Competing electron-transfer pathways in hydrocarbon frameworks: Short-circuiting through-bond coupling by nonbonded contacts in rigid U-shaped norbornylogous systems containing a cavity-bound aromatic pendant group

Journal of the American Chemical Society

Volumn 129, Issue 11, 2007, Pages 3247-3256

  Chakrabarti, Subhasis ^a   Liu, Min ^a   Waldeck, David H ^a   Oliver, Anna M ^b   Paddon Row, Michael N ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC PENDANT GROUP; DICYANOVINYL (DCV); ELECTRON TRANSFER; U-SHAPED NORBORNYLOGOUS FRAMEWORKS;

AROMATIC COMPOUNDS; CHARGE TRANSFER; HYDROCARBONS; MOLECULAR DYNAMICS; ORGANIC SOLVENTS; SHORT CIRCUIT CURRENTS;

ELECTRON TRANSITIONS;

AROMATIC COMPOUND; DICYANOVINYL; DIPHENYLDIMETHOXYNAPHTHALENE; HYDROCARBON; NAPHTHALENE DERIVATIVE; ORGANIC SOLVENT; PHENYL GROUP; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CALCULATION; CHROMATOPHORE; ELECTRICITY; ELECTRON TRANSPORT; ENERGY; FLUORESCENCE; MOLECULE; PHYSICS; REACTION ANALYSIS;

BENZENE DERIVATIVES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; NAPHTHALENES; NORBORNANES; THERMODYNAMICS;

EID: 33947364317     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067266b     Document Type: Article

References (39)

1. (a) Barbara, P. F.; Meyer, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148.
2. (b) Jortner, J., Bixon, M., Eds. Electron Transfer-From Isolated Molecules to Biomolecules. In Advances in Chemical Physics; Wiley: New York, 1999.
3. (a) Hush, N. S.; Paddon-Row, M. N.; Cotsaris, E.; Oevering, H.; Verhoeven, J. W.; Heppener, M. Chem. Phys. Lett. 1985, 117, 8.
4. (b) Oliver, A. M.; Craig, D. C.; Paddon-Row, M. N.; Kroon, J.; Verhoeven, J. W. Chem. Phys. Lett. 1988, 150, 366.
5. (c) Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18.
6. (a) Zeng, Y.; Zimmt, M. B. J. Phys. Chem. 1992, 96, 8395.
7. (b) Oliver, A. M.; Paddon-Row, M. N.; Kroon, J.; Verhoeven, J. W. Chem. Phys. Lett. 1992, 191, 371.
8. (a) Closs, G. L.; Miller, J. R. Science 1988, 240, 440.
9. (b) Guldi, D. M.; Luo, C.; Prato, M.; Troisi, A.; Zerbetto, F.; Scheloske, M.; Dietel, E.; Bauer, W.; Hirsch, A. J. Am. Chem. Soc. 2001, 123, 9166.
10. Napper, A. M.; Head, N. J.; Oliver, A. M.; Shephard, M. J.; Paddon-Row, M. N.; Read, I.; Waldeck, D. H. J. Am. Chem. Soc. 2002, 124, 10171.
11. Liu, M.; Chakrabarti, S.; Waldeck, D. H.; Oliver, A. M.; Paddon-Row, M. N. Chem. Phys. 2006, 324, 72.
12. Napper, A. M.; Read, I.; Waldeck, D. H.; Head, N. J.; Oliver, A. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 2000, 122, 5220.
13. (a) Oevering, H.; Verhoeven, J. W.; Paddon-Row, M. N.; Warman, J. M. Tetrahedron 1989, 45, 4751.
14. (b) Oevering, M. N.; Paddon-Row, M. N.; Heppener, H.; Oliver, A. M.; Cotsaris, E.; Verhoeven, J. H.; Hush, N. S. J. Am. Chem. Soc. 1987, 109, 3258.
15. Kumar, K.; Kurnikov, I. V.; Beratan, D. N.; Waldeck, D. H.; Zimmt, M. B. J. Phys. Chem. A 1998, 102, 5529.
16. Read, I.; Napper, A. M.; Zimmt, M. B.; Waldeck, D. H. J. Phys. Chem. A 2000, 104, 9385.
17. Matyushov, D. V.; Voth, G. A. J. Chem. Phys. 1999, 111, 3630.
18. (a) Paddon-Row, M. N.; Oliver, A. M.; Warman, J. M.; Smit, K. J.; de Hass, M.P.; Oevering, H.; Verhoeven, J. W. J. Phys. Chem. 1988, 92, 6958.
19. (b) Warman, J. M.; Smit, K. J.; de Hass, M. P.; Jonker, S. A.; Paddon-Row, M. N.; Oliver, A. M.; Kroon, J.; Oevering, H.; Verhoeven, J. W. J. Phys. Chem. 1991, 95, 1979.
20. Head, N. J.; Oliver, A. M.; Look, K.; Lokan, N. R.; Jones, G. A.; Paddon-Row, M. N. Angew. Chem., Int. Ed. 1999, 38, 3219.
21. Wasielewski, M. R.; Minsek, D. W.; Niemczyk, M. P.; Svec, W. A.; Yang, N. C. J. Am. Chem. Soc. 1990, 112, 2823.
22. Morais, J.; Huang, R. R.; Grabowski, J. J.; Zimmt, M. B. J. Phys. Chem. 1993, 97, 13138.
23. (a) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1955, 28, 690.
24. (b) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1955, 29, 465.
25. (a) Marcus, R. A. J. Phys. Chem. 1989, 93, 3078.
26. (b) Cortes, J.; Heitele, H.; Jortner, J. J. Phys. Chem. 1994, 98, 2527.
27. ET for 2DBA than for 1DBA but leads to a bad fit between the experimental and theoretical prediction of 2DBA.
28. Koeberg, M.; deGroot, M.; Verhoeven, J. W.; Lokan, N. R.; Shephard, M. J.; Paddon-Row, M. N. J. Phys. Chem. A 2001, 105, 3417.
29. Frisch, M. J.; et al. Gaussian, Inc.: Pittsburgh PA, 2003.
30. Liu, M.; Waldeck, D. H.; Oliver, A.; Head, N. J.; Paddon-Row, M. N. J. Am. Chem. Soc. 2004, 126, 10778.
31. Jordan, K. D.; Burrow, P. D. Acc. Chem. Res. 1978, 11, 341.
32. Toluene: Kimura, K. Handbook of He(I) photoelectron spectra of fundamental organic molecules; Japan Scientific Societies Press: Tokyo. 1981.
33. Anisole: Kobayashi, T.; Nagakura, S. Bull. Chem. Soc. Japan 1974, 47, 2563.
34. (a) Shephard, M. J.; Paddon-Row, M. N. J. Phys. Chem. A 1999, 103, 3347.
35. (b) Shephard, M. J.; Paddon-Row, M. N. J. Phys. Chem. A 2000, 104, 11628.
36. Fully optimized charge-separated state geometries, with no symmetry constraints, could be calculated using some sort of CI procedure, the simplest being CIS. However, preliminary attempts to optimize the charge-separated state of 1DBA′. even using the relatively small 3-21G basis set, met with such huge computational overheads that they were aborted.
37. Paddon-Row, M. N.; Jordan, K. D. Through-Bond and Through-Space Interactions in Unsaturated Hydrocarbons: Their Implications for Chemical Reactivity and Long-Range Electron Transfer. In Modern Models of Bonding and Delocalisation; Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: New York, 1988; Vol. 6, p 115.
38. (a) Jolliffe, K. A.; Bell, T. D. M.; Ghiggino, K. P.; Langford, S. J.; Paddon-Row, M. N. Angew. Chem., Int. Ed. 1998, 37, 916.
39. (b) Bell, T. D. M.; Jolliffe, K. A.; Ghiggino, K. P.; Oliver, A. M.; Shephard, M. J.; Langford, S. J.; Paddon-Row, M. N. J. Am. Chem. Soc. 2000, 122, 10661.