Spin control of the lifetime of an intramolecular charge-transfer excited state

Photochemical and Photobiological Sciences

Volumn 2, Issue 10, 2003, Pages 995-1001

  Hviid, Lene ^a   Bouwman, Wim G ^b   Paddon Row, Michael N ^c   Van Ramesdonk, Hendrik J ^a   Verhoeven, Jan W ^a   Brouwer, Albert M ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^c UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALKANE; NITRILE;

ABSORPTION SPECTROSCOPY; ARTICLE; ELECTRON; ELECTRON TRANSPORT; ENERGY; LIFESPAN; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

EID: 3042685067     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b306052g     Document Type: Article

References (51)

1. R. A. Marcus, Electron-transfer reactions in chemistry - theory and experiment (Nobel lecture), Angew. Chem., Int. Ed. Engl., 1993, 32, 1111.
2. M. R. Wasielewski, Photoinduced electron transfer in supramolecular systems for artificial photosynthesis, Chem. Rev., 1992, 92, 435.
3. D. Gust, T. A. Moore and A. L. Moore, Molecular mimicry of photosynthetic energy and electron transfer, Acc. Chem. Res., 1993, 26, 198-205.
4. M. R. Roest, J. W. Verhoeven, W. Schuddeboom, J. M. Warman, J. M. Lawson and M. N. Paddon-Row, Solvent and distance dependent charge separation in rigid trichromophoric systems, J. Am. Chem. Soc., 1996, 118, 1762-1768.
5. A. Osuka, N. Mataga and T. Okada, A chemical approach towards the photosynthetic reaction center, Pure Appl. Chem., 1997, 69, 797.
6. C. Luo, D. M. Guldi, H. Imahori, K. Tamaki and S. Sakata, Sequential energy and electron transfer in an artificial reaction center: formation of a lone-lived charge-separated state, J. Am. Chem. Soc., 2000, 122, 6535-6551.
7. D. Gust, T. A. Moore and A. L. Moore, Mimicking photosynthetic solar energy transduction, Acc. Chem. Res., 2001, 34, 40-48.
8. H. Imahori, D. M. Guldi, K. Tamaki, Y. Yoshida, C. P. Luo, Y. Sakata and S. Fukuzumi, Charge separation in a novel artificial photosynthetic reaction center lives 380 ms, J. Am. Chem. Soc., 2001, 123, 6617-6628.
9. 2)- tetrachlorophthalimide compounds studied by time-resolved microwave conductivity, J. Lumin., 1988, 42, 149-154.
10. D. Anglos, V. Bindra and A. Kuki, Photoinduced electron transfer and long-lived charge separation in rigid peptide architectures, J. Chem. Soc., Chem. Commun., 1994, 2, 213.
11. K. Lee and D. E. Falvey, Photochemically removable protecting groups based on covalently linked electron donor-acceptor systems, J. Am. Chem. Soc., 2000, 122, 9361-9366.
12. S. I. van Dijk, C. P. Groen, F. Hartl, A. M. Brouwer and J. W. Verhoeven, Long-lived triplet state charge separation in novel piperidine-bridged donor-acceptor systems, J. Am. Chem. Soc., 1996, 118, 8425-8432.
13. L. Hviid, J. W. Verhoeven, A. M. Brouwer, M. N. Paddon-Row, J. Yang and M. V. George, Characterization by time-resolved UV/ Vis and infrared absorption spectroscopy of an intramolecular charge-transfer state in an organic electron-donor-bridge-acceptor system, manuscript in preparation.
14. H. Oevering, M. N. Paddon-Row, M. Heppener, A. M. Oliver, E. Cotsaris, J. W. Verhoeven and N. S. Hush, Long-range photoinduced through-bond electron transfer and radiative recombination via rigid nonconjugated bridges: distance and solvent dependence, J. Am. Chem. Soc., 1987, 109, 3258-3269.
15. 1 spectra of naphthalene and anthracene, Chem. Phys., 1974, 3, 205-216.
16. J. W. Verhoeven, B. Wegewijs, J. Kroon, R. P. H. Rettschnick, M. N. Paddon-Row and A. M. Oliver, Rigid donor-bridge-acceptor systems - photoinduced charge-transfer in solution and in a supersonic jet, J. Photochem. Photobiol., A, 1994, 82, 161-170.
17. J. M. Warman, K. J. Smit, S. A. Jonker, J. W. Verhoeven, H. Oevering, J. Kroon, M. N. Paddon-Row and A. M. Oliver, Intramolecular charge separation and recombination in non-polar environments via long-distance electron transfer through saturated hydrocarbon barriers, Chem. Phys., 1993, 170, 359-380.
18. J. Morais, R. R. Hung, J. J. Grabowski and M. B. Zimmt, Charge transfer state photophysics in a rigid molecule: competition between electron transfer processes in the Marcus normal and inverted regions, J. Phys. Chem., 1993, 97, 13 138.
19. H. Oevering, Electron- and Energy Transfer via Saturated Hydrocarbon Bridges, Ph.D. Thesis, University of Amsterdam, The Netherlands, 1988.
20. S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry, Marcel Dekker, New York, 1993.
21. G. S. Hammond, J. Saltiel, A. A. Lamola, N. J. Turro, J. S. Bradshaw, D. O. Cowan, R. C. Counsell, V. Vogt and C. Dalton, Mechanism of photochemical reactions in solution. XXII. Photochemical cis-trans isomerization, J. Am. Chem. Soc., 1964, 86, 3197.
22. R. Sustman, K. Luecking, G. Kopp and M. Rese, [4+2]-Cyclo-additions with 1,4-bis(N,N-dimethylamino)-1,3-dicnes: stereochemical studies and observation of radical ions, Angew. Chem., Int. Ed. Engl., 1989, 28, 1713.
23. D. A. Tyssee and M. M. Baizer, Electrocarboxylation. I. Mono- and dicarboxylation of activated olefins, J. Org. Chem., 1974, 39, 2819.
24. A. Weller, Photoinduced electron transfer in solution: exciplex and radical ion pair formation free enthalpies and their solvent dependence, Z. Phys. Chem., Neue Folge, 1982, 133, 93.
25. N. J. Turro, Modern Molecular Photochemistry, Benjamin/ Cummings, San Fransisco, 1978.
26. I. Carmichael, W. P. Helman and G. L. Hug, Extinction coefficients of triplet-triplet absorption spectra of organic molecules in condensed phases: a least-squares analysis, J. Phys. Chem. Ref. Data, 1987, 16, 239-260.
27. W. H. Press, B. P. Flannery, S. A. Teukolsky and W. T. Vetterling, Numerical Recipes. The Art of Scientific Computing, Cambridge University Press, Cambridge, 1986.
28. I. H. M. Van Stokkum, T. Scherer, A. M. Brouwer and J. W. Verhoeven, Conformational dynamics of flexibly and semirigidly bridged electron donor-acceptor systems as revealed by spectrotemporal parameterization of fluorescence, J. Phys. Chem., 1994, 98, 852-866.
29. Igor Pro, version 4.06, Program for Graphing and Data Analysis, Wavemetrics, Inc., Lake Oswego, OR, USA.
30. P. R. Bevington, Data Reduction and Error Analysis for the Physical Sciences, McGraw-Hill, New York, 1969.
31. D. Rehm and A. Weller, Kinetics of fluorescence quenching by electron and H-atom transfer, Isr. J. Chem., 1970, 8, 259-271.
32. L. Hviid, A. M. Brouwer, M. N. Paddon-Row and J. W. Verhoeven, Long-lived short-distance intramolecular charge separation via intermolecular triplet sensitation, ChemPhysChem, 2001, 4, 232-235.
33. L. Hviid, Charge Separation and Recombination in Photoexcited Triplet States of Electron Donor Acceptor Systems, Ph.D. Thesis, University of Amsterdam, The Netherlands, 2001.
34. M. R. Roest, Electron Transfer via Hydrocarbon Bridges with and without an Intermediate π-System, Ph.D. Thesis, University of Amsterdam, The Netherlands, 1996.
35. T. Shida, Electronic Absorption Spectra of Radical Ions, Elsevier, Amsterdam, 1988.
36. Y. Mori, Y. Sakaguchi and H. Hayashi, Spin effects on decay dynamics of charge-separated states generated by photoinduced electron transfer in zinc porphyrin-naphthalenediimide dyads, J. Phys. Chem. A, 2002, 106, 4453-4467.
37. R. A. Marcus, On the theory of oxidation-reduction reactions involving electron transfer. I., J. Chem. Phys., 1956, 24, 966.
38. A. Weller, Exciplex and radical pairs in photochemical electron transfer, Pure Appl. Chem., 1982, 54, 1885-1888.
39. N. Malaga, T. Okada and N. Yamamoto, Electronic processes in hetero-excimers and the mechanism of fluorescence quenching, Chem. Phys. Lett., 1967, 1, 119-121.
40. H. Beens and A. Weller, Classification and formation of charge-transfer complexes in the triplet state, in Molecular Luminescence, ed. E. C. Lim, W. A. Benjamin, New York, 1969.
41. H. Beens, Exciplexes. An Experimental and Theoretical Study, Ph.D. Thesis, Vrije Universtiteit, Amsterdam, The Netherlands, 1970.
42. I. R. Gould, R. H. Young, L. J. Mueller, A. C. Albrecht and S. Farid, Electronic structures of exciplexes and excited CT complexes, J. Am. Chem. Soc., 1994, 116, 8188-8199.
43. M. Bixon, J. Jortner and J. W. Verhoeven, Lifetimes for radiative charge recombination in donor-acceptor molecules, J. Am. Chem. Soc., 1994, 116, 7349-7355.
44. H. Oevering, J. W. Verhoeven, M. N. Paddon-Row and J. M. Warman, Charge-transfer absorption and emission resulting from long-range through-bond interaction; exploring the relation between electronic coupling and electron-transfer in bridged donor-acceptor systems, Tetrahedron, 1989, 45, 4751-4766.
45. H. Hayashi, S. Nagakura and S. Iwata, E.S.R. of the charge-transfer triplet state of the durene-tetracyanobenzene complex, Mol. Phys., 1967, 13, 489-490.
46. S. Iwata, J. Tanaka and S. Nagakura, Phosphorescence of the charge-transfer triplet states of some molecular complexes, J. Chem. Phys., 1967, 47, 2203-2209.
47. S. Sekiguchi, Y. Kobori, K. Akiyama and S. Tero-Kubota, Marcus free energy dependence of the sign of exchange interactions in radical ion pairs generated by photoinduced electron transfer reactions, J. Am. Chem. Soc., 1998, 120, 1325-1326.
48. Y. Kobori, K. Akiyama and S. Tero-Kubota, Theoretical analysis of singlet-triplet energy splitting generated by charge-transfer interaction in electron donor- acceptor radical pair systems, J. Chem. Phys., 2000, 113, 465-468.
49. T. Tachikawa, Y. Kobori, K. Akiyama, A. Katsuki, U. E. Steiner and S. Tero-Kubota, Spin dynamics and zero-field splitting constants of the triplet exciplex generated by photoinduced electron transfer reaction between erythrosin B and duroquinone. Chem. Phys. Lett., 2002, 360, 13-21.
50. M. N. Paddon-Row and M. J. Shephard, A time-dependent density functional study of the singlet- triplet energy gap in charge-separated states of rigid bichromophoric molecules, J. Phys. Chem. A, 2002, 106, 2935-2944.
51. M. Wegner, H. Fischer, M. Koeberg, J. W. Verhoeven, A. M. Oliver and M. N. Paddon-Row, Time-resolved CIDNP from photochemically generated radical ion pairs in rigid bichromophoric systems, Chem. Phys., 1999, 242, 227.