skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Precise Control of Noncovalent Interactions in Semiconducting Polymers for High-Performance Organic Field-Effect Transistors

Journal Article · · Chemistry of Materials

Performed through side-chain engineering or by incorporating intramolecular locking units, the directionality and dynamic nature of noncovalent interactions are particularly attractive for the design of novel semiconducting materials in a wide variety of applications. This work investigates the nature and position of hydrogen bonding (intra- versus intermolecular), with the objective of developing a rational approach to the design of new semiconducting materials with improved properties in the solid state. To control the polymer chains’ self-assembly, a π-conjugated polymer incorporating a moiety capable of generating intramolecular hydrogen bonding is evaluated against a polymer that allows for intermolecular hydrogen bonding. Characterization through various techniques, optical spectroscopies, grazing incidence wide-angle x-ray scattering, and solution small-angle neutron scattering showed that intramolecular hydrogen bonds resulted in materials with improved crystallinity and higher effective conjugation in the solid state. Additionally, the effect of the noncovalent interaction configuration on the optoelectronic properties was analyzed in organic field-effect transistor fabrication. Devices prepared from the materials with intramolecular hydrogen bonds showed significantly higher performance, with three orders of magnitude higher charge mobility than their counterparts fabricated from polymers with intermolecular hydrogen bonds. These results confirm the importance of chemical design on polymer structures and offer a novel route for the design of high-efficiency semiconducting polymers for next-generation electronics.

Research Organization:
Univ. of Southern Mississippi, Hattiesburg, MS (United States); University of Southern Mississippi, Hattiesburg, MS (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES); Natural Sciences and Engineering Research Council of Canada (NSERC); Canadian Foundation for Innovation; Ministry of Science and Technology, Taiwan
Grant/Contract Number:
SC0019361; RGPIN-2017-06611; 110-2221-E-011-009
OSTI ID:
1865521
Alternate ID(s):
OSTI ID: 1985410
Journal Information:
Chemistry of Materials, Vol. 33, Issue 21; ISSN 0897-4756
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English

References (56)

High-Performance Organic Semiconducting Polymers by a Resonance-Assisted Hydrogen Bonding Approach journal January 2021
Quantification of Thin Film Crystallographic Orientation Using X-ray Diffraction with an Area Detector journal June 2010
Low-Cost and Green Fabrication of Polymer Electronic Devices by Push-Coating of the Polymer Active Layers journal July 2017
Nonhalogenated Solvent Processable and Printable High-Performance Polymer Semiconductor Enabled by Isomeric Nonconjugated Flexible Linkers journal June 2018
A Fully Non‐fused Ring Acceptor with Planar Backbone and Near‐IR Absorption for High Performance Polymer Solar Cells journal October 2020
Influence of amide-containing side chains on the mechanical properties of diketopyrrolopyrrole-based polymers journal January 2018
Pyrazine-Flanked Diketopyrrolopyrrole (DPP): A New Polymer Building Block for High-Performance n-Type Organic Thermoelectrics journal November 2019
Correlations between Mechanical and Electrical Properties of Polythiophenes journal November 2010
Probing the Viscoelastic Property of Pseudo Free-Standing Conjugated Polymeric Thin Films journal May 2018
Characterization of Hydrogen Bonding Formation and Breaking in Semiconducting Polymers under Mechanical Strain journal March 2019
Importance of C 2 Symmetry for the Device Performance of a Newly Synthesized Family of Fused-Ring Thiophenes journal March 2010
A general relationship between disorder, aggregation and charge transport in conjugated polymers journal August 2013
Systematic Investigation of Isoindigo-Based Polymeric Field-Effect Transistors: Design Strategy and Impact of Polymer Symmetry and Backbone Curvature journal May 2012
Crystalline Ultrasmooth Self-Assembled Monolayers of Alkylsilanes for Organic Field-Effect Transistors journal July 2009
25th Anniversary Article: The Evolution of Electronic Skin (E-Skin): A Brief History, Design Considerations, and Recent Progress journal October 2013
Siloxane-Terminated Solubilizing Side Chains: Bringing Conjugated Polymer Backbones Closer and Boosting Hole Mobilities in Thin-Film Transistors journal December 2011
Morphology and Charge Transport in Conjugated Polymers journal January 2006
Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks journal July 2017
Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding journal December 2015
“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
Intrinsically stretchable and healable semiconducting polymer for organic transistors journal November 2016
Soft Poly(butyl acrylate) Side Chains toward Intrinsically Stretchable Polymeric Semiconductors for Field-Effect Transistor Applications journal June 2017
Regulating the Packing of Non-Fullerene Acceptors via Multiple Noncovalent Interactions for Enhancing the Performance of Organic Solar Cells journal January 2020
Exploring the origin of high optical absorption in conjugated polymers journal May 2016
Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale journal June 2012
Density‐functional thermochemistry. III. The role of exact exchange journal April 1993
Developments of Diketopyrrolopyrrole‐Dye‐Based Organic Semiconductors for a Wide Range of Applications in Electronics journal December 2019
Stretchable electronics: recent progress in the preparation of stretchable and self-healing semiconducting conjugated polymers journal December 2017
Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells journal July 2019
Microstructural Characterization and Charge Transport in Thin Films of Conjugated Polymers journal July 2010
Iron-coordinating π-conjugated semiconducting polymer: morphology and charge transport in organic field-effect transistors journal January 2020
Recent Progress in Materials and Devices toward Printable and Flexible Sensors journal February 2016
Molecularly Stretchable Electronics journal May 2014
Pd 2 (dba) 3 as a Precursor of Soluble Metal Complexes and Nanoparticles: Determination of Palladium Active Species for Catalysis and Synthesis journal March 2012
Pyrazine as a noncovalent conformational lock in semiconducting polymers for enhanced charge transport and stability in thin film transistors journal January 2019
Branched Polyethylene as a Plasticizing Additive to Modulate the Mechanical Properties of π-Conjugated Polymers journal October 2019
Molecularly Engineered Intrinsically Healable and Stretchable Conducting Polymers journal October 2017
Conjugation-Break Spacers in Semiconducting Polymers: Impact on Polymer Processability and Charge Transport Properties journal March 2015
Elastomer–Polymer Semiconductor Blends for High-Performance Stretchable Charge Transport Networks journal February 2016
Taming Charge Transport in Semiconducting Polymers with Branched Alkyl Side Chains journal July 2017
The adjustment of bandgap and coplanarity of diketopyrrolopyrrole-based copolymers through fine-tuning of the conjugated backbones and applications in thin film field effect transistors journal January 2016
Structural Engineering in Polymer Semiconductors with Aromatic N-Heterocycles journal February 2021
Tuning the Mechanical Properties of a Polymer Semiconductor by Modulating Hydrogen Bonding Interactions journal June 2020
Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties journal February 2018
Melt-Processing of Complementary Semiconducting Polymer Blends for High Performance Organic Transistors journal December 2016
Review of electronic and optical properties of semiconductingπ-conjugated polymers: applications in optoelectronics journal September 2004
Exploiting Noncovalently Conformational Locking as a Design Strategy for High Performance Fused-Ring Electron Acceptor Used in Polymer Solar Cells journal February 2017
Fluoro-Modulated Molecular Geometry in Diketopyrrolopyrrole-Based Low-Bandgap Copolymers for Tuning the Photovoltaic Performance journal May 2019
Polymer Chain Shape of Poly(3-alkylthiophenes) in Solution Using Small-Angle Neutron Scattering journal February 2013
Toward the Prediction and Control of Glass Transition Temperature for Donor–Acceptor Polymers journal May 2020
Charge Mobility Enhancement for Conjugated DPP-Selenophene Polymer by Simply Replacing One Bulky Branching Alkyl Chain with Linear One at Each DPP Unit journal April 2018
π-Conjugated Donor Polymers: Structure Formation and Morphology in Solution, Bulk and Photovoltaic Blends journal August 2017
Organic Semiconductor/Polymer Blend Films for Organic Field‐Effect Transistors journal June 2019
The Critical Role of Electron‐Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers journal March 2019
The Polymer Physics of Multiscale Charge Transport in Conjugated Systems journal August 2019
Stretchable and self-healing polymers and devices for electronic skin journal December 2013

Similar Records

Enhancing the Solubility of Semiconducting Polymers in Eco-Friendly Solvents with Carbohydrate-Containing Side Chains
Journal Article · Wed May 19 00:00:00 EDT 2021 · ACS Applied Materials and Interfaces · OSTI ID:1865521

Carbohydrate-Containing Conjugated Polymers: Solvent-Resistant Materials for Greener Organic Electronics
Journal Article · Wed Dec 08 00:00:00 EST 2021 · ACS Applied Electronic Materials · OSTI ID:1865521

Molecular Origin of Strain-Induced Chain Alignment in PDPP-Based Semiconducting Polymeric Thin Films
Journal Article · Thu Mar 18 00:00:00 EDT 2021 · Advanced Functional Materials · OSTI ID:1865521

Related Subjects