Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Tuning the Mechanical Properties of a Polymer Semiconductor by Modulating Hydrogen Bonding Interactions

Journal Article · · Chemistry of Materials
 [1];  [2];  [3];  [4];  [5];  [5];  [6];  [5];  [5];  [5];  [5];  [5];  [3];  [5]
  1. Stanford Univ., CA (United States); University of Southern Mississippi
  2. Stanford Univ., CA (United States); Tokyo Institute of Technology (Japan)
  3. Univ. of Southern Mississippi, Hattiesburg, MI (United States)
  4. Stanford Univ., CA (United States); Korea Advanced Inst. Science and Technology (KAIST), Daejeon (Korea, Republic of)
  5. Stanford Univ., CA (United States)
  6. Stanford Univ., CA (United States); Yamagata Univ. (Japan)
Conjugation breakers (CBs) with different H-bonding chemistry and linker flexibility are designed and incorporated into a Diketopyrrolopyrrole (DPP)-based conjugated polymer backbone. The effects of H-bonding interactions on polymer semiconductor morphology, mechanical properties and electrical performance are systematically investigated. We observe that CBs with H-bonding self-association constant >0.7 or denser packing tendency are able to induce higher polymer chain aggregation and crystallinity in as-casted thin film, resulting in higher modulus and crack on-set strain. Additionally, the rDoC (relative degree of crystallinity) of the stretched thin film with the highest crack on-set strain only suffers a small decrease, suggesting the main energy dissipation mechanism is the breakage of H-bonding interactions. By contrast, other less stretchable polymer films dissipate strain energy through the breakage of crystalline domains, indicated by drastic decrease in rDoC. Furthermore, we evaluate their electrical performance under mechanical strain in fully stretchable field-effect transistors. The polymer with the highest crack on-set strain has the least degradation in mobility as a function of strain. Overall, these observations suggest that we can aptly tune the mechanical properties in polymer semiconductors by modulating intermolecular interactions, such as H-bonding chemistry and linker flexibility. Such understanding provides molecular design guidelines for future stretchable semiconductors.
Research Organization:
Univ. of Southern Mississippi, Hattiesburg, MI (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division
Grant/Contract Number:
SC0019361
OSTI ID:
1659427
Journal Information:
Chemistry of Materials, Journal Name: Chemistry of Materials Journal Issue: 13 Vol. 32; ISSN 0897-4756
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English

References (60)

Structure-property relationships of degradable polyurethane elastomers containing an amino acid-based chain extender journal March 2000
Effect of Nonconjugated Spacers on Mechanical Properties of Semiconducting Polymers for Stretchable Transistors journal September 2018
An Intrinsically Stretchable High‐Performance Polymer Semiconductor with Low Crystallinity journal September 2019
Charge Transport in Organic and Polymeric Semiconductors for Flexible and Stretchable Devices journal December 2015
Extremely Stretchable and Fast Self-Healing Hydrogels journal April 2016
Recent Progress on Stretchable Electronic Devices with Intrinsically Stretchable Components journal November 2016
Exploring the Charge Transport in Conjugated Polymers journal August 2017
Tough and Water-Insensitive Self-Healing Elastomer for Robust Electronic Skin journal February 2018
Recent Progress in High-Mobility Organic Transistors: A Reality Check journal July 2018
Conjugated Carbon Cyclic Nanorings as Additives for Intrinsically Stretchable Semiconducting Polymers journal September 2019
Recent Advances in Stretchable and Transparent Electronic Materials journal March 2016
Connecting the Mechanical and Conductive Properties of Conjugated Polymers journal December 2017
Stretchable Polymer Semiconductors for Plastic Electronics journal January 2018
The Critical Role of Electron‐Donating Thiophene Groups on the Mechanical and Thermal Properties of Donor–Acceptor Semiconducting Polymers journal March 2019
Probing the Viscoelastic Property of Pseudo Free-Standing Conjugated Polymeric Thin Films journal May 2018
H-bond and conformations of donors and acceptors in model polyether based polyurethanes journal September 2003
Comparison of hydrogen bonding in polydimethylsiloxane and polyether based urethane and urea copolymers journal February 2000
Dimer self-association via hydrogen bonding: Measurement and comparison of binding constants with 2-amidopyrimidine derivatives journal September 2012
New polyamine-sensitive inhibitors of the NMDA receptor: Syntheses and pharmacological evaluation journal February 2007
Backbone orientation in semiconducting polymers journal February 2015
The impact of molecular weight on microstructure and charge transport in semicrystalline polymer semiconductors–poly(3-hexylthiophene), a model study journal December 2013
Intrinsically stretchable conjugated polymer semiconductors in field effect transistors journal January 2020
Skin-Inspired Electronics: An Emerging Paradigm journal April 2018
Tuning the Cross-Linker Crystallinity of a Stretchable Polymer Semiconductor journal November 2018
Importance of Critical Molecular Weight of Semicrystalline n-Type Polymers for Mechanically Robust, Efficient Electroactive Thin Films journal April 2019
Robust and Stretchable Polymer Semiconducting Networks: From Film Microstructure to Macroscopic Device Performance journal December 2018
Mechanical Properties of Organic Semiconductors for Stretchable, Highly Flexible, and Mechanically Robust Electronics journal March 2017
Soft Poly(butyl acrylate) Side Chains toward Intrinsically Stretchable Polymeric Semiconductors for Field-Effect Transistor Applications journal June 2017
Correlating Crack Onset Strain and Cohesive Fracture Energy in Polymer Semiconductor Films journal October 2017
Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties journal February 2018
Nonhalogenated Solvent Processable and Printable High-Performance Polymer Semiconductor Enabled by Isomeric Nonconjugated Flexible Linkers journal June 2018
Characterization of Hydrogen Bonding Formation and Breaking in Semiconducting Polymers under Mechanical Strain journal March 2019
Branched Polyethylene as a Plasticizing Additive to Modulate the Mechanical Properties of π-Conjugated Polymers journal October 2019
Molecularly Stretchable Electronics journal May 2014
Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale journal June 2012
Hydrogen bonding ability of the amide group journal June 1974
Enhanced Solid-State Order and Field-Effect Hole Mobility through Control of Nanoscale Polymer Aggregation journal December 2013
Tough Stimuli-Responsive Supramolecular Hydrogels with Hydrogen-Bonding Network Junctions journal May 2014
Crystalline Ultrasmooth Self-Assembled Monolayers of Alkylsilanes for Organic Field-Effect Transistors journal July 2009
Enhancing Mechanical Performance of a Covalent Self-Healing Material by Sacrificial Noncovalent Bonds journal April 2015
Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding journal December 2015
Fine-Tuning of Crystal Packing and Charge Transport Properties of BDOPV Derivatives through Fluorine Substitution journal December 2015
Role of Molecular Weight on the Mechanical Device Properties of Organic Polymer Solar Cells journal January 2014
Effect of Confinement on Stiffness and Fracture of Thin Amorphous Polymer Films journal November 2011
Intrinsically stretchable and healable semiconducting polymer for organic transistors journal November 2016
Tensile testing of ultra-thin films on water surface journal October 2013
A general relationship between disorder, aggregation and charge transport in conjugated polymers journal August 2013
Next-generation organic photovoltaics based on non-fullerene acceptors journal February 2018
Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor journal January 2016
Flexible thiophene polymers: a concerted macromolecular architecture for dielectrics journal January 2016
Morphological/nanostructural control toward intrinsically stretchable organic electronics journal January 2019
Progress and perspective of polymer white light-emitting devices and materials journal January 2009
Preparation of 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene from Two Versatile 1,3,5-Tri(halosubstituted) 2,4,6-Triethylbenzene Derivatives journal January 2005
Competition between deformability and charge transport in semiconducting polymers for flexible and stretchable electronics journal June 2016
Preparation of 3-(n-Alkenoxy)propanoic Acids journal February 1993
A short history of SHELX journal December 2007
Crystal structure determination and refinement via SIR2014 journal January 2015
Highly stretchable polymer semiconductor films through the nanoconfinement effect journal January 2017
Mechanically robust, readily repairable polymers via tailored noncovalent cross-linking journal December 2017
H- and J-Aggregate Behavior in Polymeric Semiconductors journal April 2014


Similar Records

Conjugated Carbon Cyclic Nanorings as Additives for Intrinsically Stretchable Semiconducting Polymers
Journal Article · Thu Sep 05 20:00:00 EDT 2019 · Advanced Materials · OSTI ID:1560698