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Title: Synthesis and Properties of New N;#8208;Heteroheptacenes for Solution;#8208;Based Organic Field Effect Transistors

Authors:
; ; ; ; ; ;  [1]
  1. UIC
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
NSFUNIVERSITYFOREIGN
OSTI Identifier:
1597993
Resource Type:
Journal Article
Journal Name:
Chem.-Eur. J.
Additional Journal Information:
Journal Volume: 23; Journal Issue: (51) ; 09, 2017
Country of Publication:
United States
Language:
ENGLISH

Citation Formats

Zhou, Fei, Liu, Sheng, Santarsiero, Bernard D., Wink, Donald J., Boudinet, Damien, Facchetti, Antonio, and Driver, Tom. Synthesis and Properties of New N;#8208;Heteroheptacenes for Solution;#8208;Based Organic Field Effect Transistors. United States: N. p., 2020. Web. doi:10.1002/chem.201701966.
Zhou, Fei, Liu, Sheng, Santarsiero, Bernard D., Wink, Donald J., Boudinet, Damien, Facchetti, Antonio, & Driver, Tom. Synthesis and Properties of New N;#8208;Heteroheptacenes for Solution;#8208;Based Organic Field Effect Transistors. United States. doi:10.1002/chem.201701966.
Zhou, Fei, Liu, Sheng, Santarsiero, Bernard D., Wink, Donald J., Boudinet, Damien, Facchetti, Antonio, and Driver, Tom. Fri . "Synthesis and Properties of New N;#8208;Heteroheptacenes for Solution;#8208;Based Organic Field Effect Transistors". United States. doi:10.1002/chem.201701966.
@article{osti_1597993,
title = {Synthesis and Properties of New N;#8208;Heteroheptacenes for Solution;#8208;Based Organic Field Effect Transistors},
author = {Zhou, Fei and Liu, Sheng and Santarsiero, Bernard D. and Wink, Donald J. and Boudinet, Damien and Facchetti, Antonio and Driver, Tom},
abstractNote = {},
doi = {10.1002/chem.201701966},
journal = {Chem.-Eur. J.},
number = (51) ; 09, 2017,
volume = 23,
place = {United States},
year = {2020},
month = {1}
}

Works referenced in this record:

Organic Semiconducting Oligomers for Use in Thin Film Transistors
journal, April 2007

  • Murphy, Amanda R.; Fréchet, Jean M. J.
  • Chemical Reviews, Vol. 107, Issue 4
  • DOI: 10.1021/cr0501386

Advances in Molecular Design and Synthesis of Regioregular Polythiophenes
journal, September 2008

  • Osaka, Itaru; McCullough, Richard D.
  • Accounts of Chemical Research, Vol. 41, Issue 9
  • DOI: 10.1021/ar800130s

Spectral Engineering in π-Conjugated Polymers with Intramolecular Donor−Acceptor Interactions
journal, November 2010

  • Beaujuge, Pierre M.; Amb, Chad M.; Reynolds, John R.
  • Accounts of Chemical Research, Vol. 43, Issue 11
  • DOI: 10.1021/ar100043u

π-Conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications
journal, January 2010

  • Wu, Weiping; Liu, Yunqi; Zhu, Daoben
  • Chem. Soc. Rev., Vol. 39, Issue 5
  • DOI: 10.1039/B813123F

Thienoacene-Based Organic Semiconductors
journal, August 2011

  • Takimiya, Kazuo; Shinamura, Shoji; Osaka, Itaru
  • Advanced Materials, Vol. 23, Issue 38
  • DOI: 10.1002/adma.201102007

π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications
journal, February 2011


Experimental Techniques for the Fabrication and Characterization of Organic Thin Films for Field-Effect Transistors
journal, May 2011

  • Wen, Yugeng; Liu, Yunqi; Guo, Yunlong
  • Chemical Reviews, Vol. 111, Issue 5
  • DOI: 10.1021/cr1001904

Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics
journal, November 2011

  • Wang, Chengliang; Dong, Huanli; Hu, Wenping
  • Chemical Reviews, Vol. 112, Issue 4
  • DOI: 10.1021/cr100380z

Organic Semiconductors toward Electronic Devices: High Mobility and Easy Processability
journal, May 2012

  • Ruiz, Constanza; García-Frutos, Eva M.; Hennrich, Gunther
  • The Journal of Physical Chemistry Letters, Vol. 3, Issue 11
  • DOI: 10.1021/jz300251u

Comprehensive Approach to Intrinsic Charge Carrier Mobility in Conjugated Organic Molecules, Macromolecules, and Supramolecular Architectures
journal, May 2012

  • Saeki, Akinori; Koizumi, Yoshiko; Aida, Takuzo
  • Accounts of Chemical Research, Vol. 45, Issue 8
  • DOI: 10.1021/ar200283b

Chemical and Engineering Approaches To Enable Organic Field-Effect Transistors for Electronic Skin Applications
journal, October 2011

  • Sokolov, Anatoliy N.; Tee, Benjamin C-K.; Bettinger, Christopher J.
  • Accounts of Chemical Research, Vol. 45, Issue 3
  • DOI: 10.1021/ar2001233

Organic transistors in the new decade: Toward n-channel, printed, and stabilized devices
journal, February 2012

  • Kola, Srinivas; Sinha, Jasmine; Katz, Howard E.
  • Journal of Polymer Science Part B: Polymer Physics, Vol. 50, Issue 15
  • DOI: 10.1002/polb.23054

Design of Semiconducting Indacenodithiophene Polymers for High Performance Transistors and Solar Cells
journal, January 2012

  • McCulloch, Iain; Ashraf, Raja Shahid; Biniek, Laure
  • Accounts of Chemical Research, Vol. 45, Issue 5
  • DOI: 10.1021/ar200208g

Toward high-mobility organic field-effect transistors: Control of molecular packing and large-area fabrication of single-crystal-based devices
journal, January 2013

  • Li, Hanying; Giri, Gaurav; Tok, Jeffrey B. -H.
  • MRS Bulletin, Vol. 38, Issue 1
  • DOI: 10.1557/mrs.2012.309

25th Anniversary Article: Recent Advances in n-Type and Ambipolar Organic Field-Effect Transistors
journal, August 2013


Designing π-conjugated polymers for organic electronics
journal, December 2013


Advances in Charge Carrier Mobilities of Semiconducting Polymers Used in Organic Transistors
journal, September 2013

  • Holliday, Sarah; Donaghey, Jenny E.; McCulloch, Iain
  • Chemistry of Materials, Vol. 26, Issue 1
  • DOI: 10.1021/cm402421p

Imide- and Amide-Functionalized Polymer Semiconductors
journal, September 2014

  • Guo, Xugang; Facchetti, Antonio; Marks, Tobin J.
  • Chemical Reviews, Vol. 114, Issue 18
  • DOI: 10.1021/cr500225d

Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives:  The Brick and Mortar of Organic Electronics
journal, November 2004

  • Bendikov, Michael; Wudl, Fred; Perepichka, Dmitrii F.
  • Chemical Reviews, Vol. 104, Issue 11
  • DOI: 10.1021/cr030666m

Functionalized Acenes and Heteroacenes for Organic Electronics
journal, December 2006


The Larger Acenes: Versatile Organic Semiconductors
journal, January 2008


Höhere Acene: vielseitige organische Halbleiter
journal, January 2008


Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors
journal, April 2013

  • Mei, Jianguo; Diao, Ying; Appleton, Anthony L.
  • Journal of the American Chemical Society, Vol. 135, Issue 18
  • DOI: 10.1021/ja400881n

Recent Highlights and Perspectives on Acene Based Molecules and Materials
journal, July 2014

  • Ye, Qun; Chi, Chunyan
  • Chemistry of Materials, Vol. 26, Issue 14
  • DOI: 10.1021/cm501536p

Interface-Controlled, High-Mobility Organic Transistors
journal, March 2007

  • Jurchescu, O. D.; Popinciuc, M.; van Wees, B. J.
  • Advanced Materials, Vol. 19, Issue 5
  • DOI: 10.1002/adma.200600929

Elastomeric Transistor Stamps: Reversible Probing of Charge Transport in Organic Crystals
journal, March 2004

  • Sundar, Vikram C.; Zaumseil, Jana; Podzorov, Vitaly
  • Science, Vol. 303, Issue 5664, p. 1644-1646
  • DOI: 10.1126/science.1094196

Organic thin-film electronics from vitreous solution-processed rubrene hypereutectics
journal, July 2005

  • Stingelin-Stutzmann, Natalie; Smits, Edsger; Wondergem, Harry
  • Nature Materials, Vol. 4, Issue 8
  • DOI: 10.1038/nmat1426

Very high-mobility organic single-crystal transistors with in-crystal conduction channels
journal, March 2007

  • Takeya, J.; Yamagishi, M.; Tominari, Y.
  • Applied Physics Letters, Vol. 90, Issue 10
  • DOI: 10.1063/1.2711393

Organic field-effect transistors using single crystals
journal, April 2009


Very High Mobility in Solution-Processed Organic Thin-Film Transistors of Highly Ordered [1]Benzothieno[3,2-b]benzothiophene Derivatives
journal, November 2009

  • Uemura, Takafumi; Hirose, Yuri; Uno, Mayumi
  • Applied Physics Express, Vol. 2, Issue 11, Article No. 111501
  • DOI: 10.1143/APEX.2.111501

Rubrenes: Planar and Twisted
journal, October 2008

  • Paraskar, Abhimanyu S.; Reddy, A. Ravikumar; Patra, Asit
  • Chemistry - A European Journal, Vol. 14, Issue 34
  • DOI: 10.1002/chem.200800802

A Photopatternable Pentacene Precursor for Use in Organic Thin-Film Transistors
journal, October 2004

  • Weidkamp, Kevin P.; Afzali, Ali; Tromp, Rudolf M.
  • Journal of the American Chemical Society, Vol. 126, Issue 40
  • DOI: 10.1021/ja045228r

Effect of impurities on the mobility of single crystal pentacene
journal, April 2004

  • Jurchescu, Oana D.; Baas, Jacob; Palstra, Thomas T. M.
  • Applied Physics Letters, Vol. 84, Issue 16
  • DOI: 10.1063/1.1704874

High mobility solution processed 6,13-bis(triisopropyl-silylethynyl) pentacene organic thin film transistors
journal, August 2007

  • Park, Sung Kyu; Jackson, Thomas N.; Anthony, John E.
  • Applied Physics Letters, Vol. 91, Issue 6
  • DOI: 10.1063/1.2768934

Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties
journal, May 2013

  • McGarry, Kathryn A.; Xie, Wei; Sutton, Christopher
  • Chemistry of Materials, Vol. 25, Issue 11
  • DOI: 10.1021/cm400736s

Connecting Molecular Structure and Exciton Diffusion Length in Rubrene Derivatives
journal, June 2013

  • Mullenbach, Tyler K.; McGarry, Kathryn A.; Luhman, Wade A.
  • Advanced Materials, Vol. 25, Issue 27
  • DOI: 10.1002/adma.201300641

Control of Rubrene Polymorphs via Polymer Binders: Applications in Organic Field-Effect Transistors
journal, May 2015


Impact of Molecular Packing on Electronic Polarization in Organic Crystals: The Case of Pentacene vs TIPS-Pentacene
journal, April 2014

  • Ryno, Sean M.; Risko, Chad; Brédas, Jean-Luc
  • Journal of the American Chemical Society, Vol. 136, Issue 17
  • DOI: 10.1021/ja501725s

Epitaxially Grown Strained Pentacene Thin Film on Graphene Membrane
journal, January 2015


Highly Soluble [1]Benzothieno[3,2- b ]benzothiophene (BTBT) Derivatives for High-Performance, Solution-Processed Organic Field-Effect Transistors
journal, December 2007

  • Ebata, Hideaki; Izawa, Takafumi; Miyazaki, Eigo
  • Journal of the American Chemical Society, Vol. 129, Issue 51
  • DOI: 10.1021/ja074841i

Doping Molecular Semiconductors:  n-Type Doping of a Liquid Crystal Perylene Diimide
journal, August 2001

  • Gregg, Brian A.; Cormier, Russell A.
  • Journal of the American Chemical Society, Vol. 123, Issue 32, p. 7959-7960
  • DOI: 10.1021/ja016410k

All-Polymer Solar Cells from Perylene Diimide Based Copolymers: Material Design and Phase Separation Control
journal, February 2011

  • Zhou, Erjun; Cong, Junzi; Wei, Qingshuo
  • Angewandte Chemie International Edition, Vol. 50, Issue 12, p. 2799-2803
  • DOI: 10.1002/anie.201005408

Rylene and Related Diimides for Organic Electronics
journal, December 2010

  • Zhan, Xiaowei; Facchetti, Antonio; Barlow, Stephen
  • Advanced Materials, Vol. 23, Issue 2, p. 268-284
  • DOI: 10.1002/adma.201001402

Annealing-Free High-Mobility Diketopyrrolopyrrole−Quaterthiophene Copolymer for Solution-Processed Organic Thin Film Transistors
journal, February 2011

  • Li, Yuning; Sonar, Prashant; Singh, Samarendra P.
  • Journal of the American Chemical Society, Vol. 133, Issue 7
  • DOI: 10.1021/ja1085996

High-Performance Ambipolar Diketopyrrolopyrrole-Thieno[3,2- b ]thiophene Copolymer Field-Effect Transistors with Balanced Hole and Electron Mobilities
journal, October 2011

  • Chen, Zhuoying; Lee, Mi Jung; Shahid Ashraf, Raja
  • Advanced Materials, Vol. 24, Issue 5
  • DOI: 10.1002/adma.201102786

Importance of Solubilizing Group and Backbone Planarity in Low Band Gap Polymers for High Performance Ambipolar field-effect Transistors
journal, March 2012

  • Lee, Joong Suk; Son, Seon Kyoung; Song, Sanghoon
  • Chemistry of Materials, Vol. 24, Issue 7
  • DOI: 10.1021/cm2037487

Highly π-Extended Copolymers with Diketopyrrolopyrrole Moieties for High-Performance Field-Effect Transistors
journal, June 2012


Diketopyrrolopyrrole–Diketopyrrolopyrrole-Based Conjugated Copolymer for High-Mobility Organic Field-Effect Transistors
journal, October 2012

  • Kanimozhi, Catherine; Yaacobi-Gross, Nir; Chou, Kang Wei
  • Journal of the American Chemical Society, Vol. 134, Issue 40
  • DOI: 10.1021/ja308211n

Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics
journal, January 2012


Recent Advances in the Development of Semiconducting DPP-Containing Polymers for Transistor Applications
journal, September 2012

  • Nielsen, Christian B.; Turbiez, Mathieu; McCulloch, Iain
  • Advanced Materials, Vol. 25, Issue 13
  • DOI: 10.1002/adma.201201795

Diketopyrrolopyrrole Polymers for Organic Solar Cells
journal, December 2015


Inkjet printing of single-crystal films
journal, July 2011

  • Minemawari, Hiromi; Yamada, Toshikazu; Matsui, Hiroyuki
  • Nature, Vol. 475, Issue 7356, p. 364-367
  • DOI: 10.1038/nature10313

Functionalized Higher Acenes:  Hexacene and Heptacene
journal, June 2005

  • Payne, Marcia M.; Parkin, Sean R.; Anthony, John E.
  • Journal of the American Chemical Society, Vol. 127, Issue 22
  • DOI: 10.1021/ja051798v

Organic Field-Effect Transistors from Solution-Deposited Functionalized Acenes with Mobilities as High as 1 cm 2 /V·s
journal, April 2005

  • Payne, Marcia M.; Parkin, Sean R.; Anthony, John E.
  • Journal of the American Chemical Society, Vol. 127, Issue 14
  • DOI: 10.1021/ja042353u

Functionalized Pentacene:  Improved Electronic Properties from Control of Solid-State Order
journal, September 2001

  • Anthony, John E.; Brooks, James S.; Eaton, David L.
  • Journal of the American Chemical Society, Vol. 123, Issue 38
  • DOI: 10.1021/ja0162459

High-Performance Transistors and Complementary Inverters Based on Solution-Grown Aligned Organic Single-Crystals
journal, March 2012

  • Li, Hanying; Tee, Benjamin C.-K.; Giri, Gaurav
  • Advanced Materials, Vol. 24, Issue 19, p. 2588-2591
  • DOI: 10.1002/adma.201200151

Theory-Driven Insight into the Crystal Packing of Trialkylsilylethynyl Pentacenes
journal, November 2016


Dibenzothiopheno[6,5- b :6′,5′- f ]thieno[3,2- b ]thiophene (DBTTT): High-Performance Small-Molecule Organic Semiconductor for Field-Effect Transistors
journal, April 2015

  • Park, Jeong-Il; Chung, Jong Won; Kim, Joo-Young
  • Journal of the American Chemical Society, Vol. 137, Issue 38
  • DOI: 10.1021/jacs.5b01108

Synthesis of Ladder-Type Thienoacenes and Their Electronic and Optical Properties
journal, January 2016

  • Zheng, Tianyue; Cai, Zhengxu; Ho-Wu, Rosina
  • Journal of the American Chemical Society, Vol. 138, Issue 3
  • DOI: 10.1021/jacs.5b10175

Fused Thiophene-Pyrrole-Containing Ring Systems up to a Heterodecacene
journal, July 2015

  • Wetzel, Christoph; Brier, Eduard; Vogt, Astrid
  • Angewandte Chemie International Edition, Vol. 54, Issue 42
  • DOI: 10.1002/anie.201502840

Anellierte Thiophen-Pyrrol-haltige Ringsysteme bis zu einem Heterodecacen
journal, July 2015

  • Wetzel, Christoph; Brier, Eduard; Vogt, Astrid
  • Angewandte Chemie, Vol. 127, Issue 42
  • DOI: 10.1002/ange.201502840

Indolo[3,2-b]indole-based crystalline hole-transporting material for highly efficient perovskite solar cells
journal, January 2017

  • Cho, Illhun; Jeon, Nam Joong; Kwon, Oh Kyu
  • Chemical Science, Vol. 8, Issue 1
  • DOI: 10.1039/C6SC02832B

A Highly π-Stacked Organic Semiconductor for Field-Effect Transistors Based on Linearly Condensed Pentathienoacene
journal, September 2005

  • Xiao, Kai; Liu, Yunqi; Qi, Ting
  • Journal of the American Chemical Society, Vol. 127, Issue 38
  • DOI: 10.1021/ja052816b

Molecular Ordering of High-Performance Soluble Molecular Semiconductors and Re-evaluation of Their Field-Effect Transistor Characteristics
journal, July 2008

  • Izawa, Takafumi; Miyazaki, Eigo; Takimiya, Kazuo
  • Advanced Materials, Vol. 20, Issue 18
  • DOI: 10.1002/adma.200800799

Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions
journal, May 2013

  • Jackson, Nicholas E.; Savoie, Brett M.; Kohlstedt, Kevin L.
  • Journal of the American Chemical Society, Vol. 135, Issue 28
  • DOI: 10.1021/ja403667s

Noncovalent Intermolecular Interactions in Organic Electronic Materials: Implications for the Molecular Packing vs Electronic Properties of Acenes
journal, November 2015


Efficient Conversion of Aromatic Amines into Azides:  A One-Pot Synthesis of Triazole Linkages
journal, April 2007

  • Barral, Karine; Moorhouse, Adam D.; Moses, John E.
  • Organic Letters, Vol. 9, Issue 9
  • DOI: 10.1021/ol070527h

Expanding the Scope of C−H Amination through Catalyst Design
journal, December 2004

  • Espino, Christine G.; Fiori, Kristin Williams; Kim, Mihyong
  • Journal of the American Chemical Society, Vol. 126, Issue 47
  • DOI: 10.1021/ja0446294

Synthesis and Structure of Alkyl-Substituted Fused Thiophenes Containing up to Seven Rings
journal, January 2007

  • He, Mingqian; Zhang, Feixia
  • The Journal of Organic Chemistry, Vol. 72, Issue 2
  • DOI: 10.1021/jo061853y

Copolymers of Cyclopentadithiophene and Electron-Deficient Aromatic Units Designed for Photovoltaic Applications
journal, October 2009

  • Bijleveld, Johan C.; Shahid, Munazza; Gilot, Jan
  • Advanced Functional Materials, Vol. 19, Issue 20
  • DOI: 10.1002/adfm.200900412

Poly(3,4-alkylenedioxypyrroles): The PXDOPs as Versatile Yet Underutilized Electroactive and Conducting Polymers
journal, May 2006


London Dispersion in Molecular Chemistry-Reconsidering Steric Effects
journal, August 2015

  • Wagner, J. Philipp; Schreiner, Peter R.
  • Angewandte Chemie International Edition, Vol. 54, Issue 42
  • DOI: 10.1002/anie.201503476

Do Special Noncovalent π–π Stacking Interactions Really Exist?
journal, April 2008


Substituent Effects in the Benzene Dimer are Due to Direct Interactions of the Substituents with the Unsubstituted Benzene
journal, August 2008

  • Wheeler, Steven E.; Houk, K. N.
  • Journal of the American Chemical Society, Vol. 130, Issue 33
  • DOI: 10.1021/ja802849j

Local Nature of Substituent Effects in Stacking Interactions
journal, July 2011

  • Wheeler, Steven E.
  • Journal of the American Chemical Society, Vol. 133, Issue 26
  • DOI: 10.1021/ja202932e

Highly Accurate Coupled Cluster Potential Energy Curves for the Benzene Dimer:  Sandwich, T-Shaped, and Parallel-Displaced Configurations
journal, November 2004

  • Sinnokrot, Mutasem Omar; Sherrill, C. David
  • The Journal of Physical Chemistry A, Vol. 108, Issue 46
  • DOI: 10.1021/jp0469517

Physical origins of interactions in dimers of polycyclic aromatic hydrocarbons
journal, January 2008

  • Podeszwa, Rafał; Szalewicz, Krzysztof
  • Physical Chemistry Chemical Physics, Vol. 10, Issue 19
  • DOI: 10.1039/b719725j

The Magnitude of the CH/π Interaction between Benzene and Some Model Hydrocarbons
journal, April 2000

  • Tsuzuki, Seiji; Honda, Kazumasa; Uchimaru, Tadafumi
  • Journal of the American Chemical Society, Vol. 122, Issue 15
  • DOI: 10.1021/ja993972j

CH/? hydrogen bonds in crystals
journal, January 2004


Influence of the Substituents on the CH...π Interaction: Benzene–Methane Complex
journal, July 2013

  • Karthikeyan, S.; Ramanathan, V.; Mishra, Brijesh Kumar
  • The Journal of Physical Chemistry A, Vol. 117, Issue 30
  • DOI: 10.1021/jp404972f

Enhanced Mobility of Poly(3-hexylthiophene) Transistors by Spin-Coating from High-Boiling-Point Solvents
journal, November 2004

  • Chang, Jui-Fen; Sun, Baoquan; Breiby, Dag W.
  • Chemistry of Materials, Vol. 16, Issue 23, p. 4772-4776
  • DOI: 10.1021/cm049617w