Diradical character view of singlet fission

Journal of Physical Chemistry Letters

Volumn 3, Issue 2, 2012, Pages 145-150

  Minami, Takuya ^a   Nakano, Masayoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIRADICALS; ENERGY DIFFERENCES; FEASIBILITY CONDITION; FULL CONFIGURATION INTERACTION; MOLECULAR SYSTEMS; NATURAL ORBITALS; OPEN-SHELL;

HYDROCARBONS; POLYCYCLIC AROMATIC HYDROCARBONS;

ENERGY EFFICIENCY;

EID: 84856002733     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz2015346     Document Type: Article

References (43)

1. Geacintov, N.; Pope, M.; Vogel, F. Effect on Magnetic Field on the Fluorescence of Tetracene Crystals: Exciton Fission Phys. Rev. Lett. 1969, 22, 593-596
2. Merrifield, R. E.; Avakian, P.; Groff, R. P. Fission of Singlet Excitons into Pairs of Triplet Excitons in Tetracene Crystals Chem. Phys. Lett. 1969, 3, 386-388
3. Smith, M. J.; Michl, J. Singlet Fission Chem. Rev. 2010, 110, 6891-6936
4. Paci, I.; Johnson, J. C.; Chen, X.; Rana, G.; Popovic, D.; David, D. E.; Nojik, A. J.; Ratner, M. A.; Michl, J. Singlet Fission for Dye-Sensitized Solar Cells: Can a Suitable Sensitizer Be Found ? J. Am. Chem. Soc. 2006, 128, 16546-16553 (Pubitemid 46032734)
5. Jadhav, P. J.; Mohanty, A.; Sussman, J.; Lee, J.; Baldo, M. A. Singlet Exciton Fission in Nanostructured Organic Solar Cells Nano Lett. 2011, 11, 1495-1498
6. 60 Bilayers J. Am. Chem. Soc. 2010, 132, 12698-12703
7. Hanna, M. C.; Nojik, A. J. Solar Conversion Efficiency of Photovoltaic and Photoelectrolysis Cells with Carrier Multiplication Absorbers J. Appl. Phys. 2006, 100, 074510-1-8
8. Bendikov, M.; Duong, H. M.; Starkey, K.; Houk, K. N.; Carter, E. A.; Wudi, F. Oligoacenes: Theoretical Prediction of Open-Shell Singlet Diradical Ground States J. Am. Chem. Soc. 2004, 126, 7416-7417 (Pubitemid 38781456)
9. Greyson, G. C.; Vura-Weis, J.; Michl, J.; Ratner, M. A. Maximizing Singlet Fission in Organic Dimers: Theoretical Investigation of Triplet Yield in the Regime of Localized Excitation and Fast Coherent Electron Transfer J. Phys. Chem. B 2010, 114, 14168-14177
10. Zimmerman, P. M.; Bell, F.; Casanova, D.; Head-Gordon, M. Mechanism for Singlet Fission in Pentacene and Tetracene: From Single Exciton to Two Triplets J. Am. Chem. Soc. 2011, 133, 19944-19952
11. Yamaguchi, K. Self-Consistent Field: Theory and Applications; Carbo, R.; Klobukowski, M., Eds.; Elsevier: Amsterdam, The Netherands, 1990; p 727.
12. Nakano, M.; Fukui, H.; Minami, T.; Yoneda, K.; Shigeta, Y.; Kishi, R.; Champagne, B.; Botek, E.; Kubo, T.; Ohta, K.; Kamada, K. (Hyper)polarizability Density Analysis for Open-Shell Molecular Systems Based on Natural Orbitals and Occupation Numbers Theor. Chem. Acc. 2011, 130, 711-724
13. erratum; Nakano, M.; Fukui, H.; Minami, T.; Yoneda, K.; Shigeta, Y.; Kishi, R.; Champagne, B.; Botek, E.; Kubo, T.; Ohta, K.; Kamada, K. (Hyper)polarizability Density Analysis for Open-Shell Molecular Systems Based on Natural Orbitals and Occupation Numbers Theor. Chem. Acc. 2011, 130, 725-726
14. Calzado, C.; Cabrero, J.; Malrieu, J. P.; Caballol, R. Analysis of the Magnetic Coupling in Binuclear Complexes. I. Physics of the Coupling J. Chem. Phys. 2002, 116, 2728-2747 (Pubitemid 34207539)
15. Nakano, M.; Kishi, R.; Ohta, S.; Takahashi, H.; Kubo, T.; Kamada, K.; Ohta, K.; Botek, E.; Champagne, B. Relationship between Third-Order Nonlinear Optical Properties and Magnetic Interactions in Open-Shell Systems: A New Paradigm for Nonlinear Optics Phys. Rev. Lett. 2007, 99, 033001-1-4
16. Kamada, K.; Ohta, K.; Shimizu, A.; Kubo, T.; Kishi, R.; Takahashi, H.; Botek, E.; Champagne, B.; Nakano, M. Singlet Diradical Character from Experiment J. Phys. Chem. Lett. 2010, 1, 937-940
17. Nakano, M.; Kishi, R.; Nitta, T.; Kubo, T.; Nakasuji, K.; Kamada, K.; Ohta, K.; Champagne, B.; Botek, E.; Yamaguchi, K. Second Hyperpolarizability () of Singlet Diradical System: Dependence of on the Diradical Character J. Phys. Chem. A 2005, 109, 885-891 (Pubitemid 40213230)
18. Nakano, M.; Yoneda, K.; Kishi, R.; Takahashi, H.; Kubo, T.; Kamada, K.; Ohta, K.; Botek, E.; Champagne, B. Remarkable Two-Photon Absorption in Open-Shell Singlet Systems J. Chem. Phys. 2009, 131, 114316-1-7
19. Kamada, K.; Ohta, K.; Kubo, T.; Shimizu, A.; Morita, Y.; Nakasuji, K.; Kishi, R.; Ohta, S.; Furukawa, S.; Takahashi, H.; Nakano, M. Strong Two-Photon Absorption of Singlet Diradical Hydrocarbons Angew. Chem., Int. Ed. 2007, 46, 3544-3546 (Pubitemid 46973452)
20. Schulten, K.; Karplus, M. On The Origin of a Low-Lying Forbidden Transition in Polyenes and Related Molecules Chem. Phys. Lett. 1972, 14, 305-309
21. Motomura, S.; Nakano, M.; Fukui, H.; Yoneda, K.; Kubo, T.; Carison, R.; Champagne, B. Size Dependences of the Diradical Character and the Second Hyperpolarizabilities in Dicyclopenta-Fused Acenes: Relationships with Their Aromaticity/Antiaromaticity Phys. Chem. Chem. Phys. 2011, 13, 20575-20583
22. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, M. A. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
23. Nakano, M.; Takebe, A.; Kishi, R.; Ohta, S.; Nate, M.; Kubo, T.; Kamada, K.; Ohta, K.; Champagne, B.; Botek, E.; Takahashi, H.; Furukawa, S.; Morita, Y.; Nakatsuji, K. Second Hyperpolarizabilities (?) of Open-Shell Singlet One-Dimensional Systems: Intersite Interaction Effects on the Average Diradical Character and Size Dependences of ? Chem. Phys. Lett. 2006, 432, 473-479 (Pubitemid 44828010)
24. 4 Model Compound: Summation-Over-States Analysis and Interplay with Diradical Characters. J. Chem. Phys., in press.
25. Thorsmølle, V. K.; Averitt, R. D.; Demsar, J.; Smith, D. L.; Tretiak, S.; Martin, R. L.; Chi, X.; Crone, B. K.; Ramirez, A. P.; Taylor, A. J. Morphology Effectively Controls Singlet-Triplet Exciton Relaxation and Charge Transport in Organic Semiconductors Phys. Rev. Lett. 2009, 102, 017401-1-4
26. Zimmerman, P. M.; Zhang, Z.; Musgrave, C. B. Singlet Fission in Pentacene through Multi-Exciton Quantum States Nat. Chem. 2010, 2, 648-652
27. Johnson., J. C.; Nojik, A. J.; Michl, J. High Triplet Yield from Singlet Fission in a Thin Film of 1,3-Diphenylisobenzofuran J. Am. Chem. Soc. 2010, 132, 16302-16303
28. Jundt, C.; Klein, G.; Sipp, B.; Moigne, J.; Le.; Joucla, M.; Villaeys, A. A. Exciton Dynamics in Pentacene Thin Films Studied by Pump-Probe Spectroscopy Chem. Phys. Lett. 1995, 241, 84-88
29. Wang, C.; Tauber, M. J. High-Yield Singlet Fission in a Zeaxanthin Aggregate Observed by Picosecond Resonance Raman Spectroscopy J. Am. Chem. Soc. 2010, 132, 13988-13991
30. Frank, H. A.; Bautista, J. A.; Josue, J. S.; Young, A. Mechanism of Nonphotochemical Quenching in Green Plants: Energies of the Lowest Excited Singlet States of Violaxanthin and Zeaxanthin Biochemistry 2000, 39, 2831-2837 (Pubitemid 30159387)
31. Kawashima, Y.; Hashimoto, T.; Nakano, H.; Hirao, K. Theoretical Study of the Valence π → π* Excited States of Polyacenes: Anthracene and Naphthacene Theor. Chem. Acc. 1999, 102, 49-64
32. Schwerin, A. F.; Johnson, J. C.; Smith, M. B.; Sreearunothai, P.; Popovi, D.; erný, J.; Havlas, Z.; Paci, I.; Akdag, A.; MacLeod, M. K.; Chen, X.; Davis, D. E.; Rathner, M. A.; Miller, J. R.; Nozik, A. J.; Michl, J. Toward Designed Singlet Fission: Electronic States and Photophysics of 1,3-Diphenylisobenzofuran J. Phys. Chem. A 2010, 114, 1457-1473
33. Konishi, A.; Hirao, Y.; Nakano, M.; Shimizu, A.; Botek, E.; Champagne, B.; Shiomi, D.; Sato, K.; Takui, T.; Matsumoto, K.; Kurata, H.; Kubo, T. Synthesis and Characterization of Teranthene: A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekulé Structures J. Am. Chem. Soc. 2010, 132, 11021-11023
34. Lambert, C. Towards Polycyclic Aromatic Hydrocarbons with a Singlet Open-Shell Ground State Angew. Chem., Int. Ed. 2011, 50, 1756-1758
35. Nakano, M.; Kishi, R.; Takebe, A.; Nate, M.; Takahashi, H.; Kubo, T.; Kamada, K.; Ohta, K.; Champagne, B.; Edith, B. Second Hyperpolarizability of Zethrenes Comput. Lett. 2007, 3, 333-338
36. Nagai, H.; Nakano, M.; Yoneda, K.; Kishi, R.; Takahashi, H.; Shimizu, A.; Kubo, T.; Kamada, K.; Ohta, K.; Botek, E.; Champagne, B. Signature of Multiradical Character in Second Hyperpolarizabilities of Rectangular Graphene Nanoflakes Chem. Phys. Lett. 2010, 489, 212-218
37. Shao, Y.; Head-Gordon, H.; Krylov, A. I. The Spin-Flip Approach within Time-Dependent Density Functional Theory: Theory and Applications to Diradicals J. Chem. Phys. 2003, 118, 4807-4818
38. Rinkevicius, Z.; Vahtras, O.; Ågren, H. Spin-Flip Time Dependent Density Functional Theory Applied to Excited States with Single, Double, or Mixed Electron Excitation Character J. Chem. Phys. 2010, 133, 11404-1-12
39. Yamanaka, S.; Okumura, M.; Nakano, M.; Yamaguchi, K. EHF theory of Chemical Reactions Part 4. UNO CASSCF, UNO CASPT2 and R(U)HF Coupled-Cluster (CC) Wavefunctions J. Mol. Struct. 1994, 310, 205-218
40. Chan, W.-L.; Ligges, M.; Jailaubekov, A.; Kaake, L.; Miaja-Avila, L.; Zhu, X.-Y. Observing the Multiexciton State in Singlet Fission and Ensuing Ultrafast Multielectron Transfer Science 2011, 334, 1541-1545
41. Nakano, M.; Kubo, T.; Kamada, K.; Ohta, K.; Kishi, R.; Ohta, S.; Nakagawa, N.; Takahashi, H.; Furukawa, S.; Morita, Y.; Nakasuji, K.; Yamaguchi, K. Second Hyperpolarizabilities of Polycyclic Aromatic Hydrocarbons involving Phenalenyl Radical Units Chem. Phys. Lett. 2006, 428, 142-147 (Pubitemid 43063364)
42. Nakasuji, K.; Kubo, T. Multi-Stage Amphoteric Redox Hydrocarbons Based on a Phenalenyl Radical Bull. Chem. Soc. Jpn. 2004, 10, 1791-1801 (Pubitemid 39486280)
43. Kubo, T.; Shimizu, A.; Sakamoto, M.; Uruichi, M.; Yakushi, K.; Nakano, M.; Shimoi, D.; Sato, K.; Takui, T.; Morita, Y.; Nakasuji, K. Synthesis, Intermolecular Interaction, and Semiconductive Behavior of a Delocalized Singlet Biradical Hydrocarbon Angew. Chem., Int. Ed. 2005, 44, 6564-6568 (Pubitemid 41502799)