On the possibility of singlet fission in crystalline quaterrylene

Wang, Xiaopeng; Liu, Xingyu; Cook, Cameron; Schatschneider, Bohdan; Marom, Noa

doi:10.1063/1.5027553

Title: On the possibility of singlet fission in crystalline quaterrylene

Journal Article · Tue May 08 00:00:00 EDT 2018 · Journal of Chemical Physics

DOI:https://doi.org/10.1063/1.5027553· OSTI ID:1543862

Wang, Xiaopeng ^[1]; Liu, Xingyu ^[1]; Cook, Cameron ^[2]; Schatschneider, Bohdan ^[2];

^[1]

Carnegie Mellon Univ., Pittsburgh, PA (United States)
California State Polytechnic Univ. at Pomona, Pomona, CA (United States)

Singlet fission (SF), the spontaneous down-conversion of a singlet exciton into two triplet excitons residing on neighboring molecules, is a promising route to improve organic photovoltaic (OPV) device efficiencies by harvesting two charge carriers from one photon. However, only a few materials have been discovered that exhibit intermolecular SF in the solid state, most of which are acene derivatives. Recently, there has been a growing interest in rylenes as potential SF materials. We use many-body perturbation theory in the GW approximation and the Bethe-Salpeter equation to investigate the possibility of intermolecular SF in crystalline perylene and quaterrylene. Here, a new method is presented for determining the percent charge transfer (%CT) character of an exciton wave-function from double-Bader analysis. This enables relating exciton probability distributions to crystal packing. Based on comparison to known and predicted SF materials with respect to the energy conservation criterion (E_S-2E_T) and %CT, crystalline quaterrylene is a promising candidate for intermolecular SF. Furthermore, quaterrylene is attractive for OPV applications, thanks to its high stability and narrow optical gap. Perylene is not expected to exhibit SF; however, it is a promising candidate for harvesting sub-gap photons by triplet-triplet annihilation.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Univ. of California, Oakland, CA (United States); Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC02-05CH11231; AC02-06CH11357

OSTI ID:: 1543862

Journal Information:: Journal of Chemical Physics, Vol. 148, Issue 18; ISSN 0021-9606

Publisher:: American Institute of Physics (AIP)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 19 works

Citation information provided by
Web of Science

References (163)

High-throughput electronic band structure calculations: challenges and tools Setyawan, Wahyu; Curtarolo, Stefano arXiv https://doi.org/10.48550/arxiv.1004.2974	text	January 2010
Renormalization of Molecular Quasiparticle Levels at Metal-Molecule Interfaces: Trends Across Binding Regimes Thygesen, Kristian S.; Rubio, Angel arXiv https://doi.org/10.48550/arxiv.0810.5214	text	January 2008
Electronic and optical properties of families of polycyclic aromatic hydrocarbons: A systematic (time-dependent) density functional theory study Malloci, G.; Cappellini, G.; Mulas, G. Chemical Physics, Vol. 384, Issue 1-3 https://doi.org/10.1016/j.chemphys.2011.04.013	journal	June 2011
Short-Range to Long-Range Charge-Transfer Excitations in the Zincbacteriochlorin-Bacteriochlorin Complex: A Bethe-Salpeter Study Duchemin, I.; Deutsch, T.; Blase, X. Physical Review Letters, Vol. 109, Issue 16 https://doi.org/10.1103/physrevlett.109.167801	journal	October 2012
Analysis of exact vertex function for improving on the GW $Γ$ scheme for first-principles calculation of electron self-energy Maebashi, Hideaki; Takada, Yasutami Physical Review B, Vol. 84, Issue 24 https://doi.org/10.1103/physrevb.84.245134	journal	December 2011
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
Many-Body Dispersion Interactions in Molecular Crystal Polymorphism Marom, Noa; DiStasio, Robert A.; Atalla, Viktor Angewandte Chemie, Vol. 125, Issue 26 https://doi.org/10.1002/ange.201301938	journal	May 2013
Intermolecular Vibrational Modes Speed Up Singlet Fission in Perylenediimide Crystals Renaud, Nicolas; Grozema, Ferdinand C. The Journal of Physical Chemistry Letters, Vol. 6, Issue 3 https://doi.org/10.1021/jz5023575	journal	January 2015
GW 100: Benchmarking G0W0 for molecular systems van Setten, M. J.; Caruso, F.; Sharifzadeh, S. Universität Regensburg https://doi.org/10.5283/epub.33561	text	January 2015
Off-Diagonal Self-Energy Terms and Partially Self-Consistency in GW Calculations for Single Molecules: Efficient Implementation and Quantitative Effects on Ionization Potentials Kaplan, F.; Weigend, F.; Evers, F. Journal of Chemical Theory and Computation, Vol. 11, Issue 11 https://doi.org/10.1021/acs.jctc.5b00394	journal	October 2015
Electronic and optical properties of families of polycyclic aromatic hydrocarbons: a systematic (time-dependent) density functional theory study Malloci, G.; Cappellini, G.; Mulas, G. arXiv https://doi.org/10.48550/arxiv.1104.2978	text	January 2011
QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials Giannozzi, Paolo; Baroni, Stefano; Bonini, Nicola Journal of Physics: Condensed Matter, Vol. 21, Issue 39, Article No. 395502 https://doi.org/10.1088/0953-8984/21/39/395502	journal	September 2009
Enhanced sub-bandgap efficiency of a solid-state organic intermediate band solar cell using triplet–triplet annihilation Lin, YunHui L.; Koch, Marius; Brigeman, Alyssa N. Energy & Environmental Science, Vol. 10, Issue 6 https://doi.org/10.1039/c6ee03702j	journal	January 2017
Benchmark Many-Body GW and Bethe–Salpeter Calculations for Small Transition Metal Molecules Körbel, Sabine; Boulanger, Paul; Duchemin, Ivan Journal of Chemical Theory and Computation, Vol. 10, Issue 9 https://doi.org/10.1021/ct5003658	journal	August 2014
Microscopic theory of singlet exciton fission. II. Application to pentacene dimers and the role of superexchange Berkelbach, Timothy C.; Hybertsen, Mark S.; Reichman, David R. arXiv https://doi.org/10.48550/arxiv.1211.6459	text	January 2012
A grid-based Bader analysis algorithm without lattice bias Tang, W.; Sanville, E.; Henkelman, G. Journal of Physics: Condensed Matter, Vol. 21, Issue 8 https://doi.org/10.1088/0953-8984/21/8/084204	journal	January 2009
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
Singlet Fission in Rubrene Derivatives: Impact of Molecular Packing Sutton, Christopher; Tummala, Naga Rajesh; Beljonne, David Chemistry of Materials, Vol. 29, Issue 7 https://doi.org/10.1021/acs.chemmater.6b04633	journal	March 2017
Exciton Fission and Charge Generation via Triplet Excitons in Pentacene/C ₆₀ Bilayers Rao, Akshay; Wilson, Mark W. B.; Hodgkiss, Justin M. Journal of the American Chemical Society, Vol. 132, Issue 36 https://doi.org/10.1021/ja1042462	journal	September 2010
Bringing dark states to light Bardeen, Christopher J. Nature Materials, Vol. 13, Issue 11 https://doi.org/10.1038/nmat4112	journal	October 2014
Slow Singlet Fission Observed in a Polycrystalline Perylenediimide Thin Film Le, Aaron K.; Bender, Jon A.; Roberts, Sean T. The Journal of Physical Chemistry Letters, Vol. 7, Issue 23 https://doi.org/10.1021/acs.jpclett.6b02320	journal	November 2016
High-Throughput Investigation of the Geometry and Electronic Structures of Gas-Phase and Crystalline Polycyclic Aromatic Hydrocarbons Schatschneider, Bohdan; Monaco, Stephen; Liang, Jian-Jie The Journal of Physical Chemistry C, Vol. 118, Issue 34 https://doi.org/10.1021/jp5064462	journal	August 2014
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
Triplet exciton dynamics in rubrene single crystals Ryasnyanskiy, Aleksandr; Biaggio, Ivan Physical Review B, Vol. 84, Issue 19 https://doi.org/10.1103/physrevb.84.193203	journal	November 2011
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
Efficient pseudopotentials for plane-wave calculations Troullier, N.; Martins, José Luriaas Physical Review B, Vol. 43, Issue 3 https://doi.org/10.1103/physrevb.43.1993	journal	January 1991
The energy barrier in singlet fission can be overcome through coherent coupling and entropic gain Chan, Wai-Lun; Ligges, Manuel; Zhu, X-Y. Nature Chemistry, Vol. 4, Issue 10 https://doi.org/10.1038/nchem.1436	journal	August 2012
On the Nature of Nonplanarity in the [N]Phenylenes Holmes, Daniel; Kumaraswamy, Sriram; Matzger, Adam J. Chemistry - A European Journal, Vol. 5, Issue 11 https://doi.org/10.1002/(sici)1521-3765(19991105)5:11<3399::aid-chem3399>3.0.co;2-v	journal	November 1999
Influence of the Core-Valence Interaction and of the Pseudopotential Approximation on the Electron Self-Energy in Semiconductors Gómez-Abal, Ricardo; Li, Xinzheng; Scheffler, Matthias Physical Review Letters, Vol. 101, Issue 10 https://doi.org/10.1103/physrevlett.101.106404	journal	September 2008
Exciton Delocalization Drives Rapid Singlet Fission in Nanoparticles of Acene Derivatives Pensack, Ryan D.; Tilley, Andrew J.; Parkin, Sean R. Journal of the American Chemical Society, Vol. 137, Issue 21 https://doi.org/10.1021/ja512668r	journal	May 2015
The Low-Lying Electronic States of Pentacene and Their Roles in Singlet Fission Zeng, Tao; Hoffmann, Roald; Ananth, Nandini Journal of the American Chemical Society, Vol. 136, Issue 15 https://doi.org/10.1021/ja500887a	journal	April 2014
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
Beyond the $G W$ approximation: A second-order screened exchange correction Ren, Xinguo; Marom, Noa; Caruso, Fabio Physical Review B, Vol. 92, Issue 8 https://doi.org/10.1103/physrevb.92.081104	journal	August 2015
Enhanced sub-bandgap efficiency of a solid-state organic intermediate band solar cell using triplet-triplet annihilation Lin, Yhl; Koch, M.; Brigeman, An Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.49458	text	January 2017
Low-Lying Electronic Excited States of Pentacene Oligomers: A Comparative Electronic Structure Study in the Context of Singlet Fission Coto, Pedro B.; Sharifzadeh, Sahar; Neaton, Jeffrey B. Journal of Chemical Theory and Computation, Vol. 11, Issue 1 https://doi.org/10.1021/ct500510k	journal	December 2014
Benchmark of $G W$ methods for azabenzenes Marom, Noa; Caruso, Fabio; Ren, Xinguo Physical Review B, Vol. 86, Issue 24 https://doi.org/10.1103/physrevb.86.245127	journal	December 2012
Morphology Effectively Controls Singlet-Triplet Exciton Relaxation and Charge Transport in Organic Semiconductors Thorsmølle, V. K.; Averitt, R. D.; Demsar, J. Physical Review Letters, Vol. 102, Issue 1 https://doi.org/10.1103/physrevlett.102.017401	journal	January 2009
Microscopic theory of singlet exciton fission. III. Crystalline pentacene Berkelbach, Timothy C.; Hybertsen, Mark S.; Reichman, David R. The Journal of Chemical Physics, Vol. 141, Issue 7 https://doi.org/10.1063/1.4892793	journal	August 2014
Coulomb-hole summations and energies for $G W$ calculations with limited number of empty orbitals: A modified static remainder approach Deslippe, Jack; Samsonidze, Georgy; Jain, Manish Physical Review B, Vol. 87, Issue 16 https://doi.org/10.1103/physrevb.87.165124	journal	April 2013
Excitons and Davydov splitting in sexithiophene from first-principles many-body Green’s function theory Leng, Xia; Yin, Huabing; Liang, Dongmei The Journal of Chemical Physics, Vol. 143, Issue 11 https://doi.org/10.1063/1.4930975	journal	September 2015
1002. The intensity of ultraviolet-light absorption by monocrystals. Part IV. Absorption by naphthacene of plane-polarized light Bree, A.; Lyons, L. E. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9600005206	journal	January 1960
Molecular detail in electron micrographs of quaterrylene C40H20 Smith, David J.; Fryer, J. R. Nature, Vol. 291, Issue 5815 https://doi.org/10.1038/291481a0	journal	June 1981
High-throughput electronic band structure calculations: Challenges and tools Setyawan, Wahyu; Curtarolo, Stefano Computational Materials Science, Vol. 49, Issue 2 https://doi.org/10.1016/j.commatsci.2010.05.010	journal	August 2010
The Origin of a 650 nm Photoluminescence Band in Rubrene Chen, Yuanzhen; Lee, Bumsu; Fu, Danni Advanced Materials, Vol. 23, Issue 45 https://doi.org/10.1002/adma.201102294	journal	October 2011
Charge Transfer–Mediated Singlet Fission Monahan, N.; Zhu, X. -Y. Annual Review of Physical Chemistry, Vol. 66, Issue 1 https://doi.org/10.1146/annurev-physchem-040214-121235	journal	April 2015
Singlet fission in rubrene single crystal: direct observation by femtosecond pump–probe spectroscopy Ma, Lin; Zhang, Keke; Kloc, Christian Physical Chemistry Chemical Physics, Vol. 14, Issue 23 https://doi.org/10.1039/c2cp40449d	journal	January 2012
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
Correlations between photoelectron and ultraviolet absorption spectra of polycyclic hydrocarbons Clar, E.; Schmidt, W. Tetrahedron, Vol. 34, Issue 21 https://doi.org/10.1016/0040-4020(78)87020-3	journal	January 1978
Resonant energy transfer of triplet excitons from pentacene to PbSe nanocrystals Tabachnyk, Maxim; Ehrler, Bruno; Gélinas, Simon Nature Materials, Vol. 13, Issue 11 https://doi.org/10.1038/nmat4093	journal	October 2014
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
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
Morphology Effectively Controls Singlet-Triplet Exciton Relaxation and Charge Transport in Organic Semiconductors Thorsmølle, V. K.; Averitt, R. D.; Demsar, J. arXiv https://doi.org/10.48550/arxiv.0901.2002	text	January 2009
Benchmarking the Bethe–Salpeter Formalism on a Standard Organic Molecular Set Jacquemin, Denis; Duchemin, Ivan; Blase, Xavier Journal of Chemical Theory and Computation, Vol. 11, Issue 7 https://doi.org/10.1021/acs.jctc.5b00304	journal	June 2015
Ab initio pseudopotentials for electronic structure calculations of poly-atomic systems using density-functional theory Fuchs, Martin Mendeley https://doi.org/10.17632/kygjf563w3.1	dataset	January 2019
Atomically Flat, Large-Sized, Two-Dimensional Organic Nanocrystals Jiang, Hui; Zhang, Keke K.; Ye, Jun Small, Vol. 9, Issue 7 https://doi.org/10.1002/smll.201202390	journal	November 2012
Assessment of the Accuracy of the Bethe–Salpeter (BSE/ GW ) Oscillator Strengths Jacquemin, Denis; Duchemin, Ivan; Blondel, Aymeric Journal of Chemical Theory and Computation, Vol. 12, Issue 8 https://doi.org/10.1021/acs.jctc.6b00419	journal	July 2016
Theoretical predictions of red and near-infrared strongly emitting X -annulated rylenes Peng, Qian; Niu, Yingli; Wang, Zhaohui The Journal of Chemical Physics, Vol. 134, Issue 7 https://doi.org/10.1063/1.3549143	journal	February 2011
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
Lattice images and molecular images of organic materials Kobayashi, Takashi; Isoda, Seiji Journal of Materials Chemistry, Vol. 3, Issue 1 https://doi.org/10.1039/jm9930300001	journal	January 1993
Renormalization of Molecular Electronic Levels at Metal-Molecule Interfaces Neaton, J. B.; Hybertsen, Mark S.; Louie, Steven G. Physical Review Letters, Vol. 97, Issue 21 https://doi.org/10.1103/physrevlett.97.216405	journal	November 2006
Singlet Fission Smith, Millicent B.; Michl, Josef Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr1002613	journal	November 2010
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
Emissive spin-0 triplet-pairs are a direct product of triplet–triplet annihilation in pentacene single crystals and anthradithiophene films Bossanyi, David G.; Matthiesen, Maik; Wang, Shuangqing Nature Chemistry, Vol. 13, Issue 2 https://doi.org/10.1038/s41557-020-00593-y	journal	December 2020
Singlet Fission in a Covalently Linked Cofacial Alkynyltetracene Dimer Korovina, Nadezhda V.; Das, Saptaparna; Nett, Zachary Journal of the American Chemical Society, Vol. 138, Issue 2 https://doi.org/10.1021/jacs.5b10550	journal	January 2016
Temperature-Independent Singlet Exciton Fission in Tetracene Wilson, Mark W. B.; Rao, Akshay; Johnson, Kerr Journal of the American Chemical Society, Vol. 135, Issue 44 https://doi.org/10.1021/ja408854u	journal	October 2013
Singlet Fission in Polypentacene Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B. Chem, Vol. 1, Issue 3 https://doi.org/10.1016/j.chempr.2016.08.016	journal	September 2016
25th Anniversary Article: Bulk Heterojunction Solar Cells: Understanding the Mechanism of Operation Heeger, Alan J. Advanced Materials, Vol. 26, Issue 1 https://doi.org/10.1002/adma.201304373	journal	December 2013
The Dynamics of Singlet Fission in Crystalline Tetracene and Covalent Analogs Burdett, Jonathan J.; Bardeen, Christopher J. Accounts of Chemical Research, Vol. 46, Issue 6 https://doi.org/10.1021/ar300191w	journal	January 2013
Vibrational and nonlinear optical properties of rylenes calculated by ab initio methods Rumi, Mariacristina; Zerbi, Giuseppe; Müllen, Klaus The Journal of Chemical Physics, Vol. 108, Issue 20 https://doi.org/10.1063/1.476305	journal	May 1998
Modeling Singlet Fission in Rylene and Diketopyrrolopyrrole Derivatives: The Role of the Charge Transfer State in Superexchange and Excimer Formation Miller, Claire E.; Wasielewski, Michael R.; Schatz, George C. The Journal of Physical Chemistry C, Vol. 121, Issue 19 https://doi.org/10.1021/acs.jpcc.7b02697	journal	May 2017
The Quantum Coherent Mechanism for Singlet Fission: Experiment and Theory Chan, Wai-Lun; Berkelbach, Timothy C.; Provorse, Makenzie R. Accounts of Chemical Research, Vol. 46, Issue 6 https://doi.org/10.1021/ar300286s	journal	April 2013
Ab initio pseudopotentials for electronic structure calculations of poly-atomic systems using density-functional theory Fuchs, Martin; Scheffler, Matthias Computer Physics Communications, Vol. 119, Issue 1 https://doi.org/10.1016/s0010-4655(98)00201-x	journal	June 1999
Renormalization of Molecular Quasiparticle Levels at Metal-Molecule Interfaces: Trends across Binding Regimes Thygesen, Kristian S.; Rubio, Angel Physical Review Letters, Vol. 102, Issue 4 https://doi.org/10.1103/physrevlett.102.046802	journal	January 2009
Ionization Potentials of Solids: The Importance of Vertex Corrections Grüneis, Andreas; Kresse, Georg; Hinuma, Yoyo Physical Review Letters, Vol. 112, Issue 9 https://doi.org/10.1103/physrevlett.112.096401	journal	March 2014
The Crystal and Molecular Structure of Quaterrylene: A Redetermination Kerr, K. A.; Ashmore, J. P.; Speakman, J. C. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 344, Issue 1637 https://doi.org/10.1098/rspa.1975.0098	journal	June 1975
Fission and fusion of excitons in perylene crystal studied with VUV and X-ray excitation Takeda, Y. Journal of Electron Spectroscopy and Related Phenomena, Vol. 78, Issue 1-3 https://doi.org/10.1016/0368-2048(96)02765-x	journal	May 1996
Singlet Exciton Fission in Thin Films of tert -Butyl-Substituted Terrylenes Eaton, Samuel W.; Miller, Stephen A.; Margulies, Eric A. The Journal of Physical Chemistry A, Vol. 119, Issue 18 https://doi.org/10.1021/acs.jpca.5b02719	journal	April 2015
Communication: Exciton analysis in time-dependent density functional theory: How functionals shape excited-state characters Mewes, Stefanie A.; Plasser, Felix; Dreuw, Andreas The Journal of Chemical Physics, Vol. 143, Issue 17 https://doi.org/10.1063/1.4935178	journal	November 2015
Detailed Balance Limit of Efficiency of p‐n Junction Solar Cells Shockley, William; Queisser, Hans J. Journal of Applied Physics, Vol. 32, Issue 3, p. 510-519 https://doi.org/10.1063/1.1736034	journal	March 1961
BerkeleyGW: A massively parallel computer package for the calculation of the quasiparticle and optical properties of materials and nanostructures Deslippe, Jack Mendeley https://doi.org/10.17632/dzk6frrs69.1	dataset	January 2019
Theoretical Investigation of Singlet Fission in Molecular Dimers: The Role of Charge Transfer States and Quantum Interference Mirjani, Fatemeh; Renaud, Nicolas; Gorczak, Natalie The Journal of Physical Chemistry C, Vol. 118, Issue 26 https://doi.org/10.1021/jp503398a	journal	June 2014
Laser Generation of Excitons and Fluorescence in Anthracene Crystals Singh, S.; Jones, W. J.; Siebrand, W. The Journal of Chemical Physics, Vol. 42, Issue 1 https://doi.org/10.1063/1.1695695	journal	January 1965
Microscopic theory of singlet exciton fission. I. General formulation Berkelbach, Timothy C.; Hybertsen, Mark S.; Reichman, David R. The Journal of Chemical Physics, Vol. 138, Issue 11 https://doi.org/10.1063/1.4794425	journal	March 2013
Enabling singlet fission by controlling intramolecular charge transfer in π-stacked covalent terrylenediimide dimers Margulies, Eric A.; Miller, Claire E.; Wu, Yilei Nature Chemistry, Vol. 8, Issue 12 https://doi.org/10.1038/nchem.2589	journal	August 2016
Absorption and photoluminescence spectroscopy of rubrene single crystals Irkhin, Pavel; Ryasnyanskiy, Aleksandr; Koehler, Marlus Physical Review B, Vol. 86, Issue 8 https://doi.org/10.1103/physrevb.86.085143	journal	August 2012
Benchmark of Bethe-Salpeter for Triplet Excited-States Jacquemin, Denis; Duchemin, Ivan; Blondel, Aymeric Journal of Chemical Theory and Computation, Vol. 13, Issue 2 https://doi.org/10.1021/acs.jctc.6b01169	journal	February 2017
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
The Bethe–Salpeter equation in chemistry: relations with TD-DFT, applications and challenges Blase, Xavier; Duchemin, Ivan; Jacquemin, Denis Chemical Society Reviews, Vol. 47, Issue 3 https://doi.org/10.1039/c7cs00049a	journal	January 2018
Organic photovoltaics Kippelen, Bernard; Brédas, Jean-Luc Energy & Environmental Science, Vol. 2, Issue 3 https://doi.org/10.1039/b812502n	journal	January 2009
Microscopic theory of singlet exciton fission. II. Application to pentacene dimers and the role of superexchange Berkelbach, Timothy C.; Hybertsen, Mark S.; Reichman, David R. The Journal of Chemical Physics, Vol. 138, Issue 11 https://doi.org/10.1063/1.4794427	journal	March 2013
Singlet Exciton Fission in a Hexacene Derivative Lee, Jiye; Bruzek, Matthew J.; Thompson, Nicholas J. Advanced Materials, Vol. 25, Issue 10 https://doi.org/10.1002/adma.201203982	journal	January 2013
Exciton Delocalization and Superradiance in Tetracene Thin Films and Nanoaggregates Lim, Sang-Hyun; Bjorklund, Thomas G.; Spano, Frank C. Physical Review Letters, Vol. 92, Issue 10 https://doi.org/10.1103/physrevlett.92.107402	journal	March 2004
Electronic Properties of Quaterrylene, C ₄₀ H ₂₀ Maruyama, Yusei; Inokuchi, Hiroo; Harada, Yoshiya Bulletin of the Chemical Society of Japan, Vol. 36, Issue 9 https://doi.org/10.1246/bcsj.36.1193	journal	September 1963
Rylene and Rylene Diimides: Comparison of Theoretical and Experimental Results and Prediction for High-Rylene Derivatives Zhao, Xiaohong; Xiong, Yushuai; Ma, Jie The Journal of Physical Chemistry A, Vol. 120, Issue 38 https://doi.org/10.1021/acs.jpca.6b07552	journal	September 2016
Rubrene micro-crystals from solution routes: their crystallography, morphology and optical properties Huang, Liwei; Liao, Qing; Shi, Qiang J. Mater. Chem., Vol. 20, Issue 1 https://doi.org/10.1039/b914334c	journal	January 2010
Excited state dynamics in solid and monomeric tetracene: The roles of superradiance and exciton fission Burdett, Jonathan J.; Müller, Astrid M.; Gosztola, David The Journal of Chemical Physics, Vol. 133, Issue 14 https://doi.org/10.1063/1.3495764	journal	October 2010
Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers Hanna, M. C.; Nozik, A. J. Journal of Applied Physics, Vol. 100, Issue 7 https://doi.org/10.1063/1.2356795	journal	October 2006
The Electronic Spectra of Aromatic Molecular Crystals. II. The Crystal Structure and Spectra of Perylene Tanaka, Jiro Bulletin of the Chemical Society of Japan, Vol. 36, Issue 10 https://doi.org/10.1246/bcsj.36.1237	journal	October 1963
A systematic benchmark of the ab initio Bethe-Salpeter equation approach for low-lying optical excitations of small organic molecules Bruneval, Fabien; Hamed, Samia M.; Neaton, Jeffrey B. The Journal of Chemical Physics, Vol. 142, Issue 24 https://doi.org/10.1063/1.4922489	journal	June 2015
The Structure and Dynamics of Molecular Excitons Bardeen, Christopher J. Annual Review of Physical Chemistry, Vol. 65, Issue 1 https://doi.org/10.1146/annurev-physchem-040513-103654	journal	April 2014
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
Quantum dissipation driven by electron transfer within a single molecule investigated with atomic force microscopy Berger, Jan; Ondráček, Martin; Stetsovych, Oleksandr Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-15054-w	journal	March 2020
Coulomb-hole summations and energies for GW calculations with limited number of empty orbitals: a modified static remainder approach Deslippe, Jack; Samsonidze, Georgy; Jain, Manish arXiv https://doi.org/10.48550/arxiv.1208.0266	text	January 2012
Effect of crystal packing on the excitonic properties of rubrene polymorphs Wang, Xiaopeng; Garcia, Taylor; Monaco, Stephen CrystEngComm, Vol. 18, Issue 38 https://doi.org/10.1039/c6ce00873a	journal	January 2016
Charge-Transfer Excitations Steer the Davydov Splitting and Mediate Singlet Exciton Fission in Pentacene Beljonne, D.; Yamagata, H.; Brédas, J. L. Physical Review Letters, Vol. 110, Issue 22 https://doi.org/10.1103/physrevlett.110.226402	journal	May 2013
The triplet state energies of rubrene and diphenylisobenzofuran Herkstroeter, W. G.; Merkel, P. B. Journal of Photochemistry, Vol. 16, Issue 4 https://doi.org/10.1016/0047-2670(81)80055-x	journal	August 1981
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
Accurate Ionization Potentials and Electron Affinities of Acceptor Molecules III: A Benchmark of GW Methods Knight, Joseph W.; Wang, Xiaopeng; Gallandi, Lukas Journal of Chemical Theory and Computation, Vol. 12, Issue 2 https://doi.org/10.1021/acs.jctc.5b00871	journal	January 2016
998. Photo- and semi-conductance of organic crystals. Part VI. Effect of oxygen on the surface photo-current and some photochemical properties of solid anthracene Bree, A.; Lyons, L. E. Journal of the Chemical Society (Resumed) https://doi.org/10.1039/jr9600005179	journal	January 1960
Optical properties of acene molecules and pentacene crystal from the many-body Green's function method Leng, Xia; Feng, Jin; Chen, Tingwei Physical Chemistry Chemical Physics, Vol. 18, Issue 44 https://doi.org/10.1039/c6cp05902c	journal	January 2016
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
Polymorphism influences singlet fission rates in tetracene thin films Arias, Dylan H.; Ryerson, Joseph L.; Cook, Jasper D. Chemical Science, Vol. 7, Issue 2 https://doi.org/10.1039/c5sc03535j	journal	January 2016
Optical Excitations in Conjugated Polymers Rohlfing, Michael; Louie, Steven G. Physical Review Letters, Vol. 82, Issue 9 https://doi.org/10.1103/physrevlett.82.1959	journal	March 1999
Oxygen-Related Band Gap State in Single Crystal Rubrene Mitrofanov, Oleg; Lang, David V.; Kloc, Christian Physical Review Letters, Vol. 97, Issue 16 https://doi.org/10.1103/physrevlett.97.166601	journal	October 2006
Origins of singlet fission in solid pentacene from an ab initio Green's-function approach Refaely-Abramson, Sivan; da Jornada, Felipe H.; Louie, Steven G. arXiv https://doi.org/10.48550/arxiv.1706.01564	text	January 2017
Charge Photogeneration in Organic Solar Cells Clarke, Tracey M.; Durrant, James R. Chemical Reviews, Vol. 110, Issue 11, p. 6736-6767 https://doi.org/10.1021/cr900271s	journal	November 2010
Quantitative Intramolecular Singlet Fission in Bipentacenes Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B. Journal of the American Chemical Society, Vol. 137, Issue 28 https://doi.org/10.1021/jacs.5b04986	journal	July 2015
Accurate description of the electronic structure of organic semiconductors by GW methods Marom, Noa Journal of Physics: Condensed Matter, Vol. 29, Issue 10 https://doi.org/10.1088/1361-648x/29/10/103003	journal	February 2017
Origins of Singlet Fission in Solid Pentacene from an ab initio Green’s Function Approach Refaely-Abramson, Sivan; da Jornada, Felipe H.; Louie, Steven G. Physical Review Letters, Vol. 119, Issue 26 https://doi.org/10.1103/physrevlett.119.267401	journal	December 2017
Femtosecond Transient Absorption Studies of trans - and cis -1,3,5-Hexatriene in Solution Ohta, Kaoru; Naitoh, Yukito; Tominaga, Keisuke The Journal of Physical Chemistry A, Vol. 102, Issue 1 https://doi.org/10.1021/jp9725994	journal	January 1998
Singlet Exciton Fission Photovoltaics Lee, Jiye; Jadhav, Priya; Reusswig, Philip D. Accounts of Chemical Research, Vol. 46, Issue 6 https://doi.org/10.1021/ar300288e	journal	April 2013
Elimination of the linearization error in GW calculations based on the linearized augmented-plane-wave method Friedrich, Christoph; Schindlmayr, Arno; Blügel, Stefan arXiv https://doi.org/10.48550/arxiv.cond-mat/0606605	text	January 2006
Exciton dynamics in pentacene thin films studied by pump-probe spectroscopy Jundt, C.; Klein, G.; Sipp, B. Chemical Physics Letters, Vol. 241, Issue 1-2 https://doi.org/10.1016/0009-2614(95)00603-2	journal	July 1995
BerkeleyGW: A massively parallel computer package for the calculation of the quasiparticle and optical properties of materials and nanostructures Deslippe, Jack Mendeley https://doi.org/10.17632/dzk6frrs69	dataset	January 2019
Optical response and emission waveguiding in rubrene crystals Tavazzi, S.; Borghesi, A.; Papagni, A. Physical Review B, Vol. 75, Issue 24 https://doi.org/10.1103/physrevb.75.245416	journal	June 2007
Singlet exciton fission in solution Walker, Brian J.; Musser, Andrew J.; Beljonne, David Nature Chemistry, Vol. 5, Issue 12 https://doi.org/10.1038/nchem.1801	journal	November 2013
Singlet Fission for Dye-Sensitized Solar Cells: Can a Suitable Sensitizer Be Found? Paci, Irina; Johnson, Justin C.; Chen, Xudong Journal of the American Chemical Society, Vol. 128, Issue 51 https://doi.org/10.1021/ja063980h	journal	December 2006
Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials Würthner, Frank; Saha-Möller, Chantu R.; Fimmel, Benjamin Chemical Reviews, Vol. 116, Issue 3 https://doi.org/10.1021/acs.chemrev.5b00188	journal	August 2015
Accurate and efficient algorithm for Bader charge integration Yu, Min; Trinkle, Dallas R. The Journal of Chemical Physics, Vol. 134, Issue 6 https://doi.org/10.1063/1.3553716	journal	February 2011
Mechanism for Singlet Fission in Pentacene and Tetracene: From Single Exciton to Two Triplets Zimmerman, Paul M.; Bell, Franziska; Casanova, David Journal of the American Chemical Society, Vol. 133, Issue 49 https://doi.org/10.1021/ja208431r	journal	December 2011
Polarized Absorption in Crystalline Pentacene: Theory vs Experiment Hestand, N. J.; Yamagata, H.; Xu, Bolei The Journal of Physical Chemistry C, Vol. 119, Issue 38 https://doi.org/10.1021/acs.jpcc.5b07163	journal	September 2015
Singlet Exciton Fission in Polycrystalline Thin Films of a Slip-Stacked Perylenediimide Eaton, Samuel W.; Shoer, Leah E.; Karlen, Steven D. Journal of the American Chemical Society, Vol. 135, Issue 39 https://doi.org/10.1021/ja4053174	journal	September 2013
The triplet state energies of rubrene and diphenylisobenzofuran Herkstroeter, W. G.; Merkel, P. B. Journal of Photochemistry, Vol. 16, Issue 3 https://doi.org/10.1016/0047-2670(81)80043-3	journal	January 1981
GW 100: Benchmarking G ₀ W ₀ for Molecular Systems van Setten, Michiel J.; Caruso, Fabio; Sharifzadeh, Sahar Journal of Chemical Theory and Computation, Vol. 11, Issue 12 https://doi.org/10.1021/acs.jctc.5b00453	journal	November 2015
Aromaticity in benzene-like rings — An experimental electron density investigation Ranganathan, Anupama; Kulkarni, G. U. Journal of Chemical Sciences, Vol. 115, Issue 5-6 https://doi.org/10.1007/bf02708254	journal	October 2003
Controlling Polarization at Insulating Surfaces: Quasiparticle Calculations for Molecules Adsorbed on Insulator Films Freysoldt, Christoph; Rinke, Patrick; Scheffler, Matthias Physical Review Letters, Vol. 103, Issue 5 https://doi.org/10.1103/physrevlett.103.056803	journal	July 2009
Perylene, Oligorylenes, and Aza-Analogs Markiewicz, John T.; Wudl, Fred ACS Applied Materials & Interfaces, Vol. 7, Issue 51 https://doi.org/10.1021/acsami.5b02243	journal	October 2015
Organic Photovoltaics Jørgensen, Mikkel Technical University of Denmark (DTU), The Department of Energy Conversion and Storage https://doi.org/10.5446/18210	audiovisual	January 2015
Theory-Driven Insight into the Crystal Packing of Trialkylsilylethynyl Pentacenes Thorley, Karl J.; Finn, Tristan W.; Jarolimek, Karol Chemistry of Materials, Vol. 29, Issue 6 https://doi.org/10.1021/acs.chemmater.6b04211	journal	November 2016
Ab initio pseudopotentials for electronic structure calculations of poly-atomic systems using density-functional theory Fuchs, Martin Mendeley https://doi.org/10.17632/kygjf563w3	dataset	January 2019
Singlet Exciton Fission for Solar Cell Applications: Energy Aspects of Interchromophore Coupling ^† Greyson, Eric C.; Stepp, Brian R.; Chen, Xudong The Journal of Physical Chemistry B, Vol. 114, Issue 45 https://doi.org/10.1021/jp909002d	journal	November 2010
Energy harvesting of non-emissive triplet excitons in tetracene by emissive PbS nanocrystals Thompson, Nicholas J.; Wilson, Mark W. B.; Congreve, Daniel N. Nature Materials, Vol. 13, Issue 11 https://doi.org/10.1038/nmat4097	journal	October 2014
Accurate and Efficient Method for Many-Body van der Waals Interactions Tkatchenko, Alexandre; DiStasio, Robert A.; Car, Roberto Physical Review Letters, Vol. 108, Issue 23 https://doi.org/10.1103/physrevlett.108.236402	journal	June 2012
Accurate Molecular Van Der Waals Interactions from Ground-State Electron Density and Free-Atom Reference Data Tkatchenko, Alexandre; Scheffler, Matthias Physical Review Letters, Vol. 102, Issue 7 https://doi.org/10.1103/physrevlett.102.073005	journal	February 2009
Accurate Quasiparticle Spectra from Self-Consistent GW Calculations with Vertex Corrections Shishkin, M.; Marsman, M.; Kresse, G. Physical Review Letters, Vol. 99, Issue 24 https://doi.org/10.1103/physrevlett.99.246403	journal	December 2007
Benchmarking the Starting Points of the GW Approximation for Molecules Bruneval, Fabien; Marques, Miguel A. L. Journal of Chemical Theory and Computation, Vol. 9, Issue 1 https://doi.org/10.1021/ct300835h	journal	December 2012
Direct Observation of a Charge-Transfer State Preceding High-Yield Singlet Fission in Terrylenediimide Thin Films Margulies, Eric A.; Logsdon, Jenna L.; Miller, Claire E. Journal of the American Chemical Society, Vol. 139, Issue 2 https://doi.org/10.1021/jacs.6b07721	journal	December 2016
Noncovalent Intermolecular Interactions in Organic Electronic Materials: Implications for the Molecular Packing vs Electronic Properties of Acenes Sutton, Christopher; Risko, Chad; Brédas, Jean-Luc Chemistry of Materials, Vol. 28, Issue 1 https://doi.org/10.1021/acs.chemmater.5b03266	journal	November 2015
Optical pump-probe spectroscopy of photocarriers in rubrene single crystals Tao, Shoichi; Matsuzaki, Hiroyuki; Uemura, Hirotaka Physical Review B, Vol. 83, Issue 7 https://doi.org/10.1103/physrevb.83.075204	journal	February 2011
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
First principles methods using CASTEP Clark, Stewart J.; Segall, Matthew D.; Pickard, Chris J. Zeitschrift für Kristallographie - Crystalline Materials, Vol. 220, Issue 5/6 https://doi.org/10.1524/zkri.220.5.567.65075	journal	January 2005
An assessment of low-lying excitation energies and triplet instabilities of organic molecules with an ab initio Bethe-Salpeter equation approach and the Tamm-Dancoff approximation Rangel, Tonatiuh; Hamed, Samia M.; Bruneval, Fabien The Journal of Chemical Physics, Vol. 146, Issue 19 https://doi.org/10.1063/1.4983126	journal	May 2017
Many-Body Dispersion Interactions in Molecular Crystal Polymorphism Marom, Noa; DiStasio, Robert A.; Atalla, Viktor Angewandte Chemie International Edition, Vol. 52, Issue 26 https://doi.org/10.1002/anie.201301938	journal	May 2013
Theoretical Study of Singlet Fission in Oligorylenes Minami, Takuya; Ito, Soichi; Nakano, Masayoshi The Journal of Physical Chemistry Letters, Vol. 3, Issue 18 https://doi.org/10.1021/jz3011749	journal	September 2012
A Qualitative Index of Spatial Extent in Charge-Transfer Excitations Le Bahers, Tangui; Adamo, Carlo; Ciofini, Ilaria Journal of Chemical Theory and Computation, Vol. 7, Issue 8 https://doi.org/10.1021/ct200308m	journal	July 2011
Structural and excited-state properties of oligoacene crystals from first principles Rangel, Tonatiuh; Berland, Kristian; Sharifzadeh, Sahar arXiv https://doi.org/10.48550/arxiv.1604.00041	text	January 2016
Excitation spectra of aromatic molecules within a real-space $G W$ -BSE formalism: Role of self-consistency and vertex corrections Hung, Linda; da Jornada, Felipe H.; Souto-Casares, Jaime Physical Review B, Vol. 94, Issue 8 https://doi.org/10.1103/physrevb.94.085125	journal	August 2016
Understanding the Structure and Electronic Properties of Molecular Crystals Under Pressure: Application of Dispersion Corrected DFT to Oligoacenes Schatschneider, Bohdan; Monaco, Stephen; Tkatchenko, Alexandre The Journal of Physical Chemistry A, Vol. 117, Issue 34 https://doi.org/10.1021/jp406573n	journal	May 2013
Elimination of the linearization error in GW calculations based on the linearized augmented-plane-wave method Friedrich, Christoph; Schindlmayr, Arno; Blügel, Stefan Physical Review B, Vol. 74, Issue 4 https://doi.org/10.1103/physrevb.74.045104	journal	July 2006
Mapping the Relation between Stacking Geometries and Singlet Fission Yield in a Class of Organic Crystals Renaud, Nicolas; Sherratt, Paul A.; Ratner, Mark A. The Journal of Physical Chemistry Letters, Vol. 4, Issue 7 https://doi.org/10.1021/jz400176m	journal	March 2013
A transferable model for singlet-fission kinetics Yost, Shane R.; Lee, Jiye; Wilson, Mark W. B. Nature Chemistry, Vol. 6, Issue 6 https://doi.org/10.1038/nchem.1945	journal	May 2014
Molecular Orientation and Absorption Spectra of Quaterrylene Evaporated Film Maruyama, Yusei; Iwaki, Tohru; Kajiwara, Takashi Bulletin of the Chemical Society of Japan, Vol. 43, Issue 4 https://doi.org/10.1246/bcsj.43.1259	journal	April 1970
Singlet Fission Tykwinski, Rik R.; Guldi, Dirk M. ChemPhotoChem, Vol. 5, Issue 5 https://doi.org/10.1002/cptc.202100053	journal	April 2021

Cited By (2)

Dimensionality of excitons in stacked van der Waals materials: The example of hexagonal boron nitride Aggoune, Wahib; Cocchi, Caterina; Nabok, Dmitrii Physical Review B, Vol. 97, Issue 24 https://doi.org/10.1103/physrevb.97.241114	journal	June 2018
Dimensionality of excitons in stacked van der Waals materials: The example of hexagonal boron nitride Aggoune, Wahib; Cocchi, Caterina; Nabok, Dmitrii arXiv https://doi.org/10.48550/arxiv.1806.09324	text	January 2018

Similar Records

Phenylated Acene Derivatives as Candidates for Intermolecular Singlet Fission

Journal Article · Mon Feb 18 00:00:00 EST 2019 · Journal of Physical Chemistry. C · OSTI ID:1543862

Wang, Xiaopeng; Liu, Xingyu; Tom, Rithwik; +3 more

New insights into the design of conjugated polymers for intramolecular singlet fission

Journal Article · Tue Jul 31 00:00:00 EDT 2018 · Nature Communications · OSTI ID:1543862

Hu, Jiahua; Xu, Ke; Shen, Lei; +6 more

Quantitative intramolecular fission in oligoacenes, materials, and methods of use thereof

Patent · Tue Aug 25 00:00:00 EDT 2020 · OSTI ID:1543862

Campos, Luis Miguel; Sfeir, Matthew Y.; Sanders, Samuel Nathan; +3 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Chemistry
Physics

Title: On the possibility of singlet fission in crystalline quaterrylene

Citation Formats

References (163)

Cited By (2)

Similar Records

Related Subjects