DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Optimal arrangements of 1,3-diphenylisobenzofuran molecule pairs for fast singlet fission

Abstract

Best molecular pair packing geometries for singlet fission in 1,3-diphenylisobenzofuran are predicted.

Authors:
ORCiD logo [1]; ORCiD logo [2]
  1. Univ. of Colorado, Boulder, CO (United States)
  2. Univ. of Colorado, Boulder, CO (United States); Academy of Sciences of the Czech Republic, Prague (Czech Republic)
Publication Date:
Research Org.:
Univ. of Colorado, Boulder, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1688401
Alternate Identifier(s):
OSTI ID: 1559343
Grant/Contract Number:  
SC0007004
Resource Type:
Accepted Manuscript
Journal Name:
Photochemical & Photobiological Sciences
Additional Journal Information:
Journal Volume: 18; Journal Issue: 9; Journal ID: ISSN 1474-905X
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Buchanan, Eric A., and Michl, Josef. Optimal arrangements of 1,3-diphenylisobenzofuran molecule pairs for fast singlet fission. United States: N. p., 2019. Web. doi:10.1039/c9pp00283a.
Buchanan, Eric A., & Michl, Josef. Optimal arrangements of 1,3-diphenylisobenzofuran molecule pairs for fast singlet fission. United States. https://doi.org/10.1039/c9pp00283a
Buchanan, Eric A., and Michl, Josef. Wed . "Optimal arrangements of 1,3-diphenylisobenzofuran molecule pairs for fast singlet fission". United States. https://doi.org/10.1039/c9pp00283a. https://www.osti.gov/servlets/purl/1688401.
@article{osti_1688401,
title = {Optimal arrangements of 1,3-diphenylisobenzofuran molecule pairs for fast singlet fission},
author = {Buchanan, Eric A. and Michl, Josef},
abstractNote = {Best molecular pair packing geometries for singlet fission in 1,3-diphenylisobenzofuran are predicted.},
doi = {10.1039/c9pp00283a},
journal = {Photochemical & Photobiological Sciences},
number = 9,
volume = 18,
place = {United States},
year = {2019},
month = {8}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 13 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers
journal, October 2006

  • Hanna, M. C.; Nozik, A. J.
  • Journal of Applied Physics, Vol. 100, Issue 7
  • DOI: 10.1063/1.2356795

Efficient Singlet Fission Discovered in a Disordered Acene Film
journal, March 2012

  • Roberts, Sean T.; McAnally, R. Eric; Mastron, Joseph N.
  • Journal of the American Chemical Society, Vol. 134, Issue 14
  • DOI: 10.1021/ja300504t

Property-optimized Gaussian basis sets for molecular response calculations
journal, October 2010

  • Rappoport, Dmitrij; Furche, Filipp
  • The Journal of Chemical Physics, Vol. 133, Issue 13
  • DOI: 10.1063/1.3484283

Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans
journal, November 2017

  • Dron, Paul I.; Michl, Josef; Johnson, Justin C.
  • The Journal of Physical Chemistry A, Vol. 121, Issue 45
  • DOI: 10.1021/acs.jpca.7b07362

Different Rates of Singlet Fission in Monoclinic versus Orthorhombic Crystal Forms of Diphenylhexatriene
journal, November 2013

  • Dillon, Robert J.; Piland, Geoffrey B.; Bardeen, Christopher J.
  • Journal of the American Chemical Society, Vol. 135, Issue 46
  • DOI: 10.1021/ja409266s

Electron transfers in chemistry and biology
journal, August 1985

  • Marcus, R. A.; Sutin, Norman
  • Biochimica et Biophysica Acta (BBA) - Reviews on Bioenergetics, Vol. 811, Issue 3
  • DOI: 10.1016/0304-4173(85)90014-X

Recent Advances in Singlet Fission
journal, April 2013


Polymorphism influences singlet fission rates in tetracene thin films
journal, January 2016

  • Arias, Dylan H.; Ryerson, Joseph L.; Cook, Jasper D.
  • Chemical Science, Vol. 7, Issue 2
  • DOI: 10.1039/C5SC03535J

Effects of Charge Transfer State and Exciton Migration on Singlet Fission Dynamics in Organic Aggregates
journal, June 2016

  • Zang, Hang; Ke, Yaling; Zhao, Yi
  • The Journal of Physical Chemistry C, Vol. 120, Issue 25
  • DOI: 10.1021/acs.jpcc.6b02943

An Extended Hückel Theory. I. Hydrocarbons
journal, September 1963

  • Hoffmann, Roald
  • The Journal of Chemical Physics, Vol. 39, Issue 6
  • DOI: 10.1063/1.1734456

Magneto-optical activity: Gauge-invariant calculations in the random-phase approximation
journal, December 1972


High Triplet Yield from Singlet Fission in a Thin Film of 1,3-Diphenylisobenzofuran
journal, November 2010

  • Johnson, Justin C.; Nozik, Arthur J.; Michl, Josef
  • Journal of the American Chemical Society, Vol. 132, Issue 46
  • DOI: 10.1021/ja104123r

Analytical Self-Consistent Field Functions for the Atomic Configurations 1 s 2 , 1 s 2 2 s , and 1 s 2 2 s 2
journal, April 1960

  • Roothaan, C. C. J.; Sachs, Lester M.; Weiss, A. W.
  • Reviews of Modern Physics, Vol. 32, Issue 2
  • DOI: 10.1103/RevModPhys.32.186

Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions
journal, January 1980

  • Krishnan, R.; Binkley, J. S.; Seeger, R.
  • The Journal of Chemical Physics, Vol. 72, Issue 1
  • DOI: 10.1063/1.438955

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


The density functional formalism, its applications and prospects
journal, July 1989


NBO 6.0 : Natural bond orbital analysis program
journal, March 2013

  • Glendening, Eric D.; Landis, Clark R.; Weinhold, Frank
  • Journal of Computational Chemistry, Vol. 34, Issue 16
  • DOI: 10.1002/jcc.23266

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

Predicting Accurate Electronic Excitation Transfer Rates via Marcus Theory with Boys or Edmiston−Ruedenberg Localized Diabatization
journal, August 2010

  • Subotnik, Joseph E.; Vura-Weis, Josh; Sodt, Alex J.
  • The Journal of Physical Chemistry A, Vol. 114, Issue 33
  • DOI: 10.1021/jp101235a

Molecular Packing and Singlet Fission: The Parent and Three Fluorinated 1,3-Diphenylisobenzofurans
journal, March 2019

  • Buchanan, Eric A.; Kaleta, Jiří; Wen, Jin
  • The Journal of Physical Chemistry Letters, Vol. 10, Issue 8
  • DOI: 10.1021/acs.jpclett.8b03875

An overlap fitted chain of spheres exchange method
journal, October 2011

  • Izsák, Róbert; Neese, Frank
  • The Journal of Chemical Physics, Vol. 135, Issue 14
  • DOI: 10.1063/1.3646921

Mechanism of Singlet Fission in Thin Films of 1,3-Diphenylisobenzofuran
journal, May 2014

  • Schrauben, Joel N.; Ryerson, Joseph L.; Michl, Josef
  • Journal of the American Chemical Society, Vol. 136, Issue 20
  • DOI: 10.1021/ja501337b

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

1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission
journal, September 2017


Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
journal, January 2005

  • Weigend, Florian; Ahlrichs, Reinhart
  • Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305
  • DOI: 10.1039/b508541a

Hartree–Fock exchange fitting basis sets for H to Rn
journal, January 2007

  • Weigend, Florian
  • Journal of Computational Chemistry, Vol. 29, Issue 2
  • DOI: 10.1002/jcc.20702

Theoretical Modeling of Singlet Fission
journal, April 2018


Packing Guidelines for Optimizing Singlet Fission Matrix Elements in Noncovalent Dimers
journal, October 2017

  • Buchanan, Eric A.; Michl, Josef
  • Journal of the American Chemical Society, Vol. 139, Issue 44
  • DOI: 10.1021/jacs.7b07963

Singlet Fission
journal, November 2010

  • Smith, Millicent B.; Michl, Josef
  • Chemical Reviews, Vol. 110, Issue 11
  • DOI: 10.1021/cr1002613

Electron transfer reactions in chemistry. Theory and experiment
journal, July 1993


The triplet state energies of rubrene and diphenylisobenzofuran
journal, January 1981


Triplet Pair States in Singlet Fission
journal, January 2019


Deduction of the Zero Differential Overlap Approximation from an Orthogonal Atomic Orbital Basis
journal, March 1965

  • Fischer‐Hjalmars, Inga
  • The Journal of Chemical Physics, Vol. 42, Issue 6
  • DOI: 10.1063/1.1696232

A note on triplet-triplet fission of singlet excitons in molecular crystals
journal, July 1972


Toward reliable density functional methods without adjustable parameters: The PBE0 model
journal, April 1999

  • Adamo, Carlo; Barone, Vincenzo
  • The Journal of Chemical Physics, Vol. 110, Issue 13
  • DOI: 10.1063/1.478522

The Quantum Coherent Mechanism for Singlet Fission: Experiment and Theory
journal, April 2013

  • Chan, Wai-Lun; Berkelbach, Timothy C.; Provorse, Makenzie R.
  • Accounts of Chemical Research, Vol. 46, Issue 6
  • DOI: 10.1021/ar300286s

Time-dependent density functional theory within the Tamm–Dancoff approximation
journal, December 1999


Functional Mode Singlet Fission Theory
journal, February 2017

  • Elenewski, Justin E.; Cubeta, Ulyana S.; Ko, Edward
  • The Journal of Physical Chemistry C, Vol. 121, Issue 8
  • DOI: 10.1021/acs.jpcc.6b11722

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

Automatic Generation of Auxiliary Basis Sets
journal, January 2017

  • Stoychev, Georgi L.; Auer, Alexander A.; Neese, Frank
  • Journal of Chemical Theory and Computation, Vol. 13, Issue 2
  • DOI: 10.1021/acs.jctc.6b01041

The Role of Chromophore Coupling in Singlet Fission
journal, January 2013

  • Johnson, Justin C.; Nozik, Arthur J.; Michl, Josef
  • Accounts of Chemical Research, Vol. 46, Issue 6
  • DOI: 10.1021/ar300193r

Singlet Exciton Fission in Thin Films of tert -Butyl-Substituted Terrylenes
journal, April 2015

  • Eaton, Samuel W.; Miller, Stephen A.; Margulies, Eric A.
  • The Journal of Physical Chemistry A, Vol. 119, Issue 18
  • DOI: 10.1021/acs.jpca.5b02719

Detailed Balance Limit of Efficiency of p‐n Junction Solar Cells
journal, March 1961

  • Shockley, William; Queisser, Hans J.
  • Journal of Applied Physics, Vol. 32, Issue 3, p. 510-519
  • DOI: 10.1063/1.1736034

Monte Carlo Wavefunction Approach to Singlet Fission Dynamics of Molecular Aggregates
journal, February 2019


Toward Designed Singlet Fission: Electronic States and Photophysics of 1,3-Diphenylisobenzofuran
journal, January 2010

  • Schwerin, Andrew F.; Johnson, Justin C.; Smith, Millicent B.
  • The Journal of Physical Chemistry A, Vol. 114, Issue 3
  • DOI: 10.1021/jp907401t

Two Thin Film Polymorphs of the Singlet Fission Compound 1,3-Diphenylisobenzofuran
journal, May 2014

  • Ryerson, Joseph L.; Schrauben, Joel N.; Ferguson, Andrew J.
  • The Journal of Physical Chemistry C, Vol. 118, Issue 23
  • DOI: 10.1021/jp502122d

Singlet Fission in 9,10-Bis(phenylethynyl)anthracene Thin Films
journal, October 2018

  • Bae, Youn Jue; Kang, Gyeongwon; Malliakas, Christos D.
  • Journal of the American Chemical Society, Vol. 140, Issue 45
  • DOI: 10.1021/jacs.8b07498

Triplet Excitons in Crystals of Aromatic Molecules
journal, January 1965

  • Jortner, Joshua; Rice, Stuart A.; Katz, Joseph L.
  • The Journal of Chemical Physics, Vol. 42, Issue 1
  • DOI: 10.1063/1.1695693

Deploying RMACC Summit: An HPC Resource for the Rocky Mountain Region
conference, January 2017

  • Anderson, Jonathon; Burns, Patrick J.; Milroy, Daniel
  • Proceedings of the Practice and Experience in Advanced Research Computing 2017 on Sustainability, Success and Impact - PEARC17
  • DOI: 10.1145/3093338.3093379

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

The Spectra and Electronic Structure of the Tetrahedral Ions MnO 4 , CrO 4 −− , and ClO 4
journal, May 1952

  • Wolfsberg, Max; Helmholz, Lindsay
  • The Journal of Chemical Physics, Vol. 20, Issue 5
  • DOI: 10.1063/1.1700580

Singlet Fission
journal, April 2021


Electron transfer reactions in chemistry theory and experiment
journal, November 1997


Works referencing / citing this record:

Structure and photophysics of indigoids for singlet fission: Cibalackrot
journal, November 2019

  • Ryerson, Joseph L.; Zaykov, Alexandr; Aguilar Suarez, Luis E.
  • The Journal of Chemical Physics, Vol. 151, Issue 18
  • DOI: 10.1063/1.5121863

Lessons from intramolecular singlet fission with covalently bound chromophores
journal, January 2020

  • Korovina, Nadezhda V.; Pompetti, Nicholas F.; Johnson, Justin C.
  • The Journal of Chemical Physics, Vol. 152, Issue 4
  • DOI: 10.1063/1.5135307