Porphyrin-β-01igo-ethynylenephenylene-[60]fullerene triads: Synthesis and electrochemical and photophysical characterization of the new porphyrin-oligo-PPE-[60]fullerene systems

Journal of Physical Chemistry A

Volumn 113, Issue 9, 2009, Pages 1779-1793

  Lembo, Angelo ^a   Tagliatesta, Pietro ^a   Guldi, Dirk M ^b   Wielopolski, Mateusz ^b   Nuccetelli, Marzia ^a  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

[60] FULLERENES; DAMPING FACTORS; DONOR-BRIDGE-ACCEPTOR SYSTEMS; ELECTRON DONOR ACCEPTORS; ELECTRONIC INTERACTIONS; EXCITED-STATE; EXCITED-STATE ENERGIES; MACROCYCLE; MOLECULAR BRIDGES; NONPOLAR MEDIAS; PHENYL RINGS; PHENYLENE-ETHYNYLENES; PHENYLENEETHYNYLENE; PHOTOPHYSICAL CHARACTERIZATIONS; PHOTOPHYSICAL STUDIES; POLAR MEDIAS; PORPHYRIN RINGS; RADICAL ION PAIRS; TETRAHYDROFURAN; TETRAPYRROLE; TIME-RESOLVED FLUORESCENCES; TRANSIENT ABSORPTION MEASUREMENTS;

CHARGE TRANSFER; CHEMICAL MODIFICATION; EXCITED STATES; FULLERENES; ION EXCHANGE; NITROGEN COMPOUNDS; TOLUENE;

PORPHYRINS;

FULLERENE C60; FULLERENE DERIVATIVE; POLY(PHENYLENE ETHYNYLENE); POLYMER; PORPHYRIN; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTROCHEMISTRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; PHYSICAL CHEMISTRY; QUANTUM THEORY; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ELECTROCHEMISTRY; FULLERENES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHYSICOCHEMICAL PROCESSES; POLYMERS; PORPHYRINS; QUANTUM THEORY; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 63849241010     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp809557e     Document Type: Article

References (86)

1. (a). Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
2. (b). Jordan, P.; Fromme, P.; Witt, H. T.; Klukas, O.; Saenger, W.; Krauss, N. Nature 2001, 411, 909-917.
3. Ben-Shem, A.; Frolow, F.; Nelson, N. Nature 2003, 426, 630-635.
4. Liu, Z.; Yan, H.; Wang, K.; Kuang, T.; Zhang, J.; Gui, L.; An, X.; Chang, W. Nature 2004, 428, 287-292.
5. (a). Nelson, N.; Ben-Shem, A. Nat. Rev. 2004, 5, 1-12.
6. (b). Zinth, W.; Wachtveitl, J. ChemPhysChem 2005, 6, 871-880.
7. Ivashin, N.; Larsson, S. J. Phys. Chem. B 2005, 109, 23051-23060.
8. Ziolek, M.; Pawlowicz, N.; Naskrecki, R.; Dobek, A. J. Phys. Chem. B 2005, 109, 18171-18176.
9. (e). Kirmaier, C; Holten, D. Biochemistry 1991, 30, 609-613.
10. (f). Lauterwasser, C; Finkele, U.; Scheer, H.; Zinth, W. Chem. Phys. Lett. 1991, 183, 471-477.
11. (g). Holzapfel, W.; Finkele, U.; Kaiser, W.; Oesterhelt, D.; Scheer, H.; Stilz, H. U.; Zinth, W. Chem. Phys. Lett. 1989, 160, 1-7.
12. (a). Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863-1933.
13. Creager, S.; Yu, C. J.; Bamdad, C; O'Connor, S.; MacLean, T.; Lam, E.; Chong, Y.; Olsen, G. T.; Luo, J.; Gozin, M.; Kayyem, J. F. J. Am. Chem. Soc. 1999, 121, 1059-1064.
14. Segura, J. L.; Martin, N. J. Mater. Chem. 2000, 10, 2403-2435.
15. Kertesz, M.; Choi, C. H.; Yang, S. Chem. Rev. 2005, 105, 3448-3481.
16. Weder, C. Chem. Commun. 2005, 5378-5389. (f) Benniston, A. C; Harriman, A.; Rewinska, D. B.; Yang, S.; Zhi, Y. G. Chem. Eur. J. 2007, 13, 10194-10203.
17. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322.
18. Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155-196.
19. Newton, M. D.; Sutin, N. Annu. Rev. Phys. Chem. 1984, 35, 437-480.
20. Bolton, J. R.; Mataga, R.; McLendon, G. Advances in Chemistry Series CSC Symposium Series; American Chemical Society and Canadian Society for Chemistry; Oxford University Press: New York, 1991; Chapter 3.
21. Winters, M. U.; Pettersson, K.; Mirtensson, J.; Albinsson, B. Chem. Eur. J. 2005, 11, 562-573.
22. Pettersson, K.; Kyrychenko, A.; Ronnow, E.; Ljungdahl, T.; Mirtensson, J.; Albinsson, B. J. Phys. Chem. A 2006, 110, 310-318.
23. Eng, M. P.; Albinsson, B. Angew. Chem., Int. Ed. 2006, 45, 5626-5629.
24. Van Hal, P. A.; Meskers, S. C. J.; Janssen, R. A. J. Appl. Phys. A: Mater. Sci. Process. 2004, 79, 41-46.
25. Giacalone, F.; Segura, J. L.; Martin, N.; Ramey, J.; Guldi, D. M. Chem. Eur. J. 2005, 11, 4819-4834.
26. De la Torre, G.; Giacalone, F.; Segura, J. L.; Martin, N.; Guldi, D. M. Chem. Eur. J. 2005, 11, 1267-1280.
27. Figueira-Duarte, T. M.; Gegout, A.; Nierengarten, J. F. Chem. Commun. 2007, 109-119.
28. Toivonen, T. L. J.; Hukka, T. I. J. Phys. Chem. A 2007, 111, 4821-4828.
29. Nierengarten, J. F.; Gu, T.; Aernouts, T.; Geens, W.; Poortmans, J.; Hadziioannou, G.; Tsamouras, D. Appl. Phys. A: Mater. Sci. Process. 2004, 79, 47-49.
30. Koynov, K.; Bahtiar, A.; Bubeck, C; Miihling, B.; Meier, H. J. Phys. Chem. B 2005, 109, 10184-10188.
31. Chaignon, F.; Torroba, J.; Blart, E.; Borgstrom, M.; Hammarstrom, L.; Odobel, F. New J. Chem. 2005, 29, 1272-1284.
32. Zhao, Y.; Shirai, Y.; Slepkov, A. D.; Cheng, L.; Alemany, L. B.; Sasaki, T.; Hegmann, F. A.; Tour, J. M. Chem. Eur. J. 2005, 11, 3643-3658.
33. Atienza, C; Martin, N.; Wielopolski, M.; Haworth, N.; Clark, T.; Guldi, D. M. Chem. Commun. 2006, 3202-3204.
34. Wielopolski, M.; Atienza, C; Clark, T.; Guldi, D. M.; Martin, N. Chem. Eur. J. 2008, 14, 6379-6390.
35. Fortage, J.; Goransonn, E.; Blart, E.; Becker, H. C; Hammarstrom, L.; Odobel, F. Chem. Commun. 2007, 4629-4631.
36. Pu, K. Y.; Qi, X. Y.; Yang, Y. L.; Lu, X. M.; Li, T. C.; Fan, Q. L.; Whang, C.; Liu, B.; On Chan, H. S.; Huang, W. Chem. Eur. J. 2008, 14, 1205-1215.
37. Vail, S. A.; Krawczuk, P. J.; Guldi, D. M.; Palkar, A.; Echegoyen, L.; Tome, J. P. C.; Fazio, M. A.; Schuster, D. I. Chem. Eur. J. 2005, 11, 3375-3388.
38. Vail, S. A.; Schuster, D. I.; Guldi, D. M.; Isosomppi, M.; Tkachenko, N.; Lemmetyinen, H.; Palkar, A.; Echegoyen, L.; Chen, X.; Zhang, J. Z. H. J. Phys. Chem. B 2006, 110, 14155-14166.
39. Yamanaka, K.; Fujitsuka, M.; Araki, Y.; Tashiro, K.; Sato, A.; Yuzawa, T.; Aida, T. J. Porphyrins Phthalocyanines 2007, 11, 397-405.
40. Nakamura, T.; Fujitsuka, M.; Araki, Y.; Osamu, I.; Ikemoto, J.; Takimiya, K.; Aso, Y.; Otsubo, T. J. Phys. Chem. B 2004, 108, 10700-10710.
41. Huang, C. H.; McClenaghan, N. D.; Kuhn, A.; Hofstraat, J. W.; Bassani, D. M. Org. Lett. 2005, 7, 3409-3412.
42. Petrella, A.; Cremer, J.; De Cola, L.; Bauerle, P.; Williams, R. M. J. Phys. Chem. A 2005, 109, 11687-11695.
43. Sivula, K.; Luscombe, C. K.; Thompson, B. C; Frechet, J. M. J. J. Am. Chem. Soc. 2006, 128, 13988-13989.
44. Narutaki, M.; Takimiya, K.; Otsubo, T.; Harima, Y.; Zhang, H.; Araki, Y.; Osamu, I. J. Org. Chem. 2006, 71, 1761-1768.
45. Barigelletti, F.; Flamigni, L.; Guardigli, M.; Juris, A.; Beley, M.; Chodorowski-Kimmes, S.; Collin, J.-P.; Sauvage, J.-P. Inorg. Chem. 1996, 35, 136-142.
46. Berresheim, A. J.; Miiller, M.; Mullen, K. Chem. Rev. 1999, 99, 1747-1785.
47. Schlicke, B.; Belser, P.; De Cola, L.; Sabbioni, E.; Balzani, V. J. Am. Chem. Soc. 1999, 121, 4207-4214.
48. Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6238.
49. Cohen, R.; Stokbro, K.; Martin, J. M. L.; Ratner, M. A. J. Phys. Chem. C 2007, 111, 14893-14902.
50. Winters, M. U.; Dahlstedt, E.; Blades, H. E.; Wilson, C. J.; Frampton, M. J.; Anderson, H. L.; Albinsson, B. J. Am. Chem. Soc. 2007, 129, 4291-4297.
51. Pettersson, K.; Wiberg, J.; Ljungdahl, T.; Martensson, J.; Albinsson, B. J. Phys. Chem. A 2006, 110, 319-326.
52. Xiao, X.; Nagahara, L. A.; Rawlett, A. M.; Tao, N. J. Am. Chem. Soc. 2005, 127, 9235-9240.
53. Lewis, P. A.; Inman, C. E.; Maya, F.; Tour, J. M.; Hutchinson, J. E.; Weiss, P. S. J. Am. Chem. Soc. 2005, 127, 17421-17426.
54. Huber, R.; Gonzalez, M. T.; Wu, S.; Langer, M.; Grunder, S.; Horhoiu, V.; Mayor, M.; Bryce, M. R.; Wang, C; Jitchati, R.; Schonenberger, C; Calame, M. J. Am. Chem. Soc. 2008, 130, 1080-1084.
55. Fan, F.-R. F.; Lai, R. Y.; Cornil, J.; Karzazi, Y.; Bredas, J. L.; Cai, L.; Cheng, L.; Yao, Y.; Price, D. W., Jr.; Dirk, S. M.; Tour, J. M.; Bard, A. J. J. Am. Chem. Soc. 2004, 126, 2568-2573.
56. Zangmeister, C. D.; Robey, S. W.; van Zee, R. D.; Yao, Y.; Tour, J. M. J. Am. Chem. Soc. 2004, 126, 3420-3421.
57. Fan, F.-R. F.; Yao, Y.; Cai, L.; Cheng, L.; Tour, J. M.; Bard, A. J. J. Am. Chem. Soc. 2004, 126, 4035-4042.
58. Meier, H.; Miihling, B.; Kolshorn, H. Eur. J. Org. Chem. 2004, 103, 3-1042.
59. Gholap, A. R.; Venkatesan, K.; Pasricha, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2005, 70, 4869-4872.
60. Liang, Y.; Xie, Y. X.; Li, J. H. J. Org. Chem. 2006, 71, 379-381.
61. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874-922.
62. Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1993, 115, 9798-9799.
63. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280-2286.
64. Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551-8553.
65. Yao, Y.; Tour, J. M. J. Org. Chem. 1999, 64, 1968-1971.
66. Lembo, A.; Tagliatesta, P.; Guldi, D. M. J. Phys. Chem. A 2006, 111, 11424-11434.
67. Noteworthy, the reduction process is not reproducible once passing the first scan. A side reaction at the working electrode-solution interface generates adsorbed films on the electrode surface, which requires removal prior to continuing the measurements. It is plausible to suppose that the aldehyde group is involved in these side reactions.
68. Wielopolski, M.; Atienza-Castellanos, A.; Clark, T.; Guldi, D. M.; Martin, N. Chem. Eur. J. 2008, 14, 6379-6390.
69. Clark T.; Alex A.; Beck B.; Burkhardt F.; Chandrasekhar J.; Gedeck P.; Horn A. H. C; Hutter M.; Martin B.; Rauhut G.; Sauer W.; Schindler T.; Steinke T. VAMP 10.0; Erlangen, Germany, 2003.
70. Winget, P.; Horn, A. H. C; Selcuki, C; Martin, B.; Clark, T. J. Mol. Model. 2003, 9, 408-414.
71. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
72. Burke, K.; Perdew, J. P.; Wang, Y. In Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F., Vignale, G., Das, M. P., Eds.; Plenum: New York, 1998.
73. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C; Millam, J. M.; Iyengar, S. S.; Tomasi, J. J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe,
74. M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C; Pople, J. A. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.
75. James, P. V.; Sudeep, P. K.; Suresh, C. H.; Thomas, K. G. J. Phys. Chem. A 2006,110, 4329-4337.
76. Levitus, M.; Schmieder, K.; Ricks, H.; Shimizu, K. D.; Bunz, U. H. F.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2002, 124, 8181-8181.
77. Schmieder, K.; Levitus, M.; Dang, H.; Garcia-Garibay, M. A. J. Phys. Chem. A 2002,106, 1551-1556.
78. Sudeep, P. K.; James, P. V.; Thomas, K. G.; Kamat, P. V. J. Phys. Chem. A 2006, 110, 5642-5649.
79. Eng, M. P.; Martensson, J.; Albinsson, B. Chem. Eur. J. 2008, 14, 2819-2826.
80. Calculated energies in vacuum are higher due to a lack of solvent stabilization.
81. Clark, T.; Lin, Jr.-H.; Horn, A. H. C. Parasurf 07; Cepos InSilico Ltd.: Ryde, U.K., 2007; www.ceposinsilico.com
82. Ehresmann, B.; Martin, B.; Horn, A. H. C; Clark, T. J. Mol. Model. 2003, 9, 342-348.
83. Clark, T. J. Mol. Graphics Modell. 2004, 22, 519-525.
84. Lanig, H.; Koenig, R.; Clark, T. Tramp 1.Id.; University of Erlangen, Erlangen, Germany, 2005.
85. Weller, A. Z. Phys. Chem. (Munich) 1982, 133, 93-98.
86. Ventura, B.; Flamigni, L.; Marconi, G.; Lodato, F.; Officer, D. L. New J. Chem. 2008, 32, 166-178.