Structural analysis of porphyrin multilayer films on ITO assembled using copper(I)-catalyzed azide-alkyne cycloaddition by ATR IR

ACS Applied Materials and Interfaces

Volumn 3, Issue 12, 2011, Pages 4703-4713

  Palomaki, Peter K B ^a   Dinolfo, Peter H ^a  

^a Research Rensselaer Polytechnic Institute   (United States)

Author keywords

CuAAC; GATR IR; layer by layer; multilayers; porphyrin; thin films

Indexed keywords

ABSORBANCES; ADDITIONAL REACTIONS; ATTENUATED TOTAL REFLECTANCE; AZIDE-ALKYNE CYCLOADDITION; AZIDO GROUP; CHARACTERISTIC PEAKS; CUAAC; GATR-IR; IR INTENSITIES; LAYER-BY-LAYER; LAYER-BY-LAYERS; MOLECULAR MULTILAYERS; MULTILAYER FABRICATION; MULTILAYER STRUCTURES; PHOTOPHYSICAL; PLANE ANGLES; POTENTIAL APPLICATIONS; UV-VIS ABSORBANCE MEASUREMENTS;

ACETYLENE; CATALYSIS; COPPER; ELECTROCHEMICAL PROPERTIES; MOLECULAR ORIENTATION; MULTILAYERS; PORPHYRINS; SPECTRUM ANALYSIS; SUBSTRATES;

MULTILAYER FILMS;

ALKYNE; AZIDE; COPPER; INDIUM TIN OXIDE; PORPHYRIN; TIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SPECTROSCOPY;

ALKYNES; AZIDES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; PORPHYRINS; SPECTRUM ANALYSIS; TIN COMPOUNDS;

EID: 84857729265     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am201125p     Document Type: Article

References (73)

1. George, S. M.; Yoon, B.; Dameron, A. A. Acc. Chem. Res. 2009, 42, 498-508
2. van der Boom, M. E.; Marks, T. J. In Polymers for Microelectronics and Nanoelectronics; American Chemical Society: Washington, D.C., 2004; Vol. 874, pp 30-43.
3. Cao, G.; Hong, H. G.; Mallouk, T. E. Acc. Chem. Res. 2002, 25, 420-427
4. Lee, H.; Kepley, L. J.; Hong, H. G.; Akhter, S.; Mallouk, T. E. J. Phys. Chem. 2002, 92, 2597-2601
5. Yang, H. C.; Aoki, K.; Hong, H. G.; Sackett, D. D.; Arendt, M. F.; Yau, S. L.; Bell, C. M.; Mallouk, T. E. J. Am. Chem. Soc. 2002, 115, 11855-11862
6. Altman, M.; Shukla, A. D.; Zubkov, T.; Evmenenko, G.; Dutta, P.; van der Boom, M. E. J. Am. Chem. Soc. 2006, 128, 7374-7382
7. Altman, M.; Zenkina, O.; Evmenenko, G.; Dutta, P.; van der Boom, M. E. J. Am. Chem. Soc. 2008, 130, 5040-5041
8. Motiei, L.; Sassi, M.; Kaminker, R.; Evmenenko, G.; Dutta, P.; Iron, M. A.; van der Boom, M. E. Langmuir 2010, 27, 1319-1325
9. Motiei, L.; Lahav, M.; Gulino, A.; Iron, M. A.; van der Boom, M. E. J. Phys. Chem. B 2010, 114, 14283-14286
10. Altman, M.; Zenkina, O. V.; Ichiki, T.; Iron, M. A.; Evmenenko, G.; Dutta, P.; van der Boom, M. E. Chem. Mater. 2009, 21, 4676-4684
11. Li, D.; Ratner, M. A.; Marks, T. J.; Zhang, C.; Yang, J.; Wong, G. K. J. Am. Chem. Soc. 1990, 112, 7389-7390
12. Netzer, L.; Sagiv, J. J. Am. Chem. Soc. 1983, 105, 674-676
13. van der Boom, M. E.; Richter, A. G.; Malinsky, J. E.; Lee, P. A.; Armstrong, N. R.; Dutta, P.; Marks, T. J. Chem. Mater. 2000, 13, 15-17
14. van der Boom, M. E.; Zhu, P.; Evmenenko, G.; Malinsky, J. E.; Lin, W.; Dutta, P.; Marks, T. J. Langmuir 2002, 18, 3704-3707
15. Zhu, P.; van der Boom, M. E.; Kang, H.; Evmenenko, G.; Dutta, P.; Marks, T. J. Chem. Mater. 2002, 14, 4982-4989
16. Jiao, J.; Anariba, F.; Tiznado, H.; Schmidt, I.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. J. Am. Chem. Soc. 2006, 128, 6965-6974
17. Kohli, P.; Blanchard, G. J. Langmuir 2000, 16, 4655-4661
18. Li, D.; Buscher, C. T.; Swanson, B. I. Chem. Mater. 1994, 6, 803-810
19. Li, D.; Ratner, M. A.; Marks, T. J.; Zhang, C.; Yang, J.; Wong, G. K. J. Am. Chem. Soc. 2002, 112, 7389-7390
20. Li, Y.-h.; Wang, D.; Buriak, J. M. Langmuir 2010, 26, 1232-1238
21. Schmidt, I.; Jiao, J.; Thamyongkit, P.; Sharada, D. S.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2006, 71, 3033-3050
22. Decher, G. In Photonic and Optoelectronic Polymers; American Chemical Society: Washington, D.C., 1997; Vol. 672, pp 445-459.
23. Palomaki, P. K. B.; Dinolfo, P. H. Langmuir 2010, 26, 9677-9685
24. Palomaki, P. K. B.; Krawicz, A.; Dinolfo, P. H. Langmuir 2011, 27, 4613-4622
25. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
26. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
27. Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051-1053
28. Collman, J. P.; Devaraj, N. K.; Eberspacher, T. P. A; Chidsey, C. E. D. Langmuir 2006, 22, 2457-2464
29. Devaraj, N. K.; Collman, J. P. QSAR Comb. Sci. 2007, 26, 1253-1260
30. Devaraj, N. K.; Decreau, R. A.; Ebina, W.; Collman, J. P.; Chidsey, C. E. D. J. Phys. Chem. B 2006, 110, 15955-15962
31. Devaraj, N. K.; Dinolfo, P. H.; Chidsey, C. E. D.; Collman, J. P. J. Am. Chem. Soc. 2006, 128, 1794-1795
32. Ku, S.-Y.; Wong, K.-T.; Bard, A. J. J. Am. Chem. Soc. 2008, 130, 2392-2393
33. Lummerstorfer, T.; Hoffmann, H. J. Phys. Chem. B 2004, 108, 3963-3966
34. Prakash, S.; Long, T. M.; Selby, J. C.; Moore, J. S.; Shannon, M. A. Anal. Chem. 2006, 79, 1661-1667
35. Bergbreiter, D. E.; Chance, B. S. Macromolecules 2007, 40, 5337-5343
36. Such, G. K.; Quinn, J. F.; Quinn, A.; Tjipto, E.; Caruso, F. J. Am. Chem. Soc. 2006, 128, 9318-9319
37. Rydzek, G.; Thomann, J.-S.; Ameur, N. B.; Jierry, L.; Msini, P.; Ponche, A.; Contal, C.; Haitami, A. E. E.; Voegel, J.-C.; Senger, B.; Schaaf, P.; Frisch, B.; Boulmedais, F. Langmuir 2009, 26, 2816-2824
38. Vestberg, R.; Malkoch, M.; Kade, M.; Wu, P.; Fokin, V. V.; Sharpless, K. B.; Drockenmuller, E.; Hawker, C. J. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 2835-2846
39. Luo, L.; Frisbie, C. D. J. Am. Chem. Soc. 2010, 132, 8854-8855
40. Kadish, K.; Smith, K. M.; Guilard, R. The Porphyrin Handbook; Academic Press: New York, 1999.
41. Jurowa, M.; Schuckmanb, A. E.; Batteasb, J. D.; Drain, C. M. Coord. Chem. Rev. 2010, 254, 2297-2310
42. Thamyongkit, P.; Yu, L.; Padmaja, K.; Jiao, J.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2006, 71, 1156-1171
43. Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461
44. Abdelrazzaq, F. B.; Kwong, R. C.; Thompson, M. E. J. Am. Chem. Soc. 2002, 124, 4796-4803
45. Cho, Y.-J.; Ahn, T. K.; Song, H.; Kim, K. S.; Lee, C. Y.; Seo, W. S.; Lee, K.; Kim, S. K.; Kim, D.; Park, J. T. J. Am. Chem. Soc. 2005, 127, 2380-2381
46. Campbell, W. M.; Jolley, K. W.; Wagner, P.; Wagner, K.; Walsh, P. J.; Gordon, K. C.; Schmidt-Mende, L.; Nazeeruddin, M. K.; Wang, Q.; Grätzel, M.; David L., Officer J. Phys. Chem. C 2007, 111, 11760-11762
47. Odobel, F.; Blart, E.; Lagree, M.; Villieras, M.; Boujtita, H.; El Murr, N.; Caramori, S.; Bignozzi, A. C. J. Mater. Chem. 2003, 13, 502-510
48. Monti, D.; Nardis, S.; Stefanelli, M.; Paolesse, R.; Natale, C. D.; D'Amico, A. J. Sens. 2009, 2009, Article ID 856053, 10 pages.
49. Li, X. Y.; Czernuszewicz, R. S.; Kincaid, J. R.; Spiro, T. G. J. Am. Chem. Soc. 1989, 111, 7012-7023
50. Li, X. Y.; Czernuszewicz, R. S.; Kincaid, J. R.; Su, Y. O.; Spiro, T. G. J. Phys. Chem. 1990, 94, 31-47
51. Colthup, N. B. J. Opt. Soc. Am. 1950, 40, 397-400
52. Tolstoy, V. P.; Chernyshova, I.; Skryshevsky, V. A. Handbook of Infrared Spectroscopy of Ultrathin Films; Wiley-Interscience: Hoboken, NJ, 2003.
53. Bohn, P. W. Annu. Rev. Phys. Chem. 1993, 44, 37-60
54. Bard, A. J.; Faulkner, L. R. In Electrochemical Methods: Fundamentals and Applications; 2 nd ed.; John Wiley & Sons, Inc.: New York, 2001.
55. Rhodes, C. P.; Long, J. W.; Doescher, M. S.; Fontanella, J. J.; Rolison, D. R. J. Phys. Chem. B 2004, 108, 13079-13087
56. Wahab, A.; Bhattacharya, M.; Ghosh, S.; Samuelson, A. G.; Das, P. K. J. Phys. Chem. B 2008, 112, 2842-2847
57. Padmaja, K.; Wei, L.; Lindsey, J. S.; Bocian, D. F. J. Org. Chem. 2005, 70, 7972-7978
58. Chidsey, C. E. D.; Bertozzi, C. R.; Putvinski, T. M.; Mujsce, A. M. J. Am. Chem. Soc. 1990, 112, 4301-4306
59. Meldal, M.; Tornã̧e, C. W. Chem. Rev. 2008, 108, 2952-3015
60. Yasseri, A. A.; Syomin, D.; Malinovskii, V. L.; Loewe, R. S.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. J. Am. Chem. Soc. 2004, 126, 11944-11953
61. Arnold, R.; Terfort, A.; Wöll, C. Langmuir 2001, 17, 4980-4989
62. Debe, M. K. J. Appl. Phys. 1984, 55, 3354-3366
63. Zhang, Z.; Hu, R.; Liu, Z. Langmuir 1999, 16, 1158-1162
64. Blasie, J. K.; Ereckinska, M.; Samuels, S.; Leigh, J. S. Biochim. Biophys. Acta 1978, 501, 33-52
65. Qian, D.-J.; Nakamura, C.; Ishida, T.; Wenk, S.-O.; Wakayama, T.; Takeda, S.; Miyake, J. Langmuir 2002, 18, 10237-10242
66. Fu, Y.-S.; Yu, S. J. Angew. Chem. Int. Ed. 2001, 40, 437-440
67. Onitsuka, K.; Kitajima, H.; Fujimoto, M.; Iuchi, A.; Takei, F.; Takahashi, S. Chem. Commun. 2002, 2576-2577
68. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855
69. Song, Y.; Kohlmeir, E. K.; Meade, T. J. J. Am. Chem. Soc. 2008, 130, 6662-6663
70. Xu, L. Q.; Yao, F.; Fu, G.-D.; Shen, L. Macromolecules 2009, 42, 6385-6392
71. Cameron, D. G.; Moffatt, D. J. J. Test. Eval. 1984, 12, 78-85
72. Kauppinen, J. K.; Moffatt, D. J.; Mantsch, H. H.; Cameron, D. G. Appl. Spectrosc. 1981, 35, 271-276
73. Robinson, D. B.; Chidsey, C. E. D. J. Phys. Chem. B 2002, 106, 10706-10713