Semiquantitative study of the EDC/NHS activation of acid terminal groups at modified porous silicon surfaces

Langmuir

Volumn 26, Issue 2, 2010, Pages 809-814

  Sam, S ^a,b,c   Touahir, L ^a   Salvador Andresa, J ^a   Allongue, P ^a   Chazalviel, J N ^a   Gouget Laemmel, A C ^a   De Villeneuve, C H ^a   Moraillon, A ^a   Ozanam, F ^a   Gabouze, N ^b   Djebbar, S ^c  

^a LABORATOIRE DE PHYSIQUE DE LA MATIÈRE CONDENSÉE   (France)

^b L'Unite de Developpement de la Technologie du Silicium   (Algeria)

^c UNIVERSITY OF SCIENCES AND TECHNOLOGY HOUARI BOUMEDIENE   (Algeria)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHAINS; ALKYL CHAIN; AQUEOUS SOLUTIONS; CARBODIIMIDES; CROSS SECTION; DETECTING TRACE; MODIFIED POROUS SILICON; N-HYDROXYSUCCINIMIDE; REACTION CONDITIONS; REACTION PATHS; REACTION PRODUCTS; SEMI-QUANTITATIVE; SOLUTION COMPOSITION; SUCCINIMIDYL ESTER; SURFACE ADSORPTION; SURFACE COMPOSITIONS; SURFACE PRODUCTS; TERMINAL GROUPS;

ACIDS; ADSORPTION; ESTERIFICATION; ESTERS; INFRARED SPECTROSCOPY; POROUS SILICON;

SURFACE REACTIONS;

1 (3 DIMETHYLAMINOPROPYL) 3 ETHYLCARBODIIMIDE; 10 UNDECENOIC ACID; N HYDROXYSUCCINIMIDE; N-HYDROXYSUCCINIMIDE; SILICON; SUCCINIMIDE DERIVATIVE;

ARTICLE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; INFRARED SPECTROSCOPY; POROSITY; THEORETICAL MODEL;

ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE; MODELS, THEORETICAL; POROSITY; SILICON; SPECTROPHOTOMETRY, INFRARED; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SUCCINIMIDES; UNDECYLENIC ACIDS;

EID: 74249117126     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la902220a     Document Type: Article

References (66)

1. Sassolas, A.; Leca-Bouvier, B. D.; Blum, L. J. Chem. Rev. 2008, 108, 109.
2. Borisov, S. M.; Wolfbeis, O. S. Chem. Rev. 2008,108, 423.
3. Luderer, F.; Walschus, U. Top. Curr. Chem, 2005, 260, 37.
4. Rusmini, F.; Zhong, Z.; Feijen, J. Biomacromolecules 2007, 8, 1775.
5. Staros, J. V.; Wright, R. W.; Swingle, D. M. Anal. Biochem. 1986, 156, 220.
6. Hermanson, G. T. Bioconjugate Techniques, 2nd ed.; Academic Press: San Diego, 2008.
7. Dordi, B.; Schönherr, H.; Vansco, G. J. Langmuir 2003, 19, 5780.
8. Taratula, O.; Galoppini, E.; Mendelsohn, R.; Reyes, P. I.; Zhang, Z.; Duan, Z.; Zhong, J.; Lu, Y. Langmuir 2009, 25, 2107.
9. Wojtyk, J. T. C.; Morin, R. A.; Boukherroub, R.; Wayner, D. D. M. Langmuir 2002, 18, 6081.
10. (a) Booking, T.; James, M.; Coster, H. G. L.; Chilcott, T. C.; Barrow, R. D. Langmuir 2004, 20, 9235.
11. (b) Yang, M.; Teeuwen, R. L. M.; Giesbers, M.; Baggennan, J.; Arafat, A.; de Wolf, F. A.; van Hest, J. C. M.; Zuilhof, H. Langmuir 2008, 24, 7931.
12. (a) Patel, N.; Davies, M, C.; Hartshorne, M.; Heaton, R. J.; Roberts, C. J.; Tendler, S. J. B.; Williams, P. M. Langmuir 1997, 13, 6485.
13. (b) Wolf, L. K.; Fullenkamp, D. E.; Georgiadis, R. M. J. Am. Chem. Soc. 2005, 127, 17453.
14. Lee, J. W.; Sim, S. J.; Cho, S. M.; Lee, J. Biosens. Bioelectron. 2005, 20, 1422.
15. (c) Jang, L.-S.; Keng, H.-K. Biomed. Microdevices 2008, 10, 203.
16. (a) Nakano, K.; Taira, H.; Takagi, M. Anal. Sci, 1993, 9, 133.
17. (b) Wagner, P.; Kernen, P.; Hegner, M.; Ungewickell, E.; Semenza, G. FEBS Lett. 1994, 356, 267.
18. Linford, M. R.; Fenter, P.; Eisenberger, P. M.; Chidsey, C E. D. J. Am. Chem. Soc. 1995, 117, 3145.
19. (a) Buriak, J. M. Chem. Rev. 2002, 102, 1271.
20. (b) Wayner, D. D. M.; Wolkow, R. A. J. Chem. Soc., Perkin Trans. 2 2002, 2, 23.
21. (c) Boukherroub, R. Curr, Opin. Solid State Mater. Sci. 2005, 9, 66.
22. (d) Shirahata, N.; Hozumi, A.; Yonezawa, T. Chem. Rec. 2005, 5, 145.
23. Lehner, A.; Steinhoff, G.; Brandt, M. S.; Eickhoff, M.; Stutzmann, M. J. Appl. Phys. 2003, 94, 2289.
24. (a) Bunimovich, Y. L.; Ge, G.; Beverly, R. C.; Ries, R. S.; Hood, L.; Heath, J. R. Langmuir 2004, 20, 10630.
25. (b) Streifer, J. A.; Kim, H.; Nichols, B. M.; Hamers, R. J. Nanotechnology 2005, 16, 1868.
26. (c) Scheibal, Z. R.; Xu, W; Audifrred, J. F.; Flake, J. C. Electrochem. Solid-State Lett. 2008, 11, K81.
27. Wagner, P.; Nock, S.; Spudick, J. A.; Volkmuth, W. D.; Chu, S.; Cicero, R. L.; Wade, C. P.; Linford, M. R.; Chidsey, C. E. D. J. Struct. Biol. 1997, 119, 189.
28. (a) Strother, T.; Cai, W.; Zhao, X.; Hamers, R. J.; Smith, L. M. J. Am. Chem. Soc. 2000, 122, 1205.
29. (b) Pike, A. R.; Lie, L. H.; Eagling, R. A.; Ryder, L. C.; Patole, S. N.; Connoly, B. A.; Horrocks, B. R.; Houlton, A. Angew. Chem., Int. Ed. 2002, 41, 615.
30. (c) Guo, D.-J.; Xiao, S.-J.; Xia, B.; Wei, S.; Pei. Pan, Y.; You, X.-Z.; Gu, Z.-Z.; Lu, Z. J. Phys. Chem, B 2005, 109, 20620.
31. (d) Booking, T.; Kilián, K. A.; Hanley, T.; Ilyas, S.; Gaus, K.; Gal, M.; Gooding, J. J. Langmuir 2005, 21, 10522.
32. Voicu, R.; Boukherroub, R.; Bartzoka, V.; Ward, T.; Wojtyk, J. T. C.; Wayner, D. D. M. Langmuir 2004, 20, 11713.
33. (a) Stewart, MTP.; Buriak, J. M. J. Am. Chem. Soc. 2001, 123, 7821.
34. (b)Sun, Q.-Y.; de Smet, L. C. P. M.; van Lagen, B.; Wright, A.; Zuilhof, H.; Sudhölter, E. J. R. Angew. Chem., Int. Ed. 2004, 43, 1352.
35. (c) Liu, Y.; Yamazaki, S.; Yamabe, S.; Nakato, Y. J. Mater. Chem. 2005, 15, 4906.
36. (a) Sieval, A. B.; van den Hout, B.; Zuilhof, H.; Sudhölter, E. R. J. Langmuir 2001, 17, 2172.
37. (b) Zhang, L.; Wesley, K.; Jiang, S. Langmuir 2001, 17, 6275.
38. Cicero, R. L.; Linford, M. R.; Chidsey, C E. D. Langmuir 2000, 16, 5688.
39. Moraillon, A.; Gouget-Laemmel, A. C.; Ozanam, F.; Chazalviel, J.-N. J. Phys. Chem. C 2008, 112, 7158.
40. (a) Lahiri, J.; Isaacs, L.; Tien, J.; Whitesides, G. M, Anal. Chem. 1999, 71, 777.
41. (b) Chi, Y. S.; Jung, Y. H.; Choi, I. S.; Kim, Y.-G. Langmuir 2005, 21, 4669.
42. (c) Briand, E.; Salmain, M.; Compère, C; Pradier, C.-M. Colloids Surf., B 2006, 53, 215.
43. Wei, F.; Sun, B.; Guo, Y.; Zhao, X. S. Biosens. Bioelectron, 2003, 18, 1157.
44. Mirsky, V. M.; Riepl, M.; Wolfbeis, O. S. Biosens. Bioelectron. 1997, 12, 977.
45. Grubor, N. M.; Shinar, R.; Jankowiak, R.; Porter, M. D.; Small, G. J. Biosens. Bioelectron. 2004, 19, 547.
46. Seghal, D.; Vijay, I. R. Anal. Biochem. 1994, 218, 87.
47. Boukherroub, R.; Wojtyk, T. C.; Wayner, D. D. M.; Lockwood, D. J. J. Electrochem. Soc. 2002, 149, H59.
48. Faucheux, A.; Gouget-Laemmel, A. C.; Henry de Villeneuve, C.; Boukherroub, R.; Ozanam, F.; Allongue, P.; Chazalviel, J.-N. Lanemuir 2006, 22, 153.
49. Ogata, Y.; Niki, H.; Sakka, T.; Iwasaki, M. J. Electrochem. Soc. 1995, 142, 195.
50. da Fonseca, C.; Ozanam, F.; Chazalviel, J.-N. Surf Sci. 1995, 365, 1.
51. (a) Lucovsky, G. Solid State Commun. 1979, 29, 571.
52. (b) Ubara, H.; Imura, T.; Hiraki, A. Solid State Commun, 1984, 50, 673.
53. (c) Chazalviel, J.-N.; Ozanam, F. In EMIS Datarev., Ser. 18 (Properties of Porous Silicon); Canham, L., Ed.; The Institution, of Electrical Engineers: London, 1997; pp 59-65.
54. (a) Yan, L.; Marzolin, C.; Terfort, A.; Whitesides, G. M. Langmuir 1997, 13, 6704.
55. (b) Faucheux, A.; Gouget-Laemmel, A. C.; Allongue, P.; Henryae Villeneuve, C.; Ozanam, F.; Chazalviel, J.-N. Langmuir 2007, 23, 1326.
56. Rhorana, H. G. Chem. Rev. 1953, 53, 145.
57. Hoare, D. G.; Koshland, D. E., Jr. J. Biol. Chem. 1967, 242, 2447.
58. Iwasawa, T.; Wash, P.; Gibson, C.; Rebek, J., Jr. Tetrahedron 2007, 63, 6506.
59. (a) Frey, B. L.; Corn, R. M. Anal. Chem. 1996, 68, 3187.
60. (b) Xiao, S.-J.; Brunner, S.; Wieland, M. J. Phys. Chem. B 2004, 108, 16508.
61. Lin-Vien, D.; Colthup, N. B.; Fateley, W. G.; Grasselli, J. G. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; Academic Press: San Diego, 1991.
62. Aureau, D.; Ozanam, F.; Allongue,P.; Chazalviel, J.-N. Langmuir 2008, 24, 9440.
63. Nakajima, N.; Ikada, Y. Bioconjugate Chem. 1995, 6, 123.
64. In previous experiments [see ref 23 and (a) Douarche, C.; Cortés, R.; Henry de Villeneuve, C.; Roser, S. J.; Breslau, A. J. Chem. Phys. 2008, 128, 225108.
65. (b) Douarche, C. PhD Thesis, Université de Lille 1 (USTL), 2007], surface activation was performed by exposing the acid surface to EDC alone (30 min) and then adding NHS (60 min). Applying this procedure here with [EDC] = [NHS] = 5 mM yields an incomplete reaction, (η = 1.6), consistent with, irreversible formation of N-acylurea during the first step of the procedure.
66. Touahir, L.; Moraillon, A.; Sam, S.; Gouget-Laemmel, A. C.; Allongue, P.; Chazalviel, J.-N.; Henry de Villeneuve, C.; Ozanam, F. ECS Trans. 2009, 19, 283.