Driving force and electronic coupling effects on photoinduced electron transfer in a fullerene-based molecular triad

Photochemistry and Photobiology

Volumn 72, Issue 5, 2000, Pages 598-611

  Bahr, Jeffrey L ^a   Kuciauskas, Darius ^a   Liddell, Paul A ^a   Moore, Ana L ^a   Moore, Thomas A ^a   Gust, Devens ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLTETRAHYDROFURAN; CAROTENE; FULLERENE; FURAN DERIVATIVE; PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; ELECTRON; ELECTRON TRANSPORT; ELECTRONICS; ENERGY TRANSFER; EXCITATION; LIGHT; MOLECULE; THERMODYNAMICS;

EID: 0034335299     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2000)072<0598:DFAECE>2.0.CO;2     Document Type: Article

References (53)

1. Gust, D. and T. A. Moore (1999) Intramolecular photoinduced electron transfer reactions of porphyrins. In The Porphyrin Handbook (Edited by K. M. Kadish, K. M. Smith and R. Guilard), pp. 153-190. Academic Press, New York.
2. 60 dyads. Photochem. Photobiol. 60, 537-541.
3. Imahori, H., K. Hagiwara, T. Akiyama, S. Taniguchi, T. Okada and Y. Sakata (1995) Synthesis and photophysical property of porphyrin-linked fullerene. Chem. Lett. 1995, 265-266.
4. Linssen, T. G., K. Dürr, M. Hanack and Q. Hirsch (1995) A green fullerene: Synthesis and electrochemistry of a Diels-Alder adduct of [60] fullerene with a phthalocyanine. J. Chem. Soc., Chem. Commun. 1995, 103-104.
5. Maggini, M., A. Dono, G. Scorrano and M. Prato (1995) Synthesis of a [60]fullerene derivative covalently linked to a ruthenium(II) tris (bipyridine) complex. J. Chem. Soc., Chem. Commun. 1995, 843-845.
6. Maggini, M., A. Karlsson, G. Scorrano, G. Sandona, G. Farina and M. Prato (1994) Ferrocenyl fulleropyrrolidines - a cyclic voltammetry study. J. Chem. Soc., Chem. Commun. 1994, 589-590.
7. Drovetskaya, T., C. A. Reed and P. D. W. Boyd (1995) A fullerene porphyrin conjugate. Tetrahedron Lett. 36, 7971-7974.
8. Imahori, H., S. L. Cardoso, D. Tatman, S. Lin, A. N. Macpherson, L. Noss, G. R. Seely, L. Sereno, J. Chessa de Silber, T. A. Moore, A. L. Moore and D. Gust (1995) Photoinduced electron transfer in a carotenobuckminsterfullerene dyad. Photochem. Photobiol. 62, 1009-1014.
9. 60 (acceptor)-aniline (donor) system. Photophysical properties of the first "active" fullerene diad. J. Am. Chem. Soc. 117, 4093-4099.
10. Kuciauskas, D., S. Lin, G. R. Seely, A. L. Moore, T. A. Moore, D. Gust, T. Drovetskaya, C. A. Reed and P. D. W. Boyd (1996) Energy and photoinduced electron transfer in porphyrin-fullerene dyads. J. Phys. Chem. 100, 15 926-15 932.
11. Imahori, H. and Y. Sakata (1996) Synthesis of closely spaced porphyrin-fullerene. Chem. Lett. 1996, 199-200.
12. 60 across extended 3- and 11-bond hydrocarbon bridges: creation of a long-lived charge-separated state. J. Org. Chem. 61, 5055-5062.
13. 60 dyads. J. Am. Chem. Soc. 118, 11 771-11 782.
14. Baran, P. S., R. R. Monaco, A. U. Kahn, D. I. Schuster and S. R. Wilson (1997) Synthesis and cation-mediated electronic interactions of two novel classes of porphyrin-fullerene hybrids. J. Am. Chem. Soc. 119, 8363-8364.
15. Bell, T. D. M., T. A. Smith, K. P. Ghiggino, M. G. Ranasinghe, M. J. Shephard and M. N. Paddon-Row (1997) Long-lived photoinduced charge separation in a bridged C60-porphyrin dyad. Chem. Phys. Lett. 268, 223-228.
16. 60. Helv. Chim. Acta 81, 1835-1844.
17. Carbonera, D., M. Di Valentin, C. Corvaja, G. Agostini, G. Giacometti, P. A. Liddell, D. Kuciauskas, A. L. Moore, T. A. Moore and D. Gust (1998) EPR investigation of photoinduced radical pair formation and decay to a triplet state in a caroteneporphyrin-fullerene triad. J. Am. Chem. Soc. 120, 4398-4405.
18. Guldi, D. M., M. Maggini, G. Scorrano and M. Prato (1997) Intramolecular electron transfer in fullerene/ferrocene based donor-bridge-acceptor dyads. J. Am. Chem. Soc. 119, 974-980.
19. Gust, D., T. A. Moore, A. L. Moore, P. A. Liddell, D. Kuciauskas, J. P. Sumida, B. Nash and D. Nguyen (1997) A caroteneporphyrin-fullerene triad: photoinduced charge separation and charge recombination to a triplet state. In Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials (Edited by K. M. Kadish and A. W. Rutherford), pp. 9-24. The Electrochemical Society, Pennington.
20. Gust, D., T. A. Moore and A. L. Moore (1997) Fullerenes linked to photosynthetic pigments. Res. Chem. Int. 23, 621-651.
21. Gust, D., T. A. Moore, A. L. Moore, D. Kuciauskas, P. A. Liddell and B. D. Halbert (1998) Mimicry of carotenoid photoprotection in artificial photosynthetic reaction centers: triplet-triplet energy transfer by a relay mechanism. J. Photochem. Photobiol. B: Biol. 43, 209-216.
22. Higashida, S., H. Imahori, T. Kaneda and Y. Sakata (1998) Synthesis and photophysical behavior of porphyrins with two C60 units. Chem. Lett. 1998, 605-606.
23. Imahori, H., K. Hagiwara, T. Akiyama, M. Aoki, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata (1996) The small reorganization energy of C60 in electron transfer. Chem. Phys. Lett. 263, 545-550.
24. Imahori, H. and Y. Sakata (1997) Donor-linked fullerenes: photoinduced electron transfer and its potential application. Adv. Mater. 9, 537-546.
25. Kuciauskas, D., P. A. Liddell, T. A. Moore, A. L. Moore and D. Gust (1998) Solvent effects and electron transfer dynamics in a porphyrin-fullerene dyad and a carotenoporphyrin-fullerene triad. In Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials (Edited by K. M. Kadish and R. S. Ruoff), pp. 242-261. The Electrochemical Society, Pennington.
26. Kuciauskas, D., P. A. Liddell, A. L. Moore, T. A. Moore and D. Gust (1998) Magnetic switching of charge separation life-times in artificial photosynthetic reaction centers. J. Am. Chem. Soc. 120, 10 880-10 886.
27. Kuciauskas, D., P. A. Liddell, S. Lin, T. E. Johnson, S. J. Weghorn, J. S. Lindsey, A. L. Moore, T. A. Moore and D. Gust (1999) An artificial photosynthetic antenna-reaction center complex. J. Am. Chem. Soc. 121, 8604-8614.
28. Liddell, P. A., D. Kuciauskas, J. P. Sumida, B. Nash, D. Nguyen, A. L. Moore, T. A. Moore and D. Gust (1997) Photoinduced charge separation and charge recombination to a triplet state in a carotene-porphyrin-fullerene triad. J. Am. Chem. Soc. 119, 1400-1405.
29. Nierengarten, J.-F., C. Schall and J.-F. Nicoud (1998) A tetraphenylporphyrin with four fullerene substitutes. Angew. Chem. Int. Ed. Engl. 37, 1934-1936.
30. Safonov, I. G., P. S. Baran and D. I. Schuster (1997) Synthesis and photophysics of a novel porphyrin-C60 hybrid Tetrahedron Lett. 38, 8133-8136.
31. Sakata, Y., H. Imahori, H. Tsue, S. Higashida, T. Akiyama, E. Yoshizawa, M. Aoki, K. Yamada, K. Hagiwara, S. Taniguchi and T. Okada (1997) Control of electron transfer and its utilization. Pure Appl. Chem. 69, 1951-1956.
32. Kuciauskas, D., P. A. Liddell, S. Lin, S. Stone, A. L. Moore, T. A. Moore and D. Gust (2000) Photoinduced electron transfer in carotenoporphyrin-fullerene triads: temperature and solvent effects. J. Phys. Chem. B 104, 4307-4321.
33. Anton, J. A. and P. A. Loach (1975) Synthesis of some mono, di, and trisubstituted tetraarylporphyrins. J. Heterocyclic Chem. 12, 573-576.
34. Gust, D., T. A. Moore, A. L. Moore, A. N. Macpherson, A. Lopez, J. M. DeGraziano, I. Gouni, E. Bittersmann, G. R. Seely, F. Gao, R. A. Nieman, X. C. Ma, L. J. Demanche, D. K. Luttrull, S.-J. Lee and P. K. Kerrigan (1993) Photoinduced electron and energy transfer in molecular pentads. J. Am. Chem. Soc. 115, 11 141-11 152.
35. 60: synthesis, characterization, and functionalization of fullerene pyrrolidines. J. Am. Chem. Soc. 115, 9798-9799.
36. Kuciauskas, D., P. A. Liddell, S.-C. Hung, S. Lin, S. Stone, G. R. Seely, A. L. Moore, T. A. Moore and D. Gust (1997) Structural effects on photoinduced electron transfer in carotenoidporphyrin-quinone triads. J. Phys. Chem. 101, 429-440.
37. Kadish, K. M., L. R. Shiue, R. K. Rhodes and L. A. Bottomley (1981) Reactions of metalloporphyrin pi radicals. I. Complexation of zinc tetraphenylporphyrin cation and anion radicals with nitrogenous bases. Inorg. Chem. 20, 1274-1277.
38. Bensasson, R. V., E. J. Land and T. G. Truscott (1983) Flash Photolysis and Pulse Radiolysis. Contributions to the Chemistry of Biology and Medicine. Pergamon Press, New York.
39. Marcus, R. A. (1956) The theory of oxidation-reduction reactions involving electron transfer. J. Chem. Phys. 24, 966-978.
40. Marcus, R. A. and N. Sutin (1985) Electron transfers in chemistry and biology. Biochim. Biophys. Acta 811, 265-322.
41. Noss, L., P. A. Liddell, A. L. Moore, T. A. Moore and D. Gust (1997) Aryl ring rotation in porphyrins. A carbon-13 NMR spinlattice relaxation time study. J. Phys. Chem. B 101, 458-465.
42. Strachan, J. P., S. Gentemann, J. Seth, W. A. Kalsbeck, J. S. Lindsey, D. Holten and D. F. Bocian (1997) Effects of orbital ordering on electronic communication in multiporphyrin arrays. J. Am. Chem. Soc. 119, 11 191-11 201.
43. Yang, S. I., J. Seth, T. Balasubramanian, D. Kim, J. S. Lindsey, D. Holten and D. F. Bocian (1999) Interplay of orbital tuning and linker location in controlling electronic communication in porphyrin-based nanostructures. J. Am. Chem. Soc. 121, 4008-4018.
44. Yang, S. I., J. Seth, J. P. Strachan, S. Gentemann, D. Kim, D. Holten, J. S. Lindsey and D. F. Bocian (1999) Ground- and excited-state electronic properties of halogenated tetraarylporphyrins. Tuning the building blocks for porphyrin-based photonic devices. J. Porphyrins Phthalocyanines 3, 117-147.
45. Closs, G. L. and J. R. Miller (1988) Intramolecular long-distance electron transfer in organic molecules. Science 240, 440-446.
46. Gust, D., T. A. Moore, L. R. Makings, P. A. Liddell, G. A. Nemeth and A. L. Moore (1986) Photodriven electron transfer in triad molecules: a two-step charge recombination reaction. J. Am. Chem. Soc. 108, 8028-8031.
47. Osuka, A., H. Yamada, T. Shinoda, K. Nozaki and O. Ohno (1995) Intramolecular charge recombination in carotenoid-porphyrin-pyromellitimide triads. Chem. Phys. Lett. 238, 37-41.
48. Gust, D., T. A. Moore, A. L. Moore, H.-K. Kang, J. M. De-Graziano, P. A. Liddell and G. R. Seely (1993) The effect of coordinated ligands on interporphyrin photoinduced electron transfer rates. J. Phys. Chem. 97, 13637-13642.
49. Seely, G. R., D. Gust, T. A. Moore and A. L. Moore (1994) The effect of anions on the electrochemistry of zinc tetraphenylporphyrin. J. Phys. Chem. 98, 10659-10664.
50. Gust, D., T. A. Moore, D. K. Luttrull, G. R. Seely, E. Bittersmann, R. V. Bensasson, M. Rougée, E. J. Land, F. C. de Schryver and M. Van der Auweraer (1990) Photophysical properties of 2-nitro-5,10,15,20-tetra-p-tolylporphyrins. Photochem. Photobiol. 51, 419-426.
51. Davis, F. S., G. A. Nemeth, D. M. Anjo, L. R. Makings, D. Gust and T. A. Moore (1987) Digital back off for computer controlled flash spectrometers. Rev. Sci. Instrum. 58, 1629-1631.
52. Freiberg, A., K. Timpmann, S. Lin and N. W. Woodbury (1998) Exciton relaxation and transfer in the LH2 antenna network of photosynthetic bacteria. J. Phys. Chem. B 102, 10974-10982.
53. Gust, D., T. A. Moore, A. L. Moore and P. A. Liddell (1992) Synthesis of carotenoporphyrin models for photosynthetic energy and electron transfer. Methods Enzymol. 213, 87-100.