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

Controlled Dedoping and Redoping of N‐Doped Poly(benzodifurandione) (n‐PBDF)

Journal Article · · Advanced Functional Materials
 [1];  [1];  [2];  [3];  [3];  [1];  [1];  [3];  [2];  [1]
  1. Department of Chemistry Purdue University West Lafayette IN 47907 USA
  2. Materials Measurement Laboratory National Institute of Standards and Technology Gaithersburg MD 20899 USA
  3. Department of Chemistry University of Kentucky Lexington KY 40506 USA

Abstract

The doping levels of conjugated polymers significantly influence their conductivity, energetics, and optical properties. Recently, a highly conductive n‐doped polymer called poly (3,7‐dihydrobenzo[1,2‐b:4,5‐b′]difuran‐2,6‐dione) (poly(benzodifurandione), n‐PBDF) is discovered, opening new possibilities for n‐type conducting polymers in printed electronics and other fields. Controlling the doping level of n‐PBDF is of great interest due to its wide range of potential applications. Here controlled dedoping and redoping of n‐PBDF is reported and a mechanistic understating of such a process is provided. Dedoping occurs through electron transfer and proton capture, wherein the ionic dopants, tris(4‐bromophenyl)ammoniumyl hexachloroantimonate (Magic Blue), exhibit efficient proton capture ability and stronger interaction with n‐PBDF, resulting in high dedoping efficiency. Moreover, chemically dedoped PBDF can be redoped using various proton‐coupled electron transfer agents. By manipulating the doping levels of n‐PBDF thin films, ranging from highly doped to dedoped states, the system demonstrates controllable conductivity in five orders of magnitude, adjustable optical properties, and energetics. As a result, these characteristics demonstrate the potential applications of n‐PBDF in organic electrochemical transistors and thermoelectrics.

Sponsoring Organization:
USDOE
Grant/Contract Number:
NONE; SC0012704
OSTI ID:
2337543
Alternate ID(s):
OSTI ID: 2337544
OSTI ID: 2580514
Journal Information:
Advanced Functional Materials, Journal Name: Advanced Functional Materials Journal Issue: 33 Vol. 34; ISSN 1616-301X
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English

References (41)

Controlling Molecular Doping in Organic Semiconductors journal September 2017
Enhancement‐Mode PEDOT:PSS Organic Electrochemical Transistors Using Molecular De‐Doping journal March 2020
Organic Hole‐Transport Layers for Efficient, Stable, and Scalable Inverted Perovskite Solar Cells journal September 2022
Interface Engineering for Highly Efficient Organic Solar Cells journal July 2023
Probing transport energies and defect states in organic semiconductors using energy resolved electrochemical impedance spectroscopy journal April 2023
Remarkable Enhancement of the Hole Mobility in Several Organic Small-Molecules, Polymers, and Small-Molecule:Polymer Blend Transistors by Simple Admixing of the Lewis Acid p-Dopant B(C 6 F 5 ) 3 journal October 2017
Advances in n‐Type Organic Thermoelectric Materials and Devices journal February 2019
Chemical Doping of Conjugated Polymers with the Strong Oxidant Magic Blue journal July 2020
Near-ultraviolet inverse photoemission spectroscopy using ultra-low energy electrons journal June 2012
Device physics of organic electrochemical transistors journal December 2018
FTIR Spectroelectrochemistry of F4TCNQ Reduction Products and Their Protonated Forms journal May 2020
Electronic and Magnetic Properties of Oligomers and Chains of Poly(benzodifurandione) (PBDF), A Highly Conducting n-Type Polymer journal July 2023
Doping Approaches for Organic Semiconductors journal November 2021
Conductive Polymers: Opportunities and Challenges in Biomedical Applications journal July 2018
Thin-Film Texture and Optical Properties of Donor/Acceptor Complexes. Diindenoperylene/F6TCNNQ vs Alpha-Sexithiophene/F6TCNNQ journal July 2018
Mechanism of Efficient Viologen Radical Generation by Ultrafast Electron Transfer from CdS Quantum Dots journal March 2018
The Mechanism of Dedoping PEDOT:PSS by Aliphatic Polyamines journal September 2019
Thermally Induced Formation of HF 4 TCNQ in F 4 TCNQ-Doped Regioregular P3HT journal July 2020
Intercalation and Ordering of F6TCNNQ and F4TCNQ Dopants in Regioregular Poly(3-hexylthiophene) Crystals: Impact on Anisotropic Thermoelectric Properties of Oriented Thin Films journal June 2021
Anion-Dependent Molecular Doping and Charge Transport in Ferric Salt-Doped P3HT for Thermoelectric Application journal February 2021
Polarons, Bipolarons, And Absorption Spectroscopy of PEDOT journal December 2018
Strategic Insights into Semiconducting Polymer Thermoelectrics by Leveraging Molecular Structures and Chemical Doping journal November 2022
Electronic Properties of Transparent Conductive Films of PEDOT:PSS on Stretchable Substrates journal December 2011
Lewis Acid Doped Polyaniline. Part II:  Spectroscopic Studies of Emeraldine Base and Emeraldine Hydrochloride Complexation with FeCl3 journal March 2000
Molecular Design of Semiconducting Polymers for High-Performance Organic Electrochemical Transistors journal August 2016
Double doping of conjugated polymers with monomer molecular dopants journal January 2019
Towards understanding the doping mechanism of organic semiconductors by Lewis acids journal September 2019
n-type charge transport in heavily p-doped polymers journal January 2021
The journey of conducting polymers from discovery to application journal August 2020
A solution-processed n-type conducting polymer with ultrahigh conductivity journal September 2022
Mind the gap! journal January 2014
Increased power factors of organic–inorganic nanocomposite thermoelectric materials and the role of energy filtering journal January 2017
Influence of dopant size and electron affinity on the electrical conductivity and thermoelectric properties of a series of conjugated polymers journal January 2018
Modulation of the doping level of PEDOT:PSS film by treatment with hydrazine to improve the Seebeck coefficient journal January 2020
Chemical doping of organic semiconductors for thermoelectric applications journal January 2020
n-Type organic semiconducting polymers: stability limitations, design considerations and applications journal January 2021
Self‐Consistent Molecular‐Orbital Methods. I. Use of Gaussian Expansions of Slater‐Type Atomic Orbitals journal September 1969
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals journal January 1985
Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction journal February 1992
Density-functional exchange-energy approximation with correct asymptotic behavior journal September 1988
High-Resolution ac Measurements of the Hall Effect in Organic Field-Effect Transistors journal March 2016

Similar Records

Electronic and Magnetic Properties of Oligomers and Chains of Poly(benzodifurandione) (PBDF), A Highly Conducting n-Type Polymer
Journal Article · Fri Jul 21 00:00:00 EDT 2023 · Chemistry of Materials · OSTI ID:1996008

Related Subjects