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Title: Lessons from intramolecular singlet fission with covalently bound chromophores

Abstract

Molecular dimers, oligomers, and polymers are versatile components in photophysical and optoelectronic architectures that could impact a large variety of applications. We present a perspective on such systems in the field of singlet fission, which effectively multiplies excitons and produces a unique excited state species, the triplet pair. The choice of chromophore and the nature of the attachment between units, both geometrical and chemical, play a defining role in the dynamical scheme that evolves upon photoexcitation. Specific final outcomes (e.g., separated and uncorrelated triplet pairs) are being sought through rational design of covalently bound chromophore architectures built with guidance from recent fundamental studies that correlate structure with excited state population flow kinetics.

Authors:
 [1];  [1]; ORCiD logo [1]
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  1. National Renewable Energy Lab. (NREL), Golden, CO (United States)
Publication Date:
Research Org.:
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1600904
Alternate Identifier(s):
OSTI ID: 1595504
Report Number(s):
NREL/JA-5900-75360
Journal ID: ISSN 0021-9606; TRN: US2103600
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Chemical Physics
Additional Journal Information:
Journal Volume: 152; Journal Issue: 4; Journal ID: ISSN 0021-9606
Publisher:
American Institute of Physics (AIP)
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; isomerism; photochemistry; ultrafast molecular spectra; molecular dynamics; photoexcitations; delocalization; electronic coupling; chemical compounds; excitons; chemical bonding

Citation Formats

Korovina, Nadezhda, Pompetti, Nicholas, and Johnson, Justin C. Lessons from intramolecular singlet fission with covalently bound chromophores. United States: N. p., 2020. Web. doi:10.1063/1.5135307.
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Korovina, Nadezhda, Pompetti, Nicholas, & Johnson, Justin C. Lessons from intramolecular singlet fission with covalently bound chromophores. United States. https://doi.org/10.1063/1.5135307
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Korovina, Nadezhda, Pompetti, Nicholas, and Johnson, Justin C. Tue . "Lessons from intramolecular singlet fission with covalently bound chromophores". United States. https://doi.org/10.1063/1.5135307. https://www.osti.gov/servlets/purl/1600904.
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@article{osti_1600904,
title = {Lessons from intramolecular singlet fission with covalently bound chromophores},
author = {Korovina, Nadezhda and Pompetti, Nicholas and Johnson, Justin C.},
abstractNote = {Molecular dimers, oligomers, and polymers are versatile components in photophysical and optoelectronic architectures that could impact a large variety of applications. We present a perspective on such systems in the field of singlet fission, which effectively multiplies excitons and produces a unique excited state species, the triplet pair. The choice of chromophore and the nature of the attachment between units, both geometrical and chemical, play a defining role in the dynamical scheme that evolves upon photoexcitation. Specific final outcomes (e.g., separated and uncorrelated triplet pairs) are being sought through rational design of covalently bound chromophore architectures built with guidance from recent fundamental studies that correlate structure with excited state population flow kinetics.},
doi = {10.1063/1.5135307},
journal = {Journal of Chemical Physics},
number = 4,
volume = 152,
place = {United States},
year = {Tue Jan 28 00:00:00 EST 2020},
month = {Tue Jan 28 00:00:00 EST 2020}
}
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New insights into the design of conjugated polymers for intramolecular singlet fission
journal, July 2018

Fission of a higher excited state generated by singlet exciton fusion in an anthracene crystal
journal, August 1992

Exergonic Intramolecular Singlet Fission of an Adamantane-Linked Tetracene Dyad via Twin Quintet Multiexcitons
journal, July 2019

  • Matsui, Yasunori; Kawaoka, Shuhei; Nagashima, Hiroki
  • The Journal of Physical Chemistry C, Vol. 123, Issue 31
  • DOI: 10.1021/acs.jpcc.9b04503

Singlet Fission from Upper Excited Electronic States of Cofacial Perylene Dimer
journal, April 2019

  • Ni, Wenjun; Gurzadyan, Gagik G.; Zhao, Jianzhang
  • The Journal of Physical Chemistry Letters, Vol. 10, Issue 10
  • DOI: 10.1021/acs.jpclett.9b00717

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
journal, December 2011

  • Ramanan, Charusheela; Smeigh, Amanda L.; Anthony, John E.
  • Journal of the American Chemical Society, Vol. 134, Issue 1
  • DOI: 10.1021/ja2080482

Pentacenes: A Molecular Ruler for Singlet Fission
journal, April 2019

Exciton Fission and Fusion in Bis(tetracene) Molecules with Different Covalent Linker Structures
journal, November 2007

  • Müller, Astrid M.; Avlasevich, Yuri S.; Schoeller, Wolfgang W.
  • Journal of the American Chemical Society, Vol. 129, Issue 46, p. 14240-14250
  • DOI: 10.1021/ja073173y

Theoretical Investigation of Singlet Fission in Molecular Dimers: The Role of Charge Transfer States and Quantum Interference
journal, June 2014

  • Mirjani, Fatemeh; Renaud, Nicolas; Gorczak, Natalie
  • The Journal of Physical Chemistry C, Vol. 118, Issue 26
  • DOI: 10.1021/jp503398a

Exciton fission in excimer forming crystal. Dynamics of an excimer build-up in α-perylene
journal, December 1978

Singlet fission in pancake-bonded systems
journal, January 2017

  • Ito, S.; Nagami, T.; Nakano, M.
  • Physical Chemistry Chemical Physics, Vol. 19, Issue 8
  • DOI: 10.1039/C6CP07641F

Long-Lived Triplet Excited States of Bent-Shaped Pentacene Dimers by Intramolecular Singlet Fission
journal, March 2016

  • Sakuma, Takao; Sakai, Hayato; Araki, Yasuyuki
  • The Journal of Physical Chemistry A, Vol. 120, Issue 11
  • DOI: 10.1021/acs.jpca.6b00988

Multiexciton Dynamics Depending on Intramolecular Orientations in Pentacene Dimers: Recombination and Dissociation of Correlated Triplet Pairs
journal, May 2018

  • Sakai, Hayato; Inaya, Ryutaro; Nagashima, Hiroki
  • The Journal of Physical Chemistry Letters, Vol. 9, Issue 12
  • DOI: 10.1021/acs.jpclett.8b01184

Observing the Multiexciton State in Singlet Fission and Ensuing Ultrafast Multielectron Transfer
journal, December 2011

Tunable Electronic Coupling and Driving Force in Structurally Well-Defined Tetracene Dimers for Molecular Singlet Fission: A Computational Exploration Using Density Functional Theory
journal, September 2013

  • Vallett, Paul J.; Snyder, Jamie L.; Damrauer, Niels H.
  • The Journal of Physical Chemistry A, Vol. 117, Issue 42
  • DOI: 10.1021/jp407426q

Blue-Green Up-Conversion: Noncoherent Excitation by NIR Light
journal, October 2007

  • Baluschev, Stanislav; Yakutkin, Vladimir; Miteva, Tzenka
  • Angewandte Chemie International Edition, Vol. 46, Issue 40
  • DOI: 10.1002/anie.200700414

Excited Singlet States of Covalently Bound, Cofacial Dimers and Trimers of Perylene-3,4:9,10-bis(dicarboximide)s
journal, March 2008

  • Giaimo, Jovan M.; Lockard, Jenny V.; Sinks, Louise E.
  • The Journal of Physical Chemistry A, Vol. 112, Issue 11
  • DOI: 10.1021/jp710847q

Singlet exciton fission in solution
journal, November 2013

  • Walker, Brian J.; Musser, Andrew J.; Beljonne, David
  • Nature Chemistry, Vol. 5, Issue 12
  • DOI: 10.1038/nchem.1801

Singlet Fission for Dye-Sensitized Solar Cells:  Can a Suitable Sensitizer Be Found?
journal, December 2006

  • Paci, Irina; Johnson, Justin C.; Chen, Xudong
  • Journal of the American Chemical Society, Vol. 128, Issue 51
  • DOI: 10.1021/ja063980h

Understanding the Bound Triplet-Pair State in Singlet Fission
journal, August 2019

A Direct Mechanism of Ultrafast Intramolecular Singlet Fission in Pentacene Dimers
journal, May 2016

Heavy-atom effects on intramolecular singlet fission in a conjugated polymer
journal, July 2019

  • Musser, Andrew J.; Al-Hashimi, Mohammed; Heeney, Martin
  • The Journal of Chemical Physics, Vol. 151, Issue 4
  • DOI: 10.1063/1.5110269

Harvesting Singlet Fission for Solar Energy Conversion: One- versus Two-Electron Transfer from the Quantum Mechanical Superposition
journal, October 2012

  • Chan, Wai-Lun; Tritsch, John R.; Zhu, X. -Y.
  • Journal of the American Chemical Society, Vol. 134, Issue 44
  • DOI: 10.1021/ja306271y

Photophysics of a Butadiyne-Linked Porphyrin Dimer:  Influence of Conformational Flexibility in the Ground and First Singlet Excited State
journal, May 2007

  • Winters, Mikael U.; Kärnbratt, Joakim; Eng, Mattias
  • The Journal of Physical Chemistry C, Vol. 111, Issue 19
  • DOI: 10.1021/jp0683519

Evidence for Charge-Transfer Mediation in the Primary Events of Singlet Fission in a Weakly Coupled Pentacene Dimer
journal, May 2018

Morphology-Independent Efficient Singlet Exciton Fission in Perylene Diimide Thin Films
journal, February 2018

  • Aulin, Yaroslav V.; Felter, Kevin M.; Günbas, D. Deniz
  • ChemPlusChem, Vol. 83, Issue 4
  • DOI: 10.1002/cplu.201700449

Singlet fission in pentacene dimers
journal, April 2015

  • Zirzlmeier, Johannes; Lehnherr, Dan; Coto, Pedro B.
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 17
  • DOI: 10.1073/pnas.1422436112

Ultrafast Singlet Fission in a Push–Pull Low-Bandgap Polymer Film
journal, December 2015

  • Kasai, Yukitomo; Tamai, Yasunari; Ohkita, Hideo
  • Journal of the American Chemical Society, Vol. 137, Issue 51
  • DOI: 10.1021/jacs.5b09361

Triplet Harvesting from Intramolecular Singlet Fission in Polytetracene
journal, September 2017

  • Pun, Andrew B.; Sanders, Samuel N.; Kumarasamy, Elango
  • Advanced Materials, Vol. 29, Issue 41
  • DOI: 10.1002/adma.201701416

Quantum Beats in Crystalline Tetracene Delayed Fluorescence Due to Triplet Pair Coherences Produced by Direct Singlet Fission
journal, May 2012

  • Burdett, Jonathan J.; Bardeen, Christopher J.
  • Journal of the American Chemical Society, Vol. 134, Issue 20
  • DOI: 10.1021/ja301683w

External Quantum Efficiency Above 100% in a Singlet-Exciton-Fission-Based Organic Photovoltaic Cell
journal, April 2013

Enabling singlet fission by controlling intramolecular charge transfer in π-stacked covalent terrylenediimide dimers
journal, August 2016

  • Margulies, Eric A.; Miller, Claire E.; Wu, Yilei
  • Nature Chemistry, Vol. 8, Issue 12
  • DOI: 10.1038/nchem.2589

Resonant energy transfer of triplet excitons from pentacene to PbSe nanocrystals
journal, October 2014

  • Tabachnyk, Maxim; Ehrler, Bruno; Gélinas, Simon
  • Nature Materials, Vol. 13, Issue 11
  • DOI: 10.1038/nmat4093

Tuning the role of charge-transfer states in intramolecular singlet exciton fission through side-group engineering
journal, December 2016

  • Lukman, Steven; Chen, Kai; Hodgkiss, Justin M.
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms13622

Singlet Exciton Fission in Polycrystalline Thin Films of a Slip-Stacked Perylenediimide
journal, September 2013

  • Eaton, Samuel W.; Shoer, Leah E.; Karlen, Steven D.
  • Journal of the American Chemical Society, Vol. 135, Issue 39
  • DOI: 10.1021/ja4053174

Charge transfer exciton fission in anthracene crystals
journal, April 1972

Synthesis and photophysical properties of a “face-to-face” stacked tetracene dimer
journal, January 2015

  • Liu, Heyuan; Nichols, Valerie M.; Shen, Li
  • Physical Chemistry Chemical Physics, Vol. 17, Issue 9
  • DOI: 10.1039/C4CP05444J

Excimer Formation and Symmetry-Breaking Charge Transfer in Cofacial Perylene Dimers
journal, February 2017

  • Cook, Rita E.; Phelan, Brian T.; Kamire, Rebecca J.
  • The Journal of Physical Chemistry A, Vol. 121, Issue 8
  • DOI: 10.1021/acs.jpca.6b12644

Annihilator dimers enhance triplet fusion upconversion
journal, January 2019

  • Pun, Andrew B.; Sanders, Samuel N.; Sfeir, Matthew Y.
  • Chemical Science, Vol. 10, Issue 14
  • DOI: 10.1039/C8SC03725F

Spin density encodes intramolecular singlet exciton fission in pentacene dimers
journal, January 2019

Guidance for Mutual Disposition of Chromophores for Singlet Fission
journal, October 2015

Energy harvesting of non-emissive triplet excitons in tetracene by emissive PbS nanocrystals
journal, October 2014

  • Thompson, Nicholas J.; Wilson, Mark W. B.; Congreve, Daniel N.
  • Nature Materials, Vol. 13, Issue 11
  • DOI: 10.1038/nmat4097

High Yield Ultrafast Intramolecular Singlet Exciton Fission in a Quinoidal Bithiophene
journal, April 2015

  • Varnavski, Oleg; Abeyasinghe, Neranga; Aragó, Juan
  • The Journal of Physical Chemistry Letters, Vol. 6, Issue 8
  • DOI: 10.1021/acs.jpclett.5b00198

Direct Observation of a Charge-Transfer State Preceding High-Yield Singlet Fission in Terrylenediimide Thin Films
journal, December 2016

  • Margulies, Eric A.; Logsdon, Jenna L.; Miller, Claire E.
  • Journal of the American Chemical Society, Vol. 139, Issue 2
  • DOI: 10.1021/jacs.6b07721

Toward Designed Singlet Fission: Solution Photophysics of Two Indirectly Coupled Covalent Dimers of 1,3-Diphenylisobenzofuran
journal, November 2012

  • Johnson, Justin C.; Akdag, Akin; Zamadar, Matibur
  • The Journal of Physical Chemistry B, Vol. 117, Issue 16
  • DOI: 10.1021/jp310979q

Intra- and Intermolecular Singlet Fission in Covalently Linked Dimers
journal, August 2016

  • Feng, Xintian; Casanova, David; Krylov, Anna I.
  • The Journal of Physical Chemistry C, Vol. 120, Issue 34
  • DOI: 10.1021/acs.jpcc.6b07666

Exciton Correlations in Intramolecular Singlet Fission
journal, June 2016

  • Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B.
  • Journal of the American Chemical Society, Vol. 138, Issue 23
  • DOI: 10.1021/jacs.6b00657

Origins of Singlet Fission in Solid Pentacene from an ab initio Green’s Function Approach
journal, December 2017

Solution-Phase Singlet Fission in a Structurally Well-Defined Norbornyl-Bridged Tetracene Dimer
journal, June 2016

  • Cook, Jasper D.; Carey, Thomas J.; Damrauer, Niels H.
  • The Journal of Physical Chemistry A, Vol. 120, Issue 26
  • DOI: 10.1021/acs.jpca.6b04367

Exploiting Singlet Fission in Organic Light‐Emitting Diodes
journal, July 2018

  • Nagata, Ryo; Nakanotani, Hajime; Potscavage, William J.
  • Advanced Materials, Vol. 30, Issue 33
  • DOI: 10.1002/adma.201801484

Quintet-triplet mixing determines the fate of the multiexciton state produced by singlet fission in a terrylenediimide dimer at room temperature
journal, April 2019

  • Chen, Michelle; Krzyaniak, Matthew D.; Nelson, Jordan N.
  • Proceedings of the National Academy of Sciences, Vol. 116, Issue 17
  • DOI: 10.1073/pnas.1820932116

Maximizing Singlet Fission in Organic Dimers: Theoretical Investigation of Triplet Yield in the Regime of Localized Excitation and Fast Coherent Electron Transfer †
journal, November 2010

  • Greyson, Eric C.; Vura-Weis, Josh; Michl, Josef
  • The Journal of Physical Chemistry B, Vol. 114, Issue 45
  • DOI: 10.1021/jp907392q

Two-Dimensional Electronic Spectroscopy Reveals Excitation Energy-Dependent State Mixing during Singlet Fission in a Terrylenediimide Dimer
journal, December 2018

  • Mandal, Aritra; Chen, Michelle; Foszcz, Eileen D.
  • Journal of the American Chemical Society, Vol. 140, Issue 51
  • DOI: 10.1021/jacs.8b08627

Distinct properties of the triplet pair state from singlet fission
text, January 2017

  • Trinh, M. Tuan; Pinkard, Andrew; Pun, Andrew Brian
  • Columbia University
  • DOI: 10.7916/d8zg843k

Quantitative Intramolecular Singlet Fission in Bipentacenes
journal, July 2015

  • Sanders, Samuel N.; Kumarasamy, Elango; Pun, Andrew B.
  • Journal of the American Chemical Society, Vol. 137, Issue 28
  • DOI: 10.1021/jacs.5b04986

Mapping the Relation between Stacking Geometries and Singlet Fission Yield in a Class of Organic Crystals
journal, March 2013

  • Renaud, Nicolas; Sherratt, Paul A.; Ratner, Mark A.
  • The Journal of Physical Chemistry Letters, Vol. 4, Issue 7
  • DOI: 10.1021/jz400176m

A transferable model for singlet-fission kinetics
journal, May 2014

  • Yost, Shane R.; Lee, Jiye; Wilson, Mark W. B.
  • Nature Chemistry, Vol. 6, Issue 6
  • DOI: 10.1038/nchem.1945

Singlet Fission Involves an Interplay between Energetic Driving Force and Electronic Coupling in Perylenediimide Films
journal, January 2018

  • Le, Aaron K.; Bender, Jon A.; Arias, Dylan H.
  • Journal of the American Chemical Society, Vol. 140, Issue 2
  • DOI: 10.1021/jacs.7b11888

Singlet Fission
journal, April 2021

Tuning the role of charge-transfer states in intramolecular singlet exciton fission through side-group engineering
text, January 2016

  • Lukman, Steven; Chen, K.; Hodgkiss, Jm
  • Apollo - University of Cambridge Repository
  • DOI: 10.17863/cam.6798

Exploiting Excited-State Aromaticity To Design Highly Stable Singlet Fission Materials
collection, January 2019

  • Fallon, Kealan J.; Budden, Peter; Salvadori, Enrico
  • Universität des Saarlandes
  • DOI: 10.22028/d291-29308

Davydov splitting and singlet fission in excitonically coupled pentacene dimers
null, January 2019

  • Basel, Bettina Sabine; Hetzer, Constantin; Zirzlmeier, Johannes
  • Cambridge : RSC
  • DOI: 10.34657/5836

Intramolecular Singlet Fission in an Antiaromatic Polycyclic Hydrocarbon
journal, July 2017

  • Wu, Yishi; Wang, Yuancheng; Chen, Jianwei
  • Angewandte Chemie International Edition, Vol. 56, Issue 32
  • DOI: 10.1002/anie.201704668

Tuning Singlet Fission in π-Bridge-π Chromophores
journalarticle, January 2017

  • Kumarasamy, E.; Sanders, Sn; Tayebjee, Mjy
  • American Chemical Society
  • DOI: 10.17863/cam.13699
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