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Title: PAH/PAH(CF3)n Donor/Acceptor Charge-Transfer Complexes in Solution and in Solid-State Co-Crystals

Abstract

2 ABSTRACT We report a solution, solid-state, and computational study of PAH/PAH(CF3)n donor/acceptor (D/A) charge-transfer complexes that involve six PAH(CF3)n acceptors with known gas-phase electron affinities that range from 2.11(2) to 2.805(15) eV and four PAH donors, including seven CT co-crystal X-ray structures that exhibit hexagonal arrays of mixed p stacks with 1/1, 1/2, or 2/1 D/A stoichiometries (PAH = anthracene, azulene, perylene, pyrene, triphenylene; n = 4, 5). These are the first D/A CT complexes with PAH(CF3)n acceptors to be studied in detail. The nine D/A combinations were chosen to allow several structural and electronic comparisons to be made, providing new insights about controlling D/A interactions and the structures of CT co-crystals. They include, among others, CT complexes of the same PAH(CF3)n acceptor with four PAH donors and CT complexes of the same donor with four PAH(CF3)n acceptors. All nine CT complexes exhibit charge-transfer bands in solution with ?max between 466 and 600 nm. A plot of E(?max) vs. [IE(donor) - EA(acceptor)] for the nine CT complexes studied is linear with a slope of 0.72 ± 0.03 eV/eV. This plot is the first of its kind for CT complexes with structurally related donors and acceptors for which precise experimentalmore » gas-phase IEs and EAs are known. It demonstrates that conclusions based on the common assumption that the slope of a CT E(?max) vs. [IE - EA] plot is unity may be incorrect in at least some cases and should be reconsidered.« less

Authors:
 [1];  [1];  [2];  [1];  [3];  [4]; ORCiD logo [4];  [5];  [1];  [1]
  1. Colorado State University
  2. COLORADO STATE UNIVERSITY
  3. University of Chicago
  4. BATTELLE (PACIFIC NW LAB)
  5. VISITORS
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1577081
Report Number(s):
PNNL-SA-145003
DOE Contract Number:  
AC05-76RL01830
Resource Type:
Journal Article
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 25; Journal Issue: 59
Country of Publication:
United States
Language:
English

Citation Formats

Castro, Karlee P., Bukovsky, Eric V., Kuvychko, Igor V., DeWeerd, Nicholas J., Chen, Yu-Sheng, Deng, Shihu, Wang, Xue-Bin, Popov, Alexey, Strauss, Steven H., and Boltalina, Olga V. PAH/PAH(CF3)n Donor/Acceptor Charge-Transfer Complexes in Solution and in Solid-State Co-Crystals. United States: N. p., 2019. Web. doi:10.1002/chem.201902712.
Castro, Karlee P., Bukovsky, Eric V., Kuvychko, Igor V., DeWeerd, Nicholas J., Chen, Yu-Sheng, Deng, Shihu, Wang, Xue-Bin, Popov, Alexey, Strauss, Steven H., & Boltalina, Olga V. PAH/PAH(CF3)n Donor/Acceptor Charge-Transfer Complexes in Solution and in Solid-State Co-Crystals. United States. doi:10.1002/chem.201902712.
Castro, Karlee P., Bukovsky, Eric V., Kuvychko, Igor V., DeWeerd, Nicholas J., Chen, Yu-Sheng, Deng, Shihu, Wang, Xue-Bin, Popov, Alexey, Strauss, Steven H., and Boltalina, Olga V. Tue . "PAH/PAH(CF3)n Donor/Acceptor Charge-Transfer Complexes in Solution and in Solid-State Co-Crystals". United States. doi:10.1002/chem.201902712.
@article{osti_1577081,
title = {PAH/PAH(CF3)n Donor/Acceptor Charge-Transfer Complexes in Solution and in Solid-State Co-Crystals},
author = {Castro, Karlee P. and Bukovsky, Eric V. and Kuvychko, Igor V. and DeWeerd, Nicholas J. and Chen, Yu-Sheng and Deng, Shihu and Wang, Xue-Bin and Popov, Alexey and Strauss, Steven H. and Boltalina, Olga V.},
abstractNote = {2 ABSTRACT We report a solution, solid-state, and computational study of PAH/PAH(CF3)n donor/acceptor (D/A) charge-transfer complexes that involve six PAH(CF3)n acceptors with known gas-phase electron affinities that range from 2.11(2) to 2.805(15) eV and four PAH donors, including seven CT co-crystal X-ray structures that exhibit hexagonal arrays of mixed p stacks with 1/1, 1/2, or 2/1 D/A stoichiometries (PAH = anthracene, azulene, perylene, pyrene, triphenylene; n = 4, 5). These are the first D/A CT complexes with PAH(CF3)n acceptors to be studied in detail. The nine D/A combinations were chosen to allow several structural and electronic comparisons to be made, providing new insights about controlling D/A interactions and the structures of CT co-crystals. They include, among others, CT complexes of the same PAH(CF3)n acceptor with four PAH donors and CT complexes of the same donor with four PAH(CF3)n acceptors. All nine CT complexes exhibit charge-transfer bands in solution with ?max between 466 and 600 nm. A plot of E(?max) vs. [IE(donor) - EA(acceptor)] for the nine CT complexes studied is linear with a slope of 0.72 ± 0.03 eV/eV. This plot is the first of its kind for CT complexes with structurally related donors and acceptors for which precise experimental gas-phase IEs and EAs are known. It demonstrates that conclusions based on the common assumption that the slope of a CT E(?max) vs. [IE - EA] plot is unity may be incorrect in at least some cases and should be reconsidered.},
doi = {10.1002/chem.201902712},
journal = {Chemistry - A European Journal},
number = 59,
volume = 25,
place = {United States},
year = {2019},
month = {10}
}

Works referenced in this record:

Organic Donor–Acceptor Complexes as Novel Organic Semiconductors
journal, June 2017


Development of Novel Functional Organic Crystals by Utilizing Proton- and π-Electron-Donating/Accepting Abilities
journal, November 2017


Two-component organic crystals without hydrogen bonding: structure and intermolecular interactions in bimolecular stacking
journal, January 2017

  • Colombo, Valentina; Presti, Leonardo Lo; Gavezzotti, Angelo
  • CrystEngComm, Vol. 19, Issue 17
  • DOI: 10.1039/C7CE00311K

Impact of Hydrogen and Halogen Bonding Interactions on the Packing and Ionicity of Charge-Transfer Cocrystals
journal, December 2016


From charge-transfer excitations to charge-transport phenomena in organic molecular crystals
journal, June 2017

  • Zoppi, Laura; Baldridge, Kim K.
  • International Journal of Quantum Chemistry, Vol. 118, Issue 1
  • DOI: 10.1002/qua.25413

Recent progress on organic donor–acceptor complexes as active elements in organic field-effect transistors
journal, January 2018

  • Zhang, Jing; Jin, Jianqun; Xu, Haixiao
  • Journal of Materials Chemistry C, Vol. 6, Issue 14
  • DOI: 10.1039/C7TC04389A

Molecular cocrystals: design, charge-transfer and optoelectronic functionality
journal, January 2018

  • Sun, Lingjie; Zhu, Weigang; Yang, Fangxu
  • Physical Chemistry Chemical Physics, Vol. 20, Issue 9
  • DOI: 10.1039/C7CP07167A

Controllable Synthesis of Organic Microcrystals with Tunable Emission Color and Morphology Based on Molecular Packing Mode
journal, November 2017


Organic Cocrystals: New Strategy for Molecular Collaborative Innovation
journal, November 2016


Rigid, Branched Porphyrin Antennas: Control over Cascades of Unidirectional Energy Funneling and Charge Transfer
journal, August 2017

  • Wolf, Maximilian; Herrmann, Astrid; Hirsch, Andreas
  • Journal of the American Chemical Society, Vol. 139, Issue 34
  • DOI: 10.1021/jacs.7b04589

Control of π–π Stacking via Crystal Engineering in Organic Conjugated Small Molecule Crystals
journal, December 2017


Tuning of the degree of charge transfer and the electronic properties in organic binary compounds by crystal engineering: a perspective
journal, January 2018

  • Jiang, Hui; Hu, Peng; Ye, Jun
  • Journal of Materials Chemistry C, Vol. 6, Issue 8
  • DOI: 10.1039/C7TC04982J

Impact of C–H···X (X = F, N) and π–π Interactions on Tuning the Degree of Charge Transfer in F 6 TNAP-Based Organic Binary Compound Single Crystals
journal, January 2018

  • Hu, Peng; Wang, Shancheng; Chaturvedi, Apoorva
  • Crystal Growth & Design, Vol. 18, Issue 3
  • DOI: 10.1021/acs.cgd.7b01669

Solvent-free mechanochemical synthesis of π–π stacked arene–perfluoroarene co-crystals
journal, September 2013


Engineering polar crystal structures by π–π stacking of N-perfluoroarylbenzimidazoles
journal, October 2014


Halogenation of a Nonplanar Molecular Semiconductor to Tune Energy Levels and Bandgaps for Electron Transport
journal, February 2015


Mixed stack charge transfer crystals: Crossing the neutral-ionic borderline by chemical substitution
journal, February 2018


“Though It Be but Little, It Is Fierce”: Excited State Engineering of Conjugated Organic Materials by Fluorination
journal, December 2016

  • Milián-Medina, Begoña; Gierschner, Johannes
  • The Journal of Physical Chemistry Letters, Vol. 8, Issue 1
  • DOI: 10.1021/acs.jpclett.6b02495

Perfluoroalkylation of Square-Planar Transition Metal Complexes: A Strategy To Assemble Them into Solid State Materials with a π–π Stacked Lamellar Structure
journal, March 2016

  • BaniKhaled, Mohammad O.; Becker, John D.; Koppang, Miles
  • Crystal Growth & Design, Vol. 16, Issue 4
  • DOI: 10.1021/acs.cgd.5b01291

Understanding Polyarene Trifluoromethylation with Hot CF 3 Radicals Using Corannulene : Understanding Polyarene Trifluoromethylation with Hot CF
journal, July 2018

  • Kuvychko, Igor V.; Clikeman, Tyler; Dubceac, Cristina
  • European Journal of Organic Chemistry, Vol. 2018, Issue 31
  • DOI: 10.1002/ejoc.201800508

Arene Trifluoromethylation: An Effective Strategy to Obtain Air-Stable n-Type Organic Semiconductors with Tunable Optoelectronic and Electron Transfer Properties
journal, July 2012

  • Sun, Haoran; Putta, Anjaneyulu; Billion, Michael
  • The Journal of Physical Chemistry A, Vol. 116, Issue 30
  • DOI: 10.1021/jp301718j

A Buckybowl with a Lot of Potential: C5-C20H5(CF3)5
journal, April 2012

  • Kuvychko, Igor V.; Spisak, Sarah N.; Chen, Yu-Sheng
  • Angewandte Chemie International Edition, Vol. 51, Issue 20
  • DOI: 10.1002/anie.201200178

A Buckybowl with a Lot of Potential: C5-C20H5(CF3)5
journal, April 2012

  • Kuvychko, Igor V.; Spisak, Sarah N.; Chen, Yu-Sheng
  • Angewandte Chemie, Vol. 124, Issue 20
  • DOI: 10.1002/ange.201200178

Taming Hot CF 3 Radicals: Incrementally Tuned Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics
journal, March 2013

  • Kuvychko, Igor V.; Castro, Karlee P.; Deng, S. H. M.
  • Angewandte Chemie International Edition, Vol. 52, Issue 18
  • DOI: 10.1002/anie.201300085

Taming Hot CF 3 Radicals: Incrementally Tuned Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics
journal, March 2013

  • Kuvychko, Igor V.; Castro, Karlee P.; Deng, S. H. M.
  • Angewandte Chemie, Vol. 125, Issue 18
  • DOI: 10.1002/ange.201300085

Synthesis and Solid-State Structures of 6,13-Bis(trifluoromethyl)- and 6,13-Dialkoxypentacene: Solid-State Structures of 6,13-Disubstituted Pentacene Derivatives
journal, February 2013

  • Schwaben, Jonas; Münster, Niels; Breuer, Tobias
  • European Journal of Organic Chemistry, Vol. 2013, Issue 9
  • DOI: 10.1002/ejoc.201201714

Perfluorinated Polycyclic Aromatic Hydrocarbons: Anthracene, Phenanthrene, Pyrene, Tetracene, Chrysene, and Triphenylene
journal, February 2009

  • Feng, Xuejun; Li, Qianshu; Gu, Jiande
  • The Journal of Physical Chemistry A, Vol. 113, Issue 5
  • DOI: 10.1021/jp809110f

On the Air Stability of n -Channel Organic Field-Effect Transistors: A Theoretical Study of Adiabatic Electron Affinities of Organic Semiconductors
journal, June 2010

  • Chang, Yu-Chang; Kuo, Ming-Yu; Chen, Chih-Ping
  • The Journal of Physical Chemistry C, Vol. 114, Issue 26
  • DOI: 10.1021/jp1025625

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors
journal, January 2017

  • Dhar, Joydeep; Salzner, Ulrike; Patil, Satish
  • Journal of Materials Chemistry C, Vol. 5, Issue 30
  • DOI: 10.1039/C6TC05467F

Enhancing charge mobilities in organic semiconductors by selective fluorination: a design approach based on a quantum mechanical perspective
journal, January 2017

  • Maiti, Buddhadev; Schubert, Alexander; Sarkar, Sunandan
  • Chem. Sci., Vol. 8, Issue 10
  • DOI: 10.1039/C7SC02491F

Effect of Hexafluorobenzene on the Photophysics of Pyrene
journal, June 2007

  • Perry, Mark; Carra, Claudio; Chrétien, Michelle N.
  • The Journal of Physical Chemistry A, Vol. 111, Issue 23
  • DOI: 10.1021/jp0702797

Perfluoropentacene:  High-Performance p−n Junctions and Complementary Circuits with Pentacene
journal, July 2004

  • Sakamoto, Youichi; Suzuki, Toshiyasu; Kobayashi, Masafumi
  • Journal of the American Chemical Society, Vol. 126, Issue 26
  • DOI: 10.1021/ja0476258

Temperature dependence of thermal motion in crystalline anthracene
journal, December 1990

  • Brock, C. P.; Dunitz, J. D.
  • Acta Crystallographica Section B Structural Science, Vol. 46, Issue 6
  • DOI: 10.1107/S0108768190008382

Supramolecular synthons in crystals of partially fluorinated fused aromatics: 1,2,3,4-Tetrafluoronaphthalene and its aza-analogue 1,3,4-trifluoroisoquinoline
journal, October 2005

  • 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

A survey of Hammett substituent constants and resonance and field parameters
journal, March 1991

  • Hansch, Corwin.; Leo, A.; Taft, R. W.
  • Chemical Reviews, Vol. 91, Issue 2
  • DOI: 10.1021/cr00002a004

Toward a Physical Interpretation of Substituent Effects: The Case of Fluorine and Trifluoromethyl Groups
journal, July 2014

  • Siodła, Tomasz; Ozimiński, Wojciech P.; Hoffmann, Marcin
  • The Journal of Organic Chemistry, Vol. 79, Issue 16
  • DOI: 10.1021/jo501013p

Electron affinities of benzo-, naphtho-, and anthraquinones determined from gas-phase equilibria measurements
journal, January 1988

  • Heinis, Thomas.; Chowdhury, Swapan.; Scott, Susannah L.
  • Journal of the American Chemical Society, Vol. 110, Issue 2
  • DOI: 10.1021/ja00210a015

Meso-Disubstituted Anthracenes with Fluorine-Containing Groups: Synthesis, Light-Emitting Characteristics, and Photostability
journal, December 2008

  • Matsubara, Yoshio; Kimura, Atsushi; Yamaguchi, Yoshihiro
  • Organic Letters, Vol. 10, Issue 24
  • DOI: 10.1021/ol802337v

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

Arene–perfluoroarene interactions in crystal engineering. Part 14. 1:1 Complexes of octafluoronaphthalene with fluorene and 9,10-dihydrophenanthrene
journal, February 2006

  • Collings, Jonathan C.; Batsanov, Andrei S.; Howard, Judith AK
  • Canadian Journal of Chemistry, Vol. 84, Issue 2
  • DOI: 10.1139/v06-007

Poly(trifluoromethyl)azulenes: structures and acceptor properties
journal, January 2014

  • Clikeman, Tyler T.; Bukovsky, Eric V.; Kuvychko, Igor V.
  • Chem. Commun., Vol. 50, Issue 47
  • DOI: 10.1039/C4CC00510D

Steric and electronic effects of CF3 conformations in acene(CF3) derivatives
journal, May 2019


Self-Assembly of Aligned Hybrid One-Dimensional Stacks from Two Complementary π-Bowls
journal, December 2017

  • Dubceac, Cristina; Sevryugina, Yulia; Kuvychko, Igor V.
  • Crystal Growth & Design, Vol. 18, Issue 1
  • DOI: 10.1021/acs.cgd.7b01258

Single-Step Gas-Phase Polyperfluoroalkylation of Naphthalene Leads to Thermodynamic Products
journal, March 2014

  • San, Long K.; Bukovsky, Eric V.; Kuvychko, Igor V.
  • Chemistry - A European Journal, Vol. 20, Issue 15
  • DOI: 10.1002/chem.201304554

Incremental Tuning Up of Fluorous Phenazine Acceptors
journal, January 2016

  • Castro, Karlee P.; Clikeman, Tyler T.; DeWeerd, Nicholas J.
  • Chemistry - A European Journal, Vol. 22, Issue 12
  • DOI: 10.1002/chem.201504122

Bis-(polyfluoroalkyl)-acetylenes. II. Bicycloöctatrienes Through 1,4-Addition of Bis-(polyfluoroalkyl)-acetylenes to Aromatic Rings 1
journal, August 1961

  • Krespan, C. G.; McKusick, B. C.; Cairns, T. L.
  • Journal of the American Chemical Society, Vol. 83, Issue 16
  • DOI: 10.1021/ja01477a018

Studies on Organic Fluorine Compounds. VII. Trifluoromethylation of Aromatic Compounds
journal, January 1970

  • Kobayashi, Yoshiro; Kumadaki, Itsumaro; Sato, Susumu
  • CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 18, Issue 11
  • DOI: 10.1248/cpb.18.2334

Synthesis of β-Trifluoromethylnaphthalene Derivatives
journal, January 1972


Synthesis and [4 + 4] photodimerization of 9-trifluoromethylanthracene
journal, August 1989

  • Mintas, Mladen; Güsten, Hans; Williard, Paul G.
  • Journal of Photochemistry and Photobiology A: Chemistry, Vol. 48, Issue 2-3
  • DOI: 10.1016/1010-6030(89)87015-7

Synthesis and Structure of 1,4-Dimethoxy and 1,4-Dimethyl-9-(trifluoromethyl)triptycenes
journal, September 1995

  • Toyota, Shinji; Watanabe, Yoichi; Yoshida, Hiroyuki
  • Bulletin of the Chemical Society of Japan, Vol. 68, Issue 9
  • DOI: 10.1246/bcsj.68.2751

A Facile Synthesis of Trifluoromethyl- and 3,3,3-Trifluoropropenyl-Substituted Aromatic Compounds by the Oxidative Desulfurization-Fluorination of the Corresponding Carbodithioates
journal, April 1999

  • Furuta, Satoru; Kuroboshi, Manabu; Hiyama, Tamejiro
  • Bulletin of the Chemical Society of Japan, Vol. 72, Issue 4
  • DOI: 10.1246/bcsj.72.805

Electronic Properties of Trifluoromethylated Corannulenes
journal, October 2012

  • Schmidt, Bernd M.; Seki, Shu; Topolinski, Berit
  • Angewandte Chemie International Edition, Vol. 51, Issue 45
  • DOI: 10.1002/anie.201205757

Elektronische Eigenschaften trifluormethylierter Corannulene
journal, October 2012

  • Schmidt, Bernd M.; Seki, Shu; Topolinski, Berit
  • Angewandte Chemie, Vol. 124, Issue 45
  • DOI: 10.1002/ange.201205757

Fluorinated and Trifluoromethylated Corannulenes
journal, September 2013

  • Schmidt , Bernd M.; Topolinski , Berit; Yamada , Mihoko
  • Chemistry - A European Journal, Vol. 19, Issue 41
  • DOI: 10.1002/chem.201301910

Development of novel synthetic routes to bis(perfluoroalkyl)-substituted anthracene derivatives
journal, January 2013

  • Yamada, Shigeyuki; Kinoshita, Keita; Iwama, Shota
  • RSC Advances, Vol. 3, Issue 19
  • DOI: 10.1039/c3ra40974k

Facile synthetic protocols for perfluoroalkyl-substituted diazapentaphenes
journal, September 2014


Solid state structures of fluorine-rich fluoranthenes
journal, January 2017

  • Schmidt, Bernd M.; Meyer, Annika K.; Lentz, Dieter
  • CrystEngComm, Vol. 19, Issue 9
  • DOI: 10.1039/C6CE02558G

Synthesis of perfluoroalkylated pentacenes and evaluation of their fundamental physical properties
journal, January 2017

  • Yamada, Shigeyuki; Kinoshita, Keita; Iwama, Shota
  • Organic & Biomolecular Chemistry, Vol. 15, Issue 12
  • DOI: 10.1039/C7OB00043J

Polarographic Oxidation Potentials of Aromatic Compounds
journal, July 1963

  • Pysh, E. S.; Yang, N. C.
  • Journal of the American Chemical Society, Vol. 85, Issue 14
  • DOI: 10.1021/ja00897a019

On the determination of redox potentials of highly reactive aromatic mono- and multications
journal, June 1990

  • Dietrich, Michael; Heinze, Juergen
  • Journal of the American Chemical Society, Vol. 112, Issue 13
  • DOI: 10.1021/ja00169a023

Structure–Property Relationship of Supramolecular Rotators of Coronene in Charge-Transfer Solids
journal, February 2015

  • Yoshida, Yukihiro; Kumagai, Yoshihide; Mizuno, Motohiro
  • Crystal Growth & Design, Vol. 15, Issue 3
  • DOI: 10.1021/cg5017774

Improved Dynamic Properties of Charge-Transfer-Type Supramolecular Rotor Composed of Coronene and F 4 TCNQ
journal, October 2015

  • Yoshida, Yukihiro; Kumagai, Yoshihide; Mizuno, Motohiro
  • Crystal Growth & Design, Vol. 15, Issue 11
  • DOI: 10.1021/acs.cgd.5b01138

Octafluoronaphthalene–1,8-diaminonaphthalene (1/1)
journal, September 2001

  • Batsanov, Andrei S.; Collings, Jonathan C.; Howard, Judith A. K.
  • Acta Crystallographica Section E Structure Reports Online, Vol. 57, Issue 10
  • DOI: 10.1107/S1600536801015100

Arene–perfluoroarene interactions in crystal engineering 8: structures of 1∶1 complexes of hexafluorobenzene with fused-ring polyaromatic hydrocarbons
journal, January 2002

  • Collings, Jonathan C.; Roscoe, Karl P.; Robins, Edward G.
  • New J. Chem., Vol. 26, Issue 12
  • DOI: 10.1039/B207102A

Formation of Cocrystal Nanorods by Solid-State Reaction of Tetracyanobenzene in 9-Methylanthracene Molecular Crystal Nanorods
journal, April 2009

  • Al-Kaysi, Rabih O.; Müller, Astrid M.; Frisbee, Robert J.
  • Crystal Growth & Design, Vol. 9, Issue 4
  • DOI: 10.1021/cg800898f

Structure, Stoichiometry, and Charge Transfer in Cocrystals of Perylene with TCNQ-F x
journal, April 2016

  • Salzillo, Tommaso; Masino, Matteo; Kociok-Köhn, Gabriele
  • Crystal Growth & Design, Vol. 16, Issue 5
  • DOI: 10.1021/acs.cgd.5b01663

Crystal Growth, Dynamic and Charge Transfer Properties of New Coronene Charge Transfer Complexes
journal, November 2015

  • Kataeva, Olga; Khrizanforov, Mikhail; Budnikova, Yulia
  • Crystal Growth & Design, Vol. 16, Issue 1
  • DOI: 10.1021/acs.cgd.5b01301

X-ray Structure of a CT Complex Relevant to Diels−Alder Reactivity of Anthracenes
journal, December 2009

  • Berionni, Guillaume; Bertelle, Pierre-Alexandre; Marrot, Jérome
  • Journal of the American Chemical Society, Vol. 131, Issue 51
  • DOI: 10.1021/ja908747j

Characterization of an orientational disorder in two charge-transfer complexes: anthracene–tetracyanobenzene (A–TCNB) and naphthalene–tetracyanobenzene (N–TCNB)
journal, June 1989

  • Lefebvre, J.; Odou, G.; Muller, M.
  • Acta Crystallographica Section B Structural Science, Vol. 45, Issue 3
  • DOI: 10.1107/S0108768189001400

OLEX2 : a complete structure solution, refinement and analysis program
journal, January 2009

  • Dolomanov, Oleg V.; Bourhis, Luc J.; Gildea, Richard J.
  • Journal of Applied Crystallography, Vol. 42, Issue 2
  • DOI: 10.1107/S0021889808042726

Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913

Density functional theory with London dispersion corrections: Density functional theory with London dispersion corrections
journal, March 2011

  • Grimme, Stefan
  • Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 1, Issue 2
  • DOI: 10.1002/wcms.30

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

NWChem: A comprehensive and scalable open-source solution for large scale molecular simulations
journal, September 2010

  • Valiev, M.; Bylaska, E. J.; Govind, N.
  • Computer Physics Communications, Vol. 181, Issue 9, p. 1477-1489
  • DOI: 10.1016/j.cpc.2010.04.018

COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient
journal, January 1993


A Smooth Solvation Potential Based on the Conductor-Like Screening Model
journal, December 1999

  • York, Darrin M.; Karplus, Martin
  • The Journal of Physical Chemistry A, Vol. 103, Issue 50
  • DOI: 10.1021/jp992097l

Comprehensive photoelectron spectroscopic study of anionic clusters of anthracene and its alkyl derivatives: Electronic structures bridging molecules to bulk
journal, December 2007

  • Ando, Naoto; Mitsui, Masaaki; Nakajima, Atsushi
  • The Journal of Chemical Physics, Vol. 127, Issue 23
  • DOI: 10.1063/1.2805185

Some comments on the Benesi-Hildebrand equation
journal, January 1956


Independent determination of equilibrium constant and molar extinction coefficient of molecular complexes from spectrophotometric data by a graphical method
journal, January 1982

  • Seal, B. K.; Sil, H.; Mukherjee, D. C.
  • Spectrochimica Acta Part A: Molecular Spectroscopy, Vol. 38, Issue 2
  • DOI: 10.1016/0584-8539(82)80210-9

ExBox: A Polycyclic Aromatic Hydrocarbon Scavenger
journal, October 2012

  • Barnes, Jonathan C.; Juríček, Michal; Strutt, Nathan L.
  • Journal of the American Chemical Society, Vol. 135, Issue 1
  • DOI: 10.1021/ja307360n

Solvent Dependent Electronic Absorption Band Shifts of Charge-Transfer Complex Formed between Piperidine and Tetrachloro-1,4-Benzoquinone
journal, March 1988


On charge transfer spectra
journal, January 1962

  • Beukers, R.; Szent-Györgyi, A.
  • Recueil des Travaux Chimiques des Pays-Bas, Vol. 81, Issue 3
  • DOI: 10.1002/recl.19620810312

Nuclear Spin−Spin Coupling via Nonbonded Interactions. 8. 1 The Distance Dependence of Through-Space Fluorine−Fluorine Coupling
journal, May 2000

  • Mallory, Frank B.; Mallory, Clelia W.; Butler, Kelly E.
  • Journal of the American Chemical Society, Vol. 122, Issue 17
  • DOI: 10.1021/ja993032z

Through-Bond and Through-Space J FF Spin−Spin Coupling in Peridifluoronaphthalenes:  Accurate DFT Evaluation of the Four Contributions
journal, September 2001

  • Peralta, Juan E.; Barone, Verónica; Contreras, Rubén H.
  • Journal of the American Chemical Society, Vol. 123, Issue 37
  • DOI: 10.1021/ja011164y

Fluorine–Fluorine Interactions: NMR and AIM Analysis
journal, April 2004


Analysis of the NMR through-space coupling mechanism between 19F atoms
journal, August 2004


Variable-Temperature 19 F NMR and Theoretical Study of 1,9- and 1,7-C 60 F(CF 3 ) and C s - and C 1 -C 60 F 17 (CF 3 ):  Hindered CF 3 Rotation and Through-Space J FF Coupling
journal, August 2005

  • Kareev, Ivan E.; Quiñones, Gustavo Santiso; Kuvychko, Igor V.
  • Journal of the American Chemical Society, Vol. 127, Issue 32
  • DOI: 10.1021/ja051954y

Synthesis, Structure, and 19 F NMR Spectra of 1,3,7,10,14,17,23,28,31,40-C 60 (CF 3 ) 10
journal, June 2005

  • Kareev, Ivan E.; Kuvychko, Igor V.; Lebedkin, Sergey F.
  • Journal of the American Chemical Society, Vol. 127, Issue 23
  • DOI: 10.1021/ja050305j

Electron transfer from anthracenes. Comparison of photoionization, charge-transfer excitation and electrochemical oxidation
journal, November 1984

  • Masnovi, J. M.; Seddon, E. A.; Kochi, J. K.
  • Canadian Journal of Chemistry, Vol. 62, Issue 11
  • DOI: 10.1139/v84-436

Electron transfer from aromatic hydrocarbons and their .pi.-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials
journal, July 1984

  • Howell, J. O.; Goncalves, J. M.; Amatore, C.
  • Journal of the American Chemical Society, Vol. 106, Issue 14
  • DOI: 10.1021/ja00326a014

Formal oxidation potentials of aromatic hydrocarbons in N,N '-dimethylformamide
journal, October 1990

  • Anxolabéhère, E.; Hapiot, P.; Savéant, J. -M.
  • Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 282, Issue 1-2
  • DOI: 10.1016/0022-0728(91)85104-W

Discovery of a Neutral-to-Ionic Phase Transition in Organic Materials
journal, January 1981


Correlation of Oxidation and Ionization Potentials for Azoalkanes
journal, July 1997

  • Nau, Werner M.; Adam, Waldemar; Klapstein, Dieter
  • The Journal of Organic Chemistry, Vol. 62, Issue 15
  • DOI: 10.1021/jo970574v

Relationship between the Electron Affinities and Half-Wave Reduction Potentials of Fullerenes, Aromatic Hydrocarbons, and Metal Complexes
journal, May 1995

  • Ruoff, Rodney S.; Kadish, Karl M.; Boulas, Pierre
  • The Journal of Physical Chemistry, Vol. 99, Issue 21
  • DOI: 10.1021/j100021a060

Classification of organic molecules to obtain electron affinities from half wave reduction potentials: The aromatic hydrocarbons
journal, May 1999

  • Chen, Edward S.; Chen, Edward C. M.; Sane, Neeta
  • The Journal of Chemical Physics, Vol. 110, Issue 18
  • DOI: 10.1063/1.478854

Calculation of Electron Affinities of Polycyclic Aromatic Hydrocarbons and Solvation Energies of Their Radical Anion
journal, November 2006

  • Betowski, Leon D.; Enlow, Mark; Riddick, Lee
  • The Journal of Physical Chemistry A, Vol. 110, Issue 47
  • DOI: 10.1021/jp065785v

Electron Affinities of Polycyclic Aromatic Hydrocarbons by Means of B3LYP/6-31+G* Calculations
journal, May 2006

  • Modelli, Alberto; Mussoni, Laura; Fabbri, Daniele
  • The Journal of Physical Chemistry A, Vol. 110, Issue 20
  • DOI: 10.1021/jp0605911

Simple and accurate correlation of experimental redox potentials and DFT-calculated HOMO/LUMO energies of polycyclic aromatic hydrocarbons
journal, December 2012

  • Méndez-Hernández, Dalvin D.; Tarakeshwar, Pilarisetty; Gust, Devens
  • Journal of Molecular Modeling, Vol. 19, Issue 7
  • DOI: 10.1007/s00894-012-1694-7

Relationship between Electron Affinity and Half-Wave Reduction Potential: A Theoretical Study on Cyclic Electron-Acceptor Compounds
journal, September 2016

  • Calbo, Joaquín; Viruela, Rafael; Ortí, Enrique
  • ChemPhysChem, Vol. 17, Issue 23
  • DOI: 10.1002/cphc.201600778

Core Perylene Diimide Designs via Direct Bay- and ortho -(Poly)trifluoromethylation: Synthesis, Isolation, X-ray Structures, Optical and Electronic Properties : Core Perylene Diimide Designs
journal, September 2015

  • Clikeman, Tyler T.; Bukovsky, Eric V.; Wang, Xue-Bin
  • European Journal of Organic Chemistry, Vol. 2015, Issue 30
  • DOI: 10.1002/ejoc.201501024

Electron affinities of cyclic unsaturated dicarbonyls: maleic anhydrides, maleimides, and cyclopentenedione
journal, January 1989

  • Paul, Gary; Kebarle, Paul
  • Journal of the American Chemical Society, Vol. 111, Issue 2
  • DOI: 10.1021/ja00184a009

Charge transfer interaction between tetrachloro phthalic anhydride and aromatics
journal, January 1960

  • Chowdhury, Mihir; Basu, Sadhan
  • Transactions of the Faraday Society, Vol. 56
  • DOI: 10.1039/tf9605600335

Molecular Compounds and their Spectra. II
journal, February 1952

  • Mulliken, Robert S.
  • Journal of the American Chemical Society, Vol. 74, Issue 3
  • DOI: 10.1021/ja01123a067

Molecular Compounds and their Spectra. III. The Interaction of Electron Donors and Acceptors
journal, July 1952

  • Mulliken, Robert S.
  • The Journal of Physical Chemistry, Vol. 56, Issue 7
  • DOI: 10.1021/j150499a001

Donor-Acceptor Complexes
journal, October 1962


Semiconductive Properties of Tetracyanoethylene Complexes and Their Absorption Spectra
journal, January 1962

  • Kuroda, H.; Kobayashi, M.; Kinoshita, M.
  • The Journal of Chemical Physics, Vol. 36, Issue 2
  • DOI: 10.1063/1.1732531

Theoretical models of charge-transfer complexes
journal, January 1986


Theoretical determination of adsorption and ionisation energies of polycyclic aromatic hydrocarbons on water ice
journal, January 2018

  • Michoulier, Eric; Ben Amor, Nadia; Rapacioli, Mathias
  • Physical Chemistry Chemical Physics, Vol. 20, Issue 17
  • DOI: 10.1039/C8CP01175C

Experimental determination of electron affinities. Part 11.—Electron capture by some cyanocarbons and related compounds
journal, January 1967


Electron Affinities of Organic Molecules
journal, November 1962


π-Complexes. I. Charge Transfer Spectra of π-Complexes Formed by Trinitrobenzene with Polycyclic Aromatic Compounds 1
journal, November 1961

  • Dewar, Michael J. S.; Lepley, Arthur R.
  • Journal of the American Chemical Society, Vol. 83, Issue 22
  • DOI: 10.1021/ja01483a015

A comparison of experimental determinations of electron affinities of pi charge transfer complex acceptors
journal, October 1975

  • Chen, E. C. M.; Wentworth, W. E.
  • The Journal of Chemical Physics, Vol. 63, Issue 8
  • DOI: 10.1063/1.431807

Organic Synthesis Enabled by Light-Irradiation of EDA Complexes: Theoretical Background and Synthetic Applications
journal, January 2016

  • Lima, Carolina G. S.; de M. Lima, Thiago; Duarte, Marcelo
  • ACS Catalysis, Vol. 6, Issue 3
  • DOI: 10.1021/acscatal.5b02386

π-System Properties of Pyromellitonitrile
journal, December 1963

  • Zweig, Arnold.; Lehnsen, John E.; Hodgson, William G.
  • Journal of the American Chemical Society, Vol. 85, Issue 24
  • DOI: 10.1021/ja00907a008

Interaction of electron acceptors with bases. Part 10.—Complexes of polycyanobenzenes with electron donors
journal, January 1963


Elektronenüberführung durch Lichtabsorption und -emission in Elektronen-Donator-Acceptor-Komplexen
journal, June 1960


Langmuir−Blodgett Films of Charge-Transfer Complexes between an Amphiphilic Monopyrrolo-TTF and TCNQ Derivatives
journal, December 2003

  • Akutagawa, Tomoyuki; Uchigata, Masanori; Hasegawa, Tatsuo
  • The Journal of Physical Chemistry B, Vol. 107, Issue 50
  • DOI: 10.1021/jp036335v

Molecular Rotors of Coronene in Charge-Transfer Solids
journal, July 2013

  • Yoshida, Yukihiro; Shimizu, Yasuhiro; Yajima, Takeshi
  • Chemistry - A European Journal, Vol. 19, Issue 37
  • DOI: 10.1002/chem.201300578

Experimental determination of electron affinities. Part 9.—Benzoquinone, chloranil and related compounds
journal, January 1966


Electronic excitation spectra of doublet anion radicals of cyanobenzene and nitrobenzene derivatives: SAC-CI theoretical studies
journal, February 2015


Molecular complexes. Part XXII. Crystal and molecular structure of the molecular complex of pyrene and chloranil
journal, January 1973

  • Prout, Keith; Tickle, Ian J.
  • Journal of the Chemical Society, Perkin Transactions 2, Issue 9
  • DOI: 10.1039/p29730001212

Effects of Aromatic Trifluoromethylation, Fluorination, and Methylation on Intermolecular π–π Interactions
journal, July 2013

  • Mottishaw, Jeffery D.; Sun, Haoran
  • The Journal of Physical Chemistry A, Vol. 117, Issue 33
  • DOI: 10.1021/jp403679x

Rational Design of Lamellar π–π Stacked Organic Crystalline Materials with Short Interplanar Distance
journal, December 2013

  • Putta, Anjaneyulu; Mottishaw, Jeffery D.; Wang, Zhihua
  • Crystal Growth & Design, Vol. 14, Issue 1
  • DOI: 10.1021/cg401637a

Arene–perfluoroarene interactions in crystal engineering. 5.
journal, November 2001

  • Batsanov, Andrei S.; Collings, Jonathan C.; Howard, Judith A. K.
  • Acta Crystallographica Section C Crystal Structure Communications, Vol. 57, Issue 11
  • DOI: 10.1107/S0108270101013075

Rapid mechanochemical preparation of a sandwich-like charge transfer complex
journal, January 2013

  • Chen, Hao; Gao, Fan; Yao, Erdong
  • CrystEngComm, Vol. 15, Issue 22
  • DOI: 10.1039/c3ce40585k

Crystal Growth, Structure, and Electronic Band Structure of Tetracene−TCNQ
journal, January 2007

  • Buurma, A. J. C.; Jurchescu, O. D.; Shokaryev, I.
  • The Journal of Physical Chemistry C, Vol. 111, Issue 8
  • DOI: 10.1021/jp065944a