Control over charge transfer through molecular wires by temperature and chemical structure modifications

ACS Nano

Volumn 4, Issue 11, 2010, Pages 6449-6462

  Wielopolski, Mateusz ^a   De Miguel Rojas, Gustavo ^a   Van Der Pol, Cornelia ^b   Brinkhaus, Linda ^a   Katsukis, Georgios ^a   Bryce, Martin R ^b   Clark, Timothy ^a   Guldi, Dirk M ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Charge transfer; Cycloaddition reactions; Electron donor acceptor conjugates; Excited state calculations; Fullerenes; Molecular wires; Oligofluorenes; Temperature dependence; Transient absorption spectroscopy; Zinc porphyrins

Indexed keywords

CYCLOADDITION REACTIONS; ELECTRON DONOR-ACCEPTOR CONJUGATES; MOLECULAR WIRES; OLIGOFLUORENES; TEMPERATURE DEPENDENCE; TRANSIENT ABSORPTION SPECTROSCOPY; ZINC PORPHYRINS;

ABSORPTION; CHARGE TRANSFER; CHEMICAL MODIFICATION; CYCLIC VOLTAMMETRY; CYCLOADDITION; ELECTRONS; EXCITED STATES; FREE RADICAL REACTIONS; FULLERENES; ION EXCHANGE; MASS TRANSFER; NANOWIRES; PHOTOEXCITATION; PORPHYRINS; TEMPERATURE DISTRIBUTION; WIRE; ZINC; ZINC COMPOUNDS;

ABSORPTION SPECTROSCOPY;

EID: 78649612214     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn1013758     Document Type: Article

References (52)

1. Jortner, J., Ratner, M., Eds. Molecular Electronics; Blackwell: London, 1997.
2. Joachim, C.; Gimzewski, J. K.; Aviram, A. Electronics Using Hybrid-Molecular and Mono-molecular Devices Nature 2000, 408, 541-548
3. Troisi, A.; Ratner, M. A. Molecular Signatures in the Transport Properties of Molecular Wire Junctions: What Makes a Junction "Molecular" Small 2006, 2, 172-181
4. Scandola, F.; Chiorboli, C.; Indelli, M. T.; Rampi, M. A. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. III, Chapter 2.1.
5. De Cola, L.; Belser, P. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. V, Chapter 3.
6. Davis, W. B.; Svec, W. A.; Ratner, M. A.; Wasielewski, M. R. Molecular-Wire Behavior in p -Phenylenevinylene Oligomers Nature 1998, 396, 60-63
7. Wasielewski, M. R. Energy, Charge, and Spin Transport in Molecules and Self-Assembled Nanostructures Inspired by Photosynthesis J. Org. Chem. 2006, 71, 5051-5066
8. Aviram, A. Molecules for Memory, Logic, and Amplification J. Am. Chem. Soc. 1988, 110, 5687-5692
9. Carrol, L.; Gorman, C. B. The Genesis of Molecular Electronics Angew. Chem., Int. Ed. 2002, 41, 4378-4400
10. Review: Albinsson, B.; Eng, M. P.; Pettersson, K.; Winters, M. U. Electron and Energy Transfer in Donor-Acceptor Systems with Conjugated Molecular Bridges Phys. Chem. Chem. Phys. 2007, 9, 5847-5864
11. James, D. K.; Tour, J. M. Electrical Measurements in Molecular Electronics Chem. Mater. 2004, 16, 4423-4435
12. Creager, S. et al. Electron Transfer at Electrodes through Conjugated "Molecular Wire" Bridges J. Am. Chem. Soc. 1999, 121, 1059-1064
13. Grozema, F. C.; Berlin, Y. A.; Siebbeles, L. D. A. Mechanism of Charge Migration through DNA: Molecular Wire Behavior, Single-Step Tunneling or Hopping J. Am. Chem. Soc. 2000, 122, 10903-10909
14. Jortner, J.; Bixon, M.; Langenbacher, T.; Michel-Beyerle, M. E. Charge Transfer and Transport in DNA Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12759-12765
15. Lambert, C.; Noll, G.; Schelter, J. Bridge-Mediated Hopping or Superexchange Electron-Transfer Processes in Bis(triarylamine) Systems Nat. Mater. 2002, 1, 69-73
16. Wasielewski, M. R.; Ratner, M. A.; Mujica, V.; Nitzan, A. Electron Transfer Rates in Bridged Molecular Systems: A Phenomenological Approach to Relaxation J. Phys. Chem. A 1997, 101, 6158-6164
17. Gray, H. B.; Winkler, J. R. Long-Range Electron Transfer Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 3534-3539
18. Albinsson, B.; Martensson, J. Long-Range Electron and Excitation Energy Transfer in Donor-Bridge-Acceptor Systems J. Photochem. Photobiol. C 2008, 9, 138-155
19. Weiss, E. A.; Wasielewski, M. R.; Ratner, M. A. Molecules as Wires: Molecule-Assisted Movement of Charge and Energy Top. Curr. Chem. 2005, 257, 103-133
20. Ratner, M. A. Bridge-Assisted Electron Transfer: Effective Electronic Coupling J. Phys. Chem. 1990, 94, 4877-4883
21. Giacalone, F.; Segura, J. L.; Martín, N.; Guldi, D. M. Exceptionally Small Attenuation Factors in Molecular Wires J. Am. Chem. Soc. 2004, 126, 5340-5341
22. Giacalone, F.; Segura, J. L.; Martín, N.; Ramey, J.; Guldi, D. M. Probing Molecular Wires: Synthesis, Structural, and Electronic Study of Donor-Acceptor Assemblies Exhibiting Long-Range Electron Transfer Chem. - Eur. J. 2005, 11, 4819-4834
23. Atienza, C.; Martín, N.; Wielopolski, M.; Haworth, N.; Clark, T.; Guldi, D. M. Tuning Electron Transfer through p -Phenyleneethynylene Molecular Wires Chem. Commun. 2006, 236, 3202-3204
24. Wielopolski, M.; Atienza, C.; Clark, T.; Guldi, D. M.; Martín, N. p -Phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron-Transfer Properties Chem. - Eur. J. 2008, 14, 6379-6390
25. Lembo, A.; Tagliatesta, P.; Guldi, D. M.; Wielopolski, M.; Nuccetelli, M. Porphyrin-β-Oligo-ethynylenephenylene-[60]Fullerene Triads: Synthesis and Electrochemical and Photophysical Characterization of the New Porphyrin-Oligo-PPE-[60]Fullerene Systems J. Phys. Chem. A 2009, 113, 1779-1793
26. Atienza-Castellanos, C.; Wielopolski, M.; Guldi, D. M.; van der Pol, C.; Bryce, M. R.; Filippone, S.; Martín, N. Determination of the Attenuation Factor in Fluorene-Based Molecular Wires Chem. Commun. 2007, 48, 5164-5166
27. Goldsmith, R. H.; Sinks, L. E.; Kelley, R. F.; Betzen, L. E.; Liu, W. H.; Weiss, E. A.; Ratner, M. A.; Wasielewski, M. R. Wire-like Charge Transport at Near Constant Bridge Energy through Fluorene Oligomers Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 3540-3545
28. 60 Ensembles Chem. - Eur. J. 2005, 11, 1267-1280
29. Imahori, H.; Fukuzumi, S. Porphyrin- and Fullerene-Based Molecular Photovoltaic Devices Adv. Funct. Mater. 2004, 14, 525-536
30. Imahori, H. Porphyrin-Fullerene Linked Systems as Artificial Photosynthetic Mimics Org. Biomol. Chem. 2004, 2, 1425-1433
31. Guldi, D. M.; Rahman, G. M. A.; Sgobba, V.; Ehli, C. Multifunctional Molecular Carbon Materials - From Fullerenes to Carbon Nanotubes Chem. Soc. Rev. 2006, 35, 471-487
32. Guldi, D. M. Nanometer Scale Carbon Structures for Charge-Transfer Systems and Photovoltaic Applications Phys. Chem. Chem. Phys. 2007, 9, 1400-1420
33. Vail, S. A. et al. Energy and Electron Transfer in β-Alkynyl-Linked Porphyrin-[60]Fullerene Dyads J. Phys. Chem. B 2006, 110, 14155-14166
34. Kobori, Y.; Yamauchi, S.; Akiyama, K.; Tero-Kubota, S.; Imahori, H.; Fukuzumi, S.; Norris, J. R., Jr. Primary Charge-Recombination in an Artificial Photosynthetic Reaction Center Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10017-10022
35. Smitha, M. A.; Gopidas, K. R. Temperature Dependence of Photoinduced Electron Transfer in Hydrogen-Bonded Donor-Acceptor Systems Chem. Phys. Lett. 2001, 350, 86-92
36. 60 Connected Systems Chem. Commun. 2007, 4498-4500
37. 60 Dyads Connected through a p -Phenylenevinylene Dimer Tetrahedron 2008, 64, 11404-11408
38. Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. A Simplified Synthesis for meso -Tetraphenylporphine J. Org. Chem. 1967, 32, 476-476
39. 60 Donor-Acceptor Conjugates J. Org. Chem. 2007, 72, 6662-6671
40. Prato, M.; Maggini, M. Fulleropyrrolidines: A Family of Full-Fledged Fullerene Derivatives Acc. Chem. Res. 1998, 31, 519-526
41. 60: Synthesis, Characterization, and Functionalization of Fullerene Pyrrolidines J. Am. Chem. Soc. 1993, 115, 9798-9799
42. 36, and the Solvated Buckide Ion J. Phys. Chem. 1990, 94, 8634-8636
43. Allemand, P. M.; Koch, A.; Wudl, F.; Rubin, Y.; Diederich, F.; Alvarez, M. M.; Anz, S. J.; Whetten, R. L. Two Different Fullerenes Have the Same Cyclic Voltammetry J. Am. Chem. Soc. 1991, 113, 1050-1051
44. Echegoyen, L.; Echegoyen, L. E. Electrochemistry of Fullerenes and Their Derivatives Acc. Chem. Res. 1998, 31, 593-601
45. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. Development and Use of Quantum Mechanical Molecular Models. AM1: A New General Purpose Quantum Mechanical Molecular Model J. Am. Chem. Soc. 1985, 107, 3902-3909
46. 60 Fullerene Derivatives Acc. Chem. Res. 2000, 33, 695-703
47. Williams, A. T. R.; Winfield, S. A.; Miller, J. N. Relative Fluorescence Quantum Yields Using a Computer-Controlled Luminescence Spectrometer Analyst 1983, 108, 1067-1071
48. Brun, A. M.; Harriman, A.; Heitz, V.; Sauvage, J.-P. Charge Transfer across Oblique Bisporphyrins: Two-Center Photoactive Molecules J. Am. Chem. Soc. 1991, 113, 8657-8663 and references therein
49. Rodriguez, J.; Kirmaier, C.; Holten, D. Optical Properties of Metalloporphyrin Excited States J. Am. Chem. Soc. 1989, 111, 6500-6506
50. Guldi, D. M. Fullerene-Porphyrin Architectures; Photosynthetic Antenna and Reaction Center Models Chem. Soc. Rev. 2002, 31, 22-36
51. -1 in THF, respectively) lead, together with the large distance between donor and acceptor, to render the intersystem crossing process feasible as a deactivation pathway (Figure 10). As confirmed by molecular modeling, the energy of the charge-separated state is raised upon increasing the distance between donor and acceptor due to the linearly increasing change of dipole moments D.
52. Martin, N.; Giacalone, F.; Segura, J. L.; Guldi, D. M. Mimicking Photosynthesis: Covalent [60]Fullerene-Based Donor-Acceptor Ensembles Synth. Met. 2004, 147, 57-61