Abstract
Singlet fission is one of the internal conversion process in which a singlet exciton splits into two triplet excitons having long lifetimes . This phenomenon is expected to be useful for significantly improving the photoelectric conversion efficiency in organic photovoltaic cells. In this chapter, we present diradical character based molecular design guidelines for efficient singlet fission molecules based on the energy level matching conditions between the lowest singlet and triplet excited states, which are found to be described by the multiple diradical characters. A simple model, i.e., tetraradical hydrogen cluster, is investigated in order to reveal the multiple diradical character dependences of relative excitation energies and to build a diradical character based design guideline. On the basis of this guideline, several candidate molecules are proposed.
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A.S. Davydov, Soviet Phys. Uspekhi 82, 145 (1964)
M. Kasha, H.R. Rawls, M. Ashraf El-Bayoumi, Pure Appl. Chem 11, 371 (1965)
M.B. Smith, J. Michl, Chem. Rev. 110, 6891 (2010)
S. Singh et al., J. Chem. Phys. 42, 330 (1965)
M.C. Hanna, A.J. Nozik, J. Appl. Phys. 100, 074510 (2006)
H. Najafov, B. Lee, Q. Zhou, L.C. Feldman, V. Podzorov, Nat. Mater. 9, 938 (2010)
A. Rao, M.W.B. Wilson et al., J. Am. Chem. Soc. 132, 12698 (2010)
P.J. Jadhav, P.R. Brown et al., Adv. Mater. 24, 6169 (2012)
P.J. Jadhav et al., Nano Lett. 11, 1495 (2011)
B. Ehrler, Nano Lett. 12, 1053 (2012)
B. Ehrler et al., Appl. Phys. Lett. 101, 113304 (2012)
S.T. Roberts, J. Am. Chem. Soc. 134, 6388 (2012)
Y. Takeda, R. Katoh et al., J. Electron. Spectrosc. Relat. Phenom. 78, 423 (1996)
E.C. Greyson, J. Vura-Weis et al., J. Phys. Chem. B 114, 14168 (2010)
W.-L. Chan, M. Ligges, X.-Y. Zhu, Nat. Chem. 4, 840 (2012)
C.A. Coulson, G.S. Rushbrooke, Proc. Cambridge. Phil. Soc. 36, 193 (1940)
A. Akdag, Z. Havlas, J. Michl, J. Am. Chem. Soc. 134, 14624 (2012)
S. Ito, T. Minami, M. Nakano, J. Phys. Chem. C 116, 19729 (2012)
K. Schulten, M. Karplus, Chem. Phys. Lett. 14, 305 (1972)
M. Nakano, H. Fukui, T. Minami et al., Theor. Chem. Acc. 130, 711 (2011)
M. Nakano, H. Fukui, T. Minami et al., erratum 130, 725 (2011)
M. Nakano et al., Phys. Rev. Lett. 99, 033001 (2007)
K. Kamada et al., J. Phys. Chem. Lett. 1, 937 (2010)
T. Minami, M. Nakano, J. Phys. Chem. Lett. 3, 145 (2012)
M. Nakano, T. Minami et al., J. Chem. Phys. 136, 0243151 (2012)
M.W. Schmidt et al., J. Comput. Chem. 14, 1347 (1993)
H. Nagai, M. Nakano et al., Chem. Phys. Lett. 489, 212 (2010)
Y. Kawashima, T. Hashimoto, H. Nakano et al., Theor. Chem. Acc. 102, 49 (1999)
A.F. Schwerin, J.C. Johnson et al., J. Phys. Chem. A 114, 1457 (2010)
H.A. Frank, J.A. Bautista et al., Biochemistry 39, 2831 (2010)
A. Konishi, Y. Hirao et al., J. Am. Chem. Soc. 132, 11021 (2010)
C. Lambert, Angew. Chem. Int. Ed. 50, 1756 (2011)
K. Nakasuji, T. Kubo, Bull. Chem. Soc. Jpn 10, 1791 (2004)
T. Kubo, A. Shimizu et al., Angew. Chem. Int. Ed. 44, 6564 (2005)
T. Weil et al., Angew. Chem. Int. Ed. 49, 9068 (2010)
E. Clar, Monatsh. Chem. 87, 391 (1956)
A. Bohnen, Angew. Chem. Int. Ed. 29, 525 (1990)
F.O. Holtrup, Chem. Eur. J. 3, 219 (1997)
N.G. Pschirer, Angew. Chem. Int. Ed. 45, 1401 (2006)
T. Minami et al., J. Phys. Chem. Lett. 3, 2719 (2012)
R. Baer et al., Annu. Rev. Phys. Chem. 61, 85 (2010)
T. Minami, M. Nakano, F. Castet et al., J Phys Chem Lett 2, 1725 (2011)
I. Paci, J.C. Johnson et al., J. Am. Chem. Soc. 128, 16546 (2006)
V.K. Thorsmølle, R.D. Averitt et al., Phys. Rev. Lett. 102, 017401 (2009)
T. Minami, S. Ito, M. Nakano, J. Phys. Chem. Lett. 4, 2133 (2013)
T. Minami, S. Ito, M. Nakano, J. Phys. Chem. A 117, 2000 (2013)
S. Hirata, M. Head-Gordon, Chem. Phys. Lett. 314, 291 (1999)
Y. Shao, M. Head-Gordon, A.I. Krylov, J. Chem. Phys. 118, 4807 (2003)
A.D. Becke, Phys. Rev. A 38, 3098 (1998)
C. Lee, W. Yang, P.G. Parr, Phys. Rev. B 37, 785 (1988)
F. Wang, T. Ziegler, J. Chem. Phys. 121, 12191 (2004)
Y. Tawada, T. Tsuneda et al., J. Phys. Chem. 120, 8425 (2004)
S. Arulmozhiraja, M.L. Coote, J. Chem. Theor. Comput. 7, 1296 (2011)
Y. Shao, L. Fusti-Molnar et al., Q-CHEM Version 4.0 (Q-Chem. Inc, Pittsburgh, 2008)
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Nakano, M. (2014). Diradical Character View of Singlet Fission. In: Excitation Energies and Properties of Open-Shell Singlet Molecules. SpringerBriefs in Molecular Science(). Springer, Cham. https://doi.org/10.1007/978-3-319-08120-5_5
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DOI: https://doi.org/10.1007/978-3-319-08120-5_5
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