Unified model for singlet fission within a non-conjugated covalent pentacene dimer

Basel, Bettina S.; Zirzlmeier, Johannes; Hetzer, Constantin; Phelan, Brian T.; Krzyaniak, Matthew D.; Reddy, S. Rajagopala; Coto, Pedro B.; Horwitz, Noah E.; Young, Ryan M.; White, Fraser J.; Hampel, Frank; Clark, Timothy; Thoss, Michael; Tykwinski, Rik R.; Wasielewski, Michael R.; Guldi, Dirk M.

doi:10.1038/ncomms15171

Title: Unified model for singlet fission within a non-conjugated covalent pentacene dimer

Journal Article · 18 May 2017 · Nature Communications

DOI: https://doi.org/10.1038/ncomms15171 · OSTI ID:1389775

Basel, Bettina S. ^[1]; Zirzlmeier, Johannes ^[1]; Hetzer, Constantin ^[1]; Phelan, Brian T. ^[2]; Krzyaniak, Matthew D. ^[2]; Reddy, S. Rajagopala ^[1]; Coto, Pedro B. ^[1]; Horwitz, Noah E. ^[2]; Young, Ryan M. ^[2]; White, Fraser J. ^[3]; Hampel, Frank ^[1]; Clark, Timothy ^[1]; Thoss, Michael ^[1]; Tykwinski, Rik R. ^[4]; Wasielewski, Michael R. ^[2]; Guldi, Dirk M. ^[1]

Friedrich-Alexander-Univ. Erlangen-Nurnberg (FAU), Erlangen (Germany)
Northwestern Univ., Evanston, IL (United States)
Rigaku Europe, Sevenoaks (United Kingdom)
Friedrich-Alexander-Univ. Erlangen-Nurnberg (FAU), Erlangen (Germany); Univ. of Alberta, Edmonton, AB (Canada)

When molecular dimers, crystalline films or molecular aggregates absorb a photon to produce a singlet exciton, spin-allowed singlet fission may produce two triplet excitons that can be used to generate two electron–hole pairs, leading to a predicted B50% enhancement in maximum solar cell performance. The singlet fission mechanism is still not well understood. Here we report on the use of time-resolved optical and electron paramagnetic resonance spectroscopy to probe singlet fission in a pentacene dimer linked by a non-conjugated spacer. We observe the key intermediates in the singlet fission process, including the formation and decay of a quintet state that precedes formation of the pentacene triplet excitons. In conclusion, using these combined data, we develop a single kinetic model that describes the data over seven temporal orders of magnitude both at room and cryogenic temperatures.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Northwestern Univ., Evanston, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-99ER14999

OSTI ID:: 1389775

Journal Information:: Nature Communications, Vol. 8; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 160 works

Citation information provided by
Web of Science

References (82)

Efficient Singlet Fission Discovered in a Disordered Acene Film Roberts, Sean T.; McAnally, R. Eric; Mastron, Joseph N. Journal of the American Chemical Society, Vol. 134, Issue 14 https://doi.org/10.1021/ja300504t	journal	March 2012
Strongly exchange-coupled triplet pairs in an organic semiconductor Weiss, Leah R.; Bayliss, Sam L.; Kraffert, Felix Nature Physics, Vol. 13, Issue 2 https://doi.org/10.1038/nphys3908	journal	October 2016
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
Real-time observation of multiexcitonic states in ultrafast singlet fission using coherent 2D electronic spectroscopy Bakulin, Artem A.; Morgan, Sarah E.; Kehoe, Tom B. Nature Chemistry, Vol. 8, Issue 1 https://doi.org/10.1038/nchem.2371	journal	October 2015
Quintet multiexciton dynamics in singlet fission Tayebjee, Murad J. Y.; Sanders, Samuel N.; Kumarasamy, Elango Nature Physics, Vol. 13, Issue 2 https://doi.org/10.1038/nphys3909	journal	October 2016
Solution-based intramolecular singlet fission in cross-conjugated pentacene dimers Zirzlmeier, Johannes; Casillas, Rubén; Reddy, S. Rajagopala Nanoscale, Vol. 8, Issue 19 https://doi.org/10.1039/C6NR02493A	journal	January 2016
Charge Transport across DNA-Based Three-Way Junctions Young, Ryan M.; Singh, Arunoday P. N.; Thazhathveetil, Arun K. Journal of the American Chemical Society, Vol. 137, Issue 15 https://doi.org/10.1021/jacs.5b00931	journal	April 2015
Theory of two coupled triplet states: Application to bicarbene structures Benk, H.; Sixl, H. Molecular Physics, Vol. 42, Issue 4 https://doi.org/10.1080/00268978100100631	journal	March 1981
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
A numerical self-consistent reaction field (SCRF) model for ground and excited states in NDDO-based methods Rauhut, Guntram; Clark, Timothy; Steinke, Thomas Journal of the American Chemical Society, Vol. 115, Issue 20 https://doi.org/10.1021/ja00073a036	journal	October 1993
Self‐Consistent Molecular‐Orbital Methods. IX. An Extended Gaussian‐Type Basis for Molecular‐Orbital Studies of Organic Molecules Ditchfield, R.; Hehre, W. J.; Pople, J. A. The Journal of Chemical Physics, Vol. 54, Issue 2 https://doi.org/10.1063/1.1674902	journal	January 1971
Direct Observation of the Preference of Hole Transfer over Electron Transfer for Radical Ion Pair Recombination in Donor−Bridge−Acceptor Molecules Dance, Zachary E. X.; Ahrens, Michael J.; Vega, Amy M. Journal of the American Chemical Society, Vol. 130, Issue 3 https://doi.org/10.1021/ja077386z	journal	January 2008
A Modular Synthetic Approach to Conjugated Pentacene Di-, Tri-, and Tetramers Lehnherr, Dan; Murray, Adrian H.; McDonald, Robert Angewandte Chemie International Edition, Vol. 49, Issue 35 https://doi.org/10.1002/anie.201000555	journal	July 2010
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
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
Competition between Singlet Fission and Charge Separation in Solution-Processed Blend Films of 6,13-Bis(triisopropylsilylethynyl)pentacene with Sterically-Encumbered Perylene-3,4:9,10-bis(dicarboximide)s Ramanan, Charusheela; Smeigh, Amanda L.; Anthony, John E. Journal of the American Chemical Society, Vol. 134, Issue 1 https://doi.org/10.1021/ja2080482	journal	December 2011
Ultrafast Dynamics of Exciton Fission in Polycrystalline Pentacene Wilson, Mark W. B.; Rao, Akshay; Clark, Jenny Journal of the American Chemical Society, Vol. 133, Issue 31 https://doi.org/10.1021/ja201688h	journal	August 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
Observation of Two Triplet-Pair Intermediates in Singlet Exciton Fission Pensack, Ryan D.; Ostroumov, Evgeny E.; Tilley, Andrew J. The Journal of Physical Chemistry Letters, Vol. 7, Issue 13 https://doi.org/10.1021/acs.jpclett.6b00947	journal	June 2016
Long-Lived Triplet Excited States of Bent-Shaped Pentacene Dimers by Intramolecular Singlet Fission Sakuma, Takao; Sakai, Hayato; Araki, Yasuyuki The Journal of Physical Chemistry A, Vol. 120, Issue 11 https://doi.org/10.1021/acs.jpca.6b00988	journal	March 2016
Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements Francl, Michelle M.; Pietro, William J.; Hehre, Warren J. The Journal of Chemical Physics, Vol. 77, Issue 7, p. 3654-3665 https://doi.org/10.1063/1.444267	journal	October 1982
Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model Dewar, Michael J. S.; Zoebisch, Eve G.; Healy, Eamonn F. Journal of the American Chemical Society, Vol. 107, Issue 13 https://doi.org/10.1021/ja00299a024	journal	June 1985
Observing the Multiexciton State in Singlet Fission and Ensuing Ultrafast Multielectron Transfer Chan, W. -L.; Ligges, M.; Jailaubekov, A. Science, Vol. 334, Issue 6062 https://doi.org/10.1126/science.1213986	journal	December 2011
Correlated Pair States Formed by Singlet Fission and Exciton–Exciton Annihilation Scholes, Gregory D. The Journal of Physical Chemistry A, Vol. 119, Issue 51 https://doi.org/10.1021/acs.jpca.5b09725	journal	December 2015
Effects of Crystal Morphology on Singlet Exciton Fission in Diketopyrrolopyrrole Thin Films Hartnett, Patrick E.; Margulies, Eric A.; Mauck, Catherine M. The Journal of Physical Chemistry B, Vol. 120, Issue 7 https://doi.org/10.1021/acs.jpcb.5b10565	journal	February 2016
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
Direct diabatization of electronic states by the fourfold way. II. Dynamical correlation and rearrangement processes Nakamura, Hisao; Truhlar, Donald G. The Journal of Chemical Physics, Vol. 117, Issue 12 https://doi.org/10.1063/1.1500734	journal	September 2002
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
The photoexcited triplet state and photosynthesis Levanon, Haim.; Norris, James R. Chemical Reviews, Vol. 78, Issue 3 https://doi.org/10.1021/cr60313a001	journal	June 1978
A Direct Mechanism of Ultrafast Intramolecular Singlet Fission in Pentacene Dimers Fuemmeler, Eric G.; Sanders, Samuel N.; Pun, Andrew B. ACS Central Science, Vol. 2, Issue 5 https://doi.org/10.1021/acscentsci.6b00063	journal	May 2016
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
Extended multi-configuration quasi-degenerate perturbation theory: The new approach to multi-state multi-reference perturbation theory Granovsky, Alexander A. The Journal of Chemical Physics, Vol. 134, Issue 21 https://doi.org/10.1063/1.3596699	journal	June 2011
Singlet fission in pentacene dimers Zirzlmeier, Johannes; Lehnherr, Dan; Coto, Pedro B. Proceedings of the National Academy of Sciences, Vol. 112, Issue 17 https://doi.org/10.1073/pnas.1422436112	journal	April 2015
Singlet Fission Smith, Millicent B.; Michl, Josef Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr1002613	journal	November 2010
Theory of Magnetic Field Effects on the Mutual Annihilation of Triplet Excitons Merrifield, R. E. The Journal of Chemical Physics, Vol. 48, Issue 9 https://doi.org/10.1063/1.1669777	journal	May 1968
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
General atomic and molecular electronic structure system Schmidt, Michael W.; Baldridge, Kim K.; Boatz, Jerry A. Journal of Computational Chemistry, Vol. 14, Issue 11, p. 1347-1363 https://doi.org/10.1002/jcc.540141112	journal	November 1993
Quantum Beats in Crystalline Tetracene Delayed Fluorescence Due to Triplet Pair Coherences Produced by Direct Singlet Fission Burdett, Jonathan J.; Bardeen, Christopher J. Journal of the American Chemical Society, Vol. 134, Issue 20 https://doi.org/10.1021/ja301683w	journal	May 2012
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
Near-transform-limited visible and near-IR femtosecond pulses from optical parametric amplification using Type II β-barium borate Greenfield, Scott R.; Wasielewski, Michael R. Optics Letters, Vol. 20, Issue 12 https://doi.org/10.1364/OL.20.001394	journal	January 1995
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
Solvent response and dielectric relaxation in supercooled butyronitrile Ito, Naoki; Duvvuri, Kalyan; Matyushov, Dmitry V. The Journal of Chemical Physics, Vol. 125, Issue 2 https://doi.org/10.1063/1.2212420	journal	July 2006
High-Yield Singlet Fission in a Zeaxanthin Aggregate Observed by Picosecond Resonance Raman Spectroscopy Wang, Chen; Tauber, Michael J. Journal of the American Chemical Society, Vol. 132, Issue 40 https://doi.org/10.1021/ja102851m	journal	October 2010
Intruder state avoidance multireference Møller-Plesset perturbation theory: Multireference Møller-Plesset Perturbation Theory Witek, Henryk A.; Choe, Yoong-Kee; Finley, James P. Journal of Computational Chemistry, Vol. 23, Issue 10 https://doi.org/10.1002/jcc.10098	journal	May 2002
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
Tuneable Singlet Exciton Fission and Triplet-Triplet Annihilation in an Orthogonal Pentacene Dimer Lukman, Steven; Musser, Andrew J.; Chen, Kai Advanced Functional Materials, Vol. 25, Issue 34 https://doi.org/10.1002/adfm.201501537	journal	August 2015
Maximizing Singlet Fission in Organic Dimers: Theoretical Investigation of Triplet Yield in the Regime of Localized Excitation and Fast Coherent Electron Transfer ^† Greyson, Eric C.; Vura-Weis, Josh; Michl, Josef The Journal of Physical Chemistry B, Vol. 114, Issue 45 https://doi.org/10.1021/jp907392q	journal	November 2010
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
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
The direct calculation of diabatic states based on configurational uniformity Nakamura, Hisao; Truhlar, Donald G. The Journal of Chemical Physics, Vol. 115, Issue 22 https://doi.org/10.1063/1.1412879	journal	January 2001
Purification of Organic Chemicals Armarego, Wilfred L. F.; Chai, Christina Purification of Laboratory Chemicals https://doi.org/10.1016/B978-0-12-382161-4.00004-2	book	January 2013
Strongly exchange-coupled triplet pairs in an organic semiconductor Weiss, Leah; Bayliss, Sam L.; Kraffert, Felix Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.5906	text	January 2016
A Modular Synthetic Approach to Conjugated Pentacene Di-, Tri-, and Tetramers Lehnherr, Dan; Murray, Adrian H.; McDonald, Robert Angewandte Chemie, Vol. 122, Issue 35 https://doi.org/10.1002/ange.201000555	journal	July 2010
Singlet Fission Tykwinski, Rik R.; Guldi, Dirk M. ChemPhotoChem, Vol. 5, Issue 5 https://doi.org/10.1002/cptc.202100053	journal	April 2021
An Antifungal Polycyclic Tetramate Macrolactam, Heat-Stable Antifungal Factor (HSAF), Is a Novel Oxidative Stress Modulator in Lysobacter enzymogenes Yu, Lingjun; Li, Hui; Zhou, Zaichun Applied and Environmental Microbiology, Vol. 87, Issue 10 https://doi.org/10.1128/aem.03105-20	journal	April 2021
Deazaflavin reductive photocatalysis involves excited semiquinone radicals Graml, Andreas; Neveselý, Tomáš; Kutta, Roger Jan Universität Regensburg https://doi.org/10.5283/epub.43436	text	January 2020
Purification of Organic Chemicals Armarego, Wilfred L. F.; Chai, Christina Li Lin Purification of Laboratory Chemicals https://doi.org/10.1016/b978-1-85617-567-8.50012-3	book	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. arXiv https://doi.org/10.48550/arxiv.1211.6459	text	January 2012
A Modular Synthetic Approach to Conjugated Pentacene Di-, Tri-, and Tetramers Lehnherr, Dan; Murray, Adrian H.; McDonald, Robert Angewandte Chemie International Edition, Vol. 49, Issue 35 https://doi.org/10.1002/anie.201000555	journal	July 2010
Numerical self-consistent reaction field study of intramolecular charge transfer in p-(dimethylamino)-benzonitrile Gedeck, Peter; Schneider, Siegfried Journal of Photochemistry and Photobiology A: Chemistry, Vol. 105, Issue 2-3 https://doi.org/10.1016/s1010-6030(96)04568-6	journal	May 1997
Correlated Pair States Formed by Singlet Fission and Exciton–Exciton Annihilation Scholes, Gregory D. The Journal of Physical Chemistry A, Vol. 119, Issue 51 https://doi.org/10.1021/acs.jpca.5b09725	journal	December 2015
Long-Lived Triplet Excited States of Bent-Shaped Pentacene Dimers by Intramolecular Singlet Fission Sakuma, Takao; Sakai, Hayato; Araki, Yasuyuki The Journal of Physical Chemistry A, Vol. 120, Issue 11 https://doi.org/10.1021/acs.jpca.6b00988	journal	March 2016
Effects of Crystal Morphology on Singlet Exciton Fission in Diketopyrrolopyrrole Thin Films Hartnett, Patrick E.; Margulies, Eric A.; Mauck, Catherine M. The Journal of Physical Chemistry B, Vol. 120, Issue 7 https://doi.org/10.1021/acs.jpcb.5b10565	journal	February 2016
Observation of Two Triplet-Pair Intermediates in Singlet Exciton Fission Pensack, Ryan D.; Ostroumov, Evgeny E.; Tilley, Andrew J. The Journal of Physical Chemistry Letters, Vol. 7, Issue 13 https://doi.org/10.1021/acs.jpclett.6b00947	journal	June 2016
A Direct Mechanism of Ultrafast Intramolecular Singlet Fission in Pentacene Dimers Fuemmeler, Eric G.; Sanders, Samuel N.; Pun, Andrew B. ACS Central Science, Vol. 2, Issue 5 https://doi.org/10.1021/acscentsci.6b00063	journal	May 2016
The photoexcited triplet state and photosynthesis Levanon, Haim.; Norris, James R. Chemical Reviews, Vol. 78, Issue 3 https://doi.org/10.1021/cr60313a001	journal	June 1978
A numerical self-consistent reaction field (SCRF) model for ground and excited states in NDDO-based methods Rauhut, Guntram; Clark, Timothy; Steinke, Thomas Journal of the American Chemical Society, Vol. 115, Issue 20 https://doi.org/10.1021/ja00073a036	journal	October 1993
Direct Observation of the Preference of Hole Transfer over Electron Transfer for Radical Ion Pair Recombination in Donor−Bridge−Acceptor Molecules Dance, Zachary E. X.; Ahrens, Michael J.; Vega, Amy M. Journal of the American Chemical Society, Vol. 130, Issue 3 https://doi.org/10.1021/ja077386z	journal	January 2008
High-Yield Singlet Fission in a Zeaxanthin Aggregate Observed by Picosecond Resonance Raman Spectroscopy Wang, Chen; Tauber, Michael J. Journal of the American Chemical Society, Vol. 132, Issue 40 https://doi.org/10.1021/ja102851m	journal	October 2010
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
Ultrafast Dynamics of Exciton Fission in Polycrystalline Pentacene Wilson, Mark W. B.; Rao, Akshay; Clark, Jenny Journal of the American Chemical Society, Vol. 133, Issue 31 https://doi.org/10.1021/ja201688h	journal	August 2011
Competition between Singlet Fission and Charge Separation in Solution-Processed Blend Films of 6,13-Bis(triisopropylsilylethynyl)pentacene with Sterically-Encumbered Perylene-3,4:9,10-bis(dicarboximide)s Ramanan, Charusheela; Smeigh, Amanda L.; Anthony, John E. Journal of the American Chemical Society, Vol. 134, Issue 1 https://doi.org/10.1021/ja2080482	journal	December 2011
Efficient Singlet Fission Discovered in a Disordered Acene Film Roberts, Sean T.; McAnally, R. Eric; Mastron, Joseph N. Journal of the American Chemical Society, Vol. 134, Issue 14 https://doi.org/10.1021/ja300504t	journal	March 2012
Quantum Beats in Crystalline Tetracene Delayed Fluorescence Due to Triplet Pair Coherences Produced by Direct Singlet Fission Burdett, Jonathan J.; Bardeen, Christopher J. Journal of the American Chemical Society, Vol. 134, Issue 20 https://doi.org/10.1021/ja301683w	journal	May 2012
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
Charge Transport across DNA-Based Three-Way Junctions Young, Ryan M.; Singh, Arunoday P. N.; Thazhathveetil, Arun K. Journal of the American Chemical Society, Vol. 137, Issue 15 https://doi.org/10.1021/jacs.5b00931	journal	April 2015
Maximizing Singlet Fission in Organic Dimers: Theoretical Investigation of Triplet Yield in the Regime of Localized Excitation and Fast Coherent Electron Transfer ^† Greyson, Eric C.; Vura-Weis, Josh; Michl, Josef The Journal of Physical Chemistry B, Vol. 114, Issue 45 https://doi.org/10.1021/jp907392q	journal	November 2010
Real-time observation of multiexcitonic states in ultrafast singlet fission using coherent 2D electronic spectroscopy Bakulin, Artem A.; Morgan, Sarah E.; Kehoe, Tom B. Nature Chemistry, Vol. 8, Issue 1 https://doi.org/10.1038/nchem.2371	journal	October 2015
Solvent response and dielectric relaxation in supercooled butyronitrile Ito, Naoki; Duvvuri, Kalyan; Matyushov, Dmitry V. The Journal of Chemical Physics, Vol. 125, Issue 2 https://doi.org/10.1063/1.2212420	journal	July 2006
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
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

Cited By (45)

Intermolecular Singlet Fission in Unsymmetrical Derivatives of Pentacene in Solution Casillas, Rubén; Adam, Matthias; Coto, Pedro B. Advanced Energy Materials, Vol. 9, Issue 2 https://doi.org/10.1002/aenm.201802221	journal	November 2018
Conformational Planarization versus Singlet Fission: Distinct Excited-State Dynamics of Cyclooctatetraene-Fused Acene Dimers Yamakado, Takuya; Takahashi, Shota; Watanabe, Kazuya Angewandte Chemie, Vol. 130, Issue 19 https://doi.org/10.1002/ange.201802185	journal	March 2018
Feinabstimmung von intramolekularem resonantem Förster-Energietransfer und Aktivierung intramolekularer Singulettspaltung Lavarda, Giulia; Zirzlmeier, Johannes; Gruber, Marco Angewandte Chemie, Vol. 130, Issue 50 https://doi.org/10.1002/ange.201808652	journal	October 2018
Conformational Planarization versus Singlet Fission: Distinct Excited-State Dynamics of Cyclooctatetraene-Fused Acene Dimers Yamakado, Takuya; Takahashi, Shota; Watanabe, Kazuya Angewandte Chemie International Edition, Vol. 57, Issue 19 https://doi.org/10.1002/anie.201802185	journal	March 2018
Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission Lavarda, Giulia; Zirzlmeier, Johannes; Gruber, Marco Angewandte Chemie International Edition, Vol. 57, Issue 50 https://doi.org/10.1002/anie.201808652	journal	October 2018
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 International Edition, Vol. 58, Issue 43 https://doi.org/10.1002/anie.201907221	journal	September 2019
Pentacene Dimers as a Critical Tool for the Investigation of Intramolecular Singlet Fission Hetzer, Constantin; Guldi, Dirk M.; Tykwinski, Rik R. Chemistry - A European Journal, Vol. 24, Issue 33 https://doi.org/10.1002/chem.201705355	journal	March 2018
High‐Yield Generation of Triplet Excited States by an Efficient Sequential Photoinduced Process from Energy Transfer to Singlet Fission in Pentacene‐Modified CdSe/ZnS Quantum Dots Sakai, Hayato; Inaya, Ryutaro; Tkachenko, Nikolai V. Chemistry – A European Journal, Vol. 24, Issue 64 https://doi.org/10.1002/chem.201803257	journal	July 2018
Theoretical Studies of Singlet Fission: Searching for Materials and Exploring Mechanisms Japahuge, Achini; Zeng, Tao ChemPlusChem, Vol. 83, Issue 4 https://doi.org/10.1002/cplu.201700489	journal	February 2018
Competition between Singlet Fission and Spin‐Orbit‐Induced Intersystem Crossing in Anthanthrene and Anthanthrone Derivatives Jue Bae, Youn; Krzyaniak, Matthew D.; Majewski, Marek B. ChemPlusChem, Vol. 84, Issue 9 https://doi.org/10.1002/cplu.201900410	journal	June 2019
Charge-Transfer Character in a Covalent Diketopyrrolopyrrole Dimer: Implications for Singlet Fission Mauck, Catherine M.; Bae, Youn Jue; Chen, Michelle ChemPhotoChem, Vol. 2, Issue 3 https://doi.org/10.1002/cptc.201700135	journal	October 2017
Quantum Master Equation Approach to Singlet Fission Dynamics in Pentacene Linear Aggregate Models: Size Dependences of Excitonic Coupling Effects: Quantum Master Equation Approach to Singlet Fission Dynamics in Pentacene Linear Aggregate Models: Size Dependences of Excitonic Coupling Effects Nakano, Masayoshi; Nagami, Takanori; Tonami, Takayoshi Journal of Computational Chemistry, Vol. 40, Issue 1 https://doi.org/10.1002/jcc.25539	journal	September 2018
Robust singlet fission in pentacene thin films with tuned charge transfer interactions Broch, K.; Dieterle, J.; Branchi, F. Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-03300-1	journal	March 2018
New insights into the design of conjugated polymers for intramolecular singlet fission Hu, Jiahua; Xu, Ke; Shen, Lei Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05389-w	journal	July 2018
Identifying triplet pathways in dilute pentacene films Lubert-Perquel, Daphné; Salvadori, Enrico; Dyson, Matthew Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-06330-x	journal	October 2018
Dehydrative π-extension to nanographenes with zig-zag edges Lungerich, Dominik; Papaianina, Olena; Feofanov, Mikhail Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-07095-z	journal	November 2018
Spin density encodes intramolecular singlet exciton fission in pentacene dimers Krishnapriya, K. C.; Roy, Palas; Puttaraju, Boregowda Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-018-07736-3	journal	January 2019
Ultra-fast intramolecular singlet fission to persistent multiexcitons by molecular design Pun, Andrew B.; Asadpoordarvish, Amir; Kumarasamy, Elango Nature Chemistry, Vol. 11, Issue 9 https://doi.org/10.1038/s41557-019-0297-7	journal	August 2019
Intramolecular singlet fission in a face-to-face stacked tetracene trimer Wang, Xuemin; Wang, Rui; Shen, Li Physical Chemistry Chemical Physics, Vol. 20, Issue 9 https://doi.org/10.1039/c7cp07841b	journal	January 2018
Singlet exciton fission in a linear tetracene tetramer Liu, Heyuan; Wang, Zhiwei; Wang, Xuemin Journal of Materials Chemistry C, Vol. 6, Issue 13 https://doi.org/10.1039/c7tc05783k	journal	January 2018
Singlet fission in self-assembled PDI nanocrystals Schierl, Christoph; Niazov-Elkan, Angelica; Shimon, Linda J. W. Nanoscale, Vol. 10, Issue 43 https://doi.org/10.1039/c8nr04155e	journal	January 2018
Light-harvesting porphyrazines to enable intramolecular singlet fission Medina, Diana-Paola; Papadopoulos, Ilias; Lavarda, Giulia Nanoscale, Vol. 11, Issue 46 https://doi.org/10.1039/c9nr08161e	journal	January 2019
New synthetic approaches for hexacene and its application in thin-film transistors Han, Jian; Liu, Xinbang; Li, Yu Organic Chemistry Frontiers, Vol. 6, Issue 16 https://doi.org/10.1039/c9qo00708c	journal	January 2019
Influence of the heavy-atom effect on singlet fission: a study of platinum-bridged pentacene dimers Basel, Bettina S.; Young, Ryan M.; Krzyaniak, Matthew D. Chemical Science, Vol. 10, Issue 48 https://doi.org/10.1039/c9sc04410h	journal	January 2019
Structural origins of the electronic properties of materials via time-resolved infrared spectroscopy Munson, Kyle T.; Kennehan, Eric R.; Asbury, John B. Journal of Materials Chemistry C, Vol. 7, Issue 20 https://doi.org/10.1039/c9tc01348b	journal	January 2019
Enhancing the intermolecular singlet fission efficiency by controlling the self-assembly of amphipathic tetracene derivatives in aqueous solution Tang, Zhaofeng; Zhou, Sainan; Wang, Xiangyang Journal of Materials Chemistry C, Vol. 7, Issue 36 https://doi.org/10.1039/c9tc04070f	journal	January 2019
Quantum dynamical simulation of intramolecular singlet fission in covalently coupled pentacene dimers Reddy, S. Rajagopala; Coto, Pedro B.; Thoss, Michael The Journal of Chemical Physics, Vol. 151, Issue 4 https://doi.org/10.1063/1.5109897	journal	July 2019
Weakly coupled triplet pair states probed by quantum beating in delayed fluorescence in tetracene crystals Wang, Zhiwei; Zhang, Chunfeng; Wang, Rui The Journal of Chemical Physics, Vol. 151, Issue 13 https://doi.org/10.1063/1.5110188	journal	October 2019
Heavy-atom effects on intramolecular singlet fission in a conjugated polymer Musser, Andrew J.; Al-Hashimi, Mohammed; Heeney, Martin The Journal of Chemical Physics, Vol. 151, Issue 4 https://doi.org/10.1063/1.5110269	journal	July 2019
Substituent effects on energetics and crystal morphology modulate singlet fission in 9,10-bis(phenylethynyl)anthracenes Bae, Youn Jue; Christensen, Joseph A.; Kang, Gyeongwon The Journal of Chemical Physics, Vol. 151, Issue 4 https://doi.org/10.1063/1.5110411	journal	July 2019
Fluctuating exchange interactions enable quintet multiexciton formation in singlet fission Collins, Miles I.; McCamey, Dane R.; Tayebjee, Murad J. Y. The Journal of Chemical Physics, Vol. 151, Issue 16 https://doi.org/10.1063/1.5115816	journal	October 2019
Structure and photophysics of indigoids for singlet fission: Cibalackrot Ryerson, Joseph L.; Zaykov, Alexandr; Aguilar Suarez, Luis E. The Journal of Chemical Physics, Vol. 151, Issue 18 https://doi.org/10.1063/1.5121863	journal	November 2019
Lessons from intramolecular singlet fission with covalently bound chromophores Korovina, Nadezhda V.; Pompetti, Nicholas F.; Johnson, Justin C. The Journal of Chemical Physics, Vol. 152, Issue 4 https://doi.org/10.1063/1.5135307	journal	January 2020
Site-selective measurement of coupled spin pairs in an organic semiconductor Bayliss, S. L.; Weiss, L. R.; Mitioglu, A. Proceedings of the National Academy of Sciences, Vol. 115, Issue 20 https://doi.org/10.1073/pnas.1718868115	journal	May 2018
Quintet-triplet mixing determines the fate of the multiexciton state produced by singlet fission in a terrylenediimide dimer at room temperature Chen, Michelle; Krzyaniak, Matthew D.; Nelson, Jordan N. Proceedings of the National Academy of Sciences, Vol. 116, Issue 17 https://doi.org/10.1073/pnas.1820932116	journal	April 2019
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
Manipulating molecules with strong coupling: harvesting triplet excitons in organic exciton microcavities. Polak, Daniel; Jayaprakash, Rahul; Lyons, Thomas P. Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.51608	text	January 2019
Identifying triplet pathways in dilute pentacene films Lubert-Perquel, Daphné; Salvadori, Enrico; Dyson, Matthew Universität des Saarlandes https://doi.org/10.22028/d291-29310	collection	January 2018
Davydov splitting and singlet fission in excitonically coupled pentacene dimers Basel, Bettina Sabine; Hetzer, Constantin; Zirzlmeier, Johannes Cambridge : RSC https://doi.org/10.34657/5836	null	January 2019
Site-selective measurement of coupled spin pairs in an organic semiconductor Bayliss, S. L.; Behrends, Jan; Bittl, R. Freie Universität Berlin https://doi.org/10.17169/refubium-4217	text	January 2018
Manipulating matter with strong coupling: harvesting triplet excitons in organic exciton microcavities Polak, Daniel; Jayaprakash, Rahul; Leventis, Anastasia arXiv https://doi.org/10.48550/arxiv.1806.09990	text	January 2018
New insights into the design of conjugated polymers for intramolecular singlet fission Hu, Jiahua; Xu, Ke; Shen, Lei Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05389-w	journal	July 2018
Influence of the heavy-atom effect on singlet fission: a study of platinum-bridged pentacene dimers Basel, Bettina S.; Young, Ryan M.; Krzyaniak, Matthew D. Chemical Science, Vol. 10, Issue 48 https://doi.org/10.1039/c9sc04410h	journal	January 2019
Excited-State Processes in Covalent Dimers Investigated with Time-Resolved Electronic and Vibrational Spectroscopy Thomas, Phelan, Brian Unknown https://doi.org/10.21985/n2-z8t2-ng29	text	January 2018
Identifying triplet pathways in dilute pentacene films Lubert-Perquel, Daphné; Salvadori, Enrico; Dyson, Matthew Universität des Saarlandes https://doi.org/10.22028/d291-29310	collection	January 2018