Using Bulky Dodecaborane-Based Dopants to Produce Mobile Charge Carriers in Amorphous Semiconducting Polymers

Wu, Yutong; Salamat, Charlene Z.; León Ruiz, Alex; Simafranca, Alexander F.; Akmanşen-Kalayci, Nesibe; Wu, Eric C.; Doud, Evan; Mehmedović, Zerina; Lindemuth, Jeffrey R.; Phan, Minh D.; Spokoyny, Alexander M.; Schwartz, Benjamin J.; Tolbert, Sarah H.

doi:10.1021/acs.chemmater.4c00502

Title: Using Bulky Dodecaborane-Based Dopants to Produce Mobile Charge Carriers in Amorphous Semiconducting Polymers

Journal Article · 16 May 2024 · Chemistry of Materials

DOI: https://doi.org/10.1021/acs.chemmater.4c00502 · OSTI ID:2352304

Wu, Yutong ^[1];

^[1]; León Ruiz, Alex ^[1];

^[1];

^[1]; Wu, Eric C. ^[1];

^[1]; Mehmedović, Zerina ^[1]; Lindemuth, Jeffrey R. ^[2]; Phan, Minh D. ^[3];

^[1];

^[4]

Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095-1569, United States
Lake Shore Cryotronics, Westerville, Ohio 43082, United States
Center for Neutron Science, Department of Chemical and Biochemical Engineering, University of Delaware, Newark, Delaware 19716, United States
Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095-1569, United States, Department of Materials Science and Engineering, University of California Los Angeles, Los Angeles, California 90095-1595, United States

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Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0019381; AC02-06CH11357; AC02-76SF00515

OSTI ID:: 2352304

Alternate ID(s):: OSTI ID: 2372844

Journal Information:: Chemistry of Materials, Journal Name: Chemistry of Materials Journal Issue: 11 Vol. 36; ISSN 0897-4756

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (64)

Understanding Bipolarons in Conjugated Polymers Using a Multiparticle Holstein Approach Qarai, Mohammad Balooch; Ghosh, Raja; Spano, Frank C. The Journal of Physical Chemistry C, Vol. 125, Issue 44 https://doi.org/10.1021/acs.jpcc.1c06767	journal	October 2021
Synthesis of poly(3,4-ethylenedioxythuophene) derivatives using three-armed conjugated cross-linker and its thermoelectric properties Lee, Jun Seop; Patel, Shrayesh N. Journal of Industrial and Engineering Chemistry, Vol. 117 https://doi.org/10.1016/j.jiec.2022.10.004	journal	January 2023
The Active Layer Morphology of Organic Solar Cells Probed with Grazing Incidence Scattering Techniques Müller-Buschbaum, Peter Advanced Materials, Vol. 26, Issue 46 https://doi.org/10.1002/adma.201304187	journal	February 2014
Impact of the anion on electrochemically doped regioregular and regiorandom poly(3‐hexylthiophene) Baustert, Kyle N.; Abtahi, Ashkan; Ayyash, Ahmed N. Journal of Polymer Science, Vol. 60, Issue 3 https://doi.org/10.1002/pol.20210699	journal	November 2021
Molecular weight dependent structure and charge transport in MAPLE-deposited poly(3-hexylthiophene) thin films Dong, Ban Xuan; Smith, Mitchell; Strzalka, Joseph Journal of Polymer Science Part B: Polymer Physics, Vol. 56, Issue 8 https://doi.org/10.1002/polb.24588	journal	February 2018
P‐type Polymers in Semitransparent Organic Photovoltaics Kong, Weibo; Wang, Jiayu; Hu, Yingyue Angewandte Chemie International Edition, Vol. 62, Issue 45 https://doi.org/10.1002/anie.202307622	journal	July 2023
A general relationship between disorder, aggregation and charge transport in conjugated polymers Noriega, Rodrigo; Rivnay, Jonathan; Vandewal, Koen Nature Materials, Vol. 12, Issue 11 https://doi.org/10.1038/nmat3722	journal	August 2013
A Versatile Method to Fabricate Highly In-Plane Aligned Conducting Polymer Films with Anisotropic Charge Transport and Thermoelectric Properties: The Key Role of Alkyl Side Chain Layers on the Doping Mechanism Hamidi-Sakr, Amer; Biniek, Laure; Bantignies, Jean-Louis Advanced Functional Materials, Vol. 27, Issue 25 https://doi.org/10.1002/adfm.201700173	journal	May 2017
Controlling the Formation of Charge Transfer Complexes in Chemically Doped Semiconducting Polymers Stanfield, Dane A.; Wu, Yutong; Tolbert, Sarah H. Chemistry of Materials, Vol. 33, Issue 7 https://doi.org/10.1021/acs.chemmater.0c04471	journal	March 2021
Polymorphism controls the degree of charge transfer in a molecularly doped semiconducting polymer Jacobs, Ian E.; Cendra, Camila; Harrelson, Thomas F. Materials Horizons, Vol. 5, Issue 4 https://doi.org/10.1039/C8MH00223A	journal	January 2018
Enhanced Electrical Conductivity of Molecularly p-Doped Poly(3-hexylthiophene) through Understanding the Correlation with Solid-State Order Hynynen, Jonna; Kiefer, David; Yu, Liyang Macromolecules, Vol. 50, Issue 20 https://doi.org/10.1021/acs.macromol.7b00968	journal	October 2017
Rapid synthesis of redox-active dodecaborane B ₁₂ (OR) ₁₂ clusters under ambient conditions Wixtrom, Alex I.; Shao, Yanwu; Jung, Dahee Inorganic Chemistry Frontiers, Vol. 3, Issue 5 https://doi.org/10.1039/C5QI00263J	journal	January 2016
Thermoelectric plastics: from design to synthesis, processing and structure–property relationships Kroon, Renee; Mengistie, Desalegn Alemu; Kiefer, David Chemical Society Reviews, Vol. 45, Issue 22 https://doi.org/10.1039/C6CS00149A	journal	January 2016
Molecular Packing and Arrangement Govern the Photo-Oxidative Stability of Organic Photovoltaic Materials Mateker, William R.; Heumueller, Thomas; Cheacharoen, Rongrong Chemistry of Materials, Vol. 27, Issue 18 https://doi.org/10.1021/acs.chemmater.5b02341	journal	September 2015
Nika : software for two-dimensional data reduction Ilavsky, Jan Journal of Applied Crystallography, Vol. 45, Issue 2 https://doi.org/10.1107/S0021889812004037	journal	March 2012
Double doping of conjugated polymers with monomer molecular dopants Kiefer, David; Kroon, Renee; Hofmann, Anna I. Nature Materials, Vol. 18, Issue 2 https://doi.org/10.1038/s41563-018-0263-6	journal	January 2019
The Role of Ordering on the Thermoelectric Properties of Blends of Regioregular and Regiorandom Poly(3‐hexylthiophene) Lim, Eunhee; Glaudell, Anne M.; Miller, Rachel Advanced Electronic Materials, Vol. 5, Issue 11 https://doi.org/10.1002/aelm.201800915	journal	April 2019
General Force-Field Parametrization Scheme for Molecular Dynamics Simulations of Conjugated Materials in Solution Wildman, Jack; Repiščák, Peter; Paterson, Martin J. Journal of Chemical Theory and Computation, Vol. 12, Issue 8 https://doi.org/10.1021/acs.jctc.5b01195	journal	July 2016
Crystallinity Determines Ion Injection Kinetics and Local Ion Density in Organic Mixed Conductors Jackson, Seth R.; Kingsford, Rand L.; Collins, Garrett W. Chemistry of Materials, Vol. 35, Issue 14 https://doi.org/10.1021/acs.chemmater.3c00657	journal	July 2023
High-Resolution ac Measurements of the Hall Effect in Organic Field-Effect Transistors Chen, Y.; Yi, H. T.; Podzorov, V. Physical Review Applied, Vol. 5, Issue 3 https://doi.org/10.1103/PhysRevApplied.5.034008	journal	March 2016
Two-dimensional charge transport in self-organized, high-mobility conjugated polymers Sirringhaus, H.; Brown, P. J.; Friend, R. H. Nature, Vol. 401, Issue 6754, p. 685-688 https://doi.org/10.1038/44359	journal	October 1999
Overcoming Film Quality Issues for Conjugated Polymers Doped with F ₄ TCNQ by Solution Sequential Processing: Hall Effect, Structural, and Optical Measurements Scholes, D. Tyler; Hawks, Steven A.; Yee, Patrick Y. The Journal of Physical Chemistry Letters, Vol. 6, Issue 23 https://doi.org/10.1021/acs.jpclett.5b02332	journal	November 2015
Understanding defect distributions in polythiophenes via comparison of regioregular and regiorandom species Muntasir, Tanvir; Chaudhary, Sumit Journal of Applied Physics, Vol. 118, Issue 20 https://doi.org/10.1063/1.4936326	journal	November 2015
Band gap design of thiophene polymers based on density functional theory Lubis, Patricia; Saito, Mineo Japanese Journal of Applied Physics, Vol. 53, Issue 7 https://doi.org/10.7567/JJAP.53.071602	journal	June 2014
Web interface for reflectivity fitting Doucet, M.; Ferraz Leal, R. M.; Hobson, T. C. SoftwareX, Vol. 7 https://doi.org/10.1016/j.softx.2018.09.001	journal	January 2018
Nanomorphology in A–D–A type small molecular acceptors-based bulk heterojunction polymer solar cells Liu, Delong; Zhang, Ying; Li, Gang Journal of Energy Chemistry, Vol. 35 https://doi.org/10.1016/j.jechem.2018.11.001	journal	August 2019
P3HT Revisited – From Molecular Scale to Solar Cell Devices Ludwigs, Sabine Advances in Polymer Science https://doi.org/10.1007/978-3-662-45145-8	book	November 2014
Aggregation control in natural brush-printed conjugated polymer films and implications for enhancing charge transport Wang, Gang; Huang, Wei; Eastham, Nicholas D. Proceedings of the National Academy of Sciences, Vol. 114, Issue 47 https://doi.org/10.1073/pnas.1713634114	journal	November 2017
The Effects of Crystallinity on Charge Transport and the Structure of Sequentially Processed F ₄ TCNQ-Doped Conjugated Polymer Films Scholes, D. Tyler; Yee, Patrick Y.; Lindemuth, Jeffrey R. Advanced Functional Materials, Vol. 27, Issue 44 https://doi.org/10.1002/adfm.201702654	journal	September 2017
Molecular Electrical Doping of Organic Semiconductors: Fundamental Mechanisms and Emerging Dopant Design Rules Salzmann, Ingo; Heimel, Georg; Oehzelt, Martin Accounts of Chemical Research, Vol. 49, Issue 3 https://doi.org/10.1021/acs.accounts.5b00438	journal	February 2016
Side Chain Engineering in Solution-Processable Conjugated Polymers Mei, Jianguo; Bao, Zhenan Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm4020805	journal	September 2013
Synthesis and Applications of Perfunctionalized Boron Clusters Axtell, Jonathan C.; Saleh, Liban M. A.; Qian, Elaine A. Inorganic Chemistry, Vol. 57, Issue 5 https://doi.org/10.1021/acs.inorgchem.7b02912	journal	February 2018
Thermoelectric Properties of Poly(3-hexylthiophene) (P3HT) Doped with 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F ₄ TCNQ) by Vapor-Phase Infiltration Lim, Eunhee; Peterson, Kelly A.; Su, Gregory M. Chemistry of Materials, Vol. 30, Issue 3 https://doi.org/10.1021/acs.chemmater.7b04849	journal	January 2018
Preferential Location of Dopants in the Amorphous Phase of Oriented Regioregular Poly(3‐hexylthiophene‐2,5‐diyl) Films Helps Reach Charge Conductivities of 3000 S cm ⁻¹ Zhong, Yuhan; Untilova, Viktoriia; Muller, Dominique Advanced Functional Materials, Vol. 32, Issue 30 https://doi.org/10.1002/adfm.202202075	journal	May 2022
GIXSGUI : a MATLAB toolbox for grazing-incidence X-ray scattering data visualization and reduction, and indexing of buried three-dimensional periodic nanostructured films Jiang, Zhang Journal of Applied Crystallography, Vol. 48, Issue 3 https://doi.org/10.1107/S1600576715004434	journal	April 2015
Revealing contributions to conduction from transport within ordered and disordered regions in highly doped conjugated polymers through analysis of temperature-dependent Hall measurements Wood, William A.; Jacobs, Ian E.; Spalek, Leszek J. Physical Review Materials, Vol. 7, Issue 3 https://doi.org/10.1103/PhysRevMaterials.7.034603	journal	March 2023
Strain–Microstructure–Optoelectronic Inter-Relationship toward Engineering Mechano-Optoelectronic Conjugated Polymer Thin Films Lee, Youngmin; Mongare, Alfred; Plant, Aaron Polymers, Vol. 13, Issue 6 https://doi.org/10.3390/polym13060935	journal	March 2021
Thermoelectric Properties of Semiconducting Polymers Peterson, Kelly A.; Thomas, Elayne M.; Chabinyc, Michael L. Annual Review of Materials Research, Vol. 50, Issue 1 https://doi.org/10.1146/annurev-matsci-082219-024716	journal	July 2020
Anisotropic Polaron Delocalization in Conjugated Homopolymers and Donor–Acceptor Copolymers Ghosh, Raja; Luscombe, Christine K.; Hambsch, Mike Chemistry of Materials, Vol. 31, Issue 17 https://doi.org/10.1021/acs.chemmater.9b01704	journal	December 2018
Dopant-Induced Ordering of Amorphous Regions in Regiorandom P3HT Yee, Patrick Y.; Scholes, D. Tyler; Schwartz, Benjamin J. The Journal of Physical Chemistry Letters, Vol. 10, Issue 17 https://doi.org/10.1021/acs.jpclett.9b02070	journal	August 2019
A highly stretchable, transparent, and conductive polymer Wang, Yue; Zhu, Chenxin; Pfattner, Raphael Science Advances, Vol. 3, Issue 3 https://doi.org/10.1126/sciadv.1602076	journal	March 2017
Tuning counterion chemistry to reduce carrier localization in doped semiconducting carbon nanotube networks Murrey, Tucker L.; Aubry, Taylor J.; Ruiz, Omar Leon Cell Reports Physical Science, Vol. 4, Issue 5 https://doi.org/10.1016/j.xcrp.2023.101407	journal	May 2023
Designing π-conjugated polymer blends with improved thermoelectric power factors Abtahi, Ashkan; Johnson, Stephen; Park, So Min Journal of Materials Chemistry A, Vol. 7, Issue 34 https://doi.org/10.1039/C9TA07464C	journal	January 2019
Charge-Transfer Localization in Molecularly Doped Thiophene-Based Donor Polymers Pingel, Patrick; Zhu, Lingyun; Park, Kue Surk The Journal of Physical Chemistry Letters, Vol. 1, Issue 13 https://doi.org/10.1021/jz100492c	journal	June 2010
Effect of Crystallization on the Electronic Energy Levels and Thin Film Morphology of P3HT:PCBM Blends Tsoi, Wing C.; Spencer, Steve J.; Yang, Li Macromolecules, Vol. 44, Issue 8 https://doi.org/10.1021/ma102841e	journal	April 2011
New Opportunities for Organic Semiconducting Polymers in Biomedical Applications Kim, Kyunghun; Yoo, Hocheon; Lee, Eun Kwang Polymers, Vol. 14, Issue 14 https://doi.org/10.3390/polym14142960	journal	July 2022
Ionic Dopant‐Induced Ordering Enhances the Thermoelectric Properties of a Polythiophene‐Based Block Copolymer Dong, Ban Xuan; Liu, Ziwei; Onorato, Jonathan W. Advanced Functional Materials, Vol. 31, Issue 51 https://doi.org/10.1002/adfm.202106991	journal	September 2021
Regioisomeric Non-Fullerene Acceptors Containing Fluorobenzo[ c ][1,2,5]thiadiazole Unit for Polymer Solar Cells Zhong, Wenkai; Fan, Baobing; Cui, Jing ACS Applied Materials & Interfaces, Vol. 9, Issue 42 https://doi.org/10.1021/acsami.7b12902	journal	October 2017
Recent Progress in Conjugated Conducting and Semiconducting Polymers for Energy Devices Heydari Gharahcheshmeh, Meysam; Gleason, Karen K. Energies, Vol. 15, Issue 10 https://doi.org/10.3390/en15103661	journal	May 2022
Vibrational Stark Effect Mapping of Polaron Delocalization in Chemically Doped Conjugated Polymers Stanfield, Dane A.; Mehmedović, Zerina; Schwartz, Benjamin J. Chemistry of Materials, Vol. 33, Issue 21 https://doi.org/10.1021/acs.chemmater.1c02934	journal	October 2021
Relating the physical structure and optical properties of conjugated polymers using neutron reflectivity in combination with photoluminescence spectroscopy Mitchell, William J.; Burn, Paul L.; Thomas, Robert K. Journal of Applied Physics, Vol. 95, Issue 5 https://doi.org/10.1063/1.1644636	journal	March 2004
Spectral Signatures and Spatial Coherence of Bound and Unbound Polarons in P3HT Films: Theory Versus Experiment Ghosh, Raja; Chew, Annabel R.; Onorato, Jonathan The Journal of Physical Chemistry C, Vol. 122, Issue 31 https://doi.org/10.1021/acs.jpcc.8b03873	journal	July 2018
Tunable Dopants with Intrinsic Counterion Separation Reveal the Effects of Electron Affinity on Dopant Intercalation and Free Carrier Production in Sequentially Doped Conjugated Polymer Films Aubry, Taylor J.; Winchell, K. J.; Salamat, Charlene Z. Advanced Functional Materials, Vol. 30, Issue 28 https://doi.org/10.1002/adfm.202001800	journal	May 2020
Additive solution deposition of multi-layered semiconducting polymer films for design of sophisticated device architectures Murrey, Tucker L.; Guo, Kunping; Mulvey, Justin T. Journal of Materials Chemistry C, Vol. 7, Issue 4 https://doi.org/10.1039/C8TC05652H	journal	January 2019
Measuring the Degree of Crystallinity in Semicrystalline Regioregular Poly(3-hexylthiophene) Shen, Xiaobo; Hu, Weiguo; Russell, Thomas P. Macromolecules, Vol. 49, Issue 12 https://doi.org/10.1021/acs.macromol.6b00799	journal	June 2016
Machine Learning Aided Design of Polymer with Targeted Band Gap Based on DFT Computation Xu, Pengcheng; Lu, Tian; Ju, Lifei The Journal of Physical Chemistry B, Vol. 125, Issue 2 https://doi.org/10.1021/acs.jpcb.0c08674	journal	January 2021
Probing the evolution of conductivity and structural changes in vapor-F4TCNQ doped P3HT DiTusa, Mark F.; Grocke, Garrett L.; Ma, Tengzhou Molecular Systems Design & Engineering, Vol. 7, Issue 7 https://doi.org/10.1039/D1ME00192B	journal	January 2022
Molecular Dynamics Study of the Thermodynamics of Integer Charge Transfer vs Charge-Transfer Complex Formation in Doped Conjugated Polymers Wu, Eric Chih-Kuan; Salamat, Charlene Z.; Tolbert, Sarah H. ACS Applied Materials & Interfaces, Vol. 14, Issue 23 https://doi.org/10.1021/acsami.2c06449	journal	June 2022
Impact of varying side chain structure on organic electrochemical transistor performance: a series of oligoethylene glycol-substituted polythiophenes Chen, Shinya E.; Flagg, Lucas Q.; Onorato, Jonathan W. Journal of Materials Chemistry A, Vol. 10, Issue 19 https://doi.org/10.1039/D2TA00683A	journal	January 2022
Dodecaborane‐Based Dopants Designed to Shield Anion Electrostatics Lead to Increased Carrier Mobility in a Doped Conjugated Polymer Aubry, Taylor J.; Axtell, Jonathan C.; Basile, Victoria M. Advanced Materials, Vol. 31, Issue 11 https://doi.org/10.1002/adma.201805647	journal	January 2019
Anomalous Surface Reflection of X Rays Yoneda, Y. Physical Review, Vol. 131, Issue 5 https://doi.org/10.1103/PhysRev.131.2010	journal	September 1963
Low Band Gap Conjugated Semiconducting Polymers Scharber, Markus Clark; Sariciftci, Niyazi Serdar Advanced Materials Technologies, Vol. 6, Issue 4 https://doi.org/10.1002/admt.202000857	journal	February 2021
Understanding the Intrinsic Carrier Transport in Highly Oriented Poly(3-hexylthiophene): Effect of Side Chain Regioregularity Qu, Sanyin; Ming, Chen; Yao, Qin Polymers, Vol. 10, Issue 8 https://doi.org/10.3390/polym10080815	journal	July 2018
Highly oriented crystals at the buried interface in polythiophene thin-film transistors Joseph Kline, R.; McGehee, Michael D.; Toney, Michael F. Nature Materials, Vol. 5, Issue 3 https://doi.org/10.1038/nmat1590	journal	February 2006

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