Experimental evidence for water mediated electron transfer through bis-amino acid donor-bridge-acceptor oligomers

Journal of the American Chemical Society

Volumn 131, Issue 6, 2009, Pages 2044-2045

  Chakrabarti, Subhasis ^a   Parker, Matthew F L ^b   Morgan, Christopher W ^a   Schafmeister, Christian E ^b   Waldeck, David H ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; DIMETHYL SULFOXIDE; ELECTRON TRANSITIONS; MOLECULES; OLIGOMERS; ORGANIC ACIDS; ORGANIC SOLVENTS; RADIO RECEIVERS; RING GAGES;

ELECTRON DONORS; ELECTRON-TRANSFER RATE CONSTANTS; EXPERIMENTAL EVIDENCE; MEDIATED ELECTRON TRANSFER; PHOTO-INDUCED; SOLUTE MOLECULES; UNIMOLECULAR; WATER MOLECULE;

RATE CONSTANTS;

AMIDE; AMINO ACID; DIMETHYL SULFOXIDE; OLIGOMER; ORGANIC SOLVENT; PYRENE DERIVATIVE; WATER; ANILINE DERIVATIVE; INFUSORIAL EARTH;

ARTICLE; BINDING SITE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; EXPERIMENTATION; LIGHT; MOLECULE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY; ELECTRON; HYDROGEN BOND; THERMODYNAMICS;

AMIDES; AMINO ACIDS; ANILINE COMPOUNDS; DIATOMACEOUS EARTH; DIMETHYL SULFOXIDE; ELECTRONS; HYDROGEN BONDING; MODELS, MOLECULAR; PYRENES; THERMODYNAMICS; WATER;

EID: 67849130972     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8079324     Document Type: Article

References (32)

1. Beratan, D. N.; Onuchic, J. N. Protein Electron Transfer; Bendall, D. S., Ed.; BIOS Scientific Publishers Ltd.: Oxford, 1996; p 23.
2. th ed.; Freeman: New York, 2002.
3. Page, C. C.; Moser, C. C.; Chen, X.; Dutton, P. L. Nature 1999, 402, 47.
4. (a) Lin, J.; Balabin, I. A.; Beratan, D. N. Science 2005, 310, 1311.
5. (b) Balabin, I. A.; Beratan, D. N.; Skourtis, S. S. Phys. Rev. Lett. 2008, 201, 158102.
6. Migliore, A.; Corni, S.; Felice, R. D.; Molinari, E. J. Phys. Chem. B 2006, 110, 23796.
7. Miyashita, O.; Okamura, M. Y.; Onuchic, J. N. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 3558.
8. Wenger, O. S.; Leigh, R. M.; Villahermosa, H. B.; Gray, H. B.; Winkler, J. R. Science 2005, 307, 99.
9. Ponce, H. B.; Gray, H. B.; Winkler, J. R. J. Am. Chem. Soc. 2000, 122, 8187.
10. The distances are center-to-center distances between the pyrene and dimethylaniline group found by molecular mechanics minimization of the molecular geometries in vacuo.
11. Zimmt, M. B.; Waldeck, D. H. J. Phys. Chem. A 2003, 107, 3580.
12. Read, I.; Napper, A.; Kaplan, R.; Zimmt, M. B.; Waldeck, D. H. J. Am. Chem. Soc. 1999, 121, 10976.
13. Kumar, K.; Kurnikov, I.; Beratan, D. N.; Waldeck, D. H.; Zimmt, M. B. J. Phys. Chem. A 1998, 102, 5529.
14. Troisi, A.; Ratner, M. A.; Zimmt, M. B. J. Am. Chem. Soc. 2004, 126, 2215.
15. Levins, C. G.; Schafmeister, C. E. J. Am. Chem. Soc. 2003, 125, 4702.
16. Nadeau, J. M.; Liu, M.; Waldeck, D. H.; Zimmt, M. B. J. Am. Chem. Soc. 2003, 125, 15973.
17. Galoppini, E.; Fox, M. A. J. Am. Chem. Soc. 1996, 118, 2299.
18. a of the dimethylaniline is 5.1. At pH ∼7, 100% of the molecule will be free amine whereas, at pH 4.5, only 20% of the molecules will contain free amine group in the dimethylamine donor unit.
19. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
20. Bixon, M.; Jortner, J. Adv. Chem. Phys. 1999, 106, 35.
21. Liu, M.; Chakrabarti, S.; Waldeck, D. H.; Oliver, A. M.; Paddon-Row, M. N. Chem. Phys. 2006, 324, 72.
22. Chakrabarti, S.; Liu, M.; Waldeck, D. H.; Oliver, A. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 2007, 129, 3247.
23. Sharp, K.; Honig, B. Annu. Rev. Biophys. Chem. 1990, 19, 301.
24. Newton, M. D.; Basilevsky, M. V.; Rostov, I. V. Chem. Phys. 1998, 232, 201.
25. Matyushov, D. V.; Voth, G. A. J. Chem. Phys. 1999, 111, 3630.
26. Read, I.; Napper, A. M.; Zimmt, M. B.; Waldeck, D. H. J. Phys. Chem. A 2000, 104, 9385.
27. The reorganization energies were calculated using a continuum model that considers the solute as an ellipsoidal cavity; see Chem. Phys. Lett. 1977, 49, 299-304 and J. Phys. Chem. 1986, 90, 3657-3668). The equation and calculation are shown in the SI.
28. The thickness of an aromatic ring is ∼3.4 Å. Thus the π-orbitals of each aromatic chromophore in the D-SSS-A molecule extend into the cleft by ∼1.7 A, leaving a 1.2 Å gap between the donor and acceptor.
29. The molecular radii were estimated from volume increments given by: Bondi, A. J. Phys. Chem. 1964, 68, 441.
30. Turro, C.; Chang, C. K.; Leroi, G. E.; Cukier, R. I.; Nocera, D. G. J. Am. Chem. Soc. 1992, 114, 4013.
31. Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337.
32. Hodgkiss, J. M.; Damrauer, N. H.; Presse, S.; Rosenthal, J.; Nocera, D. G. J. Phys. Chem. B 2006, 110, 18853.