Evidence of Preformed Lewis Acid–Base and Wheland-Type Complexes Acting as Dopants for p-Type Conjugated Polymers

Mukhopadhyaya, Tushita; Lee, Taein; Ganley, Connor; Clancy, Paulette; Katz, Howard E.

doi:10.1021/acsapm.1c01906

Evidence of Preformed Lewis Acid–Base and Wheland-Type Complexes Acting as Dopants for p-Type Conjugated Polymers

Journal Article · 16 February 2022 · ACS Applied Polymer Materials

DOI:https://doi.org/10.1021/acsapm.1c01906· OSTI ID:1978295

Mukhopadhyaya, Tushita ^[1]; Lee, Taein ^[1]; Ganley, Connor ^[2]; ^[2]; ^[3]

Department of Materials Science and Engineering, Johns Hopkins University, 206 Maryland Hall, 3400 North Charles Street, Baltimore, Maryland 21218, United States
Department of Chemical and Biomolecular Engineering, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, United States
Department of Materials Science and Engineering, Johns Hopkins University, 206 Maryland Hall, 3400 North Charles Street, Baltimore, Maryland 21218, United States; Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, United States

Not provided.

Research Organization:: Johns Hopkins Univ., Baltimore, MD (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: FG02-07ER46465

OSTI ID:: 1978295

Journal Information:: ACS Applied Polymer Materials, Vol. 4, Issue 3; ISSN 2637-6105

Publisher:: ACS Publications

Country of Publication:: United States

Language:: English

References (66)

Polymer Thermoelectrics: Opportunities and Challenges Goel, Mahima; Thelakkat, Mukundan Macromolecules, Vol. 53, Issue 10 https://doi.org/10.1021/acs.macromol.9b02453	journal	April 2020
Chemical doping of organic semiconductors for thermoelectric applications Zhao, Wenrui; Ding, Jiamin; Zou, Ye Chemical Society Reviews, Vol. 49, Issue 20 https://doi.org/10.1039/D0CS00204F	journal	January 2020
Exploring Wholly Doped Conjugated Polymer Films Based on Hybrid Doping: Strategic Approach for Optimizing Electrical Conductivity and Related Thermoelectric Properties Yoon, Sang Eun; Kang, Yeongkwon; Jeon, Gyeong G. Advanced Functional Materials, Vol. 30, Issue 42 https://doi.org/10.1002/adfm.202004598	journal	August 2020
Influence of dopant size and electron affinity on the electrical conductivity and thermoelectric properties of a series of conjugated polymers Liang, Zhiming; Zhang, Yadong; Souri, Maryam Journal of Materials Chemistry A, Vol. 6, Issue 34 https://doi.org/10.1039/C8TA05922E	journal	January 2018
How intermolecular geometrical disorder affects the molecular doping of donor–acceptor copolymers Di Nuzzo, Daniele; Fontanesi, Claudio; Jones, Rebecca Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms7460	journal	March 2015
Organic-based thermoelectrics Lindorf, M.; Mazzio, K. A.; Pflaum, J. Journal of Materials Chemistry A, Vol. 8, Issue 16 https://doi.org/10.1039/C9TA11717B	journal	January 2020
Electrochemical Stability and Ambipolar Charge Transport in Diketopyrrolopyrrole-Based Organic Materials Ray, Suman; Panidi, Julianna; Mukhopadhyay, Tushita ACS Applied Electronic Materials, Vol. 1, Issue 10 https://doi.org/10.1021/acsaelm.9b00394	journal	September 2019
Data analysis for Seebeck coefficient measurements de Boor, J.; Müller, E. Review of Scientific Instruments, Vol. 84, Issue 6 https://doi.org/10.1063/1.4807697	journal	June 2013
High Thermoelectric Power Factor of a Diketopyrrolopyrrole-Based Low Bandgap Polymer via Finely Tuned Doping Engineering Jung, In Hwan; Hong, Cheon Taek; Lee, Un-Hak Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/srep44704	journal	March 2017
Review on Polymers for Thermoelectric Applications Culebras, Mario; Gómez, Clara; Cantarero, Andrés Materials, Vol. 7, Issue 9 https://doi.org/10.3390/ma7096701	journal	September 2014
Lewis acids and bases as molecular dopants for organic semiconductors Bridges, Colin R.; Baumgartner, Thomas Journal of Physical Organic Chemistry, Vol. 33, Issue 9 https://doi.org/10.1002/poc.4077	journal	May 2020
An iodine-doped polymer light-emitting diode Huang, F.; MacDiarmid, A. G.; Hsieh, B. R. Applied Physics Letters, Vol. 71, Issue 17 https://doi.org/10.1063/1.120078	journal	October 1997
Effects of FeCl3 doping on polymer-based thin film transistors Chen, Y.; Shih, I.; Xiao, S. Journal of Applied Physics, Vol. 96, Issue 1 https://doi.org/10.1063/1.1760838	journal	July 2004
High Thermoelectric Power Factor of Poly(3-hexylthiophene) through In-Plane Alignment and Doping with a Molybdenum Dithiolene Complex Untilova, Viktoriia; Hynynen, Jonna; Hofmann, Anna I. Macromolecules, Vol. 53, Issue 15 https://doi.org/10.1021/acs.macromol.0c01223	journal	July 2020
Effect of polar side chains on neutral and p-doped polythiophene Finn, Peter A.; Jacobs, Ian E.; Armitage, John Journal of Materials Chemistry C, Vol. 8, Issue 45 https://doi.org/10.1039/D0TC04290K	journal	January 2020
Influence of dopant size and doping method on the structure and thermoelectric properties of PBTTT films doped with F ₆ TCNNQ and F ₄ TCNQ Vijayakumar, Vishnu; Durand, Pablo; Zeng, Huiyan Journal of Materials Chemistry C, Vol. 8, Issue 46 https://doi.org/10.1039/D0TC02828B	journal	January 2020
Hexacyano-[3]-radialene anion-radical salts: a promising family of highly soluble p-dopants Karpov, Y.; Kiriy, N.; Al-Hussein, M. Chemical Communications, Vol. 54, Issue 3 https://doi.org/10.1039/C7CC08671G	journal	January 2018
The Critical Role of Dopant Cations in Electrical Conductivity and Thermoelectric Performance of n-Doped Polymers Lu, Yang; Yu, Zi-Di; Liu, Yi Journal of the American Chemical Society, Vol. 142, Issue 36 https://doi.org/10.1021/jacs.0c05699	journal	August 2020
Controlled steric selectivity in molecular doping towards closest-packed supramolecular conductors Kohno, Shinya; Yamashita, Yu; Kasuya, Naotaka Communications Materials, Vol. 1, Issue 1 https://doi.org/10.1038/s43246-020-00081-3	journal	November 2020
Enhanced Molecular Doping for High Conductivity in Polymers with Volume Freed for Dopants Li, Hui; DeCoster, Mallory E.; Ming, Chen Macromolecules, Vol. 52, Issue 24 https://doi.org/10.1021/acs.macromol.9b02048	journal	December 2019
Designing Conjugated Polymers for Molecular Doping: The Roles of Crystallinity, Swelling, and Conductivity in Sequentially-Doped Selenophene-Based Copolymers Scholes, D. Tyler; Yee, Patrick Y.; McKeown, George R. Chemistry of Materials, Vol. 31, Issue 1 https://doi.org/10.1021/acs.chemmater.8b02648	journal	November 2018
Doped thieno[3,4- b ]thiophene-based copolymers for p-type organic thermoelectric materials Wu, Sicheng; Xing, Weilong; Zhu, Mengsu Journal of Materials Chemistry C, Vol. 9, Issue 12 https://doi.org/10.1039/D1TC00211B	journal	January 2021
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
High Conductivity and Electron-Transfer Validation in an n-Type Fluoride-Anion-Doped Polymer for Thermoelectrics in Air Zhao, Xingang; Madan, Deepa; Cheng, Yan Advanced Materials, Vol. 29, Issue 34 https://doi.org/10.1002/adma.201606928	journal	July 2017
Brønsted Acid Doping of P3HT with Largely Soluble Tris(pentafluorophenyl)borane for Highly Conductive and Stable Organic Thermoelectrics Via One‐Step Solution Mixing Suh, Eui Hyun; Oh, Jong Gyu; Jung, Jaemin Advanced Energy Materials, Vol. 10, Issue 47 https://doi.org/10.1002/aenm.202002521	journal	October 2020
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
Protonic acids: Generally applicable dopants for conducting polymers Han, C. C.; Elsenbaumer, R. L. Synthetic Metals, Vol. 30, Issue 1 https://doi.org/10.1016/0379-6779(89)90648-6	journal	April 1989
Making weak dopants strong Yan, Han; Ma, Wei Nature Materials, Vol. 18, Issue 12 https://doi.org/10.1038/s41563-019-0493-2	journal	September 2019
Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale Mayer, Robert J.; Hampel, Nathalie; Ofial, Armin R. Chemistry – A European Journal, Vol. 27, Issue 12 https://doi.org/10.1002/chem.202003916	journal	January 2021
Doping the Backbone of π‐Conjugated Polymers with Tricoordinate Boron: Synthetic Strategies and Emerging Applications Helten, Holger Chemistry – An Asian Journal, Vol. 14, Issue 7 https://doi.org/10.1002/asia.201900016	journal	February 2019
Lewis Acid Doping Induced Synergistic Effects on Electronic and Morphological Structure for Donor and Acceptor in Polymer Solar Cells Yan, Han; Chen, Jianya; Zhou, Ke Advanced Energy Materials, Vol. 8, Issue 19 https://doi.org/10.1002/aenm.201703672	journal	March 2018
Understanding how Lewis acids dope organic semiconductors: a “complex” story Marqués, Pablo Simón; Londi, Giacomo; Yurash, Brett Chemical Science, Vol. 12, Issue 20 https://doi.org/10.1039/D1SC01268A	journal	January 2021
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 Panidi, Julianna; Paterson, Alexandra F.; Khim, Dongyoon Advanced Science, Vol. 5, Issue 1 https://doi.org/10.1002/advs.201700290	journal	October 2017
Using Preformed Meisenheimer Complexes as Dopants for n‐Type Organic Thermoelectrics with High Seebeck Coefficients and Power Factors Han, Jinfeng; Ganley, Connor; Hu, Qin Advanced Functional Materials, Vol. 31, Issue 18 https://doi.org/10.1002/adfm.202010567	journal	February 2021
Direct Observation of the Wheland Intermediate in Electrophilic Aromatic Substitution. Reversible Formation of Nitrosoarenium Cations Hubig, Stephan M.; Kochi, Jay K. Journal of the American Chemical Society, Vol. 122, Issue 34 https://doi.org/10.1021/ja001318u	journal	August 2000
Wheland Intermediates: An ab Initio Valence Bond Study Hadzic, Mélodie; Braïda, Benoît; Volatron, François Organic Letters, Vol. 13, Issue 8 https://doi.org/10.1021/ol200327s	journal	March 2011
Identification of Wheland-type intermediates Blasco, Teresa Nature Catalysis, Vol. 1, Issue 1 https://doi.org/10.1038/s41929-017-0012-2	journal	January 2018
Hard and Soft Acids and Bases: Structure and Process Reed, James L. The Journal of Physical Chemistry A, Vol. 116, Issue 26 https://doi.org/10.1021/jp301812j	journal	June 2012
Calculation of ionization energy of alkyl radicals by hybrid density functional theory methods Jursic, Branko S. Journal of Molecular Structure: THEOCHEM, Vol. 432, Issue 3 https://doi.org/10.1016/S0166-1280(98)00084-0	journal	June 1998
Lewis-Acid Doping of Triphenylamine-Based Hole Transport Materials Improves the Performance and Stability of Perovskite Solar Cells Liu, Jiang; Liu, Wenzhu; Aydin, Erkan ACS Applied Materials & Interfaces, Vol. 12, Issue 21 https://doi.org/10.1021/acsami.0c03660	journal	May 2020
Reduction of the Lattice Thermal Conductivity of Polymer Semiconductors by Molecular Doping Zapata-Arteaga, Osnat; Perevedentsev, Aleksandr; Marina, Sara ACS Energy Letters, Vol. 5, Issue 9 https://doi.org/10.1021/acsenergylett.0c01410	journal	August 2020
Correlation of Seebeck coefficient and electric conductivity in polyaniline and polypyrrole Mateeva, N.; Niculescu, H.; Schlenoff, J. Journal of Applied Physics, Vol. 83, Issue 6 https://doi.org/10.1063/1.367119	journal	March 1998
Dopant‐Dependent Increase in Seebeck Coefficient and Electrical Conductivity in Blended Polymers with Offset Carrier Energies Li, Hui; Plunkett, Evan; Cai, Zhengxu Advanced Electronic Materials, Vol. 5, Issue 11 https://doi.org/10.1002/aelm.201800618	journal	February 2019
High Seebeck Coefficient in Mixtures of Conjugated Polymers Zuo, Guangzheng; Liu, Xianjie; Fahlman, Mats Advanced Functional Materials, Vol. 28, Issue 15 https://doi.org/10.1002/adfm.201703280	journal	November 2017
A review of carrier thermoelectric-transport theory in organic semiconductors Lu, Nianduan; Li, Ling; Liu, Ming Physical Chemistry Chemical Physics, Vol. 18, Issue 29 https://doi.org/10.1039/C6CP02830F	journal	January 2016
An analytical Seebeck coefficient model for disordered organic semiconductors Shi, Xuewen; Lu, Nianduan; Xu, Guangwei Physics Letters A, Vol. 381, Issue 40 https://doi.org/10.1016/j.physleta.2017.09.006	journal	October 2017
Towards high-performance polymer-based thermoelectric materials He, Ming; Qiu, Feng; Lin, Zhiqun Energy & Environmental Science, Vol. 6, Issue 5 https://doi.org/10.1039/c3ee24193a	journal	January 2013
Effects of Disorder on Thermoelectric Properties of Semiconducting Polymers Upadhyaya, Meenakshi; Boyle, Connor J.; Venkataraman, Dhandapani Scientific Reports, Vol. 9, Issue 1 https://doi.org/10.1038/s41598-019-42265-z	journal	April 2019
Thermoelectric properties of a semicrystalline polymer doped beyond the insulator-to-metal transition by electrolyte gating Tanaka, Hisaaki; Kanahashi, Kaito; Takekoshi, Naoya Science Advances, Vol. 6, Issue 7 https://doi.org/10.1126/sciadv.aay8065	journal	February 2020
Application of the Compensated Arrhenius Formalism to Self-Diffusion: Implications for Ionic Conductivity and Dielectric Relaxation Petrowsky, Matt; Frech, Roger The Journal of Physical Chemistry B, Vol. 114, Issue 26 https://doi.org/10.1021/jp1020142	journal	June 2010
Molecular engineered conjugated polymer with high thermal conductivity Xu, Yanfei; Wang, Xiaoxue; Zhou, Jiawei Science Advances, Vol. 4, Issue 3 https://doi.org/10.1126/sciadv.aar3031	journal	March 2018
Effects of contact resistance on electrical conductivity measurements of SiC-based materials Youngblood, G. E.; Thomsen, E. C.; Henager, C. H. Journal of Nuclear Materials, Vol. 442, Issue 1-3 https://doi.org/10.1016/j.jnucmat.2013.04.096	journal	November 2013
Improved Electron Transport with Reduced Contact Resistance in N-Doped Polymer Field-Effect Transistors with a Dimeric Dopant Wang, Rong; Guo, Yikun; Zhang, Di Macromolecular Rapid Communications, Vol. 39, Issue 14 https://doi.org/10.1002/marc.201700726	journal	January 2018
Charge carrier mobility in systems with local electron-phonon interaction Prodanović, Nikola; Vukmirović, Nenad Physical Review B, Vol. 99, Issue 10 https://doi.org/10.1103/PhysRevB.99.104304	journal	March 2019
Phonon-Assisted Jump Rate in Noncrystalline Solids Emin, David Physical Review Letters, Vol. 32, Issue 6 https://doi.org/10.1103/PhysRevLett.32.303	journal	February 1974
Electric field-dependent charge transport in organic semiconductors Li, Ling; Van Winckel, Steven; Genoe, Jan Applied Physics Letters, Vol. 95, Issue 15 https://doi.org/10.1063/1.3246160	journal	October 2009
Interface dipole: Effects on threshold voltage and mobility for both amorphous and poly-crystalline organic field effect transistors Celle, C.; Suspène, C.; Ternisien, M. Organic Electronics, Vol. 15, Issue 3 https://doi.org/10.1016/j.orgel.2014.01.003	journal	March 2014
Analytical Platform To Characterize Dopant Solution Concentrations, Charge Carrier Densities in Films and Interfaces, and Physical Diffusion in Polymers Utilizing Remote Field-Effect Transistors Jang, Hyun-June; Wagner, Justine; Li, Hui Journal of the American Chemical Society, Vol. 141, Issue 12 https://doi.org/10.1021/jacs.8b13026	journal	February 2019
Ineffectiveness of energy filtering at grain boundaries for thermoelectric materials Bachmann, M.; Czerner, M.; Heiliger, C. Physical Review B, Vol. 86, Issue 11 https://doi.org/10.1103/PhysRevB.86.115320	journal	September 2012
Expression of interfacial Seebeck coefficient through grain boundary engineering with multi-layer graphene nanoplatelets Lin, Yue; Wood, Maxwell; Imasato, Kazuki Energy & Environmental Science, Vol. 13, Issue 11 https://doi.org/10.1039/D0EE02490B	journal	January 2020
Boron-11 NMR spectra of boranes, main-group heteroboranes, and substituted derivatives. Factors influencing chemical shifts of skeletal atoms Hermanek, Stanislav Chemical Reviews, Vol. 92, Issue 2 https://doi.org/10.1021/cr00010a007	journal	March 1992
The ORCA program system: The ORCA program system Neese, Frank Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 1 https://doi.org/10.1002/wcms.81	journal	June 2011
Software update: the ORCA program system, version 4.0: Software update Neese, Frank Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 8, Issue 1 https://doi.org/10.1002/wcms.1327	journal	July 2017
Donor Conjugated Polymers with Polar Side Chain Groups: The Role of Dielectric Constant and Energetic Disorder on Photovoltaic Performance Xu, Bing; Yi, Xueping; Huang, Tzu-Yen Advanced Functional Materials, Vol. 28, Issue 46 https://doi.org/10.1002/adfm.201803418	journal	October 2018
How Ethylene Glycol Chains Enhance the Dielectric Constant of Organic Semiconductors: Molecular Origin and Frequency Dependence Sami, Selim; Alessandri, Riccardo; Broer, Ria ACS Applied Materials & Interfaces, Vol. 12, Issue 15 https://doi.org/10.1021/acsami.0c01417	journal	March 2020
Entropy of Charge Separation in Organic Photovoltaic Cells: The Benefit of Higher Dimensionality Gregg, Brian A. The Journal of Physical Chemistry Letters, Vol. 2, Issue 24, p. 3013-3015 https://doi.org/10.1021/jz2012403	journal	November 2011

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