Supramolecular donor - acceptor hybrid of electropolymerized zinc porphyrin with axially coordinated fullerene: Formation, characterization, and photoelectrochemical properties

Journal of Physical Chemistry C

Volumn 113, Issue 20, 2009, Pages 8982-8989

  Subbaiyan, Navaneetha K ^a   Obraztsov, Ievgen ^b   Wijesinghe, Channa A ^a   Tran, Kim ^a   Kutner, Wlodzimierz ^b,c   D'Souza, Francis ^a  

^a WICHITA STATE UNIVERSITY   (United States)

^b INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

^c CARDINAL STEFAN WYSZY SKI UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC FORCE; AXIAL COORDINATION; CATHODIC PHOTOCURRENT; CHARACTERISTIC ABSORPTION; DENSE FILMS; DONOR-ACCEPTOR; DONOR-ACCEPTOR DYADS; DYE-SENSITIZED PHOTOELECTROCHEMICAL CELLS; ELECTROCHEMICAL QUARTZ CRYSTAL MICROBALANCE; ELECTRODE SURFACES; ELECTRON SYSTEMS; EMISSION BANDS; FLUORESCENCE EMISSION; FREE-ENERGY CALCULATIONS; HYBRID FILM; INCIDENT PHOTON-TO-CURRENT CONVERSION EFFICIENCIES; MICROGRAVIMETRY; OPTICAL ABSORPTION AND EMISSION; PHOTO-INDUCED ELECTRON TRANSFER; PHOTO-VOLTAGE; PHOTOELECTROCHEMICAL; PHOTOELECTROCHEMICAL BEHAVIOR; PHOTOELECTROCHEMICAL PROPERTIES; POLYMER-FULLERENE; REDOX POTENTIALS; SELF-ASSEMBLE; SELF-ASSEMBLED; TETRAKIS; ZINC PORPHYRINS;

ABSORPTION; ATOMIC FORCE MICROSCOPY; CONVERSION EFFICIENCY; CYCLIC VOLTAMMETRY; ELECTRODES; ELECTRON TRANSITIONS; FREE ENERGY; FULLERENES; OXIDE MINERALS; PHOTOCURRENTS; PHOTOELECTROCHEMICAL CELLS; POLYMER FILMS; POLYMERS; PORPHYRINS; QUARTZ; QUARTZ CRYSTAL MICROBALANCES; ZINC;

ZINC COMPOUNDS;

EID: 67649265380     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp900507s     Document Type: Article

References (96)

1. (a) Kadish, K. M, Smith, K. M., Guilard, R., Eds. The Porphyrin Handbook; Academic Press: San Diego, 2000.
2. (b) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
3. (c) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537-546.
4. (d) Martin, N.; Sanchez, L.; Illescas, B.; Perez, I. P. Chem. Rev. 1998, 98, 2527-2547.
5. (e) Eckert, J. F.; Nicoud, J. F.; Nierengarten, J. F.; Liu, S.; Echegoyen, L.; Barigelletti, F.; Armaroli, N.; Ouali, L.; Krasnikov, V.; Hadziioannou, G. J. Am. Chem. Soc. 2000, 122, 7467-7479.
6. (f) de la Cruz, J. L. D.; Hahn, U.; Nierengarten, J. F. Tetrahedron Lett. 2006, 47, 3715-3718.
7. (a) Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: Burlington, MA, 2000; Vol. 8; pp 153-190.
8. (b) Gust, D.; Moore, T. A.; Moore, A. L. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3; pp 272-336.
9. (a) Fukuzumi, S.; Guldi, D. M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2; pp 270-337.
10. (b) Guldi, D. M. Chem. Commun. 2000, 321-327.
11. (c) Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695-703.
12. (d) Guldi, D. M. Chem. Soc. Rev. 2002, 31, 22-36.
13. (e) Meijer, M. E.; van Klink, G. P. M.; van Koten, G. Coord. Chem. Rev. 2002, 230, 141-163.
14. (f) Kamat, P. V. J. Phys. Chem. C 2007, 111, 2834-2860.
15. (g) Imahori, H.; Fukuzumi, S. Adv. Funct. Mater. 2004, 14, 525-536.
16. (h) Imahori, H. Bull. Chem. Soc. Jpn. 2007, 80, 621-636.
17. (i) Kamat, P. V. J. Phys. Chem. C 2008, 112, 18737-18753.
18. (j) Nierengarten, J. F. Sol. Energy Mater. Sol. Cells 2004, 8, 187-199.
19. (a) El-Khouly, M. E.; Ito, O.; Smith, P. M.; D'Souza, F. J. Photochem. Photobiol. C 2004, 5, 79-104.
20. (b) D'Souza, F.; Ito, O. Coord. Chem. Rev. 2005, 249, 1410-1422.
21. (c) Sanchez, L.; Martin, N.; Guldi, D. M. Angew. Chem. Int. Ed. 2005, 44, 5374-5382.
22. (d) Bouamaied, T. I.; Coskun, E. S. In Not-Covalent Multi-Porphyrin Assemblis;Day, P., Meyer, T. J., Roesky, H. W., Sauvage, J.-P., Eds.; Springer: Berlin, 2006; Vol. 121; pp 1-47.
23. (e) Chitta, R.; D'Souza, F. J. Mater. Chem. 2008, 18, 1440-1471.
24. (f) Fukuzumi, S. Phys. Chem. Chem. Phys. 2008, 10, 2283-2297.
25. (g) D'Souza, F.; Ito, O. In Handbook of Organic Electronics and Photonics; Nalwa, H. R., Ed.; American Scientific Publishers: Los Angeles, California, 2008; Vol. 1; pp 485-521.
26. (a) Seo, E. T.; Nelson, R. F.; Fritsch, J. M.; Marcoux, L. S.; Leedy, D. W.; Adams, R. N. J. Am. Chem. Soc. 1966, 88, 3498-3503.
27. (b) Yeh, S. J.; Tsai, C. Y.; Huang, C.-Y.; Liou, G.-S.; Cheng, S.-H. Electrochem. Commun. 2003, 5, 373-377.
28. (a) Tamoto, N.; Adachi, C.; Nagai, K. Chem. Mater. 1997, 9, 1077-1085.
29. (b) Kim, M.-J.; Seo, E. M.; Vak, D.; Kim, D. Y. Chem. Mater. 2003, 15, 4021-4027
30. (c) Son, J. M.; Mori, T.; Ogino, K.; Sato, H.; Ito, H. Macromolecules 1999, 32, 4849-4854.
31. (d) Gao, G. Y.; Chen, Y.; Znang, X. P. J. Ore. Chem. 2003, 68, 6215-6221.
32. (a) Wang, Y. Z.; Epstein, A. J. Acc Chem. Res. 1999, 32, 217-224.
33. (b) Chen, C.-T.; Lin, J.-S.; Moturu, M. V. R. K.; Lin, Y.-W.; Yi, W.; Tao, Y.-T.; Chien, C.-H. Chem. Commun. 2005, 3980-3982.
34. (c) Sengupta, S.; Sadhukhan, S. K.; Muhuri, S. Tetrahedron Lett. 2002, 43, 3521-3524.
35. (a) Li, B.; Xu, X.; Sun, M.; Fu, Y.; Yu, G.; Liu, Y.; Bo, Z. Macromolecules 2006, 39, 456-461.
36. (b) Frampton, M. J.; Beavington, R.; Lupton, J. M.; Samuel, I. D. W.; Burn, P. L. Synth. Met. 2001, 121, 1671-1672.
37. (c) Huang, C.-W.; Chiu, K. Y.; Cheng, S.-H. Dalton Trans. 2005, 2417-2422.
38. (d) Clifford, J. N.; Yahioglu, G.; Milgrom, L. R.; Durrant, J. R. Chem. Commun. 2002, 1260-1261.
39. (e) Walter, M. G.; Wamser, C. C. Mater. Res. Soc. Symp. Proc. 2007, 013, Z04-07.
40. (f) Zagal, J. H., Bedioui, F., Dodelet, J. P., Eds.; N4-Macrocyclic Metal Complexes; Springer: New York, 2006.
41. (g) Yen, W.-N.; Lo, S.-S.; Kuo, M.-C; Mai, C. L.; Lee, G.-H.; Peng, S.-M.; Yeh, C. Y. Org Lett. 2006, 8, 4239-4242.
42. D'Souza, F.; Gadde, S.; Islam, D. M. S.; Wijesinghe, C. A.; Schumacher, A. L.; Zandler, M. E.; Araki, Y.; Ito, O. J. Phys. Chem. A. 2007, 111, 8552-8560.
43. (a) Thomas, S. W., III; Joly. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339-1386.
44. (b) McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574.
45. (c) Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev. 2007, 107, 1324-1338.
46. (a) Roncali, J. Chem. Soc. Rev. 2005, 34, 483-495.
47. (b) Cravino, A.; Sariciftci, N. S. J. Mater. Chem. 2002, 12, 1931-1943.
48. (c) Coakley, K. M.; McGehee, M. D. Chem. Mater. 2004, 16, 4533-4542.
49. (d) Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15-26.
50. (e) Ng, S. C.; Lu, H.-E; Chan, H. S. O.; Fujii, A.; Laga, T.; Yoshino, K. Adv. Mater. 2000, 12, 1122-1125.
51. (f) Bao, Z.; Peng, Z.; Galvin, M. E.; Chandross, E. A. Chem. Mater. 1998, 10, 1201-1204.
52. (g) Son, S.; Dodabalapur, A.; Lovinger, A. J.; Galvin, M. E. Science 1995, 269, 376-378.
53. (h) Wu, A. P.; Jikei, M.; Kakimoto, M.; Imai, Y.; Ukishima, S.; Takahashi, Y. Chem. Lett. 1994, 2319-2322.
54. (a) Leung, J. K.; Chou, M.-Y.; Su, Y. O.; Chiang, C. L.; Chen, H.-L.; Yanbg, C.-F.; Yang, C.-C; Lin, C.-C.; Chen, H.-T. Org. Lett. 2003, 5, 839-842.
55. (b) Thompson, B. C.; DuBois, C. J.; Kim, Y. G.; Reynolds, J. R. Polymer Reprints 2004, 45, 214.
56. (c) Chen, Y.-J.; Luh, T.-Y. Macromolecules 2005, 38, 4563-4568.
57. (d) Chen, Y.-J.; Luh, T.-Y. Chem-Eur. J. 2005, 10, 5361-5368.
58. (e) Ohshita, J.; Kangai, S.; Yoshida, H.; Kunai, A.; Kajiwara, S.; Ooyama, Y.; Harima, J. Organomet. Chem. 2007, 692, 801-805.
59. (f) Gomez, R.; Blanco, R.; Veldman, D.; Segura, J. L.; Janssen, R. A. J. J. Phys. Chem. B 2008, 112, 4953-4960.
60. (g) Hou, Y.; Chen, Y.; Liu, Q.; Yang, M.; Wan, X.; Yin, S.; Yu, A. Macromolecules 2008,47, 3114-3119.
61. (a) D'Souza, F.; Deviprasad, G. R.; Zandler, M. E.; Hoang, V. T.; Arkady, K.; Van Stipdonk, M.; Perera, A.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O. J. Phys. Chem. A 2002, 106, 3243-3252.
62. (b) D'Souza, F.; Deviprasad, G. R.; Zandler, M. E.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O. J. Phys. Chem. A 2003, 107, 4801-4807.
63. (c) D'Souza, E.; Gadde, S.; Zandler, M. E.; Itou, M.; Araki, Y.; Ito, O. Chem. Commun. 2004, 2276-2277.
64. (d) D'Souza, F.; Smith, P. M.; Gadde, S.; McCarty, A. L.; Kullman, M. J.; Zandler, M. E.; Itou, M.; Araki, Y.; Ito, O. J. Phys. Chem. B 2004, 108, 11133-11138.
65. (a) Troshin, P. A.; Koeppe, R.; Peregudov, A. S.; Peregudova, S. M.; Egginger, M.; Lyubovskava, R. N.; Saricifici, N. S. Chem. Mater. 2007, 19, 5363.
66. (b) Kira, A.; Umeyama, T.; Matano, Y.; Yoshida, K.; Isoda, S.; Park, J. K.; Kim, D.; Imahori, H. J. Am. Chem. Soc. 2009, 131, 3198.
67. (a) Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature (London) 1985, 318, 162-163.
68. (b) Kratschmer, W.; Lamb, L. D.; Fostiropoulos, F.; Huffman, D. R. Nature (London) 1990, 347, 354-358.
69. (c) Hirsch, A., Ed.; Fullerene and Related Structures; Springer: Berlin, 1999; Vol. 199.
70. (a) Allemand, P. M.; Koch, A.; Wudl, F.; Rubin, Y.; Diederich, F.; Alvarez, M. M.; Anz, S. J.; Whetten, R. L. J. Am. Chem. Soc. 1991, 113, 1050-1051.
71. (b) Xie, Q.; Perez-Cordero, E.; Echegoyen, L. J. Am. Chem. Soc. 1992, 114, 3978-3980.
72. (c) Fukuzumi, S.; Nakanishi, I.; Suenobu, T.; Kadish, K. M. J. Am. Chem. Soc. 1999, 121, 3468-3474.
73. (d) Fukuzumi, S.; Ohkubo, K.; Imahori, H.; Guldi, D. M. Chem.-Eur. J. 2003, 9, 1585-1593.
74. (e) Imahori, H.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2001, 105, 325-332.
75. Gratzel, M. Nature (London) 2001, 414, 338-344.
76. (b) Gratzel, M. Inore. Chem. 2005, 44, 6841-6851.
77. Thompson, M.; Kipling, A. L.; Duncan-Hewitt, W. C.; Rajaković, L. V.; Ćavić-Vlasak, B. A. Analyst 1991, 116, 881-890.
78. (a) Buttry, D. A.; Ward, M. D. Chem. Rev. 1992, 92, 1355-1379.
79. (b) Hillman, A. R. The Electrochemical Quartz Crystal Microbalance. In Encyclopedia of Electrochemistry; Wiley-VCH: Weinheim, Germany, 2003; Vol. 3; pp 230-289.
80. (c) Ward, M. D. Phys. Electrochem. 1995, 292-338.
81. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications; 2nd ed.; John Wiley: New York, 2001.
82. A possible mechanism of film formation is discussed elsewhere (see refs 8c and 8e).
83. (a) Rehm, D.; Weller, A. Isr. J. Chem. 1970, 7, 259-271.
84. (b) Mataga, N.; Miyasaka, H. In Electron Transfer; Jortner, J., Bixon, M., Eds.; John Wiley & Sons: New York, 1999; Part 2, pp 431-496.
85. 4ZnP entity in the film, was calculated to be ∼-0.75 eV. No solvent correction was applied in these calculations.
86. (a) Nazeeruddin, M. K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Muller, E.; Liska, P.; Vlachopoulos, N.; Gratzel, M. J. Am. Chem. Soc. 1993, 115, 6382-6390.
87. (b) Alebbi, M.; Bignozzi, C. A.; Heimer, T. A.; Hasselmann, G. M.; Meyer, G. J. J. Phys. Chem. B. 1998, 102, 7577-7581.
88. (c) Fillinger, A.; Parkinson, B. A. J. Electrochem. Soc. 1999, 146, 4559-4564.
89. (d) Monat, J. E.; Rodriguez, J. H.; McCusker, J. K. J. Phys. Chem. A. 2002, 106, 7399-7406.
90. Splan, K. E.; Massari, A. M.; Hupp, J. T. J. Phys. Chem. B 2004, 108, 4111-4115.
91. - redox couple see: (a) Macagno, V. A.; Giordano, M. C.; Arvia, A. J. Electrochim. Acta 1969, 14, 335-357.
92. (b) Popov, A. I.; Geske, D. H. J. Am. Chem. Soc. 1958, 80, 1340-1352.
93. (a) Moss, J. A.; Stipkala, J. M.; Yang, J. C.; Bignozzi, C. A.; Meyer, G. J.; Meyer, T. J.; Wen, X.; Linton, R. W. Chem. Mater. 1998, 10, 1748-1750.
94. (b) Taniguchi, T.; Fukasawa, Y.; Miyashita, T. J. Phys. Chem. B 1999, 103, 1920-1924.
95. (a) Hasobe, T.; Saito, K.; Kamat, P. V.; Troiani, V.; Qiu, H.; Solladie, N.; Kim, K. S.; Park, J. K.; Kim, D.; D'Souza, F.; Fukuzumi, S. J. Mater. Chem. 2007, 17, 4160-4170.
96. (b) Marczak, R.; Sgobba, V.; Kutner, W.; Gadde, S.; D'Souza, E.; Guldi, D. M. Langmuir 2007, 23, 1917-1923.