Abstract
Organic molecular materials have attracted considerable attention as a candidate for next-generation flexible electronics in the near future. However, there still remain open questions on fundamental electronic properties such as mechanisms of the carrier transport and barriers for carrier injection at organic-inorganic heterojunctions. In this review, we illustrate the progresses in first-principles electronic structure calculations of the materials for investigation of the atomic- or molecular-scale electronic properties of organic semiconductor materials, which are in general difficult to observe even with present-day experimental techniques. The theoretical studies not only help elucidate the mechanism of the experimental measurement but also may allow us to gain insights into the essences of the materials properties in terms of the electronic structure. Specifically, in this article, we focus on the first-principles theoretical treatment of the geometric configurations of organic semiconductors and their electronic structure at the level beyond the approximation to the density functional theory (DFT) such as the local density (LDA) and generalized gradient approximations (GGA), i.e., the van der Waals-inclusive methods for describing the weak intermolecular interaction in organic solids and the many-body perturbation theory within the GW approximation for treatment of the charged excitation (quasiparticle) and thus the fundamental gap and the band dispersion of the crystals. Here, we illustrate the recent studies on (i) the effect of the molecular configuration on the quasiparticle energy in organic semiconductors, (ii) the energy level alignment at organic-metal interfaces, and (iii) prediction of the charge injection levels at a surface of organic thin film, i.e., the ionization energy and the electron affinity. Further progresses in theoretical methodologies, being enhanced by rapid progress in computational resource and algorithm, might lead to in silico material simulation or design.
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References
J.R. Sheats, Manufacturing and commercialization issues in organic electronics. J. Mater. Res. 19(7), 1974 (2004). https://doi.org/10.1557/JMR.2004.0275
M.E. Gershenson, V. Podzorov, A.F. Morpurgo, Colloquium: electronic transport in single-crystal organic transistors. Rev. Mod. Phys. 78, 973 (2006). https://doi.org/10.1103/RevModPhys.78.973
J. Kleis, B.I. Lundqvist, D.C. Langreth, E. Schröder, Towards a working density-functional theory for polymers: first-principles determination of the polyethylene crystal structure. Phys. Rev. B 76, 100201 (2007)
D. Lu, Y. Li, D. Rocca, G. Galli, Ab initio calculation of van der waals bonded molecular crystals. Phys. Rev. Lett. 102, 206411 (2009)
A. Tkatchenko, M. Scheffler, Accurate molecular van der waals interactions from ground-state electron density and free-atom reference data. Phys. Rev. Lett. 102, 073005 (2009)
A. Otero-de-la-Roza, E.R. Johnson, Van der waals interactions in solids using the exchange-hole dipole moment model. J. Chem. Phys. 136, 174109 (2012)
A. Otero-de-la-Roza, E.R. Johnson, Application of the exchange-hole dipole moment (XDM) model to molecular solids. J. Chem. Phys. 137, 054103 (2012)
A. Tkatchenko, J.R.A. DiStasio, R. Car, M. Scheffler, Accurate and efficient method for many-body van der waals interactions. Phys. Rev. Lett. 108, 236402 (2012)
J. Klimeš, A. Michaelides, Perspective: advances and challenges in treating van der waals dispersion forces in density functional theory. J. Chem. Phys. 137, 120901 (2012)
I. Hamada, van der waals density functional made accurate. Phys. Rev. B 89, 121103(R) (2014)
A.M. Reilly, A. Tkatchenko, Role of dispersion interactions in the polymorphism and entropic stabilization of the aspirin crystal. Phys. Rev. Lett. 113, 055701 (2014)
L. Hedin, New method for calculating the one-particle green’s function with application to the electron-gas problem. Phys. Rev. 139, A796 (1965). https://doi.org/10.1103/PhysRev.139.A796
S. Yanagisawa, I. Hamada, Determination of geometric and electronic structures of organic crystals from first principles: role of the molecular configuration on the electronic structure. J. Appl. Phys. 121(4), 045501 (2017). https://doi.org/10.1063/1.4974844
N. Marzari, A.A. Mostofi, J.R. Yates, I. Souza, D. Vanderbilt, Maximally localized wannier functions: theory and applications. Rev. Mod. Phys. 84, 1419 (2012)
A.A. Mostofi, J.R. Yates, Y.S. Lee, I. Souza, D. Vanderbilt, N. Marzari, wannier90: a tool for obtaining maximally-localised wannier functions. Comput. Phys. Commun. 178(9), 685 (2008)
C. Motta, S. Sanvito, Charge transport properties of durene crystals from first-principles. J. Chem. Theor. Comput. 10, 4624 (2014)
H. Ishii, K. Sugiyama, E. Ito, K. Seki, Energy level alignment and interfacial electronic structures at organic/metal and organic/organic interfaces. Adv. Mater. 11, 605 (1999)
M.S. Hybertsen, S.G. Louie, Electron correlation in semiconductors and insulators: band gaps and quasiparticle energies. Phys. Rev. B 34, 5390 (1986). https://doi.org/10.1103/PhysRevB.34.5390
S.A. Wella, H. Sawada, N. Kawaguchi, F. Muttaqien, K. Inagaki, I. Hamada, Y. Morikawa, Y. Hamamoto, Hybrid image potential states in molecular overlayers on graphene. Phys. Rev. Mater. 1(6), 061001 (2017). https://doi.org/10.1103/PhysRevMaterials.1.061001
T. Yamada, M. Isobe, M. Shibuta, H.S. Kato, T. Munakata, Spectroscopic investigation of unoccupied states in nano- and macroscopic scale: naphthalene overlayers on highly oriented pyrolytic graphite studied by combination of scanning tunneling microscopy and two-photon photoemission. J. Phys. Chem. C 118(2), 1035 (2014). https://doi.org/10.1021/jp4097875
Y. Kang, S.H. Jeon, Y. Cho, S. Han, Ab initio calculation of ionization potential and electron affinity in solid-state organic semiconductors. Phys. Rev. B 93, 035131 (2016). https://doi.org/10.1103/PhysRevB.93.035131
K. Yamada, S. Yanagisawa, T. Koganezawa, K. Mase, N. Sato, H. Yoshida, Impact of the molecular quadrupole moment on ionization energy and electron affinity of organic thin films: experimental determination of electrostatic potential and electronic polarization energies. Phys. Rev. B 97, 245206 (2018). https://doi.org/10.1103/PhysRevB.97.245206
J. Li, G. D’Avino, I. Duchemin, D. Beljonne, X. Blase, Combining the many-body GW formalism with classical polarizable models: insights on the electronic structure of molecular solids. J. Phys. Chem. Lett. 7(14), 2814 (2016). https://doi.org/10.1021/acs.jpclett.6b01302
J.L. Brédas, J.P. Calbert, D.A. da Silva Filho, J. Cornil, Organic semiconductors: a theoretical characterization of the basic parameters governing charge transport. Proc. Natl. Acad. Sci. U. S. A. 99, 5804 (2002)
V. Coropceanu, J. Cornil, D.A. da Silva Filho, Y. Olivier, R. Silbey, J.L. Brédas, Charge transport in organic semiconductors. Chem. Rev. 107, 926 (2007)
A.M. Reilly, R.I. Cooper, C.S. Adjiman, S. Bhattacharya, A.D. Boese, J.G. Brandenburg, P.J. Bygrave, R. Bylsma, J.E. Campbell, R. Car, D.H. Case, R. Chadha, J.C. Cole, K. Cosburn, H.M. Cuppen, F. Curtis, G.M. Day, R.A. DiStasio Jr, A. Dzyabchenko, B.P. van Eijck, D.M. Elking, J.A. van den Ende, J.C. Facelli, M.B. Ferraro, L. Fusti-Molnar, C.A. Gatsiou, T.S. Gee, R. de Gelder, L.M. Ghiringhelli, H. Goto, S. Grimme, R. Guo, D.W.M. Hofmann, J. Hoja, R.K. Hylton, L. Iuzzolino, W. Jankiewicz, D.T. de Jong, J. Kendrick, N.J.J. de Klerk, H.Y. Ko, L.N. Kuleshova, X. Li, S. Lohani, F.J.J. Leusen, A.M. Lund, J. Lv, Y. Ma, N. Marom, A.E. Masunov, P. McCabe, D.P. McMahon, H. Meekes, M.P. Metz, A.J. Misquitta, S. Mohamed, B. Monserrat, R.J. Needs, M.A. Neumann, J. Nyman, S. Obata, H. Oberhofer, A.R. Oganov, A.M. Orendt, G.I. Pagola, C.C. Pantelides, C.J. Pickard, R. Podeszwa, L.S. Price, S.L. Price, A. Pulido, M.G. Read, K. Reuter, E. Schneider, C. Schober, G.P. Shields, P. Singh, I.J. Sugden, K. Szalewicz, C.R. Taylor, A. Tkatchenko, M.E. Tuckerman, F. Vacarro, M. Vasileiadis, A. Vazquez-Mayagoitia, L. Vogt, Y. Wang, R.E. Watson, G.A. de Wijs, J. Yang, Q. Zhu, C.R. Groom, Report on the sixth blind test of organic crystal structure prediction methods. Acta Crystallogr. B 72(4), 439 (2016). https://doi.org/10.1107/S2052520616007447
J. Hermann, R.A. DiStasio, A. Tkatchenko, First-principles models for van der waals interactions in molecules and materials: concepts, theory, and applications. Chem. Rev. 117(6), 4714 (2017). https://doi.org/10.1021/acs.chemrev.6b00446. PMID: 28272886
J. Klimeš, M. Kaltak, E. Maggio, G. Kresse, Singles correlation energy contributions in solids. J. Chem. Phys. 143(10), 102816 (2015)
J. Klimeš, Lattice energies of molecular solids from the random phase approximation with singles corrections. J. Chem. Phys. 145(9), 094506 (2016). https://doi.org/10.1063/1.4962188. http://scitation.aip.org/content/aip/journal/jcp/145/9/10.1063/1.4962188
K. Hongo, M.A. Watson, R.S. Sánchez-Carrera, T. Iitaka, A. Aspuru-Guzik, Failure of conventional density functionals for the prediction of molecular crystal polymorphism: a quantum monte carlo study. J. Phys. Chem. Lett. 1(12), 1789 (2010)
A. Zen, J.G. Brandenburg, J. Klimeš, A. Tkatchenko, D. Alfè, A. Michaelides, Fast and accurate quantum monte carlo for molecular crystals. Proc. Natl. Acad. Sci. U. S. A. 115(8), 1724 (2018). https://doi.org/10.1073/pnas.1715434115. http://www.pnas.org/content/115/8/1724
J. Yang, W. Hu, D. Usvyat, D. Matthews, M. Schütz, G.K.L. Chan, Ab initio determination of the crystalline benzene lattice energy to sub-kilojoule/mole accuracy. Science 345(6197), 640 (2014)
M. Del Ben, J. Hutter, J. VandeVondele, Forces and stress in second order møller-plesset perturbation theory for condensed phase systems within the resolution-of-identity gaussian and plane waves approach. J. Chem. Phys. 143(10), 102803 (2015)
M. Dion, H. Rydberg, E. Schröder, D.C. Langreth, B.I. Lundqvist, Van der waals density functional for general geometries. Phys. Rev. Lett. 92, 246401 (2004)
K. Berland, P. Hyldgaard, Exchange functional that tests the robustness of the plasmon description of the van der waals density functional. Phys. Rev. B 89, 035412 (2014)
J. Kilmeš, D.R. Bowler, A. Michaelides, Chemical accuracy for the van der waals density functional. J. Phys. Condens. Matter 22, 022201 (2010)
K. Lee, É.D. Murray, L. Kong, B.I. Lundqvist, D.C. Langreth, Higher-accuracy van der waals density functional. Phys. Rev. B 82, 081101(R) (2010)
V.R. Cooper, Van der waals density functional: an appropriate exchange functional. Phys. Rev. B 81, 161104(R) (2010)
J. Kilmeš, D.R. Bowler, A. Michaelides, Van derwaals density functionals applied to solids. Phys. Rev. B 83, 195131 (2011)
G. Román-Pérez, J.M. Soler, Efficient implementation of a van der waals density functional: application to double-wall carbon nanotubes. Phys. Rev. Lett. 103, 096102 (2009). https://doi.org/10.1103/PhysRevLett.103.096102
S. Yanagisawa, K. Yamauchi, T. Inaoka, T. Oguchi, I. Hamada, Origin of the band dispersion in a metal phthalocyanine crystal. Phys. Rev. B 90, 245141 (2014)
The crystal structure for the naphthalene at 5 K was taken from NAPHTA31 in Cambridge Crystallographic database. The structure of anthracene was taken from Ref. [68]. The crystal structure of the tetracene crystal was generated using the atomic coordinates given in Ref. [46]. The pentacene crystalline phase obtained by vapor deposition [48] was taken. The diffraction data measured at 123 K [57] was used for hexacene crystal
H.C. Alt, J. Kalus, X-ray powder diffraction investigation of naphthalene up to 0.5 gpa. Acta Crystallogr. B Struct. Crystallogr. Cryst. Chem. 38, 2595 (1982)
R. Mason, The crystallography of anthracene at 95 ∘K and 290 ∘K. Acta Cryst. 17, 547 (1964)
J.M. Robertson, V.C. Sinclair, J. Trotter, The crystal and molecular structure of tetracene. Acta Cryst. 14, 697 (1961)
The temperature at which the X-ray diffraction measurement is performed is not clear in Ref. [46]. The cell lengths and the volume of the tetracene crystal (\(P\overline {1}\) symmetry) measured at 295 K [54] were slightly smaller. Therefore we presume that the temperature of the measurement in Ref. [46] is 295 K or higher
T. Siegrist, C. Kloc, J.H. Schön, B. Batlogg, R.C. Haddon, S. Berg, G.A. Thomas, Enhanced physical properties in a pentacene polymorph. Angew. Chem. Int. Ed. Engl. 40, 1732 (2001)
C.C. Mattheus, A.B. Dros, J. Baas, A. Meetsma, J.L. de Boer, T.T.M. Palstra, Polymorphism in pentacene. Acta Crystallogr. C Cryst. Struct. Commun. C57, 939 (2001)
C.C. Mattheus, A.B. Dros, J. Baas, G.T. Oostergetel, A. Meetsma, J.L. de Boer, T.T.M. Palstra, Identification of polymorphs of pentacene. Synth. Met. 138, 475 (2003)
D. Holmes, S. Kumaraswamy, A. Matzeger, K.P.C. Vollhardt, On the nature of nonplanarity in the [n]phenylenes. Chem.-Eur. J. 5, 3399 (1999)
S. Yanagisawa, K. Okuma, T. Inaoka, I. Hamada, Recent progress in predicting structural and electronic properties of organic solids with the van der waals density functional. J. Electron Spectros. Relat. Phenomena 204, 159 (2015). https://doi.org/10.1016/j.elspec.2015.04.007. http://www.sciencedirect.com/science/article/pii/S0368204815000754
T. Rangel, K. Berland, S. Sharifzadeh, F. Brown-Altvater, K. Lee, P. Hyldgaard, L. Kronik, J.B. Neaton, Structural and excited-state properties of oligoacene crystals from first principles. Phys. Rev. B 93(11), 115206 (2016)
R.B. Campbell, J.M. Robertson, J. Trotter, The crystal structure of hexacene, and a revision of the crystallographic data for tetracene. Acta Cryst. 15, 289 (1962)
H. Yoshida, N. Sato, Grazing-incidence x-ray diffraction study of pentacene thin films with the bulk phase structure. Appl. Phys. Lett. 89(10), 101919 (2006). https://doi.org/10.1063/1.2349307
S. Schiefer, M. Huth, A. Dobrinevski, B. Nickel, Determination of the crystal structure of substrate-induced pentacene polymorphs in fiber structured thin films. J. Am. Chem. Soc. 129(34), 10316 (2007). https://doi.org/10.1021/ja0730516
M. Watanabe, Y.J. Chang, S.W. Liu, T.H. Chao, K. Goto, M.M. Islam, C.H. Yuan, Y.T. Tao, T. Shinmyozu, T.J. Chow, The synthesis, crystal structure and charge-transport properties of hexacene. Nat. Chem. 4, 574 (2012). https://doi.org/10.1038/nchem.1381
P.E. Blöchl, Projector augmented-wave method. Phys. Rev. B 50, 17953 (1994)
G. Kresse, J. Furthmüller, Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set. Comput. Mater. Sci. 6, 15 (1996)
G. Kresse, D. Joubert, From ultrasoft pseudopotentials to the projector augmented-wave method. Phys. Rev. B 59, 1758 (1999)
A.D. Becke, On the large-gradient behavior of the density functional exchange energy. J. Chem. Phys. 85, 7184 (1986)
We used C_h and H_h for our vdW-DF calculations
H.J. Monkhorst, J.D. Pack, Special points for Brillouin-zone integrations. Phys. Rev. B 13, 5188 (1976). https://doi.org/10.1103/PhysRevB.13.5188
F. Murnaghan, The compressibility of media under extreme pressures. Proc. Natl. Acad. Sci. U. S. A. 30(9), 244 (1944)
A.M. Reilly, A. Tkatchenko, Understanding the role of vibrations, exact exchange, and many-body van der waals interactions in the cohesive properties of molecular crystals. J. Chem. Phys. 139, 024705 (2013)
D.J. Carter, A.L. Rohl, Benchmarking calculated lattice parameters and energies of molecular crystals using van der waals density functionals. J. Chem. Theory Comput. 10(8), 3423 (2014)
S.C. Capelli, A. Albinati, S.A. Mason, B.T.M. Willis, Molecular motion in crystalline naphthalene: analysis of multi-temperature x-ray and neutron diffraction data. J. Phys. Chem. A 110(41), 11695 (2006). https://doi.org/10.1021/jp062953a
S.L. Chaplot, N. Lehner, G.S. Pawley, The structure of anthracene-d10 at 16 K using neutron diffraction. Acta Crystallogr. B 38(2), 483 (1982). https://doi.org/10.1107/S0567740882003239
M.V. Roux, M. Temprado, J.S. Chickos, Y. Nagano, Critically evaluated thermochemical properties of polycyclic aromatic hydrocarbons. J. Phys. Chem. Ref. Data 37(4), 1855 (2008). https://doi.org/10.1063/1.2955570
A.D. Becke, E.R. Johnson, Exchange-hole dipole moment and the dispersion interaction revisited. J. Chem. Phys. 127, 154108 (2007)
A.D. Becke, E.R. Johnson, A unified density-functional treatment of dynamical, nondynamical, and dispersion correlations. J. Chem. Phys. 127, 124108 (2007)
N. Geacintov, M. Pope, Low-lying valence band states and intrinsic photoconductivity in crystalline anthracene and tetracene. J. Chem. Phys. 50(2), 814 (1969)
C.L. Braun, G.M. Dobbs, Intrinsic photoconductivity in naphthalene single crystals. J. Chem. Phys. 53(7), 2718 (1970)
H. Baessler, H. Killesreiter, Hot carrier injection into molecular crystals and its relevance to the field dependence of photocurrents. Phys. Status Solidi B 53(1), 183 (1972)
H. Baessler, H. Killesreiter, Bandgap-determination from autoionization data in molecular crystals. Mol. Cryst. Liq. Cryst. 24(1–2), 21 (1973)
A.I. Belkind, V.V. Grechov, Energy levels of polyacene crystals. Phys. Status Solidi A 26(1), 377 (1974)
L. Sebastian, G. Weiser, H. Bässler, Charge transfer transitions in solid tetracene and pentacene studied by electroabsorption. Chem. Phys. 61, 125 (1981)
E.A. Silinsh, V.A. Kolesnikov, I.J. Muzikante, D.R. Balode, On charge carrier photogeneration mechanisms in organic molecular crystals. Phys. Status Solidi B 113(1), 379 (1982)
L. Sebastian, G. Weiser, G. Peter, H. Bässler, Charge-transfer transitions in crystalline anthracene and their role in photoconductivity. Chem. Phys. 75, 103 (1983)
Y. Isono, E. Morikawa, M. Kotani, Two-color pulsed photoconductivity study of naphthalene single crystal: photoionization of singlet exciton. Chem. Phys. Lett. 125, 344 (1986)
H. Yoshida, K. Yamada, J. Tsutsumi, N. Sato, Complete description of ionization energy and electron affinity in organic solids: determining contributions from electronic polarization, energy band dispersion, and molecular orientation. Phys. Rev. B 92, 075145 (2015). https://doi.org/10.1103/PhysRevB.92.075145
M.L.M. Rocco, M. Haeming, D.R. Batchelor, R. Fink, A. Schöll, E. Umbach, Electronic relaxation effects in condensed polyacenes: a high-resolution photoemission study. J. Chem. Phys. 129(7), 074702 (2008). https://doi.org/10.1063/1.2966356
M.M. Rieger, L. Steinbeck, I.D. White, H.N. Rojas, R.W. Godby, The GW space-time method for the self-energy of large systems. Comput. Phys. Commun. 117, 211 (1999)
L. Steinbeck, A. Rubio, L. Reining, M. Torrent, I.D. White, R.W. Godby, Enhancements to the GW space-time method. Comput. Phys. Commun. 125, 105 (2000)
C. Freysoldt, P. Eggert, P. Rinke, A. Schindlmayr, R.W. Godby, M. Scheffler, Dielectric anisotropy in the GW space-time method. Comput. Phys. Commun. 176, 1 (2007)
N. Troullier, J.L. Martins, Efficient pseudopotentials for place-wave calculations. Phys. Rev. B 43, 1993 (1991)
J.P. Perdew, K. Burke, M. Ernzerhof, Generalized gradient approximation made simple. Phys. Rev. Lett. 77(18), 3865 (1996)
Y. Morikawa, H. Ishii, K. Seki, Theoretical study of n-alkane adsorption on metal surfaces. Phys. Rev. B 69, 041403(R) (2004)
C. Faber, P. Boulanger, C. Attaccalite, I. Duchemin, X. Blase, Excited states properties of organic molecules: from density functional theory to the GW and bethe–salpeter green’s function formalisms. Phil. Trans. R. Soc. A 372(2011) (2014)
S. Körbel, P. Boulanger, I. Duchemin, X. Blase, M.A.L. Marques, S. Botti, Benchmark many-body GW and bethe-salpeter calculations for small transition metal molecules. J. Chem. Theory Comput. 10(9), 3934 (2014)
C. Rostgaard, K.W. Jacobsen, K.S. Thygesen, Fully self-consistent GW calculations for molecules. Phys. Rev. B 81, 085103 (2010)
X. Blase, C. Attaccalite, V. Olevano, First-principles GW calculations for fullerenes, porphyrins, phtalocyanine, and other molecules of interest for organic photovoltaic applications. Phys. Rev. B 83, 115103 (2011)
S. Sharifzadeh, A. Biller, L. Kronik, J.B. Neaton, Quasiparticle and optical spectroscopy of the organic semiconductors pentacene and ptcda from first principles. Phys. Rev. B 85, 125307 (2012)
F. Caruso, P. Rinke, X. Ren, M. Scheffler, A. Rubio, Unified description of ground and excited states of finite systems: the self-consistent GW approach. Phys. Rev. B 86, 081102 (2012)
F. Bruneval, M.A.L. Marques, Benchmarking the starting points of the GW approximation for molecules. J. Chem. Theory Comput. 9(1), 324 (2013)
M. Govoni, G. Galli, Large scale GW calculations. J. Chem. Theory Comput. 11(6), 2680 (2015)
W. Luo, S. Ismail-Beigi, M.L. Cohen, S.G. Louie, Quasiparticle band structure of zns and znse. Phys. Rev. B 66, 195215 (2002)
W. Setyawan, S. Curtarolo, High-throughput electronic band structure calculations: challenges and tools. Comput. Mater. Sci. 49, 299 (2010)
S. Yanagisawa, Y. Morikawa, A. Schindlmayr, Homo band dispersion of crystalline rubrene: effects of self-energy corrections within the GW approximation. Phys. Rev. B 88, 115438 (2013)
S. Yanagisawa, Y. Morikawa, A. Schindlmayr, Theoretical investigation of the band structure of picene single crystals within the GW approximation. Jpn. J. Appl. Phys. 53, 05FY02 (2014)
E.L. Shirley, Many-body effects on bandwidths in ionic, noble gas, and molecular solids. Phys. Rev. B 58, 9579 (1998)
E. Kwon, H. Oikawa, H. Kasai, H. Nakanishi, A fabrication method of organic nanocrystals using stabilizer-free emulsion. Cryst. Growth Des. 7(4), 600 (2007)
N. Ueno, S. Kera, Electron spectroscopy of functional organic thin films: deep insights into valence electronic structure in relation to charge transport property. Prog. Surf. Sci. 83(10–12), 490 (2008)
S. Ciuchi, R.C. Hatch, H. Höchst, C. Faber, X. Blase, S. Fratini, Molecular fingerprints in the electronic properties of crystalline organic semiconductors: from experiments to theory. Phys. Rev. Lett. 108, 256401 (2012)
K.H. Frank, P. Yannoulis, R. Dudde, E.E. Koch, Unoccupied molecular orbitals of aromatic hydrocarbons adsorbed on ag(111). J. Chem. Phys. 89(12), 7569 (1988). https://doi.org/10.1063/1.455720
Y. Li, V. Coropceanu, J.L. Brédas, Thermal narrowing of the electronic bandwidths in organic molecular semiconductors: impact of the crystal thermal expansion. J. Phys. Chem. Lett. 3(22), 3325 (2012). https://doi.org/10.1021/jz301575u
Y.C. Cheng, R.J. Silbey, D.A. da Silva Filho, J.P. Calbert, J. Cornil, J.L. Brédas, Three-dimensional band structure and bandlike mobility in oligoacene single crystals: a theoretical investigation. J. Chem. Phys. 118(8), 3764 (2003)
G.A. de Wijs, C.C. Mattheus, R.A. de Groot, T.T. Palstra, Anisotropy of the mobility of pentacene from frustration. Synth. Met. 139(1), 109 (2003)
H. Yoshida, N. Sato, Crystallographic and electronic structures of three different polymorphs of pentacene. Phys. Rev. B 77, 235205 (2008)
D.A. da Silva Filho, E.G. Kim, J.L. Brédas, Transport properties in the rubrene crystal: electronic coupling and vibrational reorganization energy. Adv. Mater. 17, 1072 (2005)
S.Y. Quek, M. Kamenetska, M.L. Steigerwald, H.J. Choi, S.G. Louie, M.S. Hybertsen, J.B. Neaton, L. Venkataraman, Mechanically controlled binary conductance switching of a single-molecule junction. Nat. Nanotechnol. 4, 230 EP (2009). https://doi.org/10.1038/nnano.2009.10
J.C. Inkson, Many-body effect at metal-semiconductor junctions. II. The self energy and band structure distortion. J. Phys. C Solid State Phys. 6(8), 1350 (1973). http://stacks.iop.org/0022-3719/6/i=8/a=004
J.B. Neaton, M.S. Hybertsen, S.G. Louie, Renormalization of molecular electronic levels at metal-molecule interfaces. Phys. Rev. Lett. 97, 216405 (2006). https://doi.org/10.1103/PhysRevLett.97.216405
J.M. Garcia-Lastra, C. Rostgaard, A. Rubio, K.S. Thygesen, Polarization-induced renormalization of molecular levels at metallic and semiconducting surfaces. Phys. Rev. B 80(24), 245427 (2009). https://doi.org/10.1103/PhysRevB.80.245427
Y. Chen, I. Tamblyn, S.Y. Quek, Energy level alignment at hybridized organic–metal interfaces: the role of many-electron effects. J. Phys. Chem. C 121(24), 13125 (2017). https://doi.org/10.1021/acs.jpcc.7b00715
I. Tamblyn, P. Darancet, S.Y. Quek, S.A. Bonev, J.B. Neaton, Electronic energy level alignment at metal-molecule interfaces with a GW approach. Phys. Rev. B 84(20), 201402 (2011). https://doi.org/10.1103/PhysRevB.84.201402
S.Y. Quek, L. Venkataraman, H.J. Choi, S.G. Louie, M.S. Hybertsen, J.B. Neaton, Amine-gold linked single-molecule circuits: experiment and theory. Nano Lett. 7(11), 3477 (2007). https://doi.org/10.1021/nl072058i
D.A. Egger, Z.F. Liu, J.B. Neaton, L. Kronik, Reliable energy level alignment at physisorbed molecule–metal interfaces from density functional theory. Nano Lett. 15(4), 2448 (2015). https://doi.org/10.1021/nl504863r
L. Kronik, T. Stein, S. Refaely-Abramson, R. Baer, Excitation gaps of finite-sized systems from optimally tuned range-separated hybrid functionals. J. Chem. Theory Comput. 8(5), 1515 (2012). https://doi.org/10.1021/ct2009363
R. Baer, E. Livshits, U. Salzner, Tuned range-separated hybrids in density functional theory. Annu. Rev. Phys. Chem. 61(1), 85 (2010). https://doi.org/10.1146/annurev.physchem.012809.103321
Z.F. Liu, D.A. Egger, S. Refaely-Abramson, L. Kronik, J.B. Neaton, Energy level alignment at molecule-metal interfaces from an optimally tuned range-separated hybrid functional. J. Chem. Phys. 146(9), 092326 (2017). https://doi.org/10.1063/1.4975321
P.M. Echenique, J.B. Pendry, The existence and detection of Rydberg states at surfaces. J. Phys. C Solid State Phys. 11(10), 2065 (1978). http://stacks.iop.org/0022-3719/11/i=10/a=017
P.M. Echenique, J.B. Pendry, Theory of image states at metal surfaces. Prog. Surf. Sci. 32(2), 111 (1989). https://doi.org/10.1016/0079-6816(89)90015-4. http://www.sciencedirect.com/science/article/pii/0079681689900154
I.R. Collins, P.T. Andrews, A.R. Law, Unoccupied electronic states of single-crystal graphite by angle-resolved ultraviolet inverse photoemission. Phys. Rev. B 38, 13348 (1988). https://doi.org/10.1103/PhysRevB.38.13348
J. Lehmann, M. Merschdorf, A. Thon, S. Voll, W. Pfeiffer, Properties and dynamics of the image potential states on graphite investigated by multiphoton photoemission spectroscopy. Phys. Rev. B 60(24), 17037 (1999). https://doi.org/10.1103/PhysRevB.60.17037
M. Zamkov, N. Woody, S. Bing, H.S. Chakraborty, Z. Chang, U. Thumm, P. Richard, Time-resolved photoimaging of image-potential states in carbon nanotubes. Phys. Rev. Lett. 93, 156803 (2004). https://doi.org/10.1103/PhysRevLett.93.156803
M. Feng, J. Zhao, H. Petek, Atomlike, hollow-core–bound molecular orbitals of c60. Science 320(5874), 359 (2008). https://doi.org/10.1126/science.1155866. http://science.sciencemag.org/content/320/5874/359
J. Zhao, M. Feng, J. Yang, H. Petek, The superatom states of fullerenes and their hybridization into the nearly free electron bands of fullerites. ACS Nano 3(4), 853 (2009). https://doi.org/10.1021/nn800834k
V.M. Silkin, J. Zhao, F. Guinea, E.V. Chulkov, P.M. Echenique, H. Petek, Image potential states in graphene. Phys. Rev. B 80(12), 121408 (2009). https://doi.org/10.1103/PhysRevB.80.121408
M. Posternak, A. Baldereschi, A.J. Freeman, E. Wimmer, Prediction of electronic surface states in layered materials: graphite. Phys. Rev. Lett. 52, 863 (1984). https://doi.org/10.1103/PhysRevLett.52.863
N.A.W. Holzwarth, S.G. Louie, S. Rabii, X-ray form factors and the electronic structure of graphite. Phys. Rev. B 26, 5382 (1982). https://doi.org/10.1103/PhysRevB.26.5382
T. Fauster, F.J. Himpsel, J.E. Fischer, E.W. Plummer, Three-dimensional energy band in graphite and lithium-intercalated graphite. Phys. Rev. Lett. 51, 430 (1983). https://doi.org/10.1103/PhysRevLett.51.430
S. Bose, V.M. Silkin, R. Ohmann, I. Brihuega, L. Vitali, C.H. Michaelis, P. Mallet, J.Y. Veuillen, M.A. Schneider, E.V. Chulkov, P.M. Echenique, K. Kern, Image potential states as a quantum probe of graphene interfaces. New J. Phys. 12(2), 023028 (2010)
I.D. White, R.W. Godby, M.M. Rieger, R.J. Needs, Dynamic image potential at an al(111) surface. Phys. Rev. Lett. 80, 4265 (1998). https://doi.org/10.1103/PhysRevLett.80.4265
I. Hamada, Y. Hamamoto, Y. Morikawa, Image potential states from the van der waals density functional. J. Chem. Phys. 147(4), 044708 (2017). https://doi.org/10.1063/1.4995441
O. Leenaerts, B. Partoens, F.M. Peeters, A. Volodin, C.V. Haesendonck, The work function of few-layer graphene. J. Phys. Condens. Matter 29(3), 035003 (2017). http://stacks.iop.org/0953-8984/29/i=3/a=035003
I. Hamada, S. Yanagisawa, Pseudopotential approximation in van der waals density functional calculations. Phys. Rev. B 84, 153104 (2011). https://doi.org/10.1103/PhysRevB.84.153104
N. Ferri, A. Ambrosetti, A. Tkatchenko, Electronic charge rearrangement at metal/organic interfaces induced by weak van der waals interactions. Phys. Rev. Mater. 1, 026003 (2017). https://doi.org/10.1103/PhysRevMaterials.1.026003
N. Ferri, R.A. DiStasio, A. Ambrosetti, R. Car, A. Tkatchenko, Electronic properties of molecules and surfaces with a self-consistent interatomic van der waals density functional. Phys. Rev. Lett. 114, 176802 (2015). https://doi.org/10.1103/PhysRevLett.114.176802
M. Shibuta, N. Hirata, T. Eguchi, A. Nakajima, Probing of an adsorbate-specific excited state on an organic insulating surface by two-photon photoemission spectroscopy. J. Am. Chem. Soc. 136(5), 1825 (2014)
M. Shibuta, N. Hirata, R. Matsui, M. Nakaya, T. Eguchi, A. Nakajima, Excitation and relaxation dynamics of two-dimensional photoexcited electrons on alkanethiolate self-assembled monolayers. J. Phys. Chem. C 119(40), 22945 (2015)
M. Shibuta, N. Hirata, T. Eguchi, A. Nakajima, Photoexcited state confinement in two-dimensional crystalline anthracene monolayer at room temperature. ACS Nano 11(4), 4307 (2017)
T. Yamada, M. Shibuta, Y. Ami, Y. Takano, A. Nonaka, K. Miyakubo, T. Munakata, Novel growth of naphthalene overlayer on Cu(111) studied by STM, LEED, and 2PPE. J. Phys. Chem. C 114(31), 13334 (2010)
C. Bondi, P. Baglioni, G. Taddei, Structure of the monolayers of aromatic molecules adsorbed on graphite. Chem. Phys. 96(2), 277 (1985). https://doi.org/10.1016/0301-0104(85)85091-6. http://www.sciencedirect.com/science/article/pii/0301010485850916
U. Bardi, S. Magnanelli, G. Rovida, Leed study of benzene and naphthalene monolayers adsorbed on the basal plane of graphite. Langmuir 3(2), 159 (1987). https://doi.org/10.1021/la00074a003
T. Yamada, Y. Takano, M. Isobe, K. Miyakubo, T. Munakata, Growth and adsorption geometry of naphthalene overlayers on HOPG studied by low-temperature scanning tunneling microscopy. Chem. Phys. Lett. 546, 136 (2012). https://doi.org/10.1016/j.cplett.2012.08.011. http://www.sciencedirect.com/science/article/pii/S0009261412009128
F. Sojka, M. Meissner, T. Yamada, T. Munakata, R. Forker, T. Fritz, Naphthalene’s six shades on graphite: a detailed study on the polymorphism of an apparently simple system. J. Phys. Chem. C 120(40), 22972 (2016). https://doi.org/10.1021/acs.jpcc.6b06702
S. Okada, Y. Enomoto, K. Shiraishi, A. Oshiyama, New electron states that float on semiconductor and metal surfaces. Surf. Sci. 585(3), L177 (2005)
M. Kutschera, M. Weinelt, M. Rohlfing, T. Fauster, Image-potential-induced surface state at si (100). Appl. Phys. A 88(3), 519 (2007)
M. Rohlfing, N.P. Wang, P. Krüger, J. Pollmann, Image states and excitons at insulator surfaces with negative electron affinity. Phys. Rev. Lett. 91(25), 256802 (2003)
B. Baumeier, P. Krüger, J. Pollmann, Bulk and surface electronic structures of alkaline-earth metal oxides: bound surface and image-potential states from first principles. Phys. Rev. B 76(20), 205404 (2007)
S. Saito, A. Oshiyama, Cohesive mechanism and energy bands of solid c60. Phys. Rev. Lett. 66, 2637 (1991). https://doi.org/10.1103/PhysRevLett.66.2637
S. Okada, A. Oshiyama, S. Saito, Nearly free electron states in carbon nanotube bundles. Phys. Rev. B 62, 7634 (2000). https://doi.org/10.1103/PhysRevB.62.7634
S. Okada, S. Saito, A. Oshiyama, Energetics and electronic structures of encapsulated C 60 in a carbon nanotube. Phys. Rev. Lett. 86, 3835 (2001). https://doi.org/10.1103/PhysRevLett.86.3835
T. Miyake, S. Saito, Electronic structure of potassium-doped carbon nanotubes. Phys. Rev. B 65, 165419 (2002). https://doi.org/10.1103/PhysRevB.65.165419
T. Miyake, S. Saito, Quasiparticle band structure of carbon nanotubes. Phys. Rev. B 68(15), 155424 (2003)
E.R. Margine, V.H. Crespi, Universal behavior of nearly free electron states in carbon nanotubes. Phys. Rev. Lett. 96, 196803 (2006). https://doi.org/10.1103/PhysRevLett.96.196803
S. Hu, J. Zhao, Y. Jin, J. Yang, H. Petek, J. Hou, Nearly free electron superatom states of carbon and boron nitride nanotubes. Nano Lett. 10(12), 4830 (2010)
N. Sato, K. Seki, H. Inokuchi, Polarization energies of organic solids determined by ultraviolet photoelectron spectroscopy. J. Chem. Soc. Faraday Trans. 2, 1621 (1981)
S. Refaely-Abramson, S. Sharifzadeh, M. Jain, R. Baer, J.B. Neaton, L. Kronik, Gap renormalization of molecular crystals from density-functional theory. Phys. Rev. B 88, 081204 (2013). https://doi.org/10.1103/PhysRevB.88.081204
J.E. Norton, J.L. Brédas, Polarization energies in oligoacene semiconductor crystals. J. Am. Chem. Soc. 130(37), 12377 (2008). https://doi.org/10.1021/ja8017797. PMID: 18715006
P.K. Nayak, N. Periasamy, Calculation of electron affinity, ionization potential, transport gap, optical band gap and exciton binding energy of organic solids using ‘solvation’ model and DFT. Org. Electron. 10(7), 1396 (2009). https://doi.org/10.1016/j.orgel.2009.06.011. http://www.sciencedirect.com/science/article/pii/S1566119909001815
N. Sato, H. Inokuchi, E.A. Silinsh, Reevaluation of electronic polarization energies in organic molecular crystals. Chem. Phys. 115(2), 269 (1987). https://doi.org/10.1016/0301-0104(87)80041-1. http://www.sciencedirect.com/science/article/pii/0301010487800411
W. Kohn, Density functional and density matrix method scaling linearly with the number of atoms. Phys. Rev. Lett. 76, 3168 (1996). https://doi.org/10.1103/PhysRevLett.76.3168
D. Deutsch, A. Natan, Y. Shapira, L. Kronik, Electrostatic properties of adsorbed polar molecules: opposite behavior of a single molecule and a molecular monolayer. J. Am. Chem. Soc. 129(10), 2989 (2007)
B.J. Topham, Z.G. Soos, Ionization in organic thin films: electrostatic potential, electronic polarization, and dopants in pentacene films. Phys. Rev. B 84, 165405 (2011). https://doi.org/10.1103/PhysRevB.84.165405
E.V. Tsiper, Z.G. Soos, Charge redistribution and polarization energy of organic molecular crystals. Phys. Rev. B 64, 195124 (2001). https://doi.org/10.1103/PhysRevB.64.195124
J. Li, G. D’Avino, I. Duchemin, D. Beljonne, X. Blase, Accurate description of charged excitations in molecular solids from embedded many-body perturbation theory. Phys. Rev. B 97, 035108 (2018). https://doi.org/10.1103/PhysRevB.97.035108
W.G. Aulbur, L. Jönsson, J.W. Wilkins, in Quasiparticle Calculations in Solids, ed. by H. Ehrenreich, F. Spaepen. Solid State Physics, vol. 54 (Academic, 2000), pp. 1–218. https://doi.org/10.1016/S0081-1947(08)60248-9. http://www.sciencedirect.com/science/article/pii/S0081194708602489
I.D. White, R.W. Godby, M.M. Rieger, R.J. Needs, Dynamic image potential at an al(111) surface. Phys. Rev. Lett. 80(19), 4265 (1998). https://doi.org/10.1103/PhysRevLett.80.4265
H. Yoshida, Near-ultraviolet inverse photoemission spectroscopy using ultra-low energy electrons. Chem. Phys. Lett. 539–540, 180 (2012). https://doi.org/10.1016/j.cplett.2012.04.058. http://www.sciencedirect.com/science/article/pii/S000926141200557X
H. Yoshida, Measuring the electron affinity of organic solids: an indispensable new tool for organic electronics. Anal. Bioanal. Chem. 406(9), 2231 (2014). https://doi.org/10.1007/s00216-014-7659-1
H. Yoshida, Principle and application of low energy inverse photoemission spectroscopy: a new method for measuring unoccupied states of organic semiconductors. J. Electron Spectros. Relat. Phenomena 204, 116 (2015). https://doi.org/10.1016/j.elspec.2015.07.003. http://www.sciencedirect.com/science/article/pii/S0368204815001486
Acknowledgements
This work was supported by Grants-in-Aid for Scientific Research (C) (No. 18K03458), on Innovative Areas “3D Active-Site Science” (No. 26105011) and “Hydrogenomics” (No. 18H05519), and for Fund for the Promotion of Joint International Research (Fostering Joint International Research) (No. 16KK0115) from the Japan Society for the Promotion of Science (JSPS), by “Joint Usage/Research Center for Interdisciplinary Large-scale Information Infrastructures” and “High Performance Computing Infrastructure” in Japan (Project ID: jh180069-NAH), and by the Cooperative Research Program of Network Joint Research Center for Materials and Devices in ISIR, Osaka University. We acknowledge the Supercomputer Center, the Institute for Solid State Physics, the University of Tokyo, and the Cyberscience Center, Tohoku University, for the use of their facilities.
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Yanagisawa, S., Hamada, I. (2020). Nanoscale First-Principles Electronic Structure Simulations of Materials Relevant to Organic Electronics. In: Onishi, T. (eds) Theoretical Chemistry for Advanced Nanomaterials. Springer, Singapore. https://doi.org/10.1007/978-981-15-0006-0_4
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