Unprecedented Intramolecular Electron Transfer from Excited Perylenediimide Radical Anion

Journal of Physical Chemistry C

Volumn 120, Issue 23, 2016, Pages 12734-12741

  Lu, Chao ^a   Fujitsuka, Mamoru ^a   Sugimoto, Akira ^a   Majima, Tetsuro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERS; ELECTRON TRANSITIONS; GROUND STATE; IONS; NEGATIVE IONS; PHOTOLYSIS; RATE CONSTANTS;

DISPROPORTIONATION REACTIONS; DRIVING FORCES; ELECTRON DONORS; INTRA-MOLECULAR ELECTRON TRANSFER; ORGANIC MOLECULAR DEVICES; PERYLENEDIIMIDES; RADICAL ANIONS; SEMICONDUCTING MATERIALS;

FREE RADICAL REACTIONS;

EID: 84975319269     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/acs.jpcc.6b02454     Document Type: Article

References (58)

1. Fulscher, M. P.; Matzinger, S.; Bally, T. Excited States in Polyene Radical Cations. An Ab Initio Theoretical Study Chem. Phys. Lett. 1995, 236, 167-176 10.1016/0009-2614(95)00208-L
2. Kawashima, Y.; Nakayama, K.; Nakano, H.; Hirao, K. Theoretical Study of the π-π∗ Excited States of Linear Polyene Radical Cations and Dications Chem. Phys. Lett. 1997, 267, 82-90 10.1016/S0009-2614(97)00084-5
3. Hirata, S.; Head-Gordon, M.; Szczepanski, J.; Vala, M. Time-Dependent Density Functional Study of the Electronic Excited States of Polycyclic Aromatic Hydrocarbon Radical Ions J. Phys. Chem. A 2003, 107, 4940-4951 10.1021/jp0301913
4. Hall, K. F.; Boggio-Pasqua, M.; Bearpark, M. J.; Robb, M. A. Photostability Via Sloped Conical Intersections: A Computational Study of the Excited States of the Naphthalene Radical Cation J. Phys. Chem. A 2006, 110, 13591-13599 10.1021/jp064711g
5. Shine, H. J.; Zhao, D. C. Electron Transfer to Excited Doublet States. Photoirradiation of 10-Methylphenothiazine Cation Radical Perchlorate in Solutions of Phenylacetylene and p-Tolylacetylene in Acetonitrile J. Org. Chem. 1990, 55, 4086-4089 10.1021/jo00300a026
6. Ishida, A.; Fukui, M.; Ogawa, H.; Tojo, S.; Majima, T.; Takamuku, S. Lifetimes and Transient Phenomena of Stilbene Radical Cations in the Second Excited Doublet State J. Phys. Chem. 1995, 99, 10808-10814 10.1021/j100027a021
7. Huang, Y.; Hopkins, J. B. Femtosecond Resonance Raman Investigation of Four Univalent Bipyridinium Radicals J. Phys. Chem. 1996, 100, 9585-9591 10.1021/jp9520198
8. Ichinose, N.; Majima, T. Transient Absorption and Fluorescence Measurements of Free Radical Cation and Radical Ion Pair during Pulse Radiolysis of 1,3,5-Trimethoxybenzene in Chlorinated Solvents Chem. Phys. Lett. 2000, 322, 15-20 10.1016/S0009-2614(00)00382-1
9. Ichinose, N.; Tanaka, T.; Kawanishi, S.; Majima, T. Energy Transfer Quenching of a Fluorescent Excited Radical Cation by Counter Radical Anion: Dissipation of Radical Ions Generated by Photoinduced Electron Transfer Chem. Phys. Lett. 2000, 326, 293-298 10.1016/S0009-2614(00)00778-8
10. Häupl, T.; Lomoth, R.; Hammarström, L. Femtosecond Dynamics of the Photoexcited Methyl Viologen Radical Cation J. Phys. Chem. A 2003, 107, 435-438 10.1021/jp0216023
11. Zhao, L.; Lian, R.; Shkrob, I. A.; Crowell, R. A.; Pommeret, S.; Chronister, E. L.; Liu, A. D.; Trifunac, A. D. Ultrafast Studies on the Photophysics of Matrix-Isolated Radical Cations of Polycyclic Aromatic Hydrocarbons J. Phys. Chem. A 2004, 108, 25-31 10.1021/jp021832h
12. Okhrimenko, A. N.; Gusev, A. V.; Rodgers, M. A. J. Excited State Relaxation Dynamics of the Zinc(II) Tetraphenylporphine Cation Radical J. Phys. Chem. A 2005, 109, 7653-7656 10.1021/jp053136y
13. Pagès, S.; Lang, B.; Vauthey, E. Ultrafast Excited State Dynamics of the Perylene Radical Cation Generated upon Bimolecular Photoinduced Electron Transfer Reaction J. Phys. Chem. A 2006, 110, 7547-7553 10.1021/jp0615252
14. Sánchez-Carrera, R. S.; Coropceanu, V.; Da Silva Filho, D. A.; Friedlein, R.; Osikowicz, W.; Murdey, R.; Suess, C.; Salaneck, W. R.; Brédas, J. Vibronic Coupling in the Ground and Excited States of Oligoacene Cations J. Phys. Chem. B 2006, 110, 18904-18911 10.1021/jp057462p
15. Cai, X.; Sakamoto, M.; Fujitsuka, M.; Majima, T. Direct Fluorescence Lifetime Measurement of Excited Radical Cation of 1,3,5-Trimethoxybenzene by Ns-Ps Two-Color Two-Laser Flash Photolysis Chem. Phys. Lett. 2006, 432, 436-440 10.1016/j.cplett.2006.10.102
16. Samori, S.; Fujitsuka, M.; Majima, T. Properties of Excited Radical Cations of Substituted Oligothiophenes J. Phys. Chem. A 2008, 112, 11312-11318 10.1021/jp804369e
17. Amarie, S.; Förster, U.; Gildenhoff, N.; Dreuw, A.; Wachtveitl, J. Excited State Dynamics of the Astaxanthin Radical Cation Chem. Phys. 2010, 373, 8-14 10.1016/j.chemphys.2010.01.017
18. Grilj, J.; Buchgraber, P.; Vauthey, E. Excited-State Dynamics of Wurster's Salts J. Phys. Chem. A 2012, 116, 7516-7522 10.1021/jp3045548
19. Shukla, S. S.; Rusling, J. F. Photoelectrocatalytic Reduction of 4-Chlorobiphenyl Using Anion Radicals and Visible Light J. Phys. Chem. 1985, 89, 3353-3358 10.1021/j100261a039
20. Compton, R. G.; Eklund, J. C.; Fisher, A. C.; Waller, A. M. The Photo-EC′ Mechanism: Reduction of t-Butyl Bromide by Excited-State Tetrachlorobenzoquinone Radical Anion J. Chem. Soc., Faraday Trans. 1990, 86, 2951-2953 10.1039/ft9908602951
21. Eggins, B. R.; Robertson, P. K. J. Photoelectrochemistry Using Quinone Radical Anions J. Chem. Soc., Faraday Trans. 1994, 90, 2249-2256 10.1039/ft9949002249
22. Breslin, D. T.; Fox, M. A. Excited-State Behavior of Thermally Stable Radical Ions J. Phys. Chem. 1994, 98, 408-411 10.1021/j100053a011
23. Fujita, M.; Ishida, A.; Majima, T.; Takamuku, S. Lifetimes of Radical Anions of Dicyanoanthracene, Phenazine, and Anthraquinone in the Excited State from the Selective Electron-transfer Quenching J. Phys. Chem. 1996, 100, 5382-5387 10.1021/jp953203w
24. Majima, T.; Fukui, M.; Ishida, A.; Takamuku, S. Stilbene Radical Anions in the Excited Doublet State J. Phys. Chem. 1996, 100, 8913-8919 10.1021/jp960282i
25. Cook, A. R.; Curtiss, L. A.; Miller, J. R. Fluorescence of the 1,4-Benzoquinone Radical Anion J. Am. Chem. Soc. 1997, 119, 5729-5734 10.1021/ja970270q
26. Debreczeny, M. P.; Svec, W. A.; Marsh, E. M.; Wasielewski, M. R. Femtosecond Optical Control of Charge Shift within Electron Donor-Acceptor Arrays: an Approach to Molecular Switches J. Am. Chem. Soc. 1996, 118, 8174-8175 10.1021/ja961804a
27. Gosztola, D.; Niemczyk, M. P.; Svec, W.; Lukas, A. S.; Wasielewski, M. R. Excited Doublet States of Electrochemically Generated Aromatic Imide and Diimide Radical Anions J. Phys. Chem. A 2000, 104, 6545-6551 10.1021/jp000706f
28. Lukas, A. S.; Miller, S. E.; Wasielewski, M. R. Femtosecond Optical Switching of Electron Transport Direction in Branched Donor-Acceptor Arrays J. Phys. Chem. B 2000, 104, 931-940 10.1021/jp993774e
29. Lukas, A. S.; Bushard, P. J.; Wasielewski, M. R. Ultrafast Molecular Logic Gate Based on Optical Switching between Two Long-Lived Radical Ion Pair States J. Am. Chem. Soc. 2001, 123, 2440-2441 10.1021/ja0041122
30. Gumy, J.; Vauthey, E. Investigation of the Excited-State Dynamics of Radical Ions in the Condensed Phase Using the Picosecond Transient Grating Technique J. Phys. Chem. A 1997, 101, 8575-8580 10.1021/jp972066v
31. Brodard, P.; Sarbach, A.; Gumy, J.; Bally, T.; Vauthey, E. Excited-State Dynamics of Organic Radical Ions in Liquids and in Low-Temperature Matrices J. Phys. Chem. A 2001, 105, 6594-6601 10.1021/jp010808l
32. Hope, M. J.; Higlett, M. P.; Andrews, D. L.; Meech, S. R.; Hands, I. D.; Dunn, J. L.; Bates, C. A. Observation of Ultrafast Internal Conversion in Fullerene Anions in Solution Chem. Phys. Lett. 2009, 474, 112-114 10.1016/j.cplett.2009.04.066
33. Horke, D. A.; Roberts, G. M.; Verlet, J. R. R. Excited States in Electron-Transfer Reaction Products: Ultrafast Relaxation Dynamics of an Isolated Acceptor Radical Anion J. Phys. Chem. A 2011, 115, 8369-8374 10.1021/jp2038202
34. Fujitsuka, M.; Kim, S. S.; Lu, C.; Tojo, S.; Majima, T. Intermolecular and Intramolecular Electron Transfer Processes from Excited Naphthalene Diimide Radical Anions J. Phys. Chem. B 2015, 119, 7275-7282 10.1021/jp510850z
35. 60 Radical Anion: Enhanced Reactivities Due to the Photoexcitation of Reaction Intermediates Phys. Chem. Chem. Phys. 2015, 17, 31030-31038 10.1039/C5CP05254H
36. Angadi, M. A.; Gosztola, D.; Wasielewski, M. R. Organic Light Emitting Diodes Using Poly(phenylenevinylene) Doped with Perylenediimide Electron Acceptors Mater. Sci. Eng., B 1999, 63, 191-194 10.1016/S0921-5107(99)00082-3
37. Briseno, A. L.; Mannsfeld, S. C. B.; Reese, C.; Hancock, J. M.; Xiong, Y.; Jenekhe, S. A.; Bao, Z.; Xia, Y. Perylenediimide Nanowires and Their Use in Fabricating Field-Effect Transistors and Complementary Inverters Nano Lett. 2007, 7, 2847-2853 10.1021/nl071495u
38. Rajaram, S.; Shivanna, R.; Kandappa, S. K.; Narayan, K. S. Nonplanar Perylene Diimides as Potential Alternatives to Fullerenes in Organic Solar Cells J. Phys. Chem. Lett. 2012, 3, 2405-2408 10.1021/jz301047d
39. Supur, M.; El-Khouly, M. E.; Seok, J. H.; Kim, J. H.; Kay, K.; Fukuzumi, S. Efficient Electron Transfer Processes of the Covalently Linked Perylenediimide-Ferrocene Systems: Femtosecond and Nanosecond Transient Absorption Studies J. Phys. Chem. C 2010, 114, 10969-10977 10.1021/jp103094v
40. Rieth, S.; Li, Z.; Hinkle, C. E.; Guzman, C. X.; Lee, J. J.; Nehme, S. I.; Braunschweig, A. B. Superstructures of Diketopyrrolopyrrole Donors and Perylenediimide Acceptors Formed by Hydrogen-Bonding and π···π Stacking J. Phys. Chem. C 2013, 117, 11347-11356 10.1021/jp400918z
41. Singh, T. B.; Erten, S.; Günes, S.; Zafer, C.; Turkmen, G.; Kuban, B.; Teoman, Y.; Sariciftci, N. S.; Icli, S. Soluble Derivatives of Perylene and Naphthalene Diimide for n-Channel Organic Field-Effect Transistors Org. Electron. 2006, 7, 480-489 10.1016/j.orgel.2006.06.010
42. Würthner, F.; Stolte, M. Naphthalene and Perylene Diimides for Organic Transistors Chem. Commun. 2011, 47, 5109-5115 10.1039/c1cc10321k
43. Mackinnon, S. M.; Wang, Z. Y. Synthesis and Characterization of Poly(aryl ether imide)s Containing Electroactive Perylene Diimide and Naphthalene Diimide Units J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 3467-3475 10.1002/1099-0518(20001001)38:19<3467::AID-POLA30>3.0.CO;2-2
44. 2-Excited Phosphorus Tetraphenylporphyrin J. Phys. Chem. A 2007, 111, 10574-10579 10.1021/jp076303y
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al., Gaussian 09, Revision C.01; Guassian, Inc.: Wallingford, CT, 2009.
46. Brown, K. E.; Salamant, W. A.; Shoer, L. E.; Young, R. M.; Wasielewski, M. R. Direct Observation of Ultrafast Excimer Formation in Covalent Perylenediimide Dimers Using Near-Infrared Transient Absorption Spectroscopy J. Phys. Chem. Lett. 2014, 5, 2588-2593 10.1021/jz5011797
47. 70) and Tetrakis(dimethylamino)ethylene in the Ground and Excited States J. Phys. Chem. B 1999, 103, 445-449 10.1021/jp983512x
48. Marcus, R. A. Chemical and Electrochemical Electron-Transfer Theory Annu. Rev. Phys. Chem. 1964, 15, 155-196 10.1146/annurev.pc.15.100164.001103
49. Marcus, R. A.; Sutin, N. Electron Transfers in Chemistry and Biology Biochim. Biophys. Acta, Rev. Bioenerg. 1985, 811, 265-322 10.1016/0304-4173(85)90014-X
50. Marcus, R. A. Electron Transfer Reactions in Chemistry: Theory and Experiment (Nobel Lecture) Angew. Chem., Int. Ed. Engl. 1993, 32, 1111-1121 10.1002/anie.199311113
51. Klimkans, A.; Larsson, S. Reorganization Energies in Benzene, Naphthalene, and Anthracene Chem. Phys. 1994, 189, 25-31 10.1016/0301-0104(94)80004-9
52. McConnell, H. M. Intramolecular Charge Transfer in Aromatic Free Radicals J. Chem. Phys. 1961, 35, 508-515 10.1063/1.1731961
53. Paulson, B. P.; Miller, J. R.; Gan, W.; Closs, G. Superexchange and Sequential Mechanisms in Charge Transfer with a Mediating State between the Donor and Acceptor J. Am. Chem. Soc. 2005, 127, 4860-4868 10.1021/ja044946a
54. 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 10.1039/b706122f
55. Hwang, I.; Moses, D.; Heeger, A. J. Photoinduced Carrier Generation in P3HT/PCBM Bulk Heterojunction Materials J. Phys. Chem. C 2008, 112, 4350-4354 10.1021/jp075565x
56. Guo, J.; Ohkita, H.; Benten, H.; Ito, S. Charge Generation and Recombination Dynamics in Poly(3-hexylthiophene)/Fullerene Blend Films with Different Regioregularities and Morphologies J. Am. Chem. Soc. 2010, 132, 6154-6164 10.1021/ja100302p
57. Heeger, A. J. Semiconducting and Metallic Polymers: The Fourth Generation of Polymeric Materials J. Phys. Chem. B 2001, 105, 8475-8491 10.1021/jp011611w
58. Da Cunha, W. F.; Ribeiro, L. A.; Fonseca, A. L. D. A.; Gargano, R.; E Silva, G. M. Reactive Scattering between Excitons and Charge Carriers in Conjugated Polymers J. Phys. Chem. C 2014, 118, 23451-23458 10.1021/jp5046673