Photoinduced carbene generation from diazirine modified task specific phosphonium salts to prepare robust hydrophobic coatings

Langmuir

Volumn 28, Issue 33, 2012, Pages 12326-12333

  Ghiassian, Sara ^a   Ismaili, Hossein ^a   Lubbock, Brett D W ^a   Dube, Jonathan W ^a   Ragogna, Paul J ^a   Workentin, Mark S ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIWETTING PROPERTIES; CARBENES; CONTROL SAMPLES; COVALENT ATTACHMENT; FUNCTIONALIZED; HIGH DURABILITY; HYDROPHOBIC COATINGS; PAPER SURFACE; PHOSPHONIUM SALTS; PHOTO PATTERNING; PHOTO-INDUCED; PROOF OF CONCEPT; WASH CYCLES;

COATINGS; CONTACT ANGLE; COTTON; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; SALTS;

HYDROPHOBICITY;

CARBENE; DIAZOMETHANE; DRUG DERIVATIVE; METHANE; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; PHOTOCHEMISTRY;

DIAZOMETHANE; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; METHANE; ORGANOPHOSPHORUS COMPOUNDS; PHOTOCHEMICAL PROCESSES;

EID: 84865526713     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la301975u     Document Type: Article

References (49)

1. Li, X.; Tian, J.; Garnier, G.; Shen, W. Fabrication of Paper-Based Microfluidic Sensors by Printing Colloids Surf., B 2010, 76, 564-570
2. Ma, M.; Hill, R. M. Superhydrophobic Surfaces Curr. Opin. Colloid Interface Sci. 2006, 11, 193-202 (Pubitemid 44738643)
3. Blossey, R. Self-Cleaning Surfaces- Virtual Realities Nat. Mater. 2003, 2, 301-306
4. Bahners, T.; Textor, T.; Opwis, K.; Schollmeyer, E. Recent Approaches to Highly Hydrophobic Textile Surfaces J. Adhes. Sci. Technol. 2008, 22, 285-309
5. Samyn, P.; Schoukens, G.; Vonck, L.; Stanssens, D.; Abbeele, H. V. D. How thermal curing of an organic paper coating changes topography, Chemistry and Wettability Langmuir 2011, 27, 8509-8521
6. Latthe, S. S.; Gurav, A. B.; Maruti, S. C.; Vhatkar, R. S. Recent Progress in Preparation of Superhydrophobic Surfaces: A Review JSEMAT 2012, 2, 76-94
7. Li, X.-M.; Reinhoudt, D.; Crego-Calama, M. What Do We Need for a Superhydrophobic Surface? A Review on the Recent Progress in the Preparation of Superhydrophobic Surfaces Chem. Soc. Rev 2007, 36, 1350-1368
8. Wang, H.; Fang, J.; Cheng, T.; Ding, J.; Qu, L.; Dai, L.; Wang, X.; Lin, T. One-Step Coating of Fluoro-Containing Silica Nanoparticles for Universal Generation of Surface Superhydrophobicity Chem. Commun. 2008, 877-879 (Pubitemid 351208219)
9. Yu, M.; Gu, G. T.; Meng, W. D.; Qing, F. L. Superhydrophobic Cotton Fabric Coating Based on a Complex Layer of Silica Nanoparticles and Perfluorooctylated Quaternary Ammonium Silane Coupling Agent Appl. Surf. Sci. 2007, 253, 3669-3673 (Pubitemid 46127810)
10. Vilčnik, A.; Jerman, I.; Vuk, A. S.; Koželj, M.; Orel, B.; Tomšič, B.; Simončič, B.; Kovač, J. Structural Properties and Antibacterial Effects of Hydrophobic and Oleophobic Sol-Gel Coatings for Cotton Fabrics Langmuir 2009, 25, 5869-5880
11. Plechkova, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry Chem. Soc. Rev. 2008, 37, 123-150
12. Merrigan, T. L.; Bates, E. D.; Dorman, S. C.; Davis, J. H., Jr. New Fluorous Ionic Liquids Function as Surfactants in Conventional Room-Temprature Ionic Liquids Chem. Commun. 2000, 2051-2052
13. Emnet, C.; Weber, K. M.; Vidal, J. A.; Consorti, C. S.; Stuart, A. M.; Gladysza, J. A. Synthesis and Properties of Fluorous Quaternary Phosphonium Salts that Bear Four Ponytails; New Candidates for Phase Transfer Catalysts and Ionic Liquids Adv. Synth. Catal. 2006, 348, 1625-1634 (Pubitemid 44318760)
14. Tindale, J. J.; Ragogna, P. J. Highly Fluorinated Phosphonium Ionic Liquids: Novel Media for the Generation of Superhydrophobic Coatings Chem. Commun. 2009, 14, 1831-1833
15. Tindale, J. J.; Mouland, K. L.; Ragogna, P. J. Thiol Appended, Fluorinated Phosphonium Ionic Liquids as Covalent Superhydrophobic Coatings J. Mol. Liq. 2010, 152, 14-18
16. Griffiths, J.-P.; Moloney, M. G. Surface functionalization using arylcarbene reactive intermediates. PCT/GB2006/000139.
17. Moloney, M. G. Functionalized Polymers by Chemical Surface Modification J. Phys. D: Appl. Phys. 2008, 41, 174006-174014
18. Leonard, D.; Moloney, M. G.; Thompson, C. Chemical modification of materials by reaction with diaryl diazomethanes Tetrahedron Lett. 2009, 50, 3499-3502
19. Griffiths, J.-P.; Maliha, B.; Moloney, M. G.; Thompson, A. L.; Hussain, I. Surface Functional Polymers by Post-Polymerization Modification using Diarylcarbenes: Introduction, Release and Regeneration of Hydrogen Peroxide and Bactericidal Activity Langmuir 2010, 26, 14142-14153
20. Ito, Y. Photoimmobilization for Microarrays Biotechnol. Prog. 2006, 22, 924-932 (Pubitemid 44230676)
21. Yan, M.; Ren, J. Covalent Immobilization of Polypropylene Thin Films J. Mater. Chem. 2005, 15, 523-527 (Pubitemid 40159884)
22. Liu, L. H.; Yan, M. Simple Method for the Covalent Immobilization of Graphene Nano Lett. 2009, 9, 3375-3378
23. Blencowe, A.; Cosstick, K.; Hayes, W. Surface Modification of Nylon 6,6 Using a Carbene Insertion Approach New J. Chem. 2006, 30, 53-58
24. Ismaili, H.; Lagugne-Labarthet, F.; Workentin, M. S. Covalently Assembled Gold Nanoparticle-Carbon Nanotube Hybrids via a Photoinitiated Carbene Addition Reaction Chem. Mater. 2011, 23, 1519-1525
25. Ismaili, H.; Workentin, M. S. Covalent Diamond-Gold Nanojewel Hybrids via Photochemically Generated Carbenes. Kantzas, T.; Workentin, M. S Chem. Commun. 2011, 47, 7788-7790
26. Ismaili, H.; Geng, D.; Kantzas, T. T.; Sun, X.; Workentin, M. S. Light activated covalent formation of gold nanoparticle(AuNP)-graphene and AuNP-glass composites Langmuir 2011, 27, 13261-13268
27. Zhao, Y.; Zhiguang, X.; Wang, X.; Lin, T. Photoreactive Azido-Containing Silica Nanoparticle/Polycation Multilayers: Durable Superhydrophobic Coating on Cotton Fabrics Langmuir 2012, 28, 6328-6335
28. Brunner, J.; Senn, H.; Richards, F. M. 3-Trifluoromethyl-3- phenyldiazirine: A New Carbene Generating Group for Photolabeling Reagents J. Biol. Chem. 1980, 255, 3313-3318
29. Hashimoto, M.; Hatanaka, Y. Recent Progress in Diazirine-Based Photoaffinity Labeling Eur. J. Org. Chem. 2008, 2513-2523
30. Blencowe, A.; Hayes, W. Development and Application of Diazirines in Biological and Synthetic Macromolecular Systems Soft Matter. 2005, 1, 178-205 (Pubitemid 41411307)
31. Admasu, A.; Gudmundsdóttir, A. D.; Platz, M. S.; Watt, D. S.; Kwiatkowski, S.; Crocker, P. J. A Laser Flash Photolysis of P- tolyl(trifluoromethyl)carbene J. Chem. Soc., Perkin Trans. 2 1998, 1093-1099
32. Das, J. Aliphatic Diazirines as Photoaffinity Probes for Proteins: Recent Developments Chem. Rev. 2011, 1111, 4405-4417
33. Blencowe, A.; Blencowe, C.; Cosstick, K.; Hayes, W. A Carbene Insertion Approach To Functionalised Poly(ethylene oxide)-based Gels React. Funct. Polym. 2008, 68, 868-875
34. Blencowe, A.; Caiulo, N.; Cosstick, K.; Fagour, W.; Heath, P.; Hayes, W. Synthesis of Hyperbranched Poly(aryl ether)s via Carbene Insertion Processes Macromolecules 2007, 40, 939-949 (Pubitemid 46383743)
35. Blencowe, A.; Fagour, W.; Blencowe, C.; Cosstick, K.; Hayes, W. Synthesis of Hyperbranched Poly(aryl amine)s via a Carbene Insertion Approach Org. Biomol. Chem. 2008, 6, 2327-2333 (Pubitemid 351852836)
36. Lawrence, E. J.; Wildgoose, G. G.; Aldous, L.; Wu, Y. A.; Warner, J. H.; Compton, R. G.; McNaughter, P. D. 3-Aryl-3-(trifluoromethyl)diazirine as Versetile Photoactivated "Linker" Molecules for the Improved Covalent Modification of Graphitic and Carbon Nanotube Surfaces Chem. Mater. 2011, 23, 3740-3751
37. Wildgoose, G. G.; Lawrence, E. J.; Bear, J. C.; McNaughter, P. D. Enabling Electrochemical Studies of Chemically-Modified Carbon Nanotubes in Non-Aqueuos Electrolysis Using Supermagnetic Nanoparticle-Nanotube Composites Co-Modified by diazirine Molecular Tethers Electrochem. Commun. 2011, 13, 1139-1142
38. Ismaili, H.; Lee, S.; Workentin, M. S. Diazirine-Modified Gold Nanoparticle: Template for Efficient Photoinduced Interfacial Carbene Insertion Reactions Langmuir 2010, 26, 14958-14964
39. Song, M.-G.; Sheridan, R. S. Regiochemical Substituent Switching of Spin States in Aryl(trifluoromethyl)carbenes J. Am. Chem. Soc. 2011, 133, 19688-19690
40. Guo, Z.-G. Sticky Superhydrophobic Surface Appl. Phys. Lett. 2007, 90, 223111-1-223111-3
41. Feng, L.; Zhang, Y.; Xi, J.; Zhu, Y.; Wang, N.; Xia, F.; Jiang, L. Petal Effect: A Superhydrophobic State with High Adhesive Force Langmuir 2008, 24, 4114-4119 (Pubitemid 351569017)
42. Geim, A. K.; Dubonos, S. V.; Grigorieva, I. V.; Novoselov, K. S.; Zhukov, A. A.; Shapoval, S. YU. Microfabricated Adhesive Mimicking Gecko Foot-Hair Nat. Mater. 2003, 2, 461-463
43. Martinez, A. W.; Phillips, S. T.; Whitesides, G. M. Three-Dimensional Microfluidic Devices Fabricated in Layered Paper and Tape Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 19606-19611
44. Balu, B.; Berry, A. D.; Hess, D. W.; Breedveld, V. Patterning of Superhydrophobic Paper to Control the Mobility of Microlitre Drops for Two-Dimensional Lab-on-Paper Applications Lab Chip 2009, 9, 3066
45. Martinez, A. W.; Phillips, S. T.; Butte, M. J.; Whitesides, G. M. Patterned Paper as a Platform for Inexpensive, Low-Volume, Portable Bioassays Angew. Chem., Int. Ed. 2007, 46, 1318-1320 (Pubitemid 46981385)
46. Martinez, A. W.; Phillips, S. T.; Wiley, B. J.; Gupta, M.; Whitesides, G. M. FLASH: A rapid method for prototyping paper-based microfluidic devices Lab Chip 2008, 8, 2146-2150
47. Yager, P.; Edwards, T.; Fu, E.; Helton, K.; Nelson, K.; Tam, M. R.; Weigl, B. H. Microfluidic diagnostic technologies for global public health Nature 2006, 442, 412-418 (Pubitemid 44264785)
48. Lubbock, B. W.; Ismaili, H.; Dube, J. W.; Ragogna, P. J.; Workentin, M. S. US Provisional Patent 61/592,418, Jan 2012.
49. Bentz, E. L.; Gibson, H.; Hudson, C.; Moloney, M. G.; Seldon, D. A.; Wearmouth, E. S. Aryldiazirine-Modified Pyroglutamates: Photoaffinity Lables for Glutamate Synlett 2006, 0247-0250