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

Title: The Effect of Alkyl Spacers on the Mixed Ionic‐Electronic Conduction Properties of N‐Type Polymers

Journal Article · · Advanced Functional Materials
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [3];  [2]; ORCiD logo [4]; ORCiD logo [4]; ORCiD logo [4]; ORCiD logo [4]; ORCiD logo [3]; ORCiD logo [5]; ORCiD logo [6]; ORCiD logo [7]
  1. Department of Chemistry and Centre for Plastic Electronics Imperial College London London SW7 2AZ UK
  2. Department of Biomedical Engineering Northwestern University Evanston IL 60208 USA
  3. Organic Bioelectronics Laboratory, Biological and Environmental Science and Engineering Division King Abdullah University of Science and Technology Thuwal 23955‐6900 Saudi Arabia
  4. KAUST Solar Center King Abdulla University of Science and Technology Thuwal 23955‐6900 Saudi Arabia
  5. Department of Biomedical Engineering Northwestern University Evanston IL 60208 USA, Simpson Querrey Institute Northwestern University Chicago IL 60611 USA
  6. KAUST Solar Center King Abdulla University of Science and Technology Thuwal 23955‐6900 Saudi Arabia, Department of Chemistry Chemistry Research Laboratory University of Oxford Oxford OX1 3TA UK
  7. Department of Materials Science and Engineering Stanford University Stanford CA 94305 USA

Abstract Conjugated polymers with mixed ionic and electronic transport are essential for developing the complexity and function of electrochemical devices. Current n‐type materials have a narrow scope and low performance compared with their p‐type counterparts, requiring new molecular design strategies. This work presents two naphthalene diimide‐bithiophene (NDI‐T2) copolymers functionalized with hybrid alkyl‐glycol side chains, where the naphthalene diimide unit is segregated from the ethylene glycol (EG) units within the side chain by an alkyl spacer. Introduction of hydrophobic propyl and hexyl spacers is investigated as a strategy to minimize detrimental swelling close to the conjugated backbone and balance the mixed conduction properties of n‐type materials in aqueous electrolytes. It is found that both polymers functionalized with alkyl spacers outperform their analogue bearing EG‐only side chains in organic electrochemical transistors (OECTs). The presence of the alkyl spacers also leads to remarkable stability in OECTs, with no decrease in the ON current after 2 h of operation. Through this versatile side chain modification, this work provides a greater understanding of the structure‐property relationships required for n‐type OECT materials operating in aqueous media.

Sponsoring Organization:
USDOE
OSTI ID:
1761236
Alternate ID(s):
OSTI ID: 1785776
Journal Information:
Advanced Functional Materials, Journal Name: Advanced Functional Materials Vol. 31 Journal Issue: 14; ISSN 1616-301X
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English

References (51)

Conjugated Polyelectrolytes as Water Processable Precursors to Aqueous Compatible Redox Active Polymers for Diverse Applications: Electrochromism, Charge Storage, and Biocompatible Organic Electronics journal May 2017
A high-mobility electron-transporting polymer for printed transistors journal January 2009
New Conjugated Polymers with Donor−Acceptor Architectures:  Synthesis and Photophysics of Carbazole−Quinoline and Phenothiazine−Quinoline Copolymers and Oligomers Exhibiting Large Intramolecular Charge Transfer journal October 2001
Organic Bioelectronics: From Functional Materials to Next‐Generation Devices and Power Sources journal July 2020
Electrochemical Investigations of the N-Type Semiconducting Polymer P(NDI2OD-T2) and Its Monomer: New Insights in the Reduction Behavior journal September 2015
Batch-to-Batch Variation of Polymeric Photovoltaic Materials: its Origin and Impacts on Charge Carrier Transport and Device Performances journal July 2014
Solution Processed PEDOT Analogues in Electrochemical Supercapacitors journal May 2016
Improving the Compatibility of Diketopyrrolopyrrole Semiconducting Polymers for Biological Interfacing by Lysine Attachment journal August 2018
Segregated versus Mixed Interchain Stacking in Highly Oriented Films of Naphthalene Diimide Bithiophene Copolymers journal October 2012
Biofuel powered glucose detection in bodily fluids with an n-type conjugated polymer journal December 2019
P(NDI2OD-T2) revisited – Aggregation control as key for high performance n-type applications journal July 2019
A non-volatile organic electrochemical device as a low-voltage artificial synapse for neuromorphic computing journal February 2017
Influence of Water on the Performance of Organic Electrochemical Transistors journal January 2019
Conjugated Polymers for Assessing and Controlling Biological Functions journal March 2019
Benchmarking organic mixed conductors for transistors journal November 2017
Complementary Logic Circuits Based on High-Performance n-Type Organic Electrochemical Transistors journal January 2018
Rotational barriers in perylene fluorescent dyes journal January 1988
Molecular Design of Semiconducting Polymers for High-Performance Organic Electrochemical Transistors journal August 2016
Synthesis and Aggregation Behavior of a Glycolated Naphthalene Diimide Bithiophene Copolymer for Application in Low-Level n-Doped Organic Thermoelectrics journal July 2020
Hybrid Alkyl–Ethylene Glycol Side Chains Enhance Substrate Adhesion and Operational Stability in Accumulation Mode Organic Electrochemical Transistors journal November 2019
Unconventional Face-On Texture and Exceptional In-Plane Order of a High Mobility n-Type Polymer journal July 2010
Quantitative analysis of lattice disorder and crystallite size in organic semiconductor thin films journal July 2011
The organic electrochemical transistor for biological applications journal January 2015
Aggregation in a High-Mobility n-Type Low-Bandgap Copolymer with Implications on Semicrystalline Morphology journal October 2012
Organic mixed ionic–electronic conductors journal August 2019
Role of the Anion on the Transport and Structure of Organic Mixed Conductors journal December 2018
Conjugated Polymers in Bioelectronics journal May 2018
N-type organic electrochemical transistors with stability in water journal October 2016
Anion-Dependent Doping and Charge Transport in Organic Electrochemical Transistors journal July 2018
Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics journal January 2018
The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes journal April 2018
Side Chain Redistribution as a Strategy to Boost Organic Electrochemical Transistor Performance and Stability journal August 2020
Solvent Engineering for High‐Performance n‐Type Organic Electrochemical Transistors journal June 2019
An Organic Mixed Ion-Electron Conductor for Power Electronics journal December 2015
Balancing Charge Storage and Mobility in an Oligo(Ether) Functionalized Dioxythiophene Copolymer for Organic‐ and Aqueous‐ Based Electrochemical Devices and Transistors journal August 2018
Temperature-resilient solid-state organic artificial synapses for neuromorphic computing journal July 2020
High transconductance organic electrochemical transistors journal July 2013
Charge Transport Anisotropy in Highly Oriented Thin Films of the Acceptor Polymer P(NDI2OD-T2) journal March 2014
Controlling the mode of operation of organic transistors through side-chain engineering journal October 2016
Direct metabolite detection with an n-type accumulation mode organic electrochemical transistor journal June 2018
Design and evaluation of conjugated polymers with polar side chains as electrode materials for electrochemical energy storage in aqueous electrolytes journal January 2019
Organic Bioelectronics: Bridging the Signaling Gap between Biology and Technology journal July 2016
Oligo(ethylene glycol)-incorporated hybrid linear alkyl side chains for n-channel polymer semiconductors and their effect on the thin-film crystalline structure journal January 2015
Electrochemical strain microscopy probes morphology-induced variations in ion uptake and performance in organic electrochemical transistors journal June 2017
Balancing Ionic and Electronic Conduction for High‐Performance Organic Electrochemical Transistors journal January 2020
Fused electron deficient semiconducting polymers for air stable electron transport journal January 2018
Why Does Matrix-assisted Laser Desorption/Ionization Time-of-flight Mass Spectrometry Give Incorrect Results for Broad Polymer Distributions? journal September 1996
The Key Role of Side Chain Linkage in Structure Formation and Mixed Conduction of Ethylene Glycol Substituted Polythiophenes journal February 2020
Polymer Crystallinity Controls Water Uptake in Glycol Side-Chain Polymer Organic Electrochemical Transistors journal February 2019
Fullerene Active Layers for n-Type Organic Electrochemical Transistors journal July 2019
Organic electrochemical transistors for cell-based impedance sensing journal January 2015