Surface-promoted thioether linkage between proto- or hemato porphyrins and thiol-silanized quartz: Formation of self-assembled monolayers and interaction with imidazole and carbon monoxide

Langmuir

Volumn 14, Issue 17, 1998, Pages 4809-4818

  Pilloud, Denis L ^a   Moser, Christopher C ^a   Reddy, Konda S ^a   Dutton, P Leslie ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; AROMATIC COMPOUNDS; CARBON MONOXIDE; CHEMISORPTION; ETHERS; FLUORESCENCE; MONOLAYERS; QUARTZ; REDUCTION; SURFACE CHEMISTRY; YTTRIUM;

HEMATOPORPHYRINS; PROTOPORPHYRINS; SELF-ASSEMBLED MONOLAYERS (SAM);

SULFUR COMPOUNDS;

EID: 0032139176     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la980596s     Document Type: Article

References (66)

1. Abbreviation used: PP, free base protoporphyrin IX; Zn(II)PP, Zn(II)protoporphyrin IX; Fe(III)PP, Fe(III)protoporphyrin IX; Fe(III)-PPDME, Fe-(III)protoporphyrin IX dimethylester; HP, free base hematoporphyrin; SAM, self-assembled monolayer; UV, ultraviolet; vis, visible; Fe(III)MP, Fe(III)mesoporphyrin; Fe(III)CP, Fe(III)coproporphyrin I; Fe(III)UP, Fe(III)uroporphyrin; PS, propyltrimethoxysilane; Tris-HCl, Tris[hydroxymethyl]aminomethane-HCl; DMSO, dimethyl sulfoxide; MPS, (3-mercaptopropyl)trimethoxysilane; HPLC, high-performance liquid chromatography;∈, molar extinction coefficient; A, absorbance; L, ligand (typically water); Im, imidazole; MPP, metalloprotoporphyrin IX.; LD, linear dichroism; IR, infrared.
2. (a) Schuitmaker, J. J.; Baas P.; van Leengoed, H. L.; van der Meulen, F. W.; Star, W. M.; van Zandwijk, N. J. Photochem. Photobiol. B 1996, 34, 3-12.
3. (b) Sinaasappel, M.; Ince, C. J. Appl. Physiol. 1996, 81, 2297-2303.
4. (c) Cespuglio R.; Burlet, S.; Marinesco, S.; Robert, F.; Jouvet, M. C. R. Acad. Sci., Ser. III 1996, 319, 191-200.
5. (a) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537-546.
6. (b) D'Souza, F.; Deviprasad, G. R.; Golapalli, R.; Hsieh, Y.-Y. J. Chem. Soc., Chem. Commun. 1997, 6, 533-534.
7. (c) Tatsuma, T.; Buttry, D. A. Anal. Chem. 1997, 69, 887-893.
8. (d) Xiao, J.; Meyerhoff, M. E. Anal. Chem. 1996, 68, 2818-2825.
9. (a) Lee, S.-Y.; Okura, I. Anal. Chim. Acta 1997, 342, 181-188.
10. (b) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119 (9), 5267-5268.
11. (c) Brunink, J. A. J.; Di Natale, C.; Bungaro F.; Davide, F. A. M.; D'Amico, A.; Paolesse, R.; Boschi, T.; Faccio, M.; Ferri G. Anal. Chim. Acta 1996, 325, 53-64.
12. (a) Kuzelova, K.; Mrhalova, M.; Hrkal, Z. Biochim. Biophys. Acta 1997, 1336, 497-501.
13. (b) White, W. J. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 5, Chapter 7.
14. (c) Brown, S. B.; Dean, T. C.; Jones, P. Biochem. J. 1970, 117, 733-739.
15. (a) Silver, J.; Lukas, B. Inorg. Chim. Acta 1983, 78, 219-224.
16. (b) James, B. R. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 5, pp 231-251.
17. (c) King, R. F. G. J.; Brown, S. B. Biochem. Soc. Trans. 1976, 4, 299-301.
18. (a) Petrich, J. W.; Poyart, C.; Martin, J. L. Biochemistry 1988, 27, 4049-4060.
19. (b) Hopf, F. R., Whitten, D. G. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 2, pp 161-195.
20. DeGrado, W. F.; Wasserman, Z. R.; Lear, J. D. Science 1989, 243, 622-628.
21. Robertson, D. E.; Farid, R. S.; Moser, C. C.; Urbauer, J. L.; Mulholland, S. E.; Pidikiti, R.; Lear, J. D.; Wand, A. J.; DeGrado, W. F.; Dutton, P. L. Nature 1994, 368, 425-432.
22. Nishide, H.; Yuasa, M.; Hasegawa, E.; Tsuchida, E. Macromolecules 1987, 20, 1913-1917.
23. (a) Lahiri, J.; Fate, G. D.; Ungashe, S. B.; Groves, J. T. J. Am. Chem. Soc. 1996, 118, 2347-2358.
24. (b) van Hesch, J. H.; Feiters, M. C.; Peters, A. M.; Nolte, R. J. M. J. Phys. Chem. 1994, 98, 5541-5551.
25. (c) Groves, J. T.; Neumann, R. J. Am. Chem. Soc. 1989, 111, 2900-2909.
26. (d) Groves, J. T.; Neumann, R. J. Am. Chem. Soc. 1987, 109, 5045-5047.
27. Tsuchida, E.; Komatsu, T.; Arai, K.; Yamada, K.; Nishide, H.; Fuhrhop, J.-H. Langmuir 1995, 11, 1877-1884.
28. Chou, H.; Chen, C.-T.; Stork, K. F.; Bohn, P. W.; Suslick, K. S. J. Phys. Chem. 1994, 98, 383-385.
29. (a) Hutchison, J. E. Postlethwaite, T. A.; Chen, C.-h.; Hatchcock, K. W.; Ingram, R. S.; Ou, W.; Linton, R. W.; Linton, R. W.; Murray, R. Langmuir 1997, 13, 2143-2148.
30. (b) Postlethwaite, T. A.; Hutchison, J. E.; Hatchcok, K. W.; Murray, R. W. Langmuir 1995, 11, 4109-4116.
31. (c) Li, D.; Buscher, C. T., Swanson, B. I. Chem. Mater. 1994, 6, 803-810.
32. (d) Akiyama, T.; Imahori, H.; Sakata, Y. Chem, Lett. 1994, 1447-1450.
33. (e) Li, D.; Swanson, B. I.; Robinson, J. M.; Hoffbauer, M. A. J. Am. Chem. Soc. 1993, 115, 6975-6980.
34. (f) Zak, J.; Yuan, H.; Ho, M.; Woo, L. K.; Porter, M. D. Langmuir 1993, 9, 2772-2774.
35. Li, D.; Moore, L. W.; Swanson, B. I. Langmuir 1994, 10, 1177-1185.
36. Pilloud, D. L.; Rabanal, F.; Gibney, B. R., Farid, R. S.; Moser, C. C.; Dutton, P. L. J. Phys. Chem. B. 1998, 102, 1926-1937.
37. -1.
38. Yanagi, H.; Ashida, M.; Harima, Y.; Yamashita, K. Chem. Lett. 1990, 385-388.
39. (a) Schick, G. A.; Schreiman, I. C.; Wagner, R. W.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1989, 111, 1344-1350.
40. (b) Schick, G. A. Thin Solid Films 1989, 179, 521-527.
41. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 4th ed.; John Wiley and Sons: New York, 1980; pp 386-387.
42. Frink, M. E.; Ferraudi, G. Chem. Phys. Lett. 1986, 124, 576-578.
43. Silver, J.; Lukas, B. Inorg. Chim. Acta 1983, 80, 107-113.
44. Hill, A. V. Biochem. J. 1913, 7, 471-480.
45. (a) Desbois, A.; Lutz, M. Eur. Biophys. J. 1992, 20, 321-335.
46. (b) Al-Jaff, G.; Silver, J.; Wilson, M. T. Inorg. Chim. Acta 1990, 176, 307-316.
47. (c) Yoshimura, T.; Ozaki, T. Bull. Chem. Soc. Jpn. 1979, 52, 2268-2275.
48. (d) Hasegawa, E.; Kaneda, M.; Nemoto, J.; Tsuchida, E. J. Inorg. Nucl. Chem. 1978, 40, 1241-1245.
49. 3: (a) O'Connor, D. B.; Goldbeck, R. A.; Hazzard, J. H.; Kliger, D. S.; Cusanovich, M. A. Biophys. J. 1993, 65, 1718-1726. Example of monohistidyl Fe(III)PP: ref 10 and (b) Tatsuma, T.; Watanabe, T. Anal. Chem. 1992, 64, 143-147.
50. 3: (a) O'Connor, D. B.; Goldbeck, R. A.; Hazzard, J. H.; Kliger, D. S.; Cusanovich, M. A. Biophys. J. 1993, 65, 1718-1726. Example of monohistidyl Fe(III)PP: ref 10 and (b) Tatsuma, T.; Watanabe, T. Anal. Chem. 1992, 64, 143-147.
51. Decatur, S. M.; Boxer, S. G. Biochem. Biophys. Res. Commun. 1995, 212, 159-164.
52. Blasie, J. K.; Erecinska, M.; Sanmuels, S.; Leigh J. S. Biochim. Biophys. Acta 1978, 501, 33-52.
53. Adar, F. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3, pp 167-206.
54. LD of LB films and SAMs measured by UV/vis/IR: (a)Möhwald, H.; Miller, A.; Stich, W.; Knoll, W.; Ruaudel-Teixier, A.; Lehman, L.; Fuhrhop, J.-H. Thin Solid Films 1986, 141, 261-275 as well as refs 13 and 15. Measured by electron spin resonance (b) Azumi, R.; Matsumoto, M.; Kawabata, Y.; Kuroda, S.; Sugi, M.; King, L. G.; Crossley, M. J. J. Phys. Chem. 1993, 97, 12862-12869 and ref 11b. Self-ordered thin films measured by polarized Raman spectroscopy (c) Melamed, D.; Darlington, B.; Brook, D. J. R.; Pan, H.-L.; Campion, A.; Fox, M.-A. J. Phys. Chem. 1994, 98, 8971-8976.
55. LD of LB films and SAMs measured by UV/vis/IR: (a)Möhwald, H.; Miller, A.; Stich, W.; Knoll, W.; Ruaudel-Teixier, A.; Lehman, L.; Fuhrhop, J.-H. Thin Solid Films 1986, 141, 261-275 as well as refs 13 and 15. Measured by electron spin resonance (b) Azumi, R.; Matsumoto, M.; Kawabata, Y.; Kuroda, S.; Sugi, M.; King, L. G.; Crossley, M. J. J. Phys. Chem. 1993, 97, 12862-12869 and ref 11b. Self-ordered thin films measured by polarized Raman spectroscopy (c) Melamed, D.; Darlington, B.; Brook, D. J. R.; Pan, H.-L.; Campion, A.; Fox, M.-A. J. Phys. Chem. 1994, 98, 8971-8976.
56. LD of LB films and SAMs measured by UV/vis/IR: (a)Möhwald, H.; Miller, A.; Stich, W.; Knoll, W.; Ruaudel-Teixier, A.; Lehman, L.; Fuhrhop, J.-H. Thin Solid Films 1986, 141, 261-275 as well as refs 13 and 15. Measured by electron spin resonance (b) Azumi, R.; Matsumoto, M.; Kawabata, Y.; Kuroda, S.; Sugi, M.; King, L. G.; Crossley, M. J. J. Phys. Chem. 1993, 97, 12862-12869 and ref 11b. Self-ordered thin films measured by polarized Raman spectroscopy (c) Melamed, D.; Darlington, B.; Brook, D. J. R.; Pan, H.-L.; Campion, A.; Fox, M.-A. J. Phys. Chem. 1994, 98, 8971-8976.
57. For example, for porphyrins with long alkyl chains: ref 11b, 19a, and Vandevyver, M.; Barraud, A.; Raudel-Teixier, A.; Maillard, P.; Gianotti, C. J. Colloid Interface Sci. 1982, 85, 571-585 and with porphyrins having bulky residues, see ref 14e.
58. Theorell, H. Biochem. Z. 1939, 301, 201-209; Theorell, H. Biochem. Z. 1938, 298, 242-267.
59. Theorell, H. Biochem. Z. 1939, 301, 201-209; Theorell, H. Biochem. Z. 1938, 298, 242-267.
60. Sano, S.; Nanzyo N.; Rimington, C. Biochem. J. 1964, 93, 270-280.
61. 562, in Escherichia coli: (a) Barker, P. D.; Nerou, E. P.; Freund, S. M. V.; Fearnley, I. M. Biochemistry 1995, 34, 15191-15203. By enzymatic activation of apocytochrome c (b) Taniuchi, H.; Basile, G.; Taniuchi, M.; Veloso, D. J. Biol. Chem. 1983, 258, 10963-10966. Protoporphyrinsc were all synthesized from free base porphyrins (ref 31) or from porphyrinogens (ref 32) under extreme experimental conditions, and from our knowledge, there is no example of reaction between Fe(III)PP and thiol compounds.
62. 562, in Escherichia coli: (a) Barker, P. D.; Nerou, E. P.; Freund, S. M. V.; Fearnley, I. M. Biochemistry 1995, 34, 15191-15203. By enzymatic activation of apocytochrome c (b) Taniuchi, H.; Basile, G.; Taniuchi, M.; Veloso, D. J. Biol. Chem. 1983, 258, 10963-10966. Protoporphyrinsc were all synthesized from free base porphyrins (ref 31) or from porphyrinogens (ref 32) under extreme experimental conditions, and from our knowledge, there is no example of reaction between Fe(III)PP and thiol compounds.
63. Steiner, H.; Kispal, G.; Zollner, A.; Haid, A.; Neupert, W.; Lill, R. J. Biol. Chem. 1996, 271, 32605-32611.
64. Wang, J. H.; Nakahara, A.; Fleischer, E. B. J. Am. Chem. Soc. 1958, 80, 1109-1113.
65. (a) Brewer, C. T.; Brewer G. J. Chem. Soc., Dalton Trans. 1990, 843-847.
66. (b) Nappa, M.; Valentine, J. S. J. Am. Chem. Soc. 1978, 100, 5075-5080.