Thermally Activated Aromatic Ionic Dopants (TA-AIDs) Enabling Stable Doping, Orthogonal Processing and Direct Patterning

Zhifan Ke; Mustafa H. Ahmed; Ashkan Abtahi; Shih Hsin Hsu; Wenting Wu; Michael F. Espenship; Kyle N. Baustert; Kenneth R. Graham; Julia Laskin; Liang Pan; Jianguo Mei

doi:10.1002/adfm.202211522

Thermally Activated Aromatic Ionic Dopants (TA-AIDs) Enabling Stable Doping, Orthogonal Processing and Direct Patterning

Zhifan Ke, Mustafa H. Ahmed, Ashkan Abtahi, Shih Hsin Hsu, Wenting Wu, Michael F. Espenship, Kyle N. Baustert, Kenneth R. Graham, Julia Laskin, Liang Pan, Jianguo Mei

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Doping plays a critical role in organic electronics, and dopant design has been central in the development of functional and stable doping. In this study, there is departure from conventional molecular dopants and a new class of dopants are reported – aromatic ionic dopants (AIDs). AIDs consist of a pair of aromatic cation and anion that are responsible for molecular doping reaction and charge balancing separately. It is shown that the first AID made from cycloheptatrienyl (tropylium) cation and pentacyanocyclopentadienide anion (PCCp), abbreviated as T-PCCp, can function as an effective p-type dopant to dope polydioxythiophenes. Here, tropylium cation induces the doping reaction while the PCCp anion stabilizes the generated polarons and bipolarons. With T-PCCp, a highly doped (≈120 S/cm) and stable system is achieved up to 150 °C, an orthogonal (sequential)solution processing resulting from the immiscibility of the dopant and the polymer host, and a high-resolution direct micropatterning with laser writing resulted from a thermally activated doping process.

Original language	English
Article number	2211522
Journal	Advanced Functional Materials
Volume	33
Issue number	8
DOIs	https://doi.org/10.1002/adfm.202211522
State	Published - Feb 16 2023

Bibliographical note

Funding Information:
The authors are grateful for the financial support from ONR N00014‐19‐1‐2027. K.N.B. and K.R.G. gratefully acknowledge support from the National Science Foundation (DMR‐1905734). The authors would like to thank A.K. in Prof. Ying Diao's group at University of Illinois at Urbana Champaign (UIUC) for obtaining the GIXD data, L.G. in Prof. Xiaodan Gu's group at University of Southern Mississippi for obtaining the TGA data, and D.M. in Prof. Chengde Mao's group at Purdue University for AFM measurement. The authors are thankful to D.T.T., K.P., I.S. and W.J.L. for their valuable contributions and insights. This work was performed in part at the Research Instrument Center (RIC) at the Department of Chemistry, Purdue University.

Publisher Copyright:
© 2022 The Authors. Advanced Functional Materials published by Wiley-VCH GmbH.

Keywords

aromatic ionic dopants
conjugated polymers
doping
organic electronics

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Chemistry (all)
Materials Science (all)
Electrochemistry
Biomaterials

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1002/adfm.202211522

Cite this

@article{c4a47b98b3e642989b88022455257ac6,

title = "Thermally Activated Aromatic Ionic Dopants (TA-AIDs) Enabling Stable Doping, Orthogonal Processing and Direct Patterning",

abstract = "Doping plays a critical role in organic electronics, and dopant design has been central in the development of functional and stable doping. In this study, there is departure from conventional molecular dopants and a new class of dopants are reported – aromatic ionic dopants (AIDs). AIDs consist of a pair of aromatic cation and anion that are responsible for molecular doping reaction and charge balancing separately. It is shown that the first AID made from cycloheptatrienyl (tropylium) cation and pentacyanocyclopentadienide anion (PCCp), abbreviated as T-PCCp, can function as an effective p-type dopant to dope polydioxythiophenes. Here, tropylium cation induces the doping reaction while the PCCp anion stabilizes the generated polarons and bipolarons. With T-PCCp, a highly doped (≈120 S/cm) and stable system is achieved up to 150 °C, an orthogonal (sequential)solution processing resulting from the immiscibility of the dopant and the polymer host, and a high-resolution direct micropatterning with laser writing resulted from a thermally activated doping process.",

keywords = "aromatic ionic dopants, conjugated polymers, doping, organic electronics",

author = "Zhifan Ke and Ahmed, {Mustafa H.} and Ashkan Abtahi and Hsu, {Shih Hsin} and Wenting Wu and Espenship, {Michael F.} and Baustert, {Kyle N.} and Graham, {Kenneth R.} and Julia Laskin and Liang Pan and Jianguo Mei",

note = "Funding Information: The authors are grateful for the financial support from ONR N00014‐19‐1‐2027. K.N.B. and K.R.G. gratefully acknowledge support from the National Science Foundation (DMR‐1905734). The authors would like to thank A.K. in Prof. Ying Diao's group at University of Illinois at Urbana Champaign (UIUC) for obtaining the GIXD data, L.G. in Prof. Xiaodan Gu's group at University of Southern Mississippi for obtaining the TGA data, and D.M. in Prof. Chengde Mao's group at Purdue University for AFM measurement. The authors are thankful to D.T.T., K.P., I.S. and W.J.L. for their valuable contributions and insights. This work was performed in part at the Research Instrument Center (RIC) at the Department of Chemistry, Purdue University. Publisher Copyright: {\textcopyright} 2022 The Authors. Advanced Functional Materials published by Wiley-VCH GmbH.",

year = "2023",

month = feb,

day = "16",

doi = "10.1002/adfm.202211522",

language = "English",

volume = "33",

number = "8",

}

TY - JOUR

T1 - Thermally Activated Aromatic Ionic Dopants (TA-AIDs) Enabling Stable Doping, Orthogonal Processing and Direct Patterning

AU - Ke, Zhifan

AU - Ahmed, Mustafa H.

AU - Abtahi, Ashkan

AU - Hsu, Shih Hsin

AU - Wu, Wenting

AU - Espenship, Michael F.

AU - Baustert, Kyle N.

AU - Graham, Kenneth R.

AU - Laskin, Julia

AU - Pan, Liang

AU - Mei, Jianguo

N1 - Funding Information: The authors are grateful for the financial support from ONR N00014‐19‐1‐2027. K.N.B. and K.R.G. gratefully acknowledge support from the National Science Foundation (DMR‐1905734). The authors would like to thank A.K. in Prof. Ying Diao's group at University of Illinois at Urbana Champaign (UIUC) for obtaining the GIXD data, L.G. in Prof. Xiaodan Gu's group at University of Southern Mississippi for obtaining the TGA data, and D.M. in Prof. Chengde Mao's group at Purdue University for AFM measurement. The authors are thankful to D.T.T., K.P., I.S. and W.J.L. for their valuable contributions and insights. This work was performed in part at the Research Instrument Center (RIC) at the Department of Chemistry, Purdue University. Publisher Copyright: © 2022 The Authors. Advanced Functional Materials published by Wiley-VCH GmbH.

PY - 2023/2/16

Y1 - 2023/2/16

N2 - Doping plays a critical role in organic electronics, and dopant design has been central in the development of functional and stable doping. In this study, there is departure from conventional molecular dopants and a new class of dopants are reported – aromatic ionic dopants (AIDs). AIDs consist of a pair of aromatic cation and anion that are responsible for molecular doping reaction and charge balancing separately. It is shown that the first AID made from cycloheptatrienyl (tropylium) cation and pentacyanocyclopentadienide anion (PCCp), abbreviated as T-PCCp, can function as an effective p-type dopant to dope polydioxythiophenes. Here, tropylium cation induces the doping reaction while the PCCp anion stabilizes the generated polarons and bipolarons. With T-PCCp, a highly doped (≈120 S/cm) and stable system is achieved up to 150 °C, an orthogonal (sequential)solution processing resulting from the immiscibility of the dopant and the polymer host, and a high-resolution direct micropatterning with laser writing resulted from a thermally activated doping process.

AB - Doping plays a critical role in organic electronics, and dopant design has been central in the development of functional and stable doping. In this study, there is departure from conventional molecular dopants and a new class of dopants are reported – aromatic ionic dopants (AIDs). AIDs consist of a pair of aromatic cation and anion that are responsible for molecular doping reaction and charge balancing separately. It is shown that the first AID made from cycloheptatrienyl (tropylium) cation and pentacyanocyclopentadienide anion (PCCp), abbreviated as T-PCCp, can function as an effective p-type dopant to dope polydioxythiophenes. Here, tropylium cation induces the doping reaction while the PCCp anion stabilizes the generated polarons and bipolarons. With T-PCCp, a highly doped (≈120 S/cm) and stable system is achieved up to 150 °C, an orthogonal (sequential)solution processing resulting from the immiscibility of the dopant and the polymer host, and a high-resolution direct micropatterning with laser writing resulted from a thermally activated doping process.

KW - aromatic ionic dopants

KW - conjugated polymers

KW - doping

KW - organic electronics

UR - http://www.scopus.com/inward/record.url?scp=85144098687&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85144098687&partnerID=8YFLogxK

U2 - 10.1002/adfm.202211522

DO - 10.1002/adfm.202211522

M3 - Article

AN - SCOPUS:85144098687

SN - 1616-301X

VL - 33

JO - Advanced Functional Materials

JF - Advanced Functional Materials

IS - 8

M1 - 2211522

ER -

Thermally Activated Aromatic Ionic Dopants (TA-AIDs) Enabling Stable Doping, Orthogonal Processing and Direct Patterning

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this