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Title: Enhancing charge mobilities in organic semiconductors by selective fluorination: a design approach based on a quantum mechanical perspective

Abstract

Selective fluorination of organic semiconducting molecules is proposed as a means to achieving enhanced hole mobility. Naphthalene is examined here as a root molecular system with fluorination performed at various sites. Our quantum chemical calculations show that selective fluorination can enhance attractive intermolecular interactions while reducing charge trapping. Those observations suggest a design principle whereby fluorination is utilized for achieving high charge mobilities in the crystalline form. The utility of this design principle is demonstrated through an application to perylene, which is an important building block of organic semiconducting materials. We also show that a quantum mechanical perspective of nuclear degrees of freedom is crucial for a reliable description of charge transport.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [3]; ORCiD logo [1]; ORCiD logo [1]
+ Show Author Affiliations
  1. Kent State Univ., Kent, OH (United States). Dept. of Chemistry and Biochemistry
  2. Kent State Univ., Kent, OH (United States). Dept. of Chemistry and Biochemistry; Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemistry
  3. Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemistry
Publication Date:
Research Org.:
Kent State Univ., Kent, OH (United States); Univ. of Michigan, Ann Arbor, MI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
OSTI Identifier:
1505531
Grant/Contract Number:  
SC0016501; CHE-1362504; CHE-1464477
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 8; Journal Issue: 10; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE

Citation Formats

Maiti, Buddhadev, Schubert, Alexander, Sarkar, Sunandan, Bhandari, Srijana, Wang, Kunlun, Li, Zhe, Geva, Eitan, Twieg, Robert J., and Dunietz, Barry D. Enhancing charge mobilities in organic semiconductors by selective fluorination: a design approach based on a quantum mechanical perspective. United States: N. p., 2017. Web. doi:10.1039/c7sc02491f.
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Maiti, Buddhadev, Schubert, Alexander, Sarkar, Sunandan, Bhandari, Srijana, Wang, Kunlun, Li, Zhe, Geva, Eitan, Twieg, Robert J., & Dunietz, Barry D. Enhancing charge mobilities in organic semiconductors by selective fluorination: a design approach based on a quantum mechanical perspective. United States. https://doi.org/10.1039/c7sc02491f
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Maiti, Buddhadev, Schubert, Alexander, Sarkar, Sunandan, Bhandari, Srijana, Wang, Kunlun, Li, Zhe, Geva, Eitan, Twieg, Robert J., and Dunietz, Barry D. Mon . "Enhancing charge mobilities in organic semiconductors by selective fluorination: a design approach based on a quantum mechanical perspective". United States. https://doi.org/10.1039/c7sc02491f. https://www.osti.gov/servlets/purl/1505531.
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@article{osti_1505531,
title = {Enhancing charge mobilities in organic semiconductors by selective fluorination: a design approach based on a quantum mechanical perspective},
author = {Maiti, Buddhadev and Schubert, Alexander and Sarkar, Sunandan and Bhandari, Srijana and Wang, Kunlun and Li, Zhe and Geva, Eitan and Twieg, Robert J. and Dunietz, Barry D.},
abstractNote = {Selective fluorination of organic semiconducting molecules is proposed as a means to achieving enhanced hole mobility. Naphthalene is examined here as a root molecular system with fluorination performed at various sites. Our quantum chemical calculations show that selective fluorination can enhance attractive intermolecular interactions while reducing charge trapping. Those observations suggest a design principle whereby fluorination is utilized for achieving high charge mobilities in the crystalline form. The utility of this design principle is demonstrated through an application to perylene, which is an important building block of organic semiconducting materials. We also show that a quantum mechanical perspective of nuclear degrees of freedom is crucial for a reliable description of charge transport.},
doi = {10.1039/c7sc02491f},
journal = {Chemical Science},
number = 10,
volume = 8,
place = {United States},
year = {Mon Aug 14 00:00:00 EDT 2017},
month = {Mon Aug 14 00:00:00 EDT 2017}
}
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https://doi.org/10.1039/c7sc02491f
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Cited by: 19 works
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Figures / Tables:

Fig. 1 Fig. 1: A schematic view of the charge donor (blue) and acceptor (red) potential energy surfaces. Er and Ea are the reorganization energy and activation energy, respectively. ΔE is the charge transfer reaction free energy.
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Works referenced in this record:

Ultrafast Charge-Transfer Dynamics at the Boron Subphthalocyanine Chloride/C 60 Heterojunction: Comparison between Experiment and Theory
journal, January 2015

  • Wilcox, Daniel E.; Lee, Myeong H.; Sykes, Matthew E.
  • The Journal of Physical Chemistry Letters, Vol. 6, Issue 3
  • DOI: 10.1021/jz502278k

Photoinduced Charge Generation and Recombination Dynamics in Model Donor/Acceptor Pairs for Organic Solar Cell Applications:  A Full Quantum-Chemical Treatment
journal, April 2005

  • Lemaur, Vincent; Steel, Michelle; Beljonne, David
  • Journal of the American Chemical Society, Vol. 127, Issue 16
  • DOI: 10.1021/ja042390l

Organic field-effect transistors
journal, January 2010

Temperature dependent activation energy for electron transfer between biological molecules
journal, June 1976

  • Jortner, Joshua
  • The Journal of Chemical Physics, Vol. 64, Issue 12
  • DOI: 10.1063/1.432142

Communication: Charge-transfer rate constants in zinc-porphyrin-porphyrin-derived dyads: A Fermi golden rule first-principles-based study
journal, September 2014

  • Manna, Arun K.; Dunietz, Barry D.
  • The Journal of Chemical Physics, Vol. 141, Issue 12
  • DOI: 10.1063/1.4896826

On the Theory of Oxidation‐Reduction Reactions Involving Electron Transfer. I
journal, May 1956

  • Marcus, R. A.
  • The Journal of Chemical Physics, Vol. 24, Issue 5
  • DOI: 10.1063/1.1742723

Electrostatic Free Energy and Other Properties of States Having Nonequilibrium Polarization. I
journal, May 1956

  • Marcus, R. A.
  • The Journal of Chemical Physics, Vol. 24, Issue 5
  • DOI: 10.1063/1.1742724

A theoretical description of charge reorganization energies in molecular organic P-type semiconductors
journal, April 2016

  • Brückner, Charlotte; Engels, Bernd
  • Journal of Computational Chemistry, Vol. 37, Issue 15
  • DOI: 10.1002/jcc.24325

Charge Density Study of Naphthalene Based on X-ray Diffraction Data at Four Different Temperatures and Theoretical Calculations
journal, February 2004

  • Oddershede, Jette; Larsen, Sine
  • The Journal of Physical Chemistry A, Vol. 108, Issue 6
  • DOI: 10.1021/jp036186g

Additivity of the Proton Affinity in Aromatics:  Fluorinated Naphthalenes ⊥
journal, February 1997

  • Kovaček, Damir; Maksić, Zvonimir B.; Novak, Igor
  • The Journal of Physical Chemistry A, Vol. 101, Issue 6
  • DOI: 10.1021/jp961925x

Charge Hopping Dynamics along a Disordered Chain in Quantum Environments: Comparative Study of Different Rate Kernels
journal, December 2014

  • Jang, Seogjoo; Montoya-Castillo, Andrés
  • The Journal of Physical Chemistry B, Vol. 119, Issue 24
  • DOI: 10.1021/jp511933m

Effects of the Duschinsky mode-mixing mechanism on temperature dependence of electron transfer processes
journal, October 2003

  • Tang, Jau; Lee, Ming Tsung; Lin, Sheng Hsien
  • The Journal of Chemical Physics, Vol. 119, Issue 14
  • DOI: 10.1063/1.1607311

Donor-to-Donor vs Donor-to-Acceptor Interfacial Charge Transfer States in the Phthalocyanine–Fullerene Organic Photovoltaic System
journal, October 2014

  • Lee, Myeong H.; Dunietz, Barry D.; Geva, Eitan
  • The Journal of Physical Chemistry Letters, Vol. 5, Issue 21
  • DOI: 10.1021/jz5017203

Theory of light absorption and non-radiative transitions in F-centres
journal, December 1950

  • Huang, Kun; Rhys, Avril
  • Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences, Vol. 204, Issue 1078, p. 406-423
  • DOI: 10.1098/rspa.1950.0184

Extracting electron transfer coupling elements from constrained density functional theory
journal, October 2006

  • Wu, Qin; Van Voorhis, Troy
  • The Journal of Chemical Physics, Vol. 125, Issue 16
  • DOI: 10.1063/1.2360263

Novel fluorinated π-conjugated oligomers as electron transport materials in organic light emitting diodes
journal, January 1998

Recent Progress on Hole-Transporting Materials for Emerging Organometal Halide Perovskite Solar Cells
journal, April 2015

Theory of multichromophoric coherent resonance energy transfer: A polaronic quantum master equation approach
journal, July 2011

  • Jang, Seogjoo
  • The Journal of Chemical Physics, Vol. 135, Issue 3
  • DOI: 10.1063/1.3608914

Charge Transport in Organic Semiconductors
journal, July 2007

  • Coropceanu, Veaceslav; Cornil, Jerome; da Silva Filho, Demetrio A.
  • ChemInform, Vol. 38, Issue 29
  • DOI: 10.1002/chin.200729266

Organic light emitting diodes
journal, April 1997

Closed-Form Expressions of Quantum Electron Transfer Rate Based on the Stationary-Phase Approximation †
journal, September 2006

  • Jang, Seogjoo; Newton, Marshall D.
  • The Journal of Physical Chemistry B, Vol. 110, Issue 38
  • DOI: 10.1021/jp061329v

Constrained density functional theory based configuration interaction improves the prediction of reaction barrier heights
journal, January 2009

  • Wu, Qin; Kaduk, Benjamin; Van Voorhis, Troy
  • The Journal of Chemical Physics, Vol. 130, Issue 3
  • DOI: 10.1063/1.3059784

Density Functional Theory with Correct Long-Range Asymptotic Behavior
journal, February 2005

Theory of charge transport in organic crystals: Beyond Holstein’s small-polaron model
journal, June 2009

Exciton Trapping in π-Conjugated Materials: A Quantum-Chemistry-Based Protocol Applied to Perylene Bisimide Dye Aggregates
journal, October 2008

  • Fink, Reinhold F.; Seibt, Joachim; Engel, Volker
  • Journal of the American Chemical Society, Vol. 130, Issue 39
  • DOI: 10.1021/ja804331b

Quantum Mechanical Continuum Solvation Models
journal, October 2005

  • Tomasi, Jacopo; Menucci, Benedetta; Cammi, Roberto
  • ChemInform, Vol. 36, Issue 42
  • DOI: 10.1002/chin.200542292

Quantum Mechanical Continuum Solvation Models
journal, August 2005

  • Tomasi, Jacopo; Mennucci, Benedetta; Cammi, Roberto
  • Chemical Reviews, Vol. 105, Issue 8
  • DOI: 10.1021/cr9904009

The dimer-approach to characterize opto-electronic properties of and exciton trapping and diffusion in organic semiconductor aggregates and crystals
journal, January 2017

  • Engels, Bernd; Engel, Volker
  • Physical Chemistry Chemical Physics, Vol. 19, Issue 20
  • DOI: 10.1039/c7cp01599b

Pyroelectricity and charge transport in a copolymer of vinylidene fluoride and tetrafluoroethylene
journal, January 1982

Metal–Organic Nanoporous Structures with Anisotropic Photoluminescence and Magnetic Properties and Their Use as Sensors
journal, January 2008

  • Harbuzaru, Bogdan V.; Corma, Avelino; Rey, Fernando
  • Angewandte Chemie, Vol. 120, Issue 6
  • DOI: 10.1002/ange.200704702

Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections
journal, January 2008

  • Chai, Jeng-Da; Head-Gordon, Martin
  • Physical Chemistry Chemical Physics, Vol. 10, Issue 44
  • DOI: 10.1039/b810189b

Substituent effects in parallel-displaced π–π interactions
journal, January 2008

  • Arnstein, Stephen A.; Sherrill, C. David
  • Physical Chemistry Chemical Physics, Vol. 10, Issue 19
  • DOI: 10.1039/b718742d

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

The crystal and molecular structure of naphthalene. II. Structure investigation by the triple Fourier series method
journal, August 1949

The Kohn–Sham gap, the fundamental gap and the optical gap: the physical meaning of occupied and virtual Kohn–Sham orbital energies
journal, January 2013

  • Baerends, E. J.; Gritsenko, O. V.; van Meer, R.
  • Physical Chemistry Chemical Physics, Vol. 15, Issue 39
  • DOI: 10.1039/c3cp52547c

Naphthalene–octafluoronaphthalene, 1:1 solid compound
journal, October 1975

  • Potenza, J.; Mastropaolo, D.
  • Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 31, Issue 10
  • DOI: 10.1107/S0567740875008011

Nanotube Molecular Wires as Chemical Sensors
journal, January 2000

The Kohn–Sham gap, the fundamental gap and the optical gap: the physical meaning of occupied and virtual Kohn–Sham orbital energies
journal, January 2013

  • Baerends, E. J.; Gritsenko, O. V.; van Meer, R.
  • Physical Chemistry Chemical Physics, Vol. 15, Issue 39
  • DOI: 10.1039/c3cp52547c

Charge-Carrier Drift Mobility in Perylene Single Crystals
journal, January 1973

  • Maruyama, Yusei; Kobayashi, Tsutomu; Inokuchi, Hiroo
  • Molecular Crystals and Liquid Crystals, Vol. 20, Issue 3-4
  • DOI: 10.1080/15421407308083054

Highly Phosphorescent Bis-Cyclometalated Iridium Complexes:  Synthesis, Photophysical Characterization, and Use in Organic Light Emitting Diodes
journal, May 2001

  • Lamansky, Sergey; Djurovich, Peter; Murphy, Drew
  • Journal of the American Chemical Society, Vol. 123, Issue 18
  • DOI: 10.1021/ja003693s

Efficient photodiodes from interpenetrating polymer networks
journal, August 1995

  • Halls, J. J. M.; Walsh, C. A.; Greenham, N. C.
  • Nature, Vol. 376, Issue 6540, p. 498-500
  • DOI: 10.1038/376498a0

Nanotube Molecular Wires as Chemical Sensors
journal, January 2000

Metal–Organic Nanoporous Structures with Anisotropic Photoluminescence and Magnetic Properties and Their Use as Sensors
journal, January 2008

  • Harbuzaru, Bogdan V.; Corma, Avelino; Rey, Fernando
  • Angewandte Chemie International Edition, Vol. 47, Issue 6
  • DOI: 10.1002/anie.200704702

Fluorine Directed Two-Dimensional Cruciform π–π Stacking in Diketopyrrolopyrroles
journal, July 2016

  • Calvo-Castro, Jesus; Morris, Graeme; Kennedy, Alan R.
  • Crystal Growth & Design, Vol. 16, Issue 9
  • DOI: 10.1021/acs.cgd.6b00887

White organic light-emitting diodes with fluorescent tube efficiency
journal, May 2009

  • Reineke, Sebastian; Lindner, Frank; Schwartz, Gregor
  • Nature, Vol. 459, Issue 7244
  • DOI: 10.1038/nature08003

Experimental Benchmark Data and Systematic Evaluation of Two a Posteriori , Polarizable-Continuum Corrections for Vertical Excitation Energies in Solution
journal, December 2014

  • Mewes, Jan-Michael; You, Zhi-Qiang; Wormit, Michael
  • The Journal of Physical Chemistry A, Vol. 119, Issue 21
  • DOI: 10.1021/jp511163y

Calculating Off-Site Excitations in Symmetric Donor–Acceptor Systems via Time-Dependent Density Functional Theory with Range-Separated Density Functionals
journal, July 2012

  • Phillips, Heidi; Geva, Eitan; Dunietz, Barry D.
  • Journal of Chemical Theory and Computation, Vol. 8, Issue 8
  • DOI: 10.1021/ct300318g

Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections
journal, January 2008

  • Chai, Jeng-Da; Head-Gordon, Martin
  • Physical Chemistry Chemical Physics, Vol. 10, Issue 44
  • DOI: 10.1039/b810189b

The Strength of Parallel-Displaced Arene−Arene Interactions in Chloroform
journal, April 2005

  • Gung, Benjamin W.; Xue, Xiaowen; Reich, Hans J.
  • The Journal of Organic Chemistry, Vol. 70, Issue 9
  • DOI: 10.1021/jo050049t

Comparison of different rate constant expressions for the prediction of charge and energy transport in oligoacenes: Prediction of charge and energy transport in oligoacenes using rate constant expressions
journal, July 2016

  • Stehr, V.; Fink, R. F.; Tafipolski, M.
  • Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 6, Issue 6
  • DOI: 10.1002/wcms.1273

Organic field‐effect transistors with high mobility based on copper phthalocyanine
journal, November 1996

  • Bao, Zhenan; Lovinger, Andrew J.; Dodabalapur, Ananth
  • Applied Physics Letters, Vol. 69, Issue 20
  • DOI: 10.1063/1.116841

Metal–Organic Framework Materials as Chemical Sensors
journal, September 2011

  • Kreno, Lauren E.; Leong, Kirsty; Farha, Omar K.
  • Chemical Reviews, Vol. 112, Issue 2, p. 1105-1125
  • DOI: 10.1021/cr200324t

Polarization Energies in Oligoacene Semiconductor Crystals
journal, September 2008

  • Norton, Joseph E.; Brédas, Jean-Luc
  • Journal of the American Chemical Society, Vol. 130, Issue 37
  • DOI: 10.1021/ja8017797

Closed-Form Expressions of Quantum Electron Transfer Rate Based on the Stationary-Phase Approximation †
journal, September 2006

  • Jang, Seogjoo; Newton, Marshall D.
  • The Journal of Physical Chemistry B, Vol. 110, Issue 38
  • DOI: 10.1021/jp061329v

π-Conjugated Materials as the Hole-Transporting Layer in Perovskite Solar Cells
journal, January 2016

  • Gheno, Alexandre; Vedraine, Sylvain; Ratier, Bernard
  • Metals, Vol. 6, Issue 1
  • DOI: 10.3390/met6010021

Multi-Length-Scale Morphologies Driven by Mixed Additives in Porphyrin-Based Organic Photovoltaics
journal, April 2016

Benzo[b]phosphole sulfides. Highly electron-transporting and thermally stable molecular materials for organic semiconductor devices
journal, January 2009

  • Tsuji, Hayato; Sato, Kosuke; Sato, Yoshiharu
  • Journal of Materials Chemistry, Vol. 19, Issue 21
  • DOI: 10.1039/b906197e

Nonequilibrium Fermi’s Golden Rule Charge Transfer Rates via the Linearized Semiclassical Method
journal, May 2016

The Effect of Interfacial Geometry on Charge-Transfer States in the Phthalocyanine/Fullerene Organic Photovoltaic System
journal, August 2015

  • Lee, Myeong H.; Geva, Eitan; Dunietz, Barry D.
  • The Journal of Physical Chemistry A, Vol. 120, Issue 19
  • DOI: 10.1021/acs.jpca.5b06196

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport
journal, April 2002

  • Bredas, J. L.; Calbert, J. P.; da Silva Filho, D. A.
  • Proceedings of the National Academy of Sciences, Vol. 99, Issue 9
  • DOI: 10.1073/pnas.092143399

The Effect of Fluorination on Pentacene/Gold Interface Energetics and Charge Reorganization Energy
journal, January 2007

Prediction of the Absolute Charge Mobility of Molecular Semiconductors: the Case of Rubrene
journal, August 2007

Ultrafast Charge-Transfer Dynamics at the Boron Subphthalocyanine Chloride/C 60 Heterojunction: Comparison between Experiment and Theory
journal, January 2015

  • Wilcox, Daniel E.; Lee, Myeong H.; Sykes, Matthew E.
  • The Journal of Physical Chemistry Letters, Vol. 6, Issue 3
  • DOI: 10.1021/jz502278k

Photoinduced Charge Generation and Recombination Dynamics in Model Donor/Acceptor Pairs for Organic Solar Cell Applications:  A Full Quantum-Chemical Treatment
journal, April 2005

  • Lemaur, Vincent; Steel, Michelle; Beljonne, David
  • Journal of the American Chemical Society, Vol. 127, Issue 16
  • DOI: 10.1021/ja042390l

The essential role of H-F substitution in the electron-phonon interactions and electron transfer in the negatively charged acenes
journal, August 2004

  • Kato, Takashi; Yamabe, Tokio
  • The Journal of Chemical Physics, Vol. 121, Issue 5
  • DOI: 10.1063/1.1766018

The crystal and molecular structure of naphthalene. I. X-ray measurements
journal, August 1949

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

Influence of disorder on the photoinduced excitations in phenyl substituted polythiophenes
journal, October 2001

  • Brabec, Christoph J.; Winder, Christoph; Scharber, Markus C.
  • The Journal of Chemical Physics, Vol. 115, Issue 15
  • DOI: 10.1063/1.1404984

Excitation Gaps of Finite-Sized Systems from Optimally Tuned Range-Separated Hybrid Functionals
journal, April 2012

  • Kronik, Leeor; Stein, Tamar; Refaely-Abramson, Sivan
  • Journal of Chemical Theory and Computation, Vol. 8, Issue 5
  • DOI: 10.1021/ct2009363

Introduction to Nanoscience and Nanotechnology
null, January 2015

Nonequilibrium Fermi’s Golden Rule Charge Transfer Rates via the Linearized Semiclassical Method
journal, May 2016

Constrained density functional theory based configuration interaction improves the prediction of reaction barrier heights
journal, January 2009

  • Wu, Qin; Kaduk, Benjamin; Van Voorhis, Troy
  • The Journal of Chemical Physics, Vol. 130, Issue 3
  • DOI: 10.1063/1.3059784

Charge Hopping Dynamics along a Disordered Chain in Quantum Environments: Comparative Study of Different Rate Kernels
journal, December 2014

  • Jang, Seogjoo; Montoya-Castillo, Andrés
  • The Journal of Physical Chemistry B, Vol. 119, Issue 24
  • DOI: 10.1021/jp511933m

Communication: Charge-transfer rate constants in zinc-porphyrin-porphyrin-derived dyads: A Fermi golden rule first-principles-based study
journal, September 2014

  • Manna, Arun K.; Dunietz, Barry D.
  • The Journal of Chemical Physics, Vol. 141, Issue 12
  • DOI: 10.1063/1.4896826

Arene-perfluoroarene interactions in crystal engineering. Part 3. Single-crystal structures of 1 : 1 complexes of octafluoronaphthalene with fused-ring polyaromatic hydrocarbonsFor part 1, see ref. 1. For part 2, see ref. 2. Presented at the 16th International Symposium on Fluorine Chemistry, University of Durham, UK, 16–21 July 2000, Abstract no. 308.Electronic supplementary information (ESI) available: experimental data for the re-determination of the crystal structure of triphenylene, tables of the average bond lengths in OFN and the polyaromatic molecules in both the complexes and pure compounds, and a table of distances and angles for intermolecular H···F contacts in the complexes which are below the sum of the van der Waals radii. See http://www.rsc.org/suppdata/nj/b1/b105502j/
journal, October 2001

  • Collings, Jonathan C.; Roscoe, Karl P.; Thomas, Rhodri Ll.
  • New Journal of Chemistry, Vol. 25, Issue 11
  • DOI: 10.1039/b105502j

Theory of multichromophoric coherent resonance energy transfer: A polaronic quantum master equation approach
journal, July 2011

  • Jang, Seogjoo
  • The Journal of Chemical Physics, Vol. 135, Issue 3
  • DOI: 10.1063/1.3608914

Exciton Trapping in π-Conjugated Materials: A Quantum-Chemistry-Based Protocol Applied to Perylene Bisimide Dye Aggregates
journal, October 2008

  • Fink, Reinhold F.; Seibt, Joachim; Engel, Volker
  • Journal of the American Chemical Society, Vol. 130, Issue 39
  • DOI: 10.1021/ja804331b

Extracting electron transfer coupling elements from constrained density functional theory
journal, October 2006

  • Wu, Qin; Van Voorhis, Troy
  • The Journal of Chemical Physics, Vol. 125, Issue 16
  • DOI: 10.1063/1.2360263

Polarization Energies in Oligoacene Semiconductor Crystals
journal, September 2008

  • Norton, Joseph E.; Brédas, Jean-Luc
  • Journal of the American Chemical Society, Vol. 130, Issue 37
  • DOI: 10.1021/ja8017797

Reliable Prediction of Charge Transfer Excitations in Molecular Complexes Using Time-Dependent Density Functional Theory
journal, March 2009

  • Stein, Tamar; Kronik, Leeor; Baer, Roi
  • Journal of the American Chemical Society, Vol. 131, Issue 8
  • DOI: 10.1021/ja8087482

Evaluation of the External Reorganization Energy of Polyacenes
journal, February 2010

  • McMahon, David P.; Troisi, Alessandro
  • The Journal of Physical Chemistry Letters, Vol. 1, Issue 6
  • DOI: 10.1021/jz1001049

The Strength of Parallel-Displaced Arene−Arene Interactions in Chloroform
journal, April 2005

  • Gung, Benjamin W.; Xue, Xiaowen; Reich, Hans J.
  • The Journal of Organic Chemistry, Vol. 70, Issue 9
  • DOI: 10.1021/jo050049t

Donor-to-Donor vs Donor-to-Acceptor Interfacial Charge Transfer States in the Phthalocyanine–Fullerene Organic Photovoltaic System
journal, October 2014

  • Lee, Myeong H.; Dunietz, Barry D.; Geva, Eitan
  • The Journal of Physical Chemistry Letters, Vol. 5, Issue 21
  • DOI: 10.1021/jz5017203

Pinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement Strategies
journal, February 2015

  • Fuchibe, Kohei; Morikawa, Toshiyuki; Shigeno, Kento
  • Organic Letters, Vol. 17, Issue 5
  • DOI: 10.1021/ol503759d

Electronic Processes at Organic−Organic Interfaces: Insight from Modeling and Implications for Opto-electronic Devices †
journal, February 2011

  • Beljonne, David; Cornil, Jérôme; Muccioli, Luca
  • Chemistry of Materials, Vol. 23, Issue 3
  • DOI: 10.1021/cm1023426

n-Type Charge Transport and Mobility of Fluorinated Perylene Bisimide Semiconductors
journal, April 2010

  • Di Donato, Eugenio; Fornari, Rocco P.; Di Motta, Simone
  • The Journal of Physical Chemistry B, Vol. 114, Issue 16
  • DOI: 10.1021/jp101040r

Effect of Donor Molecular Structure and Gate Dielectric on Charge-Transporting Characteristics for Isoindigo-Based Donor-Acceptor Conjugated Polymers
journal, May 2016

  • Park, Won-Tae; Kim, Gyoungsik; Yang, Changduk
  • Advanced Functional Materials, Vol. 26, Issue 26
  • DOI: 10.1002/adfm.201504908

Substituent effects in parallel-displaced π–π interactions
journal, January 2008

  • Arnstein, Stephen A.; Sherrill, C. David
  • Physical Chemistry Chemical Physics, Vol. 10, Issue 19
  • DOI: 10.1039/b718742d

Calculation from First Principles of Intramolecular Golden-Rule Rate Constants for Photo-Induced Electron Transfer in Molecular Donor–Acceptor Systems
journal, October 2013

  • Lee, Myeong H.; Dunietz, Barry D.; Geva, Eitan
  • The Journal of Physical Chemistry C, Vol. 117, Issue 44
  • DOI: 10.1021/jp4081417

n-Type Charge Transport and Mobility of Fluorinated Perylene Bisimide Semiconductors
journal, April 2010

  • Di Donato, Eugenio; Fornari, Rocco P.; Di Motta, Simone
  • The Journal of Physical Chemistry B, Vol. 114, Issue 16
  • DOI: 10.1021/jp101040r

A detailed refinement of the crystal and molecular structure of naphthalene
journal, August 1957

Charge Transport in Organic Semiconductors
journal, April 2007

  • Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A.
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  • DOI: 10.1021/cr050140x

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  • Physical Chemistry Chemical Physics, Vol. 9, Issue 23
  • DOI: 10.1039/b617919c

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  • DOI: 10.1021/acs.jctc.5b00296

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  • ChemInform, Vol. 36, Issue 42
  • DOI: 10.1002/chin.200542292

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  • DOI: 10.1021/ma3009788

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  • Warta, W.; Stehle, R.; Karl, N.
  • Applied Physics A Solids and Surfaces, Vol. 36, Issue 3
  • DOI: 10.1007/BF00624938

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  • Bagryanskaya, Irina Yu.; Gatilov, Yuri V.; Maksimov, Alexander M.
  • Journal of Fluorine Chemistry, Vol. 126, Issue 9-10
  • DOI: 10.1016/j.jfluchem.2005.06.011

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  • Lee, Myeong H.; Geva, Eitan; Dunietz, Barry D.
  • The Journal of Physical Chemistry A, Vol. 120, Issue 19
  • DOI: 10.1021/acs.jpca.5b06196

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  • Bredas, J. L.; Calbert, J. P.; da Silva Filho, D. A.
  • Proceedings of the National Academy of Sciences, Vol. 99, Issue 9
  • DOI: 10.1073/pnas.092143399

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  • Mewes, Jan-Michael; You, Zhi-Qiang; Wormit, Michael
  • The Journal of Physical Chemistry A, Vol. 119, Issue 21
  • DOI: 10.1021/jp511163y

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  • Journal of Chemical Theory and Computation, Vol. 8, Issue 8
  • DOI: 10.1021/ct300318g

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  • Mazzio, Katherine A.; Luscombe, Christine K.
  • Chemical Society Reviews, Vol. 44, Issue 1
  • DOI: 10.1039/C4CS00227J

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  • Coropceanu, Veaceslav; Cornil, Jerome; da Silva Filho, Demetrio A.
  • ChemInform, Vol. 38, Issue 29
  • DOI: 10.1002/chin.200729266

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Electronic mobilities of fluorinated oligoacenes
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  • Ju, Xue-Hai; Liao, Xin
  • International Journal of Materials Research, Vol. 104, Issue 1
  • DOI: 10.3139/146.110832

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  • Stein, Tamar; Kronik, Leeor; Baer, Roi
  • Journal of the American Chemical Society, Vol. 131, Issue 8
  • DOI: 10.1021/ja8087482

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  • Kronik, Leeor; Stein, Tamar; Refaely-Abramson, Sivan
  • Journal of Chemical Theory and Computation, Vol. 8, Issue 5
  • DOI: 10.1021/ct2009363

White organic light-emitting diodes with fluorescent tube efficiency
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  • Reineke, Sebastian; Lindner, Frank; Schwartz, Gregor
  • Nature, Vol. 459, Issue 7244
  • DOI: 10.1038/nature08003

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A theoretical description of charge reorganization energies in molecular organic P-type semiconductors
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  • DOI: 10.1002/jcc.24325

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  • The Journal of Chemical Physics, Vol. 121, Issue 5
  • DOI: 10.1063/1.1766018

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  • Lamansky, Sergey; Djurovich, Peter; Murphy, Drew
  • Journal of the American Chemical Society, Vol. 123, Issue 18
  • DOI: 10.1021/ja003693s

Chemical Dynamics in Condensed Phases
book, April 2006

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    PAH/PAH(CF 3 ) n Donor/Acceptor Charge‐Transfer Complexes in Solution and in Solid‐State Co‐Crystals
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    • Castro, Karlee P.; Bukovsky, Eric V.; Kuvychko, Igor V.
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    • Maiti, Buddhadev; Wang, Kunlun; Bhandari, Srijana
    • Journal of Materials Chemistry C, Vol. 7, Issue 13
    • DOI: 10.1039/c8tc06517a
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