A Nonorthogonal Configuration Interaction Approach to Singlet Fission in Perylenediimide Compounds

Sousa, C.; Sánchez-Mansilla, A.; Broer, R.; Straatsma, T. P.; de Graaf, C.

doi:10.1021/acs.jpca.3c04975

Title: A Nonorthogonal Configuration Interaction Approach to Singlet Fission in Perylenediimide Compounds

Journal Article · 13 November 2023 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI: https://doi.org/10.1021/acs.jpca.3c04975 · OSTI ID:2234368

^[1];

^[2];

^[3]; Straatsma, T. P. ^[4];

^[5]

Universitat de Barcelona (Spain)
Universitat Rovira i Virgili, Tarragona (Spain)
University of Groningen (The Netherlands)
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States); University of Alabama, Tuscaloosa, AL (United States)
Universitat Rovira i Virgili, Tarragona (Spain); ICREA, Barcelona (Spain)

Perylenediimide molecules constitute a family of chromophores that undergo singlet fission, a process in which an excited singlet state converts into lower energy triplets on two neighboring molecules, potentially increasing the efficiency of organic solar cells. Here, the nonorthogonal configuration interaction method is applied to study the effect of the different crystal packing of various perylenediimide derivatives on the relative energies of the singlet and triplet states, the intermolecular electronic couplings, and the relative rates for singlet fission. The analysis of the wave functions and electronic couplings reveals that charge transfer states play an important role in the singlet fission mechanism. Dimer conformations where the PDI molecules are at large displacements along the long axis and short on the short axis are posed as the most favorable for singlet fission. The role of the substituent at the imide group has been inspected concluding that, although it has no effect in the energies, for some conformations it significantly influences the electronic couplings, and therefore, replacing this substituent with hydrogen may introduce artifacts in the computational modeling of the PDI molecules.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER); USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 2234368

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 47 Vol. 127; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (65)

Multiphonon Relaxation Slows Singlet Fission in Crystalline Hexacene Busby, Erik; Berkelbach, Timothy C.; Kumar, Bharat Journal of the American Chemical Society, Vol. 136, Issue 30 https://doi.org/10.1021/ja503980c	journal	July 2014
High Triplet Yield from Singlet Fission in a Thin Film of 1,3-Diphenylisobenzofuran Johnson, Justin C.; Nozik, Arthur J.; Michl, Josef Journal of the American Chemical Society, Vol. 132, Issue 46 https://doi.org/10.1021/ja104123r	journal	November 2010
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
Introduction of n -electron valence states for multireference perturbation theory Angeli, C.; Cimiraglia, R.; Evangelisti, S. The Journal of Chemical Physics, Vol. 114, Issue 23 https://doi.org/10.1063/1.1361246	journal	June 2001
Singlet Fission in Perylenediimide Dimers Farag, Marwa H.; Krylov, Anna I. The Journal of Physical Chemistry C, Vol. 122, Issue 45 https://doi.org/10.1021/acs.jpcc.8b05309	journal	October 2018
Main Group Atoms and Dimers Studied with a New Relativistic ANO Basis Set Roos, Björn O.; Lindh, Roland; Malmqvist, Per-Åke https://doi.org/10.1021/jp031064+		December 2003
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
Structures of eleven perylene-3,4:9,10-bis(dicarboximide) pigments Hädicke, E.; Graser, F. Acta Crystallographica Section C Crystal Structure Communications, Vol. 42, Issue 2 https://doi.org/10.1107/S0108270186096828	journal	February 1986
Accurate and simple density functional for the electronic exchange energy: Generalized gradient approximation Perdew, John P.; Yue, Wang Physical Review B, Vol. 33, Issue 12 https://doi.org/10.1103/PhysRevB.33.8800	journal	June 1986
Theoretical Modeling of Singlet Fission Casanova, David Chemical Reviews, Vol. 118, Issue 15 https://doi.org/10.1021/acs.chemrev.7b00601	journal	April 2018
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
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
Singlet fission in pentacene through multi-exciton quantum states Zimmerman, Paul M.; Zhang, Zhiyong; Musgrave, Charles B. Nature Chemistry, Vol. 2, Issue 8 https://doi.org/10.1038/nchem.694	journal	June 2010
Structures of three perylene-3,4,9,10-bis(dicarboximide) pigments Hädicke, E.; Graser, F. Acta Crystallographica Section C Crystal Structure Communications, Vol. 42, Issue 2 https://doi.org/10.1107/S0108270186096816	journal	February 1986
Electronic couplings for molecular charge transfer: Benchmarking CDFT, FODFT, and FODFTB against high-level ab initio calculations Kubas, Adam; Hoffmann, Felix; Heck, Alexander The Journal of Chemical Physics, Vol. 140, Issue 10 https://doi.org/10.1063/1.4867077	journal	March 2014
Crystallochromy as a solid-state effect: correlation of molecular conformation, crystal packing and colour in perylene-3,4:9,10-bis(dicarboximide) pigments Klebe, G.; Graser, F.; Hädicke, E. Acta Crystallographica Section B Structural Science, Vol. 45, Issue 1 https://doi.org/10.1107/S0108768188010407	journal	February 1989
Singlet fission from upper excited singlet states and polaron formation in rubrene film Wu, Tong; Ni, Wenjun; Gurzadyan, Gagik G. RSC Advances, Vol. 11, Issue 8 https://doi.org/10.1039/D0RA10780H	journal	January 2021
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
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
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
The Electronic Couplings in Electron Transfer and Excitation Energy Transfer Hsu, Chao-Ping Accounts of Chemical Research, Vol. 42, Issue 4 https://doi.org/10.1021/ar800153f	journal	April 2009
Towards multistate multimode landscapes in singlet fission of pentacene: the dual role of charge-transfer states Walia, Rajat; Deng, Zexiang; Yang, Jun Chemical Science, Vol. 12, Issue 39 https://doi.org/10.1039/D1SC01703A	journal	January 2021
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
Singlet Fission Smith, Millicent B.; Michl, Josef Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr1002613	journal	November 2010
Influence of a polarizable surrounding on the electronically excited states of aggregated perylene materials Bellinger, Daniel; Settels, Volker; Liu, Wenlan Journal of Computational Chemistry, Vol. 37, Issue 17 https://doi.org/10.1002/jcc.24376	journal	March 2016
Systematic optimization of long-range corrected hybrid density functionals Chai, Jeng-Da; Head-Gordon, Martin The Journal of Chemical Physics, Vol. 128, Issue 8 https://doi.org/10.1063/1.2834918	journal	February 2008
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Weigend, Florian; Ahlrichs, Reinhart Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305 https://doi.org/10.1039/b508541a	journal	January 2005
Spin-flip methods in quantum chemistry Casanova, David; Krylov, Anna I. Physical Chemistry Chemical Physics, Vol. 22, Issue 8 https://doi.org/10.1039/C9CP06507E	journal	January 2020
Light Harvesting for Organic Photovoltaics Hedley, Gordon J.; Ruseckas, Arvydas; Samuel, Ifor D. W. Chemical Reviews, Vol. 117, Issue 2 https://doi.org/10.1021/acs.chemrev.6b00215	journal	March 2016
The OpenMolcas Web: A Community-Driven Approach to Advancing Computational Chemistry Li Manni, Giovanni; Fdez. Galván, Ignacio; Alavi, Ali Journal of Chemical Theory and Computation https://doi.org/10.1021/acs.jctc.3c00182	journal	May 2023
Explorative computational study of the singlet fission process Havenith, Remco W. A.; de Gier, Hilde D.; Broer, Ria Molecular Physics, Vol. 110, Issue 19-20 https://doi.org/10.1080/00268976.2012.695810	journal	April 2012
Calculating Electron-Transfer Coupling with Density Functional Theory: The Long-Range-Corrected Density Functionals You, Zhi-Qiang; Hung, Yi-Chen; Hsu, Chao-Ping The Journal of Physical Chemistry B, Vol. 119, Issue 24 https://doi.org/10.1021/jp511216c	journal	December 2014
Modern quantum chemistry with [Open]Molcas Aquilante, Francesco; Autschbach, Jochen; Baiardi, Alberto The Journal of Chemical Physics, Vol. 152, Issue 21 https://doi.org/10.1063/5.0004835	journal	June 2020
Geometry relaxation-mediated localization and delocalization of excitons in organic semiconductors: A quantum chemical study Deutsch, M.; Wirsing, S.; Kaiser, D. The Journal of Chemical Physics, Vol. 153, Issue 22 https://doi.org/10.1063/5.0028943	journal	December 2020
Electronic couplings for molecular charge transfer: benchmarking CDFT, FODFT and FODFTB against high-level ab initio calculations. II Kubas, Adam; Gajdos, Fruzsina; Heck, Alexander Physical Chemistry Chemical Physics, Vol. 17, Issue 22 https://doi.org/10.1039/C4CP04749D	journal	January 2015
Exciton Correlations in Intramolecular Singlet Fission Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B. Journal of the American Chemical Society, Vol. 138, Issue 23 https://doi.org/10.1021/jacs.6b00657	journal	June 2016
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
Density-functional exchange-energy approximation with correct asymptotic behavior Becke, A. D. Physical Review A, Vol. 38, Issue 6 https://doi.org/10.1103/PhysRevA.38.3098	journal	September 1988
Observation of long-range exciton diffusion in highly ordered organic semiconductors Najafov, H.; Lee, B.; Zhou, Q. Nature Materials, Vol. 9, Issue 11 https://doi.org/10.1038/nmat2872	journal	October 2010
On couplings and excimers: lessons from studies of singlet fission in covalently linked tetracene dimers Feng, Xintian; Krylov, Anna I. Physical Chemistry Chemical Physics, Vol. 18, Issue 11 https://doi.org/10.1039/C6CP00177G	journal	January 2016
Singlet Fission Involves an Interplay between Energetic Driving Force and Electronic Coupling in Perylenediimide Films Le, Aaron K.; Bender, Jon A.; Arias, Dylan H. Journal of the American Chemical Society, Vol. 140, Issue 2 https://doi.org/10.1021/jacs.7b11888	journal	January 2018
GronOR: Scalable and Accelerated Nonorthogonal Configuration Interaction for Molecular Fragment Wave Functions Straatsma, T. P.; Broer, R.; Sánchez-Mansilla, A. Journal of Chemical Theory and Computation, Vol. 18, Issue 6 https://doi.org/10.1021/acs.jctc.2c00266	journal	May 2022
Intra- and Intermolecular Singlet Fission in Covalently Linked Dimers Feng, Xintian; Casanova, David; Krylov, Anna I. The Journal of Physical Chemistry C, Vol. 120, Issue 34 https://doi.org/10.1021/acs.jpcc.6b07666	journal	August 2016
Chromophore Multiplication To Enable Exciton Delocalization and Triplet Diffusion Following Singlet Fission in Tetrameric Pentacene Hetzer, Constantin; Basel, Bettina S.; Kopp, Sebastian M. Angewandte Chemie, Vol. 131, Issue 43 https://doi.org/10.1002/ange.201907221	journal	September 2019
The Nature of Singlet Exciton Fission in Carotenoid Aggregates Musser, Andrew J.; Maiuri, Margherita; Brida, Daniele Journal of the American Chemical Society, Vol. 137, Issue 15 https://doi.org/10.1021/jacs.5b01130	journal	April 2015
Mechanism of Singlet Fission in Thin Films of 1,3-Diphenylisobenzofuran Schrauben, Joel N.; Ryerson, Joseph L.; Michl, Josef Journal of the American Chemical Society, Vol. 136, Issue 20 https://doi.org/10.1021/ja501337b	journal	May 2014
Reduced Common Molecular Orbital Basis for Nonorthogonal Configuration Interaction Kathir, R. K.; de Graaf, Coen; Broer, Ria Journal of Chemical Theory and Computation, Vol. 16, Issue 5 https://doi.org/10.1021/acs.jctc.9b01144	journal	April 2020
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Singlet Fission Rate: Optimized Packing of a Molecular Pair. Ethylene as a Model Zaykov, Alexandr; Felkel, Petr; Buchanan, Eric A. Journal of the American Chemical Society, Vol. 141, Issue 44 https://doi.org/10.1021/jacs.9b08173	journal	September 2019
The IPEA dilemma in CASPT2 Zobel, J. Patrick; Nogueira, Juan J.; González, Leticia Chemical Science, Vol. 8, Issue 2 https://doi.org/10.1039/C6SC03759C	journal	January 2017
On the role of dynamic electron correlation in non-orthogonal configuration interaction with fragments Sánchez-Mansilla, A.; Sousa, C.; Kathir, R. K. Physical Chemistry Chemical Physics, Vol. 24, Issue 19 https://doi.org/10.1039/D2CP00772J	journal	January 2022
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
A Simple Kinetic Model for Singlet Fission: A Role of Electronic and Entropic Contributions to Macroscopic Rates Kolomeisky, Anatoly B.; Feng, Xintian; Krylov, Anna I. The Journal of Physical Chemistry C, Vol. 118, Issue 10 https://doi.org/10.1021/jp4128176	journal	February 2014
A design strategy for intramolecular singlet fission mediated by charge-transfer states in donor–acceptor organic materials Busby, Erik; Xia, Jianlong; Wu, Qin Nature Materials, Vol. 14, Issue 4 https://doi.org/10.1038/nmat4175	journal	January 2015
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Dissecting the Effect of Morphology on the Rates of Singlet Fission: Insights from Theory Feng, Xintian; Kolomeisky, Anatoly B.; Krylov, Anna I. The Journal of Physical Chemistry C, Vol. 118, Issue 34 https://doi.org/10.1021/jp505942k	journal	August 2014
The role of CT excitations in PDI aggregates Zubiria-Ulacia, Maria; Matxain, Jon M.; Casanova, David Physical Chemistry Chemical Physics, Vol. 22, Issue 28 https://doi.org/10.1039/D0CP02344B	journal	January 2020
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
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
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 ORCA quantum chemistry program package Neese, Frank; Wennmohs, Frank; Becker, Ute The Journal of Chemical Physics, Vol. 152, Issue 22 https://doi.org/10.1063/5.0004608	journal	June 2020
Charge transfer in organic molecules for solar cells: theoretical perspective Zhao, Yi; Liang, WanZhen Chem. Soc. Rev., Vol. 41, Issue 3 https://doi.org/10.1039/C1CS15207F	journal	January 2012
A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP) Yanai, Takeshi; Tew, David P.; Handy, Nicholas C. Chemical Physics Letters, Vol. 393, Issue 1-3, p. 51-57 https://doi.org/10.1016/j.cplett.2004.06.011	journal	July 2004
GronOR: Massively parallel and GPU-accelerated non-orthogonal configuration interaction for large molecular systems Straatsma, T. P.; Broer, R.; Faraji, S. The Journal of Chemical Physics, Vol. 152, Issue 6 https://doi.org/10.1063/1.5141358	journal	February 2020
Photochemistry of 3,4,9,10-perylenetetracarboxylic dianhydride dyes. 3. Singlet and triplet excited-state properties of the bis(2,5-di-tert-butylphenyl)imide derivative Ford, William E.; Kamat, Prashant V. The Journal of Physical Chemistry, Vol. 91, Issue 25 https://doi.org/10.1021/j100309a012	journal	December 1987

Similar Records

Harvesting electrons and holes from photodriven symmetry-breaking charge separation within a perylenediimide photosynthetic model dimer

Journal Article · 2023 · Proceedings of the National Academy of Sciences of the United States of America · OSTI ID:2217252

Bradley, Jillian M.; Coleman, Adam F.; Brown, Paige J.; +3 more

Probing Chromophore Energetics and Couplings for Singlet Fission in Solar Cell Applications: Final technical report

Technical Report · 2018 · OSTI ID:1469697

Garand, Etienne

Lasing action in a family of perylene derivatives: Singlet absorption and emission spectra, triplet absorption and oxygen quenching constants, and molecular mechanics and semiempirical molecular orbital calcuations

Journal Article · 1992 · Journal of Physical Chemistry · OSTI ID:554913

Sadrai, M; Hadel, L; Sauers, R R

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Electrical energy
Monomers
Nuclear fission
Oligomers
Wave function

Title: A Nonorthogonal Configuration Interaction Approach to Singlet Fission in Perylenediimide Compounds

Citation Formats

References (65)

Similar Records

Related Subjects