Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors

Parr, Zachary S.; Rashid, Reem B.; Paulsen, Bryan D.; Poggi, Benjamin; Tan, Ellasia; Freeley, Mark; Palma, Matteo; Abrahams, Isaac; Rivnay, Jonathan; Nielsen, Christian B.

doi:10.1002/aelm.202000215

Title: Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors

Abstract

A series of semiconducting small molecules with bithiophene or bis-3,4-ethylenedioxythiophene cores are designed and synthesized. The molecules display stable reversible oxidation in solution and can be reversibly oxidized in the solid state with aqueous electrolyte when functionalized with polar triethylene glycol side chains. Evidence of promising ion injection properties observed with cyclic voltammetry is complemented by strong electrochromism probed by spectroelectrochemistry. Blending these molecules with high molecular weight polyethylene oxide (PEO) is found to improve both ion injection and thin film stability. The molecules and their corresponding PEO blends are investigated as active layers in organic electrochemical transistors (OECTs). For the most promising molecule:polymer blend (P4E4:PEO), p-type accumulation mode OECTs with µA drain currents, μS peak transconductances, and a µC* figure-of-merit value of 0.81 F V^-1 cm^-1 s^-1 are obtained.

Authors:

Parr, Zachary S. ^[1]; Rashid, Reem B. ^[2]; Paulsen, Bryan D. ^[2]; Poggi, Benjamin ^[1]; Tan, Ellasia ^[1]; Freeley, Mark ^[1]; Palma, Matteo ^[1]; Abrahams, Isaac ^[1]; Rivnay, Jonathan ^[2];

^[1]

Queen Mary Univ. of London (United Kingdom)
Northwestern Univ., Evanston, IL (United States)

Publication Date:: Fri May 15 00:00:00 EDT 2020

Research Org.:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Org.:: National Science Foundation (NSF); USDOE

OSTI Identifier:: 1701775

Resource Type:: Accepted Manuscript

Journal Name:: Advanced Electronic Materials

Additional Journal Information:: Journal Volume: 6; Journal Issue: 6; Journal ID: ISSN 2199-160X

Publisher:: Wiley

Country of Publication:: United States

Language:: ENGLISH

Subject:: 36 MATERIALS SCIENCE

Citation Formats


                    Parr, Zachary S., Rashid, Reem B., Paulsen, Bryan D., Poggi, Benjamin, Tan, Ellasia, Freeley, Mark, Palma, Matteo, Abrahams, Isaac, Rivnay, Jonathan, and Nielsen, Christian B. Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors.  United States: N. p., 2020. 
Web.  doi:10.1002/aelm.202000215.

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                    Parr, Zachary S., Rashid, Reem B., Paulsen, Bryan D., Poggi, Benjamin, Tan, Ellasia, Freeley, Mark, Palma, Matteo, Abrahams, Isaac, Rivnay, Jonathan, & Nielsen, Christian B. Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors.  United States.  https://doi.org/10.1002/aelm.202000215

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                    Parr, Zachary S., Rashid, Reem B., Paulsen, Bryan D., Poggi, Benjamin, Tan, Ellasia, Freeley, Mark, Palma, Matteo, Abrahams, Isaac, Rivnay, Jonathan, and Nielsen, Christian B. Fri .  
"Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors".  United States.  https://doi.org/10.1002/aelm.202000215.  https://www.osti.gov/servlets/purl/1701775.

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@article{osti_1701775,

  title        = {Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors},

  author       = {Parr, Zachary S. and Rashid, Reem B. and Paulsen, Bryan D. and Poggi, Benjamin and Tan, Ellasia and Freeley, Mark and Palma, Matteo and Abrahams, Isaac and Rivnay, Jonathan and Nielsen, Christian B.},

  abstractNote = {A series of semiconducting small molecules with bithiophene or bis-3,4-ethylenedioxythiophene cores are designed and synthesized. The molecules display stable reversible oxidation in solution and can be reversibly oxidized in the solid state with aqueous electrolyte when functionalized with polar triethylene glycol side chains. Evidence of promising ion injection properties observed with cyclic voltammetry is complemented by strong electrochromism probed by spectroelectrochemistry. Blending these molecules with high molecular weight polyethylene oxide (PEO) is found to improve both ion injection and thin film stability. The molecules and their corresponding PEO blends are investigated as active layers in organic electrochemical transistors (OECTs). For the most promising molecule:polymer blend (P4E4:PEO), p-type accumulation mode OECTs with µA drain currents, μS peak transconductances, and a µC* figure-of-merit value of 0.81 F V-1 cm-1 s-1 are obtained.},

  doi          = {10.1002/aelm.202000215},

  journal      = {Advanced Electronic Materials},

  number       = 6,

  volume       = 6,

  place        = {United States},

  year         = {Fri May 15 00:00:00 EDT 2020},

  month        = {Fri May 15 00:00:00 EDT 2020}

}

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Title: Semiconducting Small Molecules as Active Materials for p-Type Accumulation Mode Organic Electrochemical Transistors

Abstract

Citation Formats

Easily Processable Phenylene−Thiophene-Based Organic Field-Effect Transistors and Solution-Fabricated Nonvolatile Transistor Memory Elements journal, August 2003

The organic electrochemical transistor for biological applications journal, January 2015

Label free urea biosensor based on organic electrochemical transistors journal, June 2018

Role of the Anion on the Transport and Structure of Organic Mixed Conductors journal, December 2018

A sensitivity-enhanced field-effect chiral sensor journal, April 2008

Hydroxy-Terminated Organic Semiconductor-Based Field-Effect Transistors for Phosphonate Vapor Detection journal, August 2007

Multicomponent semiconducting polymer systems with low crystallization-induced percolation threshold journal, November 2006

PEDOT:TOS with PEG: a biofunctional surface with improved electronic characteristics journal, January 2012

Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices journal, July 2008

N-type organic electrochemical transistors with stability in water journal, October 2016

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A glucose sensor via stable immobilization of the GOx enzyme on an organic transistor using a polymer brush journal, September 2014

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Balancing Charge Storage and Mobility in an Oligo(Ether) Functionalized Dioxythiophene Copolymer for Organic‐ and Aqueous‐ Based Electrochemical Devices and Transistors journal, August 2018

Organic semiconductors for biological sensing journal, January 2019

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Direct C–H arylation of 3-methoxythiophene catalyzed by Pd. Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives journal, December 2006

Measurement of Barrier Tissue Integrity with an Organic Electrochemical Transistor journal, September 2012

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Integration of a surface-directed microfluidic system with an organic electrochemical transistor array for multi-analyte biosensors journal, January 2009

Benchmarking organic mixed conductors for transistors journal, November 2017

Balancing Ionic and Electronic Conduction for High‐Performance Organic Electrochemical Transistors journal, January 2020

Molecular Design of Semiconducting Polymers for High-Performance Organic Electrochemical Transistors journal, August 2016

Electrochemistry of Conducting Polymers—Persistent Models and New Concepts † journal, August 2010

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

In vivo recordings of brain activity using organic transistors journal, March 2013

Easily Processable Phenylene−Thiophene-Based Organic Field-Effect Transistors and Solution-Fabricated Nonvolatile Transistor Memory Elements
journal, August 2003

The organic electrochemical transistor for biological applications
journal, January 2015

Label free urea biosensor based on organic electrochemical transistors
journal, June 2018

Role of the Anion on the Transport and Structure of Organic Mixed Conductors
journal, December 2018

A sensitivity-enhanced field-effect chiral sensor
journal, April 2008

Hydroxy-Terminated Organic Semiconductor-Based Field-Effect Transistors for Phosphonate Vapor Detection
journal, August 2007

Multicomponent semiconducting polymer systems with low crystallization-induced percolation threshold
journal, November 2006

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journal, January 2012

Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices
journal, July 2008

N-type organic electrochemical transistors with stability in water
journal, October 2016

PEDOT: Dye-Based, Flexible Organic Electrochemical Transistor for Highly Sensitive pH Monitoring
journal, June 2018

A glucose sensor via stable immobilization of the GOx enzyme on an organic transistor using a polymer brush
journal, September 2014

In Situ Antibody Detection and Charge Discrimination Using Aqueous Stable Pentacene Transistor Biosensors
journal, February 2011

Glycolated Thiophene‐Tetrafluorophenylene Copolymers for Bioelectronic Applications: Synthesis by Direct Heteroarylation Polymerisation
journal, June 2019

Balancing Charge Storage and Mobility in an Oligo(Ether) Functionalized Dioxythiophene Copolymer for Organic‐ and Aqueous‐ Based Electrochemical Devices and Transistors
journal, August 2018

Organic semiconductors for biological sensing
journal, January 2019

Ultra-high mobility transparent organic thin film transistors grown by an off-centre spin-coating method
journal, January 2014

In vivo polymerization and manufacturing of wires and supercapacitors in plants
journal, February 2017

Effect of E Cigarette Emissions on Tracheal Cells Monitored at the Air–Liquid Interface Using an Organic Electrochemical Transistor
journal, December 2018

Wearable Fiber-Based Organic Electrochemical Transistors as a Platform for Highly Sensitive Dopamine Monitoring
journal, March 2019

Controlling Epileptiform Activity with Organic Electronic Ion Pumps
journal, April 2015

Controlling the mode of operation of organic transistors through side-chain engineering
journal, October 2016

Organic Electrochemical Transistor Arrays for In Vitro Electrophysiology Monitoring of 2D and 3D Cardiac Tissues
journal, November 2018

Direct C–H arylation of 3-methoxythiophene catalyzed by Pd. Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives
journal, December 2006

Measurement of Barrier Tissue Integrity with an Organic Electrochemical Transistor
journal, September 2012

Why are S–F and S–O non-covalent interactions stabilising?
journal, January 2018

Integration of a surface-directed microfluidic system with an organic electrochemical transistor array for multi-analyte biosensors
journal, January 2009

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journal, November 2017

Balancing Ionic and Electronic Conduction for High‐Performance Organic Electrochemical Transistors
journal, January 2020

Molecular Design of Semiconducting Polymers for High-Performance Organic Electrochemical Transistors
journal, August 2016

Electrochemistry of Conducting Polymers—Persistent Models and New Concepts ^†
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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

In vivo recordings of brain activity using organic transistors
journal, March 2013