Helical versus all-trans conformations of oligo(ethylene glycol)-terminated alkanethiol self-assembled monolayers

Langmuir

Volumn 30, Issue 34, 2014, Pages 10263-10269

  Johnson, Phillip S ^a   Goel, Mohit ^a   Abbott, Nicholas L ^a   Himpsel, F J ^a  

^a Wisconsin Electric Machines and Power Electronics Consortium   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PARAFFINS; POLYOLS; SELF ASSEMBLED MONOLAYERS; X RAY ABSORPTION SPECTROSCOPY;

ALKANETHIOL SELF-ASSEMBLED MONOLAYERS; ALKANETHIOLS; C 1S CORE LEVEL; COMPLEX MIXTURE; CONFORMATIONAL STATE; OLIGO(ETHYLENE GLYCOL); POLARIZATION DEPENDENCE; SYSTEMATIC FRAMEWORK;

ETHYLENE GLYCOL;

ALKANE; ETHYLENE GLYCOL; THIOL DERIVATIVE;

CHEMISTRY; CONFORMATION; X RAY ABSORPTION SPECTROSCOPY;

ALKANES; ETHYLENE GLYCOL; MOLECULAR CONFORMATION; SULFHYDRYL COMPOUNDS; X-RAY ABSORPTION SPECTROSCOPY;

EID: 84906877918     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la500978s     Document Type: Article

References (46)

1. Prime, K. L.; Whitesides, G. M. Adsorption of proteins onto surfaces containing end-attachedoligo(ethylene oxide): A model system using self-assembled monolayers J. Am. Chem. Soc. 1993, 115, 10714-10721
2. Lopez, G. P.; Albers, M. W.; Schreiber, S. L.; Carroll, R.; Peralta, E.; Whitesides, G. M. Convenient methods for patterning the adhesion of mammalian cells to surfaces using self-assembled monolayers of alkanethiolates on gold J. Am. Chem. Soc. 1993, 115, 5877-5878
3. Herrwerth, S.; Eck, W.; Reinhardt, S.; Grunze, M. Factors that determine the protein resistance of oligoether self-assembled monolayers-Internal hydrophilicity, terminal hydrophilicity, and lateral packing density J. Am. Chem. Soc. 2003, 125, 9359-9366
4. Skoda, M. W. A.; Schreiber, F.; Jacobs, R. M. J.; Webster, J. R. P.; Wolff, M.; Dahint, R.; Schwendel, D.; Grunze, M. Protein density profile at the interface of water with oligo(ethylene glycol) self-assembled monolayers Langmuir 2009, 25, 4056-4064
5. Balamurugan, S.; Ista, L. K.; Yan, J.; López, G. P.; Fick, J.; Himmelhaus, M.; Grunze, M. Reversible protein adsorption and bioadhesion on monolayers terminated with mixtures of oligo(ethylene glycol) and methyl groups J. Am. Chem. Soc. 2005, 127, 14548-14549
6. Harder, P.; Grunze, M.; Dahint, R.; Whitesides, G. M.; Laibinis, P. E. Molecular conformation in oligo(ethylene glycol)-terminated self-assembled monolayers on gold and silver surfaces determines their ability to resist protein adsorption J. Phys. Chem. B 1998, 102, 426-436
7. Schilp, S.; Rosenhahn, A.; Pettitt, M. E.; Bowen, J.; Callow, M. E.; Callow, J. A.; Grunze, M. Physicochemical properties of (ethylene glycol)-containing self-assembled monolayers relevant for protein and algal cell resistance Langmuir 2009, 25, 10077-10082
8. Gabriel, M.; Nazmi, K.; Veerman, E. C.; Nieuw Amerongen, A. V.; Zentner, A. Preparation of LL-37-grafted titanium surfaces with bactericidal activity Bioconjugate Chem. 2006, 17, 548-550
9. Lante, A.; Crapisi, A.; Pasini, G.; Scalabrini, P. Nisin released from immobilization matrices as antimicrobial agent Biotechnol. Lett. 1994, 16, 293-298
10. Zolk, M.; Eisert, F.; Pipper, J.; Herrwerth, S.; Eck, W.; Buck, M.; Grunze, M. Solvation of oligo(ethylene glycol)-terminated self-assembled monolayers studied by vibrational sum frequency spectroscopy Langmuir 2000, 16, 5849-5852
11. Skoda, M. W. A.; Jacobs, R. M. J.; Willis, J.; Schreiber, F. Hydration of oligo(ethyleneglycol) self-assembled monolayers studied using polarization modulation infrared spectroscopy Langmuir 2007, 23, 970-974
12. 6OMe on gold and immersion effects Phys. Chem. Chem. Phys. 2010, 12, 8985-8990
13. Li, L.; Chen, S.; Zheng, J.; Ratner, B. D.; Jiang, S. Protein adsorption on oligo(ethyleneglycol)-terminated alkanethiolate self-assembled monolayers: The molecular basis for nonfouling behavior J. Phys. Chem. B 2005, 109, 2934-2941
14. Wang, R. L. C.; Kreuzer, H. J.; Grunze, M. Molecular conformation and solvation of oligo(ethylene glycol)-terminated self-assembled monolayers and their resistance to protein adsorption J. Phys. Chem. B 1997, 101, 9767-9773
15. Wang, R. L. C.; Jürgen Kreuzer, H.; Grunze, M. The interaction of oligo(ethylene oxide) with water: A quantum mechanical study Phys. Chem. Chem. Phys. 2000, 2, 3613-3622
16. Wang, R. Y.; Himmelhaus, M.; Fick, J.; Herrwerth, S.; Eck, W.; Grunze, M. Interaction of self-assembled monolayers of oligo(ethylene glycol)-terminated alkanethiols with water studied by vibrational sum-frequency generation J. Chem. Phys. 2005, 122, 164702
17. Östblom, M.; Valiokas, R.; Konradsson, P.; Svensson, S. C. T.; Liedberg, B.; Garrett, M.; Allara, D. L. Ice nucleation and phase behavior on oligo(ethylene glycol) and hydroxyl self-assembled monolayers: Simulations and experiments J. Phys. Chem. B 2006, 110, 1830-1836
18. Valiokas, R.; Malysheva, L.; Onipko, A.; Lee, H.-H.; Ruželė, Ž.; Svedhem, S.; Svensson, S. C.; Gelius, U.; Liedberg, B. On the quality and structural characteristics of oligo(ethylene glycol) assemblies on gold: An experimental and theoretical study J. Electron Spectrosc. Relat. Phenom. 2009, 172, 9-20
19. Vanderah, D. J.; Valincius, G.; Meuse, C. W. Self-assembled monolayers of methyl 1-thiahexa(ethylene oxide) for the inhibition of protein adsorption Langmuir 2002, 18, 4674-4680
20. Laibinis, P. E.; Whitesides, G. M.; Allara, D. L.; Tao, Y. T.; Parikh, A. N.; Nuzzo, R. G. Comparison of the structures and wetting properties of self-assembled monolayers of nalkanethiols on the coinage metal surfaces, copper, silver, and gold J. Am. Chem. Soc. 1991, 113, 7152-7167
21. Zharnikov, M.; Frey, S.; Heister, K.; Grunze, M. An extension of the mean free path approach to X-ray absorption spectroscopy J. Electron Spectrosc. Relat. Phenom. 2002, 124, 15-24
22. Malysheva, L.; Onipko, A.; Valiokas, R.; Liedberg, B. First-principles modeling of oligo(ethylene glycol)-terminated and amide group containing alkanethiolates Appl. Surf. Sci. 2005, 246, 372-376
23. Weidner, T.; Apte, J. S.; Gamble, L. J.; Castner, D. G. Probing the orientation and conformation of -helix and -strand model peptides on self-assembled monolayers using sum frequency generation and NEXAFS spectroscopy Langmuir 2010, 26, 3433-3440
24. Beamson, G.; Pickup, B. T.; Li, W.; Mai, S.-M. XPS studies of chain conformation in PEG, PTrMO, and PTMG linear polyethers J. Phys. Chem. B 2000, 104, 2656-2672
25. Zwahlen, M.; Herrwerth, S.; Eck, W.; Grunze, M.; Hähner, G. Conformational order in oligo(ethylene glycol)-terminated self-assembled monolayers on gold determined by soft X-ray absorption Langmuir 2003, 19, 9305-9310
26. Schertel, A.; Hahner, G.; Grunze, M.; Woll, C. Near edge x-ray absorption fine structure investigation of the orientation and thermally induced order-disorder transition in thin organic films containing long chain hydrocarbons J. Vac. Sci. Technol., A 1996, 14, 1801-1806
27. Peters, R. D.; Nealey, P. F.; Crain, J. N.; Himpsel, F. J. A near edge X-ray absorption fine structure spectroscopy investigation of the structure of self-assembled films of octadecyltrichlorosilane Langmuir 2002, 18, 1250-1256
28. Fu, J.; Urquhart, S. G. Linear dichroism in the X-ray absorption spectra of linear n-alkanes J. Phys. Chem. A 2005, 109, 11724-11732
29. Hähner, G.; Wöll, C.; Buck, M.; Grunze, M. Investigation of intermediate steps in the selfassembly of n -alkanethiols on gold surfaces by soft X-ray spectroscopy Langmuir 1993, 9, 1955-1958
30. Bierbaum, K.; Kinzler, M.; Woell, C.; Grunze, M.; Haehner, G.; Heid, S.; Effenberger, F. A near edge X-ray absorption fine structure spectroscopy and X-ray photoelectron spectroscopy study of the film properties of self-assembled monolayers of organosilanes on oxidized Si(100) Langmuir 1995, 11, 512-518
31. Ho, P.-H.; Chua, L.-L.; Dipankar, M.; Gao, X.; Qi, D.; Wee, A.-S.; Chang, J.-F.; Friend, R. Solvent effects on chain orientation and interchain -interaction in conjugated polymer thin films: Direct measurements of the air and substrate interfaces by near-edge X-ray absorption spectroscopy Adv. Mater. 2007, 19, 215-221
32. Kinzler, M.; Schertel, A.; Hähner, G.; Wöll, C.; Grunze, M.; Albrecht, H.; Holzhüter, G.; Gerber, T. Structure of mono- and multilayer Langmuir-Blodgett films from Cd arachidate and Ca arachidate J. Chem. Phys. 1994, 100, 7722-7735
33. Hähner, G.; Kinzler, M.; Wöll, C.; Grunze, M.; K. Scheller, M.; Cederbaum, L. S. Near edge x-ray-absorption fine-structure determination of alkyl-chain orientation: Breakdown of the "building-block" scheme Phys. Rev. Lett. 1991, 67, 851-854
34. Nelson, K. E.; Gamble, L.; Jung, L. S.; Boeckl, M. S.; Naeemi, E.; Golledge, S. L.; Sasaki, T.; Castner, D. G.; Campbell, C. T.; Stayton, P. S. Surface characterization of mixed self-assembled monolayers designed for streptavidin immobilization Langmuir 2001, 17, 2807-2816
35. Dicke, C.; Hähner, G. Interaction between a hydrophobic probe and tri(ethylene glycol)-containing self-assembled monolayers on gold studied with force spectroscopy in aqueous electrolyte solution J. Phys. Chem. B 2002, 106, 4450-4456
36. Bai, Y.; Liu, X.; Cook, P.; Abbott, N. L.; Himpsel, F. J. Characterization of surfaces presenting covalently immobilized oligopeptides using near-edge X-ray absorption fine structure spectroscopy Langmuir 2010, 26, 6464-6470
37. Stöhr, J. NEXAFS Spectroscopy; Springer: New York, 1996.
38. Hitchcock, A.; Ishii, I. Carbon K-shell excitation spectra of linear and branched alkanes J. Electron Spectrosc. Relat. Phenom. 1987, 42, 11-26
39. Stöhr, J.; Outka, D. A.; Baberschke, K.; Arvanitis, D.; Horsley, J. A. Identification of CH resonances in the K-shell excitation spectra of gas-phase, chemisorbed, and polymeric hydrocarbons Phys. Rev. B 1987, 36, 2976-2979
40. Urquhart, S. G.; Gillies, R. Matrix effects in the carbon 1s near edge x-ray absorption fine structure spectra of condensed alkanes J. Chem. Phys. 2006, 124, 234704
41. Bagus, P.; Weiss, K.; Schertel, A.; Wöll, C.; Braun, W.; Hellwig, C.; Jung, C. Identification of transitions into Rydberg states in the X-ray absorption spectra of condensed long-chain alkanes Chem. Phys. Lett. 1996, 248, 129-135
42. Weiss, K.; Bagus, P. S.; Wöll, C. Rydberg transitions in X-ray absorption spectroscopy of alkanes: The importance of matrix effects J. Chem. Phys. 1999, 111, 6834-6845
43. Ohta, T.; Seki, K.; Yokoyama, T.; Morisada, I.; Edamatsu, K. Polarized XANES studies of oriented polyethylene and fluorinated polyethylenes Phys. Scr. 1990, 41, 150
44. Zou, Y.; Araki, T.; Appel, G.; Kilcoyne, A.; Ade, H. Solid state effects in the NEXAFS spectra of alkane-based van der Waals crystals: Breakdown of molecular model Chem. Phys. Lett. 2006, 430, 287-292
45. Liu, X.; Jang, C.-H.; Zheng, F.; Jürgensen, A.; Denlinger, J. D.; Dickson, K. A.; Raines, R. T.; Abbott, N. L.; Himpsel, F. J. Characterization of protein immobilization at silver surfaces by near edge X-ray absorption fine structure spectroscopy Langmuir 2006, 22, 7719-7725
46. Goel, M.; Marsh, E. N. G.; Chen, Z.; Abbott, N. L. Comparison of the influence of humidity and d -mannitol on the organization of tetraethylene glycol-terminated self-assembled monolayers and immobilized antimicrobial peptides Langmuir 2014, 30, 7143-7151