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Poly(naphthalene diimide) vinylene: solid state red emission and semiconducting properties for transistors

Journal Article · · ChemComm
DOI:https://doi.org/10.1039/C7CC01372H· OSTI ID:1364439
 [1];  [2];  [3];  [3];  [3];  [4];  [2];  [2];  [5];  [6]
  1. Chongqing Univ. (China). School of Chemistry and Chemical Engineering; Yunnan Minzu Univ., Kunming (China). YMU-HKBU Joint Lab. of Traditional Natural Medicine
  2. Chongqing Univ. (China). School of Chemistry and Chemical Engineering
  3. Chinese Academy of Sciences (CAS), Beijing (China). Inst. of Chemistry. Beijing National Lab. for Molecular Sciences
  4. Yunnan Minzu Univ., Kunming (China). YMU-HKBU Joint Lab. of Traditional Natural Medicine
  5. Chinese Academy of Sciences (CAS), Chongqing (China). Chongqing Inst. of Green and Intelligent Technology
  6. Argonne National Lab. (ANL), Argonne, IL (United States). Materials Science Division; Univ. of Chicago, IL (United States). Inst. for Molecular Engineering
+ Show Author Affiliations

Here in this work, a conjugated polymer PNV is developed, linking naphthalene diimide with a vinyl linkage. Owing to the C-H ∙∙∙O hydrogen bond between the carbonyl and the vinyl, PNV exhibits a high red emission with a quantum yield of 33.4% in the solid state while it shows n-type properties with an electron mobility up to 1.5 x 10-3 cm2 V-1 s-1 in organic field effect transistors, simultaneously.

Research Organization:
Argonne National Laboratory (ANL), Argonne, IL (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Natural Science Foundation of China (NNSFC); Chinese Academy of Sciences (CAS)
Grant/Contract Number:
AC02-06CH11357
OSTI ID:
1364439
Journal Information:
ChemComm, Journal Name: ChemComm Journal Issue: 36 Vol. 53; ISSN CHCOFS; ISSN 1359-7345
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (64)

Electroluminescent Conjugated Polymers—Seeing Polymers in a New Light journal March 1998
FluorescentJ-type Aggregates and Thermotropic Columnar Mesophases of Perylene Bisimide Dyes journal May 2001
Interchain Interactions in Organic π-Conjugated Materials: Impact on Electronic Structure, Optical Response, and Charge Transport journal July 2001
Integration of a Rib Waveguide Distributed Feedback Structure into a Light-Emitting Polymer Field-Effect Transistor journal May 2009
A Cruciform Electron Donor-Acceptor Semiconductor with Solid-State Red Emission: 1D/2D Optical Waveguides and Highly Sensitive/Selective Detection of H 2 S Gas journal April 2014
A novel family of amorphous molecular materials containing an oligothiophene moiety as color-tunable emitting materials for organic electroluminescent devices journal January 1997
Effect of Molecular Morphology on Amplified Spontaneous Emission of Bis-Styrylbenzene Derivatives journal October 2009
Functional Organic Field-Effect Transistors journal September 2010
Highly Efficient Single-Layer Polymer Ambipolar Light-Emitting Field-Effect Transistors journal April 2012
Multi-Functional Integration of Organic Field-Effect Transistors (OFETs): Advances and Perspectives journal August 2012
Recent Advances in the Development of Semiconducting DPP-Containing Polymers for Transistor Applications journal September 2012
Light-Emitting Field-Effect Transistors Having Combined Organic Semiconductor and Metal Oxide Layers journal April 2013
Outlook and Emerging Semiconducting Materials for Ambipolar Transistors journal October 2013
Aggregation-Induced Emission: The Whole Is More Brilliant than the Parts journal June 2014
A Vinylene-Bridged Perylenediimide-Based Polymeric Acceptor Enabling Efficient All-Polymer Solar Cells Processed under Ambient Conditions journal August 2016
Hierarchical Growth of Fluorescent Dye Aggregates in Water by Fusion of Segmented Nanostructures journal December 2013
Arylacetylene-Substituted Naphthalene Diimides with Dual Functions: Optical Waveguides and n-Type Semiconductors journal August 2014
Molecular Materials That Can Both Emit Light and Conduct Charges: Strategies and Perspectives journal October 2015
Functional organic single crystals for solid-state laser applications: Organic laser crystals journal March 2014
Thieno[3,4-c]Pyrrole-4,6-Dione and Dithiophene-Based Conjugated Polymer for Organic Field Effect Transistors: High Mobility Induced by Synergic Effect of H-Bond and Vinyl Linkage journal June 2016
Organic Solid-State Lasers book January 2013
Photophysical characterization of a 1,4,5,8-naphthalenediimide derivative journal December 1997
Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units journal November 2016
Conjugated Copolymers of Vinylene Flanked Naphthalene Diimide journal August 2016
Effect of Fluorination on Molecular Orientation of Conjugated Polymers in High Performance Field-Effect Transistors journal September 2016
Construction and Optoelectronic Properties of Organic One-Dimensional Nanostructures journal March 2010
The Spectral Signatures of Frenkel Polarons in H- and J-Aggregates journal March 2010
The C−H···O Hydrogen Bond:  Structural Implications and Supramolecular Design journal January 1996
Band Gap Tunable, Donor−Acceptor−Donor Charge-Transfer Heteroquinoid-Based Chromophores: Near Infrared Photoluminescence and Electroluminescence journal October 2008
Organic Semiconducting Oligomers for Use in Thin Film Transistors journal April 2007
Charge Transport in Organic Semiconductors journal April 2007
Charge Carrier Transporting Molecular Materials and Their Applications in Devices journal April 2007
Organic Semiconductor Lasers journal April 2007
Electron and Ambipolar Transport in Organic Field-Effect Transistors journal April 2007
Imide- and Amide-Functionalized Polymer Semiconductors journal September 2014
Inclusion Compounds of Tetrakis(4-nitrophenyl)methane:  C−H···O Networks, Pseudopolymorphism, and Structural Transformations journal May 2001
Effects of Packing Structure on the Optoelectronic and Charge Transport Properties in Poly(9,9-di- n -octylfluorene- alt -benzothiadiazole) journal September 2005
Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors journal April 2013
Electron-Deficient Poly( p -phenylene vinylene) Provides Electron Mobility over 1 cm 2 V –1 s –1 under Ambient Conditions journal May 2013
“Conformation Locked” Strong Electron-Deficient Poly( p -Phenylene Vinylene) Derivatives for Ambient-Stable n-Type Field-Effect Transistors: Synthesis, Properties, and Effects of Fluorine Substitution Position journal January 2014
Relaxation Dynamics and Structural Characterization of Organic Nanoparticles with Enhanced Emission journal July 2005
Aggregation-Induced Emissions of Fluorenonearylamine Derivatives:  A New Kind of Materials for Nondoped Red Organic Light-Emitting Diodes journal March 2008
Reactions of Brominated Naphthalene Diimide with Bis(tributylstannyl)acetylene: A Simple Approach for Conjugated Polymers and Versatile Coupling Intermediates journal May 2012
First Synthesis of 2,3,6,7-Tetrabromonaphthalene Diimide journal September 2007
Lasing from a molecular sieve journal January 1999
A high-mobility electron-transporting polymer for printed transistors journal January 2009
A bright future for organic field-effect transistors journal August 2006
Organic photonics for communications journal July 2010
The thiophene/phenylene co-oligomers: exotic molecular semiconductors integrating high-performance electronic and optical functionalities journal January 2011
Conjugated polymers based on naphthalene diimide for organic electronics journal January 2014
Organic single-crystal light-emitting field-effect transistors journal January 2014
Multifunctional materials for OFETs, LEFETs and NIR PLEDs journal January 2014
Highly planar cross-conjugated alternating polymers with multiple conformational locks: synthesis, characterization and their field-effect properties journal January 2016
Organic materials for electronic and optoelectronic devices journal January 2000
Readily synthesised arylamino fumaronitrile for non-doped red organic light-emitting diodes journal January 2003
Semiconducting polymers: the Third Generation journal January 2010
Naphthalene and perylene diimides for organic transistors journal January 2011
Aggregation-induced emission journal January 2011
New air-stable solution-processed organic n-type semiconductors based on sulfur-rich core-expanded naphthalene diimides journal January 2011
New tetrathiafulvalene fused-naphthalene diimides for solution-processible and air-stable p-type and ambipolar organic semiconductors journal January 2012
Tuning the colour and efficiency in OLEDs by using amorphous or polycrystalline emitting layers journal January 2013
Multifunctional materials for OFETs, LEFETs and NIR PLEDs journal January 2014
The fundamental photophysics of conjugated oligomer herringbone aggregates journal January 2003
Modeling of transport in polycrystalline organic semiconductor films journal February 2003

Cited By (5)

Rational Design of Perylenediimide-Substituted Triphenylethylene to Electron Transporting Aggregation-Induced Emission Luminogens (AIEgens) with High Mobility and Near-Infrared Emission journal January 2018
Reducing aggregation caused quenching effect through co-assembly of PAH chromophores and molecular barriers journal January 2019
A vinyl flanked difluorobenzothiadiazole–dithiophene conjugated polymer for high performance organic field-effect transistors journal January 2018
Persistent radical anion polymers based on naphthalenediimide and a vinylene spacer journal January 2018
A practical strategy for construction and regulation of multi-functional triazepinium salts via highly efficient I 2 -catalyzed cyclization journal January 2020

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Related Subjects

36 MATERIALS SCIENCE
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY