for capillary hydrophilic liquid chromatography based on "thiol-ene" click chemistry J. Chromatogr. A 2013, 1284, 118-125 10.1016/j.chroma.2013.02.008
23. Lin, Z.; Tan, X.; Yu, R.; Lin, J.; Yin, X.; Zhang, L.; Yang, H. One-pot preparation of glutathione-silica hybrid monolith for mixed-mode capillary liquid chromatography based on "thiol-ene" click chemistry J. Chromatogr. A 2014, 1355, 228-237 10.1016/j.chroma.2014.06.023
24. Colon, H.; Zhang, X.; Murphy, J. K.; Rivera, J. G.; Colon, L. A. Allyl-functionalized hybrid silica monoliths Chem. Commun. 2005, 2826-2828 10.1039/b502870a
25. Roux, R.; Puy, G.; Demesmay, C.; Rocca, J.-L. Synthesis of propyl-functionalized hybrid monolithic silica capillaries and evaluation of their performances in nano-LC and CEC J. Sep. Sci. 2007, 30, 3035-3042 10.1002/jssc.200700304
26. Roux, R.; Jaoudé, M. A.; Demesmay, C.; Rocca, J. L. Optimization of the single-step synthesis of hybrid C8 silica monoliths dedicated to nano-liquid chromatography and capillary electrochromatography J. Chromatogr. A 2008, 1209, 120-127 10.1016/j.chroma.2008.08.119
27. Wang, K.; Chen, Y.; Yang, H.; Li, Y.; Nie, L.; Yao, S. Modification of VTMS hybrid monolith via thiol-ene click chemistry for capillary electrochromatography Talanta 2012, 91, 52-59 10.1016/j.talanta.2012.01.009
28. Göbel, R.; Hesemann, P.; Friedrich, A.; Rothe, R.; Schlaad, H.; Taubert, A. Modular Thiol-Ene Chemistry Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls Chem.-Eur. J. 2014, 20, 17579-17589 10.1002/chem.201403982
29. Stein, A.; Melde, B. J.; Schroden, R. C. Hybrid Inorganic-Organic Mesoporous Silicates-Nanoscopic Reactors Coming of Age Adv. Mater. 2000, 12, 1403-1419 10.1002/1521-4095(200010)12:19<1403::AID-ADMA1403>3.3.CO;2-O
30. Xie, Y.; Zhang, X.; Han, Q.; Wan, W.; Ding, M. One-step synthesis of sub-2 μm vinyl functionalized silica sphere as stationary phase for liquid chromatography Talanta 2015, 134, 425-434 10.1016/j.talanta.2014.11.044
31. Lim, M. H.; Blanford, C. F.; Stein, A. Synthesis and Characterization of a Reactive Vinyl-Functionalized MCM-41: Probing the Internal Pore Structure by a Bromination Reaction J. Am. Chem. Soc. 1997, 119, 4090-4091 10.1021/ja9638824
32. Rozga-Wijas, K.; Chojnowski, J.; Scibiorek, M.; Fortuniak, W. Polysiloxane-silica hybrids from novel precursors by the sol-gel process J. Mater. Chem. 2005, 15, 2383-2392 10.1039/b501833c
33. Lim, M. H.; Stein, A. Comparative Studies of Grafting and Direct Syntheses of Inorganic-Organic Hybrid Mesoporous Materials Chem. Mater. 1999, 11, 3285-3295 10.1021/cm990369r
34. Marechal, A.; El-Debs, R.; Dugas, V.; Demesmay, C. Is click chemistry attractive for separation sciences? J. Sep. Sci. 2013, 36, 2049-2062 10.1002/jssc.201300231
35. Marechal, A.; Laaniste, A.; El-Debs, R.; Dugas, V.; Demesmay, C. Versatile ene-thiol photoclick reaction for preparation of multimodal monolithic silica capillary columns J. Chromatogr. A 2014, 1365, 140-147 10.1016/j.chroma.2014.09.017
36. Laaniste, A.; Marechal, A.; El-Debs, R.; Randon, J.; Dugas, V.; Demesmay, C. Thiol-ene" photoclick chemistry as a rapid and localizable functionalization pathway for silica capillary monolithic columns J. Chromatogr. A 2014, 1355, 296-300 10.1016/j.chroma.2014.06.031
37. Marechal, A.; Jarrosson, F.; Randon, J.; Dugas, V.; Demesmay, C. In-line coupling of an aptamer based miniaturized monolithic affinity preconcentration unit with capillary electrophoresis and Laser Induced Fluorescence detection J. Chromatogr. A 2015, 1406, 109-117 10.1016/j.chroma.2015.05.073
38. Sagiv, J. Organized monolayers by adsorption. 1. Formation and structure of oleophobic mixed monolayers on solid surfaces J. Am. Chem. Soc. 1980, 102, 92-98 10.1021/ja00521a016
39. Alekseev, S. A.; Zaitsev, V. N.; Fraissard, J. Organosilicas with Covalently Bonded Groups under Thermochemical Treatment Chem. Mater. 2006, 18, 1981-1987 10.1021/cm052776a
40. Rozga-Wijas, K.; Chojnowski, J.; Fortuniak, W.; Scibiorek, M.; Michalska, Z.; Rogalski, L. Branched functionalised polysiloxane-silica hybrids for immobilisation of catalysts J. Mater. Chem. 2003, 13, 2301-2310 10.1039/b304134d
41. Walcarius, A.; Etienne, M.; Lebeau, B. Rate of Access to the Binding Sites in Organically Modified Silicates. 2. Ordered Mesoporous Silicas Grafted with Amine or Thiol Groups Chem. Mater. 2003, 15, 2161-2173 10.1021/cm021310e
42. Walcarius, A.; Delacôte, C. Rate of Access to the Binding Sites in Organically Modified Silicates. 3. Effect of Structure and Density of Functional Groups in Mesoporous Solids Obtained by the Co-Condensation Route Chem. Mater. 2003, 15, 4181-4192 10.1021/cm031089l
43. Kruk, M.; Asefa, T.; Jaroniec, M.; Ozin, G. A. Metamorphosis of Ordered Mesopores to Micropores: Periodic Silica with Unprecedented Loading of Pendant Reactive Organic Groups Transforms to Periodic Microporous Silica with Tailorable Pore Size J. Am. Chem. Soc. 2002, 124, 6383-6392 10.1021/ja025573l
44. Hara, T.; Makino, S.; Watanabe, Y.; Ikegami, T.; Cabrera, K.; Smarsly, B.; Tanaka, N. The performance of hybrid monolithic silica capillary columns prepared by changing feed ratios of tetramethoxysilane and methyltrimethoxysilane J. Chromatogr. A 2010, 1217, 89-98 10.1016/j.chroma.2009.11.019
45. Itagaki, A.; Nakanishi, K.; Hirao, K. Phase Separation in Sol-Gel System Containing Mixture of 3- and 4-Functional Alkoxysilanes J. Sol-Gel Sci. Technol. 2003, 26, 153-156 10.1023/A:1020770209234
46. Sing, K. S. W.; Everett, D. H.; Haul, R. A. W.; Moscou, L.; Pierotti, J.; Rouquerol, J.; Siemieniewska, T. Pure Appl. Chem. 1985, 57, 603 10.1351/pac198557010069
47. El-Debs, R.; Marechal, A.; Dugas, V.; Demesmay, C. Photopolymerization of acrylamide as a new functionalization way of silica monoliths for hydrophilic interaction chromatography and coated silica capillaries for capillary electrophoresis J. Chromatogr. A 2014, 1326, 89-95 10.1016/j.chroma.2013.12.038
48. El-Debs, R.; Dugas, V.; Demesmay, C. Photografting as a versatile, localizable, and single-step surface functionalization of silica-based monoliths dedicated to microscale separation techniques J. Sep. Sci. 2013, 36, 993-1001 10.1002/jssc.201200878
49. Stoeckel, D.; Kübel, C.; Loeh, M. O.; Smarsly, B. M.; Tallarek, U. Morphological Analysis of Physically Reconstructed Silica Monoliths with Submicrometer Macropores: Effect of Decreasing Domain Size on Structural Homogeneity Langmuir 2015, 31, 7391-7400 10.1021/la5046018
50. Ou, D. L.; Seddon, A. B. Near- and mid-infrared spectroscopy of sol-gel derived ormosils: vinyl and phenyl silicates J. Non-Cryst. Solids 1997, 210, 187-203 10.1016/S0022-3093(96)00585-6
51. Hoyle, C. E.; Lowe, A. B.; Bowman, C. N. Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis Chem. Soc. Rev. 2010, 39, 1355-1387 10.1039/b901979k
52. Bertin, A.; Schlaad, H. Mild and Versatile (Bio-)Functionalization of Glass Surfaces via Thiol-Ene Photochemistry Chem. Mater. 2009, 21, 5698-5700 10.1021/cm902176n
53. Satoh, Y.; Yokoyama, Y.; Ogino, I.; Mukai, S. R. Synthesis of Sulfonic Acid Functionalized Silica Honeycombs Ind. Eng. Chem. Res. 2013, 52, 15293-15297 10.1021/ie400541d