Mesoporous organosilica nanoparticles containing superacid and click functionalities leading to cooperativity in biocidal coatings

ACS Applied Materials and Interfaces

Volumn 7, Issue 1, 2015, Pages 1021-1029

  Gehring, Julia ^a   Schleheck, David ^a   Trepka, Bastian ^a   Polarz, Sebastian ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

antifouling; click chemistry; mesoporous particles; multifunctional materials; surface immobilization

Indexed keywords

ACIDS; BIOLOGICAL MATERIALS; DURABILITY; FLUORESCENCE MICROSCOPY; FUNCTIONAL GROUPS; INORGANIC COATINGS; METAL IONS; METAL NANOPARTICLES; NANOPARTICLES; PRASEODYMIUM; SILICA; SILVER; SOL-GELS; STAINLESS STEEL; SYNTHESIS (CHEMICAL);

ANTIFOULING; CLICK CHEMISTRY; MESOPOROUS; MULTI-FUNCTIONAL MATERIALS; SURFACE IMMOBILIZATION;

MESOPOROUS MATERIALS;

ANTIINFECTIVE AGENT; ION; METAL NANOPARTICLE; ORGANOSILICON DERIVATIVE; POWDER; SULFONIC ACID DERIVATIVE; THIOL DERIVATIVE;

BIOFILM; CHEMISTRY; CLICK CHEMISTRY; DRUG EFFECTS; FLUORESCENCE MICROSCOPY; MATERIALS TESTING; MICROBIAL SENSITIVITY TEST; NANOTECHNOLOGY; PH; POWDER; PROCEDURES; PSEUDOMONAS AERUGINOSA; REPRODUCIBILITY; SPECTROPHOTOMETRY; SURFACE PROPERTY; TRANSMISSION ELECTRON MICROSCOPY;

ANTI-BACTERIAL AGENTS; BIOFILMS; CLICK CHEMISTRY; HYDROGEN-ION CONCENTRATION; IONS; MATERIALS TESTING; METAL NANOPARTICLES; MICROBIAL SENSITIVITY TESTS; MICROSCOPY, ELECTRON, TRANSMISSION; MICROSCOPY, FLUORESCENCE; NANOTECHNOLOGY; ORGANOSILICON COMPOUNDS; POWDERS; PSEUDOMONAS AERUGINOSA; REPRODUCIBILITY OF RESULTS; SPECTROPHOTOMETRY; SULFHYDRYL COMPOUNDS; SULFONIC ACIDS; SURFACE PROPERTIES;

EID: 84921291585     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am5083057     Document Type: Article

References (57)

1. Banerjee, I.; Pangule, R. C.; Kane, R. S. Antifouling Coatings: Recent Developments in the Design of Surfaces That Prevent Fouling by Proteins, Bacteria, and Marine Organisms Adv. Mater. 2011, 23, 690-718
2. Li, Q. L.; Mahendra, S.; Lyon, D. Y.; Brunet, L.; Liga, M. V.; Li, D.; Alvarez, P. J. J. Antimicrobial Nanomaterials for Water Disinfection and Microbial Control: Potential Applications and Implications Water Res. 2008, 42, 4591-4602
3. Rana, D.; Matsuura, T. Surface Modifications for Antifouling Membranes Chem. Rev. 2010, 110, 2448-2471
4. Yebra, D. M.; Kiil, S.; Dam-Johansen, K. Antifouling Technology-Past, Present and Future Steps Towards Efficient and Environmentally Friendly Antifouling Coatings Prog. Org. Coat. 2004, 50, 75-104
5. Feng, Q. L.; Wu, J.; Chen, G. Q.; Cui, F. Z.; Kim, T. N.; Kim, J. O. A Mechanistic Study of the Antibacterial Effect of Silver Ions on Escherichia Coli and Staphylococcus Aureus J. Biomed. Mater. Res. 2000, 52, 662-668
6. Mijnendonckx, K.; Leys, N.; Mahillon, J.; Silver, S.; Van Houdt, R. Antimicrobial Silver: Uses, Toxicity and Potential for Resistance Biometals 2013, 26, 609-621
7. Furno, F.; Morley, K. S.; Wong, B.; Sharp, B. L.; Arnold, P. L.; Howdle, S. M.; Bayston, R.; Brown, P. D.; Winship, P. D.; Reid, H. J. Silver Nanoparticles and Polymeric Medical Devices: A New Approach to Prevention of Infection? J. Antimicrob. Chemother. 2004, 54, 1019-1024
8. Yan, Y.; Yang, H.; Li, J.; Lu, X.; Wang, C. Release Behavior of Nano-Silver Textiles in Simulated Perspiration Fluids Text. Res. J. 2012, 82, 1422-1429
9. Raimondi, F.; Scherer, G. G.; Kotz, R.; Wokaun, A. Nanoparticles in Energy Technology: Examples from Electrochemistry and Catalysis Angew. Chem., Int. Ed. 2005, 44, 2190-2209
10. Panyala, N. R.; Pena-Mendez, E. M.; Havel, J. Silver or Silver Nanoparticles: A Hazardous Threat to the Environment and Human Health? J. Appl. Biomed. 2008, 6, 117-129
11. Nisola, G. M.; Park, J. S.; Beltran, A. B.; Chung, W.-J. Silver Nanoparticles in a Polyether-Block-Polyamide Copolymer Towards Antimicrobial and Antifouling Membranes RSC Adv. 2012, 2, 2439
12. Deng, Z.; Zhu, H.; Peng, B.; Chen, H.; Sun, Y.; Gang, X.; Jin, P.; Wang, J. Synthesis of Ps/Ag Nanocomposite Spheres with Catalytic and Antibacterial Activities ACS Appl. Mater. Interfaces 2012, 4, 5625-5632
13. Zienkiewicz-Strzalka, M.; Pasieczna-Patkowska, S.; Kozak, M.; Pikus, S. Silver Nanoparticles Incorporated onto Ordered Mesoporous Silica from Tollen's Reagent Appl. Surf. Sci. 2013, 266, 337-343
14. Kim, J. D.; Yun, H.; Kim, G. C.; Lee, C. W.; Choi, H. C. Antibacterial Activity and Reusability of Cnt-Ag and Go-Ag Nanocomposites Appl. Surf. Sci. 2013, 283, 227-233
15. Agnihotri, S.; Mukherji, S.; Mukherji, S. Immobilized Silver Nanoparticles Enhance Contact Killing and Show Highest Efficacy: Elucidation of the Mechanism of Bactericidal Action of Silver Nanoscale 2013, 5, 7328-7340
16. Sun, J. M.; Ma, D.; Zhang, H.; Liu, X. M.; Han, X. W.; Bao, X. H.; Weinberg, G.; Pfander, N.; Su, D. S. Toward Monodispersed Silver Nanoparticles with Unusual Thermal Stability J. Am. Chem. Soc. 2006, 128, 15756-15764
17. Zhu, J.; Konya, Z.; Puntes, V. F.; Kiricsi, I.; Miao, C. X.; Ager, J. W.; Alivisatos, A. P.; Somorjai, G. A. Encapsulation of Metal (Au, Ag, Pt) Nanoparticles into the Mesoporous Sba-15 Structure Langmuir 2003, 19, 4396-4401
18. Quang, D. V.; Lee, J. E.; Kim, J. K.; Kim, Y. N.; Shao, G. N.; Kim, H. T. A Gentle Method to Graft Thiol-Functional Groups onto Silica Gel for Adsorption of Silver Ions and Immobilization of Silver Nanoparticles Powder Technol. 2013, 235, 221-227
19. Xue, C.-H.; Chen, J.; Yin, W.; Jia, S.-T.; Ma, J.-Z. Superhydrophobic Conductive Textiles with Antibacterial Property by Coating Fibers with Silver Nanoparticles Appl. Surf. Sci. 2012, 258, 2468-2472
20. Qin, Y. Q.; Ji, X. H.; Jing, J.; Liu, H.; Wu, H. L.; Yang, W. S. Size Control over Spherical Silver Nanoparticles by Ascorbic Acid Reduction Colloids Surf., A 2010, 372, 172-176
21. Morones, J. R.; Elechiguerra, J. L.; Camacho, A.; Holt, K.; Kouri, J. B.; Ramirez, J. T.; Yacaman, M. J. The Bactericidal Effect of Silver Nanoparticles Nanotechnology 2005, 16, 2346-2353
22. White, R. J.; Luque, R.; Budarin, V. L.; Clark, J. H.; Macquarrie, D. J. Supported Metal Nanoparticles on Porous Materials. Methods and Applications Chem. Soc. Rev. 2009, 38, 481-494
23. Hoffmann, F.; Froba, M. Vitalising Porous Inorganic Silica Networks with Organic Functions-Pmos and Related Hybrid Materials Chem. Soc. Rev. 2011, 40, 608-620
24. Hoffmann, F.; Cornelius, M.; Morell, J.; Froba, M. Silica-Based Mesoporous Organic-Inorganic Hybrid Materials Angew. Chem., Int. Ed. 2006, 45, 3216-3251
25. Zhang, S.; Ni, W.; Kou, X.; Yeung, M. H.; Sun, L.; Wang, J.; Yan, C. Formation of Gold and Silver Nanoparticle Arrays and Thin Shells on Mesostructured Silica Nanofibers Adv. Funct. Mater. 2007, 17, 3258-3266
26. Hoffmann, F.; Cornelius, M.; Morell, J.; Froba, M. Silica-Based Mesoporous Organic-Inorganic Hybrid Materials Angew. Chem., Int. Ed. 2006, 45, 3216-3251
27. Peng, J.; Yao, Y.; Zhang, X.; Li, C.; Yang, Q. Superhydrophobic Mesoporous Silica Nanospheres Achieved Via a High Level of Organo-Functionalization Chem. Commun. 2014, 50, 10830-10833
28. Sanchez, C.; Julian, B.; Belleville, P.; Popall, M. Applications of Hybrid Organic-Inorganic Nanocomposites J. Mater. Chem. 2005, 15, 3559-3592
29. Inagaki, S.; Guan, S.; Fukushima, Y.; Ohsuna, T.; Terasaki, O. Novel Mesoporous Materials with a Uniform Distribution of Organic Groups and Inorganic Oxide in Their Frameworks J. Am. Chem. Soc. 1999, 121, 9611-9614
30. Melde, B. J.; Holland, B. T.; Blanford, C. F.; Stein, A. Mesoporous Sieves with Unified Hybrid Inorganic/Organic Frameworks Chem. Mater. 1999, 11, 3302-3308
31. Asefa, T.; MacLachlan, M. J.; Coombs, N.; Ozin, G. A. Periodic Mesoporous Organosilicas with Organic Groups inside the Channel Walls Nature 1999, 402, 867-871
32. Esquivel, D.; van den Berg, O.; Romero-Salguero, F. J.; Du Prez, F.; Van Der Voort, P. 100% Thiol-Functionalized Ethylene Pmos Prepared by Thiol Acid-Ene Chemistry Chem. Commun. 2013, 49, 2344-2346
33. Hatton, B.; Landskron, K.; Whitnall, W.; Perovic, D.; Ozin, G. A. Past, Present, and Future of Periodic Mesoporous Organosilicas-the Pmos Acc. Chem. Res. 2005, 38, 305-312
34. Wang, W. D.; Lofgreen, J. E.; Ozin, G. A. Why Pmo? Towards Functionality and Utility of Periodic Mesoporous Organosilicas Small 2010, 6, 2634-2642
35. Van der Voort, P.; Esquivel, D.; De Canck, E.; Goethals, F.; Van Driessche, I.; Romero-Salguero, F. J. Periodic Mesoporous Organosilicas: From Simple to Complex Bridges; a Comprehensive Overview of Functions, Morphologies and Applications Chem. Soc. Rev. 2013, 42, 3913-3955
36. Kuschel, A.; Sievers, H.; Polarz, S. Amino Acid Silica Hybrid Materials with Mesoporous Structure and Enantiopure Surfaces Angew. Chem., Int. Ed. 2008, 47, 9513-9517
37. Polarz, S.; Kuschel, A. Chemistry in Confining Reaction Fields with Special Emphasis on Nanoporous Materials Chem.-Eur. J. 2008, 14, 9816-9829
38. Kuschel, A.; Drescher, M.; Kuschel, T.; Polarz, S. Bifunctional Mesoporous Organosilica Materials and Their Application in Catalysis: Cooperative Effects or Not? Chem. Mater. 2010, 22, 1472-1482
39. Kuschel, A.; Luka, M.; Wessig, M.; Drescher, M.; Fonin, M.; Kiliani, G.; Polarz, S. Organic Ligands Made Porous: Magnetic and Catalytic Properties of Transition Metals Coordinated to the Surfaces of Mesoporous Organosilica Adv. Funct. Mater. 2010, 20, 1133-1143
40. Kuschel, A.; Polarz, S. Effects of Primary and Secondary Surface Groups in Enantioselective Catalysis Using Nanoporous Materials with Chiral Walls J. Am. Chem. Soc. 2010, 132, 6558-6565
41. Mascotto, S.; Wallacher, D.; Kuschel, A.; Polarz, S.; Zickler, G. A.; Timmann, A.; Smarsly, B. M. Adsorption in Periodically Ordered Mesoporous Organosilica Materials Studied by in Situ Small-Angle X-Ray Scattering and Small-Angle Neutron Scattering Langmuir 2010, 26, 6583-6592
42. Luka, M.; Polarz, S. Stimuli-Responsive Mesoporous Organosilica Materials Containing Ph-Sensitive Organic Dyes Microporous Mesoporous Mater. 2013, 171, 35-43
43. Wessig, M.; Drescher, M.; Polarz, S. Probing Functional Group Specific Surface Interactions in Porous Solids Using Esr Spectroscopy as a Sensitive and Quantitative Tool J. Phys. Chem. C 2013, 117, 2805-2816
44. Gehring, J.; Schleheck, D.; Luka, M.; Polarz, S. Aerosol-Synthesis of Mesoporous Organosilica Nanoparticles with Highly Reactive, Superacidic Surfaces Comprising Sulfonic Acid Entities Adv. Funct. Mater. 2014, 24, 1140-1150
45. Jones, E.; Moodie, I. M. 2-Thiophenethiol Org. Synth. 1988, 50-9, 979-980
46. Morell, J.; Wolter, G.; Froba, M. Synthesis and Characterization of Highly Ordered Thiophene-Bridged Periodic Mesoporous Organosilicas with Large Pores Chem. Mater. 2005, 17, 804-808
47. Morell, J.; Gungerich, M.; Wolter, G.; Jiao, J.; Hunger, M.; Klar, P. J.; Froba, M. Synthesis and Characterization of Highly Ordered Bifunctional Aromatic Periodic Mesoporous Organosilicas with Different Pore Sizes J. Mater. Chem. 2006, 16, 2809-2818
48. Barrett, E. P.; Joyner, L. G.; Halenda, P. P. The Determination of Pore Volume and Area Distributions in Porous Substances 0.1. Computations from Nitrogen Isotherms J. Am. Chem. Soc. 1951, 73, 373-380
49. Lu, Y.; Fan, H.; Stump, A.; Ward, T. L.; Rieker, T.; Brinker, C. J. Aerosol-Assisted Self-Assembly of Mesostructured Spherical Nanoparticles Nature 1999, 398, 223-226
50. Hakki, A.; Dillert, R.; Bahnemann, D. W. Arenesulfonic Acid-Functionalized Mesoporous Silica Decorated with Titania: A Heterogeneous Catalyst for the One-Pot Photocatalytic Synthesis of Quinolines from Nitroaromatic Compounds and Alcohols ACS Catal. 2013, 3, 565-572
51. Bronstein, L. M.; Polarz, S.; Smarsly, B.; Antonietti, M. Sub-Nanometer Noble-Metal Particle Host Synthesis in Porous Silica Monoliths Adv. Mater. 2001, 13, 1333-1336
52. Hoyle, C. E.; Bowman, C. N. Thiol-Ene Click Chemistry Angew. Chem., Int. Ed. 2010, 49, 1540-1573
53. Lowe, A. B. Thiol-Ene Click Reactions and Recent Applications in Polymer and Materials Synthesis Polym. Chem. 2010, 1, 17-36
54. Swihart, M. T. Vapor-Phase Synthesis of Nanoparticles Curr. Opin. Colloid Interface Sci. 2003, 8, 127-133
55. Murray, B. E. The Life and Times of the Enterococcus Clin. Microbiol. Rev. 1990, 3, 46-65
56. Guzman, M.; Dille, J.; Godet, S. Synthesis and Antibacterial Activity of Silver Nanoparticles against Gram-Positive and Gram-Negative Bacteria Nanomed.-Nanotechnol. Biol. Med. 2012, 8, 37-45
57. Weir, E.; Lawlor, A.; Whelan, A.; Regan, F. The Use of Nanoparticles in Anti-Microbial Materials and Their Characterization Analyst 2008, 133, 835-845