Low-lying excited states in crystalline perylene

Rangel, Tonatiuh; Rinn, Andre; Sharifzadeh, Sahar; da Jornada, Felipe H.; Pick, Andre; Louie, Steven G.; Witte, Gregor; Kronik, Leeor; Neaton, Jeffrey B.; Chatterjee, Sangam

doi:10.1073/pnas.1711126115

Title: Low-lying excited states in crystalline perylene

Journal Article · 26 December 2017 · Proceedings of the National Academy of Sciences of the United States of America

DOI: https://doi.org/10.1073/pnas.1711126115 · OSTI ID:1414876

Rangel, Tonatiuh ^[1]; Rinn, Andre ^[2]; Sharifzadeh, Sahar ^[3]; da Jornada, Felipe H. ^[4]; Pick, Andre ^[2]; Louie, Steven G. ^[4];

^[2]; Kronik, Leeor ^[5]; Neaton, Jeffrey B. ^[6]; Chatterjee, Sangam ^[7]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)
Philipps-Univ. Marburg, Marburg (Germany)
Boston Univ., Boston, MA (United States)
Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Weizmann Institute of Science, Rehovoth (Israel)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States); Kavli Energy NanoSciences Institute at Berkeley, Berkeley, CA (United States)
Philipps-Univ. Marburg, Marburg (Germany); Justus Liebig Univ. Giessen, Giessen (Germany)

Organic materials are promising candidates for advanced optoelectronics and are used in light-emitting diodes and photovoltaics. However, the underlying mechanisms allowing the formation of excited states responsible for device functionality, such as exciton generation and charge separation, are insufficiently understood. This is partly due to the wide range of existing crystalline polymorphs depending on sample preparation conditions. Here, we determine the linear optical response of thin-film single-crystal perylene samples of distinct polymorphs in transmission and reflection geometries. The sample quality allows for unprecedented high-resolution spectroscopy, which offers an ideal opportunity for judicious comparison between theory and experiment. Excellent agreement with first-principles calculations for the absorption based on the GW plus Bethe–Salpeter equation (GW-BSE) approach of many-body perturbation theory (MBPT) is obtained, from which a clear picture of the low-lying excitations in perylene emerges, including evidence of an exciton–polariton stopband, as well as an assessment of the commonly used Tamm–Dancoff approximation to the GW-BSE approach. Furthermore, our findings on this well-controlled system can guide understanding and development of advanced molecular solids and functionalization for applications.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division; USDOE

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1414876

Alternate ID(s):: OSTI ID: 1466699

Journal Information:: Proceedings of the National Academy of Sciences of the United States of America, Vol. 115, Issue 2; ISSN 0027-8424

Publisher:: National Academy of Sciences, Washington, DC (United States)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 31 works

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References (63)

Determination of geometric and electronic structures of organic crystals from first principles: Role of the molecular configuration on the electronic structure Yanagisawa, Susumu; Hamada, Ikutaro Journal of Applied Physics, Vol. 121, Issue 4 https://doi.org/10.1063/1.4974844	journal	January 2017
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Anisotropic optical properties of single crystalline PTCDA studied by spectroscopic ellipsometry Alonso, M. I.; Garriga, M.; Karl, N. Organic Electronics, Vol. 3, Issue 1 https://doi.org/10.1016/S1566-1199(01)00027-1	journal	March 2002
Electronic structure of polyacetylene: Optical and infrared studies of undoped semiconducting ( CH ) x and heavily doped metallic ( CH ) x Fincher, C. R.; Ozaki, M.; Tanaka, M. Physical Review B, Vol. 20, Issue 4 https://doi.org/10.1103/PhysRevB.20.1589	journal	August 1979
Gap renormalization of molecular crystals from density-functional theory Refaely-Abramson, Sivan; Sharifzadeh, Sahar; Jain, Manish Physical Review B, Vol. 88, Issue 8 https://doi.org/10.1103/PhysRevB.88.081204	journal	August 2013
Recent Advances in Singlet Fission Smith, Millicent B.; Michl, Josef Annual Review of Physical Chemistry, Vol. 64, Issue 1 https://doi.org/10.1146/annurev-physchem-040412-110130	journal	April 2013
Quasiparticle and optical spectroscopy of the organic semiconductors pentacene and PTCDA from first principles Sharifzadeh, Sahar; Biller, Ariel; Kronik, Leeor Physical Review B, Vol. 85, Issue 12 https://doi.org/10.1103/PhysRevB.85.125307	journal	March 2012
A Star-Shaped Perylene Diimide Electron Acceptor for High-Performance Organic Solar Cells Lin, Yuze; Wang, Yifan; Wang, Jiayu Advanced Materials, Vol. 26, Issue 30 https://doi.org/10.1002/adma.201400525	journal	March 2014
BerkeleyGW: A massively parallel computer package for the calculation of the quasiparticle and optical properties of materials and nanostructures Deslippe, Jack; Samsonidze, Georgy; Strubbe, David A. Computer Physics Communications, Vol. 183, Issue 6 https://doi.org/10.1016/j.cpc.2011.12.006	journal	June 2012
Excitonic Effects on the Silicon Plasmon Resonance Olevano, Valerio; Reining, Lucia Physical Review Letters, Vol. 86, Issue 26 https://doi.org/10.1103/PhysRevLett.86.5962	journal	June 2001
Optical differential reflectance spectroscopy on thin molecular films Forker, Roman; Gruenewald, Marco; Fritz, Torsten Annual Reports Section "C" (Physical Chemistry), Vol. 108 https://doi.org/10.1039/c2pc90002e	journal	January 2012
The role of polymorphism in organic thin films: oligoacenes investigated from first principles Ambrosch-Draxl, Claudia; Nabok, Dmitrii; Puschnig, Peter New Journal of Physics, Vol. 11, Issue 12 https://doi.org/10.1088/1367-2630/11/12/125010	journal	December 2009
Recent developments in the ABINIT software package Gonze, X.; Jollet, F.; Abreu Araujo, F. Computer Physics Communications, Vol. 205 https://doi.org/10.1016/j.cpc.2016.04.003	journal	August 2016
Electron correlation in semiconductors and insulators: Band gaps and quasiparticle energies Hybertsen, Mark S.; Louie, Steven G. Physical Review B, Vol. 34, Issue 8, p. 5390-5413 https://doi.org/10.1103/PhysRevB.34.5390	journal	October 1986
Molecular Packing Determines Singlet Exciton Fission in Organic Semiconductors Kolata, Kolja; Breuer, Tobias; Witte, Gregor ACS Nano, Vol. 8, Issue 7 https://doi.org/10.1021/nn502544d	journal	June 2014
Structure preserving parallel algorithms for solving the Bethe–Salpeter eigenvalue problem Shao, Meiyue; da Jornada, Felipe H.; Yang, Chao Linear Algebra and its Applications, Vol. 488 https://doi.org/10.1016/j.laa.2015.09.036	journal	January 2016
Excited-State Properties of Molecular Solids from First Principles Kronik, Leeor; Neaton, Jeffrey B. Annual Review of Physical Chemistry, Vol. 67, Issue 1 https://doi.org/10.1146/annurev-physchem-040214-121351	journal	May 2016
Towards a Complete Description of a Polymorphic Crystal: The Example of Perylene Botoshansky, Mark; Herbstein, Frank H.; Kapon, Moshe Helvetica Chimica Acta, Vol. 86, Issue 4 https://doi.org/10.1002/hlca.200390097	journal	April 2003
First-Principles Theory of Quasiparticles: Calculation of Band Gaps in Semiconductors and Insulators Hybertsen, Mark S.; Louie, Steven G. Physical Review Letters, Vol. 55, Issue 13 https://doi.org/10.1103/PhysRevLett.55.1418	journal	September 1985
Polymorph-Selective Preparation and Structural Characterization of Perylene Single Crystals Pick, André; Klues, Michael; Rinn, Andre Crystal Growth & Design, Vol. 15, Issue 11 https://doi.org/10.1021/acs.cgd.5b01130	journal	October 2015
Electronic excitations: density-functional versus many-body Green’s-function approaches Onida, Giovanni; Reining, Lucia; Rubio, Angel Reviews of Modern Physics, Vol. 74, Issue 2 https://doi.org/10.1103/RevModPhys.74.601	journal	June 2002
Oligoacene exciton binding energies: Their dependence on molecular size Hummer, Kerstin; Ambrosch-Draxl, Claudia Physical Review B, Vol. 71, Issue 8 https://doi.org/10.1103/PhysRevB.71.081202	journal	February 2005
Vibrational spectroscopy of solid state molecular dimers Kosic, Thomas J.; Schosser, Claire L.; Dlott, Dana D. Chemical Physics Letters, Vol. 96, Issue 1 https://doi.org/10.1016/0009-2614(83)80117-1	journal	March 1983
Molecular Understanding of Organic Solar Cells: The Challenges Brédas, Jean-Luc; Norton, Joseph E.; Cornil, Jérôme Accounts of Chemical Research, Vol. 42, Issue 11 https://doi.org/10.1021/ar900099h	journal	November 2009
Optical Reflection Spectroscopy of Organic Solids Philpott, M. R. Annual Review of Physical Chemistry, Vol. 31, Issue 1 https://doi.org/10.1146/annurev.pc.31.100180.000525	journal	October 1980
Energy Transfer Mechanisms and the Molecular Exciton Model for Molecular Aggregates Kasha, Michael Radiation Research, Vol. 20, Issue 1 https://doi.org/10.2307/3571331	journal	September 1963
Structural and excited-state properties of oligoacene crystals from first principles Rangel, Tonatiuh; Berland, Kristian; Sharifzadeh, Sahar Physical Review B, Vol. 93, Issue 11 https://doi.org/10.1103/PhysRevB.93.115206	journal	March 2016
Low-Energy Charge-Transfer Excitons in Organic Solids from First-Principles: The Case of Pentacene Sharifzadeh, Sahar; Darancet, Pierre; Kronik, Leeor The Journal of Physical Chemistry Letters, Vol. 4, Issue 13 https://doi.org/10.1021/jz401069f	journal	June 2013
Large-scale complementary integrated circuits based on organic transistors Crone, B.; Dodabalapur, A.; Lin, Y. -Y. Nature, Vol. 403, Issue 6769, p. 521-523 https://doi.org/10.1038/35000530	journal	February 2000
Polaritons: the electromagnetic modes of media Mills, D. L.; Burstein, E. Reports on Progress in Physics, Vol. 37, Issue 7 https://doi.org/10.1088/0034-4885/37/7/001	journal	July 1974
Structural and electronic properties of perylene from first principles calculations Fedorov, I. A.; Zhuravlev, Y. N.; Berveno, V. P. The Journal of Chemical Physics, Vol. 138, Issue 9 https://doi.org/10.1063/1.4794046	journal	March 2013
Relating the Physical Structure and Optoelectronic Function of Crystalline TIPS-Pentacene Sharifzadeh, Sahar; Wong, Cathy Y.; Wu, Hao Advanced Functional Materials, Vol. 25, Issue 13 https://doi.org/10.1002/adfm.201403005	journal	December 2014
Spectral Effects of Strong Exciton Coupling in the Lowest Electronic Transition of Perylene Hochstrasser, Robin M. The Journal of Chemical Physics, Vol. 40, Issue 9 https://doi.org/10.1063/1.1725563	journal	May 1964
Molecular versus excitonic transitions in PTCDA dimers and oligomers studied by helium nanodroplet isolation spectroscopy Wewer, M.; Stienkemeier, F. Physical Review B, Vol. 67, Issue 12 https://doi.org/10.1103/PhysRevB.67.125201	journal	March 2003
Cavity ring-down spectroscopy and theoretical calculations of the S1(B3u1)←S0(Ag1) transition of jet-cooled perylene Tan, Xiaofeng; Salama, Farid The Journal of Chemical Physics, Vol. 122, Issue 8 https://doi.org/10.1063/1.1851502	journal	February 2005
Molecular Aggregate Photophysics beyond the Kasha Model: Novel Design Principles for Organic Materials Hestand, Nicholas J.; Spano, Frank C. Accounts of Chemical Research, Vol. 50, Issue 2 https://doi.org/10.1021/acs.accounts.6b00576	journal	January 2017
Electrical and Optical Properties of a Stable Synthetic Metallic Polymer: Polypyrrole Watanabe, Atsushi; Tanaka, Masashi; Tanaka, Jiro Bulletin of the Chemical Society of Japan, Vol. 54, Issue 8 https://doi.org/10.1246/bcsj.54.2278	journal	August 1981
Vibronic structure of PTCDA stacks: the exciton–phonon-charge-transfer dimer Hennessy, M. H.; Soos, Z. G.; Pascal, R. A. Chemical Physics, Vol. 245, Issue 1-3 https://doi.org/10.1016/S0301-0104(99)00082-8	journal	July 1999
Interference between Coulombic and CT-mediated couplings in molecular aggregates: H- to J-aggregate transformation in perylene-based π-stacks Hestand, Nicholas J.; Spano, Frank C. The Journal of Chemical Physics, Vol. 143, Issue 24 https://doi.org/10.1063/1.4938012	journal	December 2015
Theory of Molecular Polaritons. Application to the Reflection Spectra of Anthracene, 1,5‐Bis(dimethylamino)pentamethinium Perchlorate, and Some Other Cationic Dye Crystals Philpott, Michael R. The Journal of Chemical Physics, Vol. 54, Issue 5 https://doi.org/10.1063/1.1675143	journal	March 1971
Exciton dispersion in molecular solids Cudazzo, Pierluigi; Sottile, Francesco; Rubio, Angel Journal of Physics: Condensed Matter, Vol. 27, Issue 11 https://doi.org/10.1088/0953-8984/27/11/113204	journal	March 2015
Exciton-Plasmon States in Nanoscale Materials: Breakdown of the Tamm−Dancoff Approximation Grüning, Myrta; Marini, Andrea; Gonze, Xavier Nano Letters, Vol. 9, Issue 8 https://doi.org/10.1021/nl803717g	journal	August 2009
Magnetic Field Splitting and Dispersion of the Lower 1S-Exciton Polariton in KI and RbI Fröhlich, D.; Kirchhoff, St.; Köhler, P. physica status solidi (b), Vol. 158, Issue 1 https://doi.org/10.1002/pssb.2221580126	journal	March 1990
Quasi-metallic reflection spectra of TCNQ single crystals Pennelly, R. R.; Eckhardt, C. J. Chemical Physics, Vol. 12, Issue 1 https://doi.org/10.1016/0301-0104(76)80115-2	journal	January 1976
Solid-state optical absorption from optimally tuned time-dependent range-separated hybrid density functional theory Refaely-Abramson, Sivan; Jain, Manish; Sharifzadeh, Sahar Physical Review B, Vol. 92, Issue 8 https://doi.org/10.1103/PhysRevB.92.081204	journal	August 2015
New Method for Calculating the One-Particle Green's Function with Application to the Electron-Gas Problem Hedin, Lars Physical Review, Vol. 139, Issue 3A https://doi.org/10.1103/PhysRev.139.A796	journal	August 1965
From organic metals to superconductors: managing conduction electrons in organic solids Wudl, F. Accounts of Chemical Research, Vol. 17, Issue 6 https://doi.org/10.1021/ar00102a005	journal	June 1984
Study of localized and extended excitons in 3,4,9,10-perylenetetracarboxylic dianhydride (PTCDA) I. Spectroscopic properties of thin films and solutions Bulović, V.; Burrows, P. E.; Forrest, S. R. Chemical Physics, Vol. 210, Issue 1-2 https://doi.org/10.1016/0301-0104(96)00114-0	journal	October 1996
A Potential Perylene Diimide Dimer-Based Acceptor Material for Highly Efficient Solution-Processed Non-Fullerene Organic Solar Cells with 4.03% Efficiency Zhang, Xin; Lu, Zhenhuan; Ye, Long Advanced Materials, Vol. 25, Issue 40 https://doi.org/10.1002/adma.201300897	journal	August 2013
Crystallochromy of perylene pigments: Interference between Frenkel excitons and charge-transfer states Gisslén, Linus; Scholz, Reinhard Physical Review B, Vol. 80, Issue 11 https://doi.org/10.1103/PhysRevB.80.115309	journal	September 2009
Understanding electron-withdrawing substituent effect on structural, electronic and charge transport properties of perylene bisimide derivatives Chai, Shuo; Wen, Shu-Hao; Han, Ke-Li Organic Electronics, Vol. 12, Issue 11 https://doi.org/10.1016/j.orgel.2011.07.008	journal	November 2011
Semiconductor Optics Klingshirn, Claus Advanced Texts in Physics https://doi.org/10.1007/b138175	book	January 2005
Ab initio calculation of the electronic and optical properties of solid pentacene Tiago, Murilo L.; Northrup, John E.; Louie, Steven G. Physical Review B, Vol. 67, Issue 11 https://doi.org/10.1103/PhysRevB.67.115212	journal	March 2003
The polarized reflection and absorption spectra of perylene crystals in monomeric and dimeric forms Fuke, Kiyokazu; Kaya, Koji; Kajiwara, Takashi Journal of Molecular Spectroscopy, Vol. 63, Issue 1 https://doi.org/10.1016/0022-2852(67)90137-3	journal	October 1976
Electronic Spectra of Perylene and Coronene Evaporated Films as a Function of Their Crystallinity Kamura, Yusuke; Shirotani, Ichimin; Ohno, Koichi Bulletin of the Chemical Society of Japan, Vol. 49, Issue 2 https://doi.org/10.1246/bcsj.49.418	journal	February 1976
Ab Initio Optoelectronic Properties of Silicon Nanoparticles: Excitation Energies, Sum Rules, and Tamm–Dancoff Approximation Rocca, Dario; Vörös, Márton; Gali, Adam Journal of Chemical Theory and Computation, Vol. 10, Issue 8 https://doi.org/10.1021/ct5000956	journal	June 2014
Excimer emission of anthracene, perylene, coronene and pyrene microcrystals dispersed in water Seko, Toshihiro; Ogura, Kazuhito; Kawakami, Yasuyuki Chemical Physics Letters, Vol. 291, Issue 3-4 https://doi.org/10.1016/S0009-2614(98)00629-0	journal	July 1998
AB-INITIO STUDY ON THE EXCITON BINDING ENERGIES IN ORGANIC SEMICONDUCTORS Hummer, Kerstin; Puschnig, Peter; Sagmeister, Stephan Modern Physics Letters B, Vol. 20, Issue 06 https://doi.org/10.1142/S0217984906010603	journal	March 2006
Excitons in molecular crystals from first-principles many-body perturbation theory: Picene versus pentacene Cudazzo, Pierluigi; Gatti, Matteo; Rubio, Angel Physical Review B, Vol. 86, Issue 19 https://doi.org/10.1103/PhysRevB.86.195307	journal	November 2012
Electron-hole excitations and optical spectra from first principles Rohlfing, Michael; Louie, Steven G. Physical Review B, Vol. 62, Issue 8 https://doi.org/10.1103/PhysRevB.62.4927	journal	August 2000
Absorption and emission spectroscopy of perylene (C20H12) isolated in Ne, Ar, and N2 matrices Joblin, C.; Salama, F.; Allamandola, L. The Journal of Chemical Physics, Vol. 110, Issue 15 https://doi.org/10.1063/1.478631	journal	April 1999
Lowest Optical Excitations in Molecular Crystals: Bound Excitons versus Free Electron-Hole Pairs in Anthracene Hummer, Kerstin; Puschnig, Peter; Ambrosch-Draxl, Claudia Physical Review Letters, Vol. 92, Issue 14 https://doi.org/10.1103/PhysRevLett.92.147402	journal	April 2004
Electronic Absorption Spectra of Neutral Perylene (C ₂₀ H ₁₂ ), Terrylene (C ₃₀ H ₁₆ ), and Quaterrylene (C ₄₀ H ₂₀ ) and Their Positive and Negative Ions: Ne Matrix-Isolation Spectroscopy and Time-Dependent Density Functional Theory Calculations Halasinski, Thomas M.; Weisman, Jennifer L.; Ruiterkamp, Richard The Journal of Physical Chemistry A, Vol. 107, Issue 19 https://doi.org/10.1021/jp027394w	journal	May 2003

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