Incremental Tuning Up of Fluorous Phenazine Acceptors

doi:10.1002/chem.201504122

Title: Incremental Tuning Up of Fluorous Phenazine Acceptors

Authors:

Castro, Karlee P. ^[1]; Clikeman, Tyler T. ^[1]; DeWeerd, Nicholas J. ^[1]; Bukovsky, Eric V. ^[1]; Rippy, Kerry C. ^[1]; Kuvychko, Igor V. ^[1]; Hou, Gao-Lei ^[2]; Chen, Yu-Sheng ^[3]; Wang, Xue-Bin ^[2]; Strauss, Steven H. ^[1]; Boltalina, Olga V. ^[1]

Department of Chemistry, Colorado State University, Fort Collins CO 80523 USA
Physical Sciences Division, Pacific Northwest National Laboratory, Richland WA 99352 USA
ChemMatCARS, University of Chicago, Advanced Photon Source, Argonne IL 60439 USA

Publication Date:: 2016-01-12

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

OSTI Identifier:: 1401639

Grant/Contract Number:: AC02-06CH11357

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Chemistry - A European Journal

Additional Journal Information:: Journal Name: Chemistry - A European Journal Journal Volume: 22 Journal Issue: 12; Journal ID: ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Castro, Karlee P., Clikeman, Tyler T., DeWeerd, Nicholas J., Bukovsky, Eric V., Rippy, Kerry C., Kuvychko, Igor V., Hou, Gao-Lei, Chen, Yu-Sheng, Wang, Xue-Bin, Strauss, Steven H., and Boltalina, Olga V. Incremental Tuning Up of Fluorous Phenazine Acceptors.  Germany: N. p., 2016. 
        Web.  doi:10.1002/chem.201504122.

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                    Castro, Karlee P., Clikeman, Tyler T., DeWeerd, Nicholas J., Bukovsky, Eric V., Rippy, Kerry C., Kuvychko, Igor V., Hou, Gao-Lei, Chen, Yu-Sheng, Wang, Xue-Bin, Strauss, Steven H., & Boltalina, Olga V. Incremental Tuning Up of Fluorous Phenazine Acceptors.  Germany.  doi:10.1002/chem.201504122.

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                    Castro, Karlee P., Clikeman, Tyler T., DeWeerd, Nicholas J., Bukovsky, Eric V., Rippy, Kerry C., Kuvychko, Igor V., Hou, Gao-Lei, Chen, Yu-Sheng, Wang, Xue-Bin, Strauss, Steven H., and Boltalina, Olga V. Tue .  
        "Incremental Tuning Up of Fluorous Phenazine Acceptors".  Germany.  doi:10.1002/chem.201504122.

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@article{osti_1401639,

  title        = {Incremental Tuning Up of Fluorous Phenazine Acceptors},

  author       = {Castro, Karlee P. and Clikeman, Tyler T. and DeWeerd, Nicholas J. and Bukovsky, Eric V. and Rippy, Kerry C. and Kuvychko, Igor V. and Hou, Gao-Lei and Chen, Yu-Sheng and Wang, Xue-Bin and Strauss, Steven H. and Boltalina, Olga V.},

  abstractNote = {},

  doi          = {10.1002/chem.201504122},

  journal      = {Chemistry - A European Journal},

  number       = 12,

  volume       = 22,

  place        = {Germany},

  year         = {2016},

  month        = {1}

}

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DOI: 10.1002/chem.201504122

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Works referenced in this record:

N-Heteroacenes
journal, July 2009

Bunz, Uwe H. F.
Chemistry - A European Journal, Vol. 15, Issue 28
DOI: 10.1002/chem.200900990

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

Ferroelectricity near room temperature in co-crystals of nonpolar organic molecules
journal, January 2005

Horiuchi, Sachio; Ishii, Fumiyuki; Kumai, Reiji
Nature Materials, Vol. 4, Issue 2
DOI: 10.1038/nmat1298

Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties
journal, May 2006

Yoon, Myung-Han; Facchetti, Antonio; Stern, Charlotte E.
Journal of the American Chemical Society, Vol. 128, Issue 17
DOI: 10.1021/ja060016a

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

Chemical oxidation of fluoroanilines to fluoroazobenzenes and fluorophenazines with potassium ferricyanide and potassium hydroxide
journal, December 2004

Leyva, Elisa; Medina, Concepción; Moctezuma, Edgar
Canadian Journal of Chemistry, Vol. 82, Issue 12
DOI: 10.1139/v04-150

Polyfluoroarenes. Part X. Polyfluoroaromatic azo-compounds
journal, January 1970

Birchall, J. M.; Haszeldine, R. N.; Kemp, J. E. G.
Journal of the Chemical Society C: Organic, Issue 3
DOI: 10.1039/j39700000449

The electrochemical oxidation of polyfluoroaromatic amines—I
journal, January 1970

Hudson, A. G.; Pedler, A. E.; Tatlow, J. C.
Tetrahedron, Vol. 26, Issue 15
DOI: 10.1016/S0040-4020(01)92956-4

High Charge-Carrier Mobility in an Amorphous Hexaazatrinaphthylene Derivative
journal, November 2005

Kaafarani, Bilal R.; Kondo, Takeshi; Yu, Junsheng
Journal of the American Chemical Society, Vol. 127, Issue 47
DOI: 10.1021/ja0553147

Synthesis, Physical Properties, and Light-Emitting Diode Performance of Phenazine-Based Derivatives with Three, Five, and Nine Fused Six-Membered Rings
journal, February 2015

Gu, Pei-Yang; Zhao, Yongbiao; He, Jing-Hui
The Journal of Organic Chemistry, Vol. 80, Issue 6
DOI: 10.1021/jo5027707

Synthesis of Tetrachloro-azapentacene as an Ambipolar Organic Semiconductor with High and Balanced Carrier Mobilities
journal, June 2011

Song, Cheng-Li; Ma, Chong-Bo; Yang, Feng
Organic Letters, Vol. 13, Issue 11
DOI: 10.1021/ol2008999

Halogenated Materials as Organic Semiconductors ^†
journal, February 2011

Tang, Ming L.; Bao, Zhenan
Chemistry of Materials, Vol. 23, Issue 3
DOI: 10.1021/cm102182x

Charge Transport Properties in Discotic Liquid Crystals: A Quantum-Chemical Insight into Structure−Property Relationships
journal, March 2004

Lemaur, Vincent; da Silva Filho, Demetrio A.; Coropceanu, Veaceslav
Journal of the American Chemical Society, Vol. 126, Issue 10
DOI: 10.1021/ja0390956

Electron affinities of organic materials used for organic light-emitting diodes: A low-energy inverse photoemission study
journal, May 2015

Yoshida, Hiroyuki; Yoshizaki, Kei
Organic Electronics, Vol. 20
DOI: 10.1016/j.orgel.2015.01.037

Reaction, identification, and fluorescence of aminoperfluorophenazines
journal, September 2008

Matsui, Masaki; Suzuki, Masayuki; Nunome, Izumi
Tetrahedron, Vol. 64, Issue 37
DOI: 10.1016/j.tet.2008.06.079

Hydrogen-Bonded Dihydrotetraazapentacenes
journal, January 2012

He, Zikai; Liu, Danqing; Mao, Renxin
Organic Letters, Vol. 14, Issue 4
DOI: 10.1021/ol203404q

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

Phenazine Natural Products: Biosynthesis, Synthetic Analogues, and Biological Activity
journal, March 2004

Laursen, Jane Buus; Nielsen, John
Chemical Reviews, Vol. 104, Issue 3
DOI: 10.1021/cr020473j

Thin films of a ferroelectric phenazine/chloranilic acid organic cocrystal
journal, July 2011

Thompson, Nicholas J.; Jandl, Adam C.; Spalenka, Josef W.
Journal of Crystal Growth, Vol. 327, Issue 1
DOI: 10.1016/j.jcrysgro.2011.05.027

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

Studies in azide chemistry. Part VI. Some reactions of perfluoroazidobenzene and perfluoro-4-azidotoluene
journal, January 1974

Banks, Ronald E.; Prakash, Ajai
Journal of the Chemical Society, Perkin Transactions 1
DOI: 10.1039/p19740001365

New highly fluorinated phenazine derivatives: Correlation between crystal structure and NMR spectroscopy
journal, February 2006

Khusniyarov, Marat M.; Harms, Klaus; Sundermeyer, Jörg
Journal of Fluorine Chemistry, Vol. 127, Issue 2
DOI: 10.1016/j.jfluchem.2005.10.018

Photodetachment photoelectron spectroscopy of mass selected anions: anthracene and the anthracene-H2O cluster
journal, February 1997

Schiedt, J.; Weinkauf, R.
Chemical Physics Letters, Vol. 266, Issue 1-2
DOI: 10.1016/S0009-2614(96)01512-6

Development of a low-temperature photoelectron spectroscopy instrument using an electrospray ion source and a cryogenically controlled ion trap
journal, July 2008

Wang, Xue-Bin; Wang, Lai-Sheng
Review of Scientific Instruments, Vol. 79, Issue 7
DOI: 10.1063/1.2957610

Dual Solvatochromism of Neutral Red
journal, July 1998

Singh, M. K.; Pal, H.; Bhasikuttan, A. C.
Photochemistry and Photobiology, Vol. 68, Issue 1
DOI: 10.1111/j.1751-1097.1998.tb03249.x

Soluble and Stable N-Heteropentacenes with High Field-Effect Mobility
journal, February 2011

Liang, Zhixiong; Tang, Qin; Xu, Jianbin
Advanced Materials, Vol. 23, Issue 13
DOI: 10.1002/adma.201004325

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

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

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

Ferroelectricity and Pressure-Induced Phenomena Driven by Neutral Ionic Valence Instability of Acid–Base Supramolecules
journal, December 2011

Kumai, Reiji; Horiuchi, Sachio; Fujioka, Jun
Journal of the American Chemical Society, Vol. 134, Issue 2
DOI: 10.1021/ja208113p

Fascinating effect of dehydrogenation on the transport properties of N-heteropentacenes: transformation from p- to n-type semiconductor
journal, January 2012

Tang, Xiao-Dan; Liao, Yi; Geng, Hua
Journal of Materials Chemistry, Vol. 22, Issue 35
DOI: 10.1039/c2jm33039c

Nitrogen-Rich Oligoacenes: Candidates for n-Channel Organic Semiconductors
journal, February 2007

Winkler, Michael; Houk, K. N.
Journal of the American Chemical Society, Vol. 129, Issue 6
DOI: 10.1021/ja067087u

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

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

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

n-Type Organic Semiconductors in Organic Electronics
journal, August 2010

Anthony, John E.; Facchetti, Antonio; Heeney, Martin
Advanced Materials, Vol. 22, Issue 34, p. 3876-3892
DOI: 10.1002/adma.200903628

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

Red solid-state fluorescent aminoperfluorophenazines
journal, September 2009

Matsui, Masaki; Ikeda, Rie; Kubota, Yasuhiro
Tetrahedron Letters, Vol. 50, Issue 35
DOI: 10.1016/j.tetlet.2009.06.095

Are N , N -Dihydrodiazatetracene Derivatives Antiaromatic?
journal, June 2008

Miao, Shaobin; Brombosz, Scott M.; Schleyer, Paul v. R.
Journal of the American Chemical Society, Vol. 130, Issue 23
DOI: 10.1021/ja077614p

Phenazines and Polyphenazines in Electrochemical Sensors and Biosensors
journal, July 2010

Pauliukaite, Rasa; Ghica, Mariana Emilia; Barsan, Madalina M.
Analytical Letters, Vol. 43, Issue 10-11
DOI: 10.1080/00032711003653791

Substituent effects in a series of 1,7-C60(RF)2 compounds (RF = CF3, C2F5, n-C3F7, i-C3F7, n-C4F9, s-C4F9, n-C8F17): electron affinities, reduction potentials and E(LUMO) values are not always correlated
journal, January 2012

Kuvychko, Igor V.; Whitaker, James B.; Larson, Bryon W.
Chemical Science, Vol. 3, Issue 5
DOI: 10.1039/c2sc01133f

Electron affinities of aza-substituted polycyclic aromatic hydrocarbons
journal, October 1989

Dillow, Glen W.; Kebarle, P.
Canadian Journal of Chemistry, Vol. 67, Issue 10
DOI: 10.1139/v89-249

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Title: Incremental Tuning Up of Fluorous Phenazine Acceptors

Citation Formats

N-Heteroacenes journal, July 2009

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

Ferroelectricity near room temperature in co-crystals of nonpolar organic molecules journal, January 2005

Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties journal, May 2006

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

Chemical oxidation of fluoroanilines to fluoroazobenzenes and fluorophenazines with potassium ferricyanide and potassium hydroxide journal, December 2004

Polyfluoroarenes. Part X. Polyfluoroaromatic azo-compounds journal, January 1970

The electrochemical oxidation of polyfluoroaromatic amines—I journal, January 1970

High Charge-Carrier Mobility in an Amorphous Hexaazatrinaphthylene Derivative journal, November 2005

Synthesis, Physical Properties, and Light-Emitting Diode Performance of Phenazine-Based Derivatives with Three, Five, and Nine Fused Six-Membered Rings journal, February 2015

Synthesis of Tetrachloro-azapentacene as an Ambipolar Organic Semiconductor with High and Balanced Carrier Mobilities journal, June 2011

Halogenated Materials as Organic Semiconductors † journal, February 2011

Charge Transport Properties in Discotic Liquid Crystals: A Quantum-Chemical Insight into Structure−Property Relationships journal, March 2004

Electron affinities of organic materials used for organic light-emitting diodes: A low-energy inverse photoemission study journal, May 2015

Reaction, identification, and fluorescence of aminoperfluorophenazines journal, September 2008

Hydrogen-Bonded Dihydrotetraazapentacenes journal, January 2012

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

Phenazine Natural Products: Biosynthesis, Synthetic Analogues, and Biological Activity journal, March 2004

Thin films of a ferroelectric phenazine/chloranilic acid organic cocrystal journal, July 2011

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

Studies in azide chemistry. Part VI. Some reactions of perfluoroazidobenzene and perfluoro-4-azidotoluene journal, January 1974

New highly fluorinated phenazine derivatives: Correlation between crystal structure and NMR spectroscopy journal, February 2006

Photodetachment photoelectron spectroscopy of mass selected anions: anthracene and the anthracene-H2O cluster journal, February 1997

Development of a low-temperature photoelectron spectroscopy instrument using an electrospray ion source and a cryogenically controlled ion trap journal, July 2008

Dual Solvatochromism of Neutral Red journal, July 1998

Soluble and Stable N-Heteropentacenes with High Field-Effect Mobility journal, February 2011

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

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

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

Ferroelectricity and Pressure-Induced Phenomena Driven by Neutral Ionic Valence Instability of Acid–Base Supramolecules journal, December 2011

Fascinating effect of dehydrogenation on the transport properties of N-heteropentacenes: transformation from p- to n-type semiconductor journal, January 2012

Nitrogen-Rich Oligoacenes: Candidates for n-Channel Organic Semiconductors journal, February 2007

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

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

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

n-Type Organic Semiconductors in Organic Electronics journal, August 2010

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

Red solid-state fluorescent aminoperfluorophenazines journal, September 2009

Are N , N -Dihydrodiazatetracene Derivatives Antiaromatic? journal, June 2008

Phenazines and Polyphenazines in Electrochemical Sensors and Biosensors journal, July 2010

Substituent effects in a series of 1,7-C60(RF)2 compounds (RF = CF3, C2F5, n-C3F7, i-C3F7, n-C4F9, s-C4F9, n-C8F17): electron affinities, reduction potentials and E(LUMO) values are not always correlated journal, January 2012

Electron affinities of aza-substituted polycyclic aromatic hydrocarbons journal, October 1989

N-Heteroacenes
journal, July 2009

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

Ferroelectricity near room temperature in co-crystals of nonpolar organic molecules
journal, January 2005

Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties
journal, May 2006

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

Chemical oxidation of fluoroanilines to fluoroazobenzenes and fluorophenazines with potassium ferricyanide and potassium hydroxide
journal, December 2004

Polyfluoroarenes. Part X. Polyfluoroaromatic azo-compounds
journal, January 1970

The electrochemical oxidation of polyfluoroaromatic amines—I
journal, January 1970

High Charge-Carrier Mobility in an Amorphous Hexaazatrinaphthylene Derivative
journal, November 2005

Synthesis, Physical Properties, and Light-Emitting Diode Performance of Phenazine-Based Derivatives with Three, Five, and Nine Fused Six-Membered Rings
journal, February 2015

Synthesis of Tetrachloro-azapentacene as an Ambipolar Organic Semiconductor with High and Balanced Carrier Mobilities
journal, June 2011

Halogenated Materials as Organic Semiconductors ^†
journal, February 2011

Charge Transport Properties in Discotic Liquid Crystals: A Quantum-Chemical Insight into Structure−Property Relationships
journal, March 2004

Electron affinities of organic materials used for organic light-emitting diodes: A low-energy inverse photoemission study
journal, May 2015

Reaction, identification, and fluorescence of aminoperfluorophenazines
journal, September 2008

Hydrogen-Bonded Dihydrotetraazapentacenes
journal, January 2012

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

Phenazine Natural Products: Biosynthesis, Synthetic Analogues, and Biological Activity
journal, March 2004

Thin films of a ferroelectric phenazine/chloranilic acid organic cocrystal
journal, July 2011

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

Studies in azide chemistry. Part VI. Some reactions of perfluoroazidobenzene and perfluoro-4-azidotoluene
journal, January 1974

New highly fluorinated phenazine derivatives: Correlation between crystal structure and NMR spectroscopy
journal, February 2006

Photodetachment photoelectron spectroscopy of mass selected anions: anthracene and the anthracene-H2O cluster
journal, February 1997

Development of a low-temperature photoelectron spectroscopy instrument using an electrospray ion source and a cryogenically controlled ion trap
journal, July 2008

Dual Solvatochromism of Neutral Red
journal, July 1998

Soluble and Stable N-Heteropentacenes with High Field-Effect Mobility
journal, February 2011

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

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

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

Ferroelectricity and Pressure-Induced Phenomena Driven by Neutral Ionic Valence Instability of Acid–Base Supramolecules
journal, December 2011

Fascinating effect of dehydrogenation on the transport properties of N-heteropentacenes: transformation from p- to n-type semiconductor
journal, January 2012

Nitrogen-Rich Oligoacenes: Candidates for n-Channel Organic Semiconductors
journal, February 2007

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

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

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

n-Type Organic Semiconductors in Organic Electronics
journal, August 2010

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

Red solid-state fluorescent aminoperfluorophenazines
journal, September 2009

Are N , N -Dihydrodiazatetracene Derivatives Antiaromatic?
journal, June 2008

Phenazines and Polyphenazines in Electrochemical Sensors and Biosensors
journal, July 2010

Substituent effects in a series of 1,7-C60(RF)2 compounds (RF = CF3, C2F5, n-C3F7, i-C3F7, n-C4F9, s-C4F9, n-C8F17): electron affinities, reduction potentials and E(LUMO) values are not always correlated
journal, January 2012

Electron affinities of aza-substituted polycyclic aromatic hydrocarbons
journal, October 1989