Curious Case of BiEDOT: MALDI-TOF Mass Spectrometry Reveals Unbalanced Monomer Incorporation with Direct (Hetero)arylation Polymerization

Jones, A; De Keersmaecker, M.; Pelse, I.; Reynolds, J.

doi:10.1021/acs.macromol.0c01093

Title: Curious Case of BiEDOT: MALDI-TOF Mass Spectrometry Reveals Unbalanced Monomer Incorporation with Direct (Hetero)arylation Polymerization

Journal Article · 01 January 2022 · Macromolecules

DOI:https://doi.org/10.1021/acs.macromol.0c01093· OSTI ID:1690215

Jones, A; De Keersmaecker, M.; Pelse, I.; Reynolds, J.

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Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States)

Sponsoring Organization:: ~OTHER

DOE Contract Number:: SC0012704

OSTI ID:: 1690215

Report Number(s):: BNL-220536-2020-JACI

Journal Information:: Macromolecules, Vol. 53, Issue 17

Country of Publication:: United States

Language:: English

References (85)

Polymer Donors for High-Performance Non-Fullerene Organic Solar Cells Fu, Huiting; Wang, Zhaohui; Sun, Yanming Angewandte Chemie International Edition, Vol. 58, Issue 14 https://doi.org/10.1002/anie.201806291	journal	January 2019
Efficient Polymer Solar Cells Based on Non-fullerene Acceptors with Potential Device Lifetime Approaching 10 Years Du, Xiaoyan; Heumueller, Thomas; Gruber, Wolfgang Joule, Vol. 3, Issue 1 https://doi.org/10.1016/j.joule.2018.09.001	journal	January 2019
A Wide Band Gap Polymer with a Deep Highest Occupied Molecular Orbital Level Enables 14.2% Efficiency in Polymer Solar Cells Li, Sunsun; Ye, Long; Zhao, Wenchao Journal of the American Chemical Society, Vol. 140, Issue 23 https://doi.org/10.1021/jacs.8b02695	journal	May 2018
All-Polymer Solar Cells: Recent Progress, Challenges, and Prospects Wang, Gang; Melkonyan, Ferdinand S.; Facchetti, Antonio Angewandte Chemie International Edition, Vol. 58, Issue 13 https://doi.org/10.1002/anie.201808976	journal	February 2019
All Donor Electrochromic Polymers Tunable across the Visible Spectrum via Random Copolymerization Christiansen, Dylan T.; Ohtani, Shunsuke; Chujo, Yoshiki Chemistry of Materials, Vol. 31, Issue 17 https://doi.org/10.1021/acs.chemmater.9b01293	journal	December 2018
Color Control in π-Conjugated Organic Polymers for Use in Electrochromic Devices Beaujuge, Pierre M.; Reynolds, John R. Chemical Reviews, Vol. 110, Issue 1, p. 268-320 https://doi.org/10.1021/cr900129a	journal	January 2010
Electrochromic organic and polymeric materials for display applications Mortimer, Roger J.; Dyer, Aubrey L.; Reynolds, John R. Displays, Vol. 27, Issue 1 https://doi.org/10.1016/j.displa.2005.03.003	journal	January 2006
π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications ^† Facchetti, Antonio Chemistry of Materials, Vol. 23, Issue 3 https://doi.org/10.1021/cm102419z	journal	February 2011
Solution processed organic thermoelectrics: towards flexible thermoelectric modules Chen, Yani; Zhao, Yan; Liang, Ziqi Energy & Environmental Science, Vol. 8, Issue 2 https://doi.org/10.1039/C4EE03297G	journal	January 2015
Semi-metallic polymers Bubnova, Olga; Khan, Zia Ullah; Wang, Hui Nature Materials, Vol. 13, Issue 2 https://doi.org/10.1038/nmat3824	journal	December 2013
Conductive, Solution‐Processed Dioxythiophene Copolymers for Thermoelectric and Transparent Electrode Applications Ponder, James F.; Menon, Akanksha K.; Dasari, Raghunath R. Advanced Energy Materials, Vol. 9, Issue 24 https://doi.org/10.1002/aenm.201900395	journal	May 2019
Solution-Processed Metallic Conducting Polymer Films as Transparent Electrode of Optoelectronic Devices Xia, Yijie; Sun, Kuan; Ouyang, Jianyong Advanced Materials, Vol. 24, Issue 18 https://doi.org/10.1002/adma.201104795	journal	April 2012
Optimization of direct arylation polymerization (DArP) through the identification and control of defects in polymer structure Rudenko, Andrey E.; Thompson, Barry C. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 2 https://doi.org/10.1002/pola.27279	journal	June 2014
Approaches for improving the sustainability of conjugated polymer synthesis using direct arylation polymerization (DArP) Pankow, Robert M.; Thompson, Barry C. Polymer Chemistry, Vol. 11, Issue 3 https://doi.org/10.1039/C9PY01534E	journal	January 2020
Direct (Hetero)arylation Polymerization: Simplicity for Conjugated Polymer Synthesis Pouliot, Jean-Rémi; Grenier, François; Blaskovits, J. Terence Chemical Reviews, Vol. 116, Issue 22 https://doi.org/10.1021/acs.chemrev.6b00498	journal	October 2016
C–H Arylation in the Synthesis of π-Conjugated Polymers Suraru, Sabin-Lucian; Lee, Jason A.; Luscombe, Christine K. ACS Macro Letters, Vol. 5, Issue 6 https://doi.org/10.1021/acsmacrolett.6b00279	journal	May 2016
Mixed-Ligand Approach to Palladium-Catalyzed Direct Arylation Polymerization: Synthesis of Donor–Acceptor Polymers Containing Unsubstituted Bithiophene Units Wakioka, Masayuki; Morita, Hazuki; Ichihara, Nobuko Macromolecules, Vol. 53, Issue 1 https://doi.org/10.1021/acs.macromol.9b02298	journal	December 2019
Green-Solvent-Processed Amide-Functionalized Conjugated Polymers Prepared via Direct Arylation Polymerization (DArP) Ye, Liwei; Pankow, Robert M.; Horikawa, Mami Macromolecules, Vol. 52, Issue 23 https://doi.org/10.1021/acs.macromol.9b02014	journal	November 2019
Exploring the Utility of Buchwald Ligands for C–H Oxidative Direct Arylation Polymerizations Collier, Graham S.; Reynolds, John R. ACS Macro Letters, Vol. 8, Issue 8 https://doi.org/10.1021/acsmacrolett.9b00395	journal	July 2019
Suppressing Defect Formation Pathways in the Direct C–H Arylation Polymerization of Photovoltaic Copolymers Aldrich, Thomas J.; Dudnik, Alexander S.; Eastham, Nicholas D. Macromolecules, Vol. 51, Issue 22 https://doi.org/10.1021/acs.macromol.8b02297	journal	November 2018
Direct arylation polymerization: A guide to optimal conditions for effective conjugated polymers Gobalasingham, Nemal S.; Thompson, Barry C. Progress in Polymer Science, Vol. 83 https://doi.org/10.1016/j.progpolymsci.2018.06.002	journal	August 2018
End-Capping Effect of a Narrow Bandgap Conjugated Polymer on Bulk Heterojunction Solar Cells Park, Jin Kuen; Jo, Jang; Seo, Jung Hwa Advanced Materials, Vol. 23, Issue 21 https://doi.org/10.1002/adma.201004629	journal	April 2011
Homocoupling Defects in Diketopyrrolopyrrole-Based Copolymers and Their Effect on Photovoltaic Performance Hendriks, Koen H.; Li, Weiwei; Heintges, Gaël H. L. Journal of the American Chemical Society, Vol. 136, Issue 31 https://doi.org/10.1021/ja505574a	journal	July 2014
Mechanistic Studies of Effect of Dispersity on the Photovoltaic Performance of PTB7 Polymer Solar Cells Lu, Luyao; Zheng, Tianyue; Xu, Tao Chemistry of Materials, Vol. 27, Issue 2 https://doi.org/10.1021/cm5042953	journal	January 2015
Molar Mass versus Polymer Solar Cell Performance: Highlighting the Role of Homocouplings Vangerven, Tim; Verstappen, Pieter; Drijkoningen, Jeroen Chemistry of Materials, Vol. 27, Issue 10 https://doi.org/10.1021/acs.chemmater.5b00939	journal	May 2015
On the Effect of Prevalent Carbazole Homocoupling Defects on the Photovoltaic Performance of PCDTBT:PC ₇₁ BM Solar Cells Lombeck, Florian; Komber, Hartmut; Fazzi, Daniele Advanced Energy Materials, Vol. 6, Issue 21 https://doi.org/10.1002/aenm.201601232	journal	August 2016
Systematic Variation of Fluorinated Diketopyrrolopyrrole Low Bandgap Conjugated Polymers: Synthesis by Direct Arylation Polymerization and Characterization and Performance in Organic Photovoltaics and Organic Field-Effect Transistors Homyak, Patrick; Liu, Yao; Liu, Feng Macromolecules, Vol. 48, Issue 19 https://doi.org/10.1021/acs.macromol.5b01275	journal	September 2015
Performance Comparisons of Polymer Semiconductors Synthesized by Direct (Hetero)Arylation Polymerization (DHAP) and Conventional Methods for Organic Thin Film Transistors and Organic Photovoltaics Hendsbee, Arthur; Li, Yuning Molecules, Vol. 23, Issue 6 https://doi.org/10.3390/molecules23061255	journal	May 2018
Every Atom Counts: Elucidating the Fundamental Impact of Structural Change in Conjugated Polymers for Organic Photovoltaics Lo, Chi Kin; Gautam, Bhoj R.; Selter, Philipp Chemistry of Materials, Vol. 30, Issue 9 https://doi.org/10.1021/acs.chemmater.8b00590	journal	April 2018
On the “True” Structure of Push-Pull-Type Low-Bandgap Polymers for Organic Electronics Pirotte, Geert; Verstappen, Pieter; Vanderzande, Dirk Advanced Electronic Materials, Vol. 4, Issue 10 https://doi.org/10.1002/aelm.201700481	journal	January 2018
Facile Syntheses of Dioxythiophene-Based Conjugated Polymers by Direct C–H Arylation Zhao, Haichao; Liu, Ching-Yuan; Luo, Shyh-Chyang Macromolecules, Vol. 45, Issue 19, p. 7783-7790 https://doi.org/10.1021/ma300719n	journal	September 2012
An Indacenodithiophene–Quinoxaline Polymer Prepared by Direct Arylation Polymerization for Organic Photovoltaics Chen, Shanshan; Lee, Kyu Cheol; Zhang, Zhi-Guo Macromolecules, Vol. 49, Issue 2 https://doi.org/10.1021/acs.macromol.5b02324	journal	January 2016
Pd-Catalysed Direct Arylation Polymerisation for Synthesis of Low-Bandgap Conjugated Polymers and Photovoltaic Performance Chang, Shu-Wei; Waters, Huw; Kettle, Jeff Macromolecular Rapid Communications, Vol. 33, Issue 22, p. 1927-1932 https://doi.org/10.1002/marc.201200368	journal	July 2012
Suppression of Homocoupling Side Reactions in Direct Arylation Polycondensation for Producing High Performance OPV Materials Kuwabara, Junpei; Fujie, Yohei; Maruyama, Keisuke Macromolecules, Vol. 49, Issue 24 https://doi.org/10.1021/acs.macromol.6b02380	journal	December 2016
Toward Perfect Control of End Groups and Polydispersity in Poly(3-hexylthiophene) via Catalyst Transfer Polymerization Lohwasser, Ruth H.; Thelakkat, Mukundan Macromolecules, Vol. 44, Issue 9 https://doi.org/10.1021/ma200119s	journal	March 2011
A Rational Design of Highly Controlled Suzuki–Miyaura Catalyst-Transfer Polycondensation for Precision Synthesis of Polythiophenes and Their Block Copolymers: Marriage of Palladacycle Precatalysts with MIDA-Boronates Seo, Kyeong-Bae; Lee, In-Hwan; Lee, Jaeho Journal of the American Chemical Society, Vol. 140, Issue 12 https://doi.org/10.1021/jacs.7b13701	journal	March 2018
Externally Initiated Regioregular P3HT with Controlled Molecular Weight and Narrow Polydispersity Bronstein, Hugo A.; Luscombe, Christine K. Journal of the American Chemical Society, Vol. 131, Issue 36 https://doi.org/10.1021/ja9054977	journal	September 2009
Regioregularity and properties of the poly(3-hexylthiophene) synthesized by palladium catalyzed direct CH arylation polycondensation under different reaction conditions Dou, Junyan; Chen, Zhouqun; Ma, Changqi Synthetic Metals, Vol. 196 https://doi.org/10.1016/j.synthmet.2014.07.022	journal	October 2014
Catalyst-Transfer Polycondensation. Mechanism of Ni-Catalyzed Chain-Growth Polymerization Leading to Well-Defined Poly(3-hexylthiophene) Miyakoshi, Ryo; Yokoyama, Akihiro; Yokozawa, Tsutomu Journal of the American Chemical Society, Vol. 127, Issue 49 https://doi.org/10.1021/ja0556880	journal	December 2005
Facile Synthesis of End-Functionalized Regioregular Poly(3-alkylthiophene)s via Modified Grignard Metathesis Reaction Jeffries-El, Malika; Sauvé, Geneviève; McCullough, Richard D. Macromolecules, Vol. 38, Issue 25 https://doi.org/10.1021/ma051096q	journal	December 2005
In Situ Formation of Pyridyl-Functionalized Poly(3-hexylthiophene)s via Quenching of the Grignard Metathesis Polymerization: Toward Ligands for Semiconductor Quantum Dots Kochemba, W. Michael; Pickel, Deanna L.; Sumpter, Bobby G. Chemistry of Materials, Vol. 24, Issue 22 https://doi.org/10.1021/cm302915h	journal	November 2012
High-resolution MALDI-TOF MS study on analysis of low-molecular-weight products from photo-oxidation of poly(3-hexylthiophene): P3HT photo-oxidation analysis using MALDI-TOF MS Mizukado, Junji; Sato, Hiroaki; Chen, Liang Journal of Mass Spectrometry, Vol. 50, Issue 8 https://doi.org/10.1002/jms.3614	journal	June 2015
End Capping Does Matter: Enhanced Order and Charge Transport in Conjugated Donor–Acceptor Polymers Koldemir, Unsal; Puniredd, Sreenivasa Reddy; Wagner, Manfred Macromolecules, Vol. 48, Issue 18 https://doi.org/10.1021/acs.macromol.5b01252	journal	September 2015
A one-pot strategy to improve end-capping efficacy in Stille poly-condensations Harris, Jared D.; Carter, Kenneth R. Polymer Chemistry, Vol. 9, Issue 9 https://doi.org/10.1039/C7PY01761H	journal	January 2018
CH Activation as a Shortcut to Conjugated Polymer Synthesis Blaskovits, J. Terence; Leclerc, Mario Macromolecular Rapid Communications, Vol. 40, Issue 1 https://doi.org/10.1002/marc.201800512	journal	September 2018
Modular Establishment of a Diketopyrrolopyrrole-Based Polymer Library via Pd-Catalyzed Direct C-H (Hetero)arylation: a Highly Efficient Approach to Discover Low-Bandgap Polymers Guo, Qiang; Dong, Jiaxing; Wan, Danyang Macromolecular Rapid Communications, Vol. 34, Issue 6 https://doi.org/10.1002/marc.201200737	journal	January 2013
Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene: An Efficient Approach to Head-to-Tail Poly(3-hexylthiophene) Wang, Qifeng; Takita, Ryo; Kikuzaki, Yuuta Journal of the American Chemical Society, Vol. 132, Issue 33 https://doi.org/10.1021/ja105767z	journal	August 2010
Minimization of the auxiliary reagent loading for direct arylation polymerization (DArP) of 2-bromo-3-hexylthiophene Rudenko, Andrey E.; Latif, Alia A.; Thompson, Barry C. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 12 https://doi.org/10.1002/pola.27581	journal	March 2015
Structural Analysis of Poly(3-hexylthiophene) Prepared via Direct Heteroarylation Polymerization Pouliot, Jean-Rémi; Wakioka, Masayuki; Ozawa, Fumiyuki Macromolecular Chemistry and Physics, Vol. 217, Issue 13 https://doi.org/10.1002/macp.201600050	journal	May 2016
Synthesis of End-capped Regioregular Poly(3-hexylthiophene)s via Direct Arylation Wang, Qifeng; Wakioka, Masayuki; Ozawa, Fumiyuki Macromolecular Rapid Communications, Vol. 33, Issue 14 https://doi.org/10.1002/marc.201200076	journal	April 2012
Influence of the Carboxylic Acid Additive Structure on the Properties of Poly(3-hexylthiophene) Prepared via Direct Arylation Polymerization (DArP) Rudenko, Andrey E.; Thompson, Barry C. Macromolecules, Vol. 48, Issue 3 https://doi.org/10.1021/ma502131k	journal	January 2015
Mixed-Ligand Approach to Palladium-Catalyzed Direct Arylation Polymerization: Highly Selective Synthesis of π-Conjugated Polymers with Diketopyrrolopyrrole Units Wakioka, Masayuki; Takahashi, Rina; Ichihara, Nobuko Macromolecules, Vol. 50, Issue 3 https://doi.org/10.1021/acs.macromol.6b02679	journal	January 2017
Defect Analysis of High Electron Mobility Diketopyrrolopyrrole Copolymers Made by Direct Arylation Polycondensation Broll, Sebastian; Nübling, Fritz; Luzio, Alessandro Macromolecules, Vol. 48, Issue 20 https://doi.org/10.1021/acs.macromol.5b01843	journal	October 2015
A Highly Efficient Catalytic System for Polycondensation of 2,7-Dibromo-9,9-dioctylfluorene and 1,2,4,5-Tetrafluorobenzene via Direct Arylation Wakioka, Masayuki; Kitano, Yutaro; Ozawa, Fumiyuki Macromolecules, Vol. 46, Issue 2 https://doi.org/10.1021/ma302558z	journal	December 2012
Direct arylation polycondensation for the synthesis of bithiophene-based alternating copolymers Kuwabara, Junpei; Nohara, Yuta; Choi, Seong Jib Polymer Chemistry, Vol. 4, Issue 4, p. 947-953 https://doi.org/10.1039/C2PY20917A	journal	January 2013
A Highly Efficient Catalyst for the Synthesis of Alternating Copolymers with Thieno[3,4- c ]pyrrole-4,6-dione Units via Direct Arylation Polymerization Wakioka, Masayuki; Ichihara, Nobuko; Kitano, Yutaro Macromolecules, Vol. 47, Issue 2 https://doi.org/10.1021/ma4023668	journal	January 2014
Tin-Free Direct C–H Arylation Polymerization for High Photovoltaic Efficiency Conjugated Copolymers Dudnik, Alexander S.; Aldrich, Thomas J.; Eastham, Nicholas D. Journal of the American Chemical Society, Vol. 138, Issue 48 https://doi.org/10.1021/jacs.6b10023	journal	November 2016
Conjugated Polymers à la Carte from Time-Controlled Direct (Hetero)Arylation Polymerization Morin, Pierre-Olivier; Bura, Thomas; Sun, Bin ACS Macro Letters, Vol. 4, Issue 1 https://doi.org/10.1021/mz500656g	journal	December 2014
Mixed-Ligand Approach to Palladium-Catalyzed Direct Arylation Polymerization: Synthesis of Donor–Acceptor Polymers with Dithienosilole (DTS) and Thienopyrroledione (TPD) Units Iizuka, Eisuke; Wakioka, Masayuki; Ozawa, Fumiyuki Macromolecules, Vol. 48, Issue 9 https://doi.org/10.1021/acs.macromol.5b00526	journal	April 2015
Direct Arylation Polycondensation of Bithiazole Derivatives with Various Acceptors Kuramochi, Masahiro; Kuwabara, Junpei; Lu, Wei Macromolecules, Vol. 47, Issue 21 https://doi.org/10.1021/ma5014397	journal	October 2014
Highly Efficient Catalysts for Direct Arylation Polymerization (DArP) Wakioka, Masayuki; Ozawa, Fumiyuki Asian Journal of Organic Chemistry, Vol. 7, Issue 7 https://doi.org/10.1002/ajoc.201800227	journal	May 2018
Mechanistic studies and optimisation of a Pd-catalysed direct arylation reaction using phosphine-free systems Kuwabara, Junpei; Sakai, Masaru; Zhang, Qiao Organic Chemistry Frontiers, Vol. 2, Issue 5 https://doi.org/10.1039/C4QO00351A	journal	January 2015
Direct (Hetero)arylation Polymerization: An Effective Route to 3,4-Propylenedioxythiophene-Based Polymers with Low Residual Metal Content Estrada, Leandro A.; Deininger, James J.; Kamenov, George D. ACS Macro Letters, Vol. 2, Issue 10 https://doi.org/10.1021/mz4003886	journal	September 2013
Heteroatom Role in Polymeric Dioxyselenophene/Dioxythiophene Systems for Color and Redox Control Ponder, James F.; Pittelli, Sandra L.; Reynolds, John R. ACS Macro Letters, Vol. 5, Issue 6 https://doi.org/10.1021/acsmacrolett.6b00250	journal	May 2016
A Fruitful Usage of a Dialkylthiophene Comonomer for Redox Stable Wide-Gap Cathodically Coloring Electrochromic Polymers Christiansen, Dylan T.; Reynolds, John R. Macromolecules, Vol. 51, Issue 22 https://doi.org/10.1021/acs.macromol.8b01789	journal	November 2018
Electrochromic Polymers Processed from Environmentally Benign Solvents Collier, Graham S.; Pelse, Ian; Österholm, Anna M. Chemistry of Materials, Vol. 30, Issue 15 https://doi.org/10.1021/acs.chemmater.8b01765	journal	July 2018
Aqueous Electrolyte Compatible Electrochromic Polymers Processed from an Environmentally Sustainable Solvent Collier, Graham S.; Pelse, Ian; Reynolds, John R. ACS Macro Letters, Vol. 7, Issue 10 https://doi.org/10.1021/acsmacrolett.8b00551	journal	September 2018
Semi-random P3HT analogs via direct arylation polymerization Rudenko, Andrey E.; Wiley, Calvin A.; Stone, Shiloh M. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 50, Issue 18, p. 3691-3697 https://doi.org/10.1002/pola.26175	journal	June 2012
Identifying Homocouplings as Critical Side Reactions in Direct Arylation Polycondensation Lombeck, Florian; Komber, Hartmut; Gorelsky, Serge I. ACS Macro Letters, Vol. 3, Issue 8 https://doi.org/10.1021/mz5004147	journal	August 2014
Scope and Limitations of a Direct Arylation Polycondensation Scheme in the Synthesis of PCPDTBT-Type Copolymers Kowalski, Sebastian; Allard, Sybille; Scherf, Ullrich Macromolecular Rapid Communications, Vol. 36, Issue 11 https://doi.org/10.1002/marc.201400557	journal	December 2014
Designing a Soluble PEDOT Analogue without Surfactants or Dispersants Ponder, James F.; Österholm, Anna M.; Reynolds, John R. Macromolecules, Vol. 49, Issue 6 https://doi.org/10.1021/acs.macromol.5b02638	journal	March 2016
Solution Processed PEDOT Analogues in Electrochemical Supercapacitors Österholm, Anna M.; Ponder, James F.; Kerszulis, Justin A. ACS Applied Materials & Interfaces, Vol. 8, Issue 21 https://doi.org/10.1021/acsami.6b02434	journal	May 2016
The Impact of Palladium(II) Reduction Pathways on the Structure and Activity of Palladium(0) Catalysts Wei, Carolyn S.; Davies, Geraint H. M.; Soltani, Omid Angewandte Chemie International Edition, Vol. 52, Issue 22 https://doi.org/10.1002/anie.201210252	journal	April 2013
Synthesis of random poly(hexyl thiophene-3-carboxylate) copolymers via oxidative direct arylation polymerization (oxi-DArP) Gobalasingham, Nemal S.; Pankow, Robert M.; Thompson, Barry C. Polymer Chemistry, Vol. 8, Issue 12 https://doi.org/10.1039/C7PY00181A	journal	January 2017
Push–pull chromophores based on 2,2′-bi(3,4-ethylenedioxythiophene) (BEDOT) π-conjugating spacer Raimundo, Jean-Manuel; Blanchard, Philippe; Frère, Pierre Tetrahedron Letters, Vol. 42, Issue 8 https://doi.org/10.1016/S0040-4039(00)02317-0	journal	February 2001
Photoinduced Electron Transfer in Naphthalene Diimide End-Capped Thiophene Oligomers Jones, Austin L.; Gish, Melissa K.; Zeman, Charles J. The Journal of Physical Chemistry A, Vol. 121, Issue 50 https://doi.org/10.1021/acs.jpca.7b09095	journal	December 2017
Role of Structure in Ultrafast Charge Separation and Recombination in Naphthalene Diimide End-Capped Thiophene Oligomers Gish, Melissa K.; Jones, Austin L.; Papanikolas, John M. The Journal of Physical Chemistry C, Vol. 122, Issue 33 https://doi.org/10.1021/acs.jpcc.8b04074	journal	July 2018
Structural, Optical, and Electronic Properties of a Series of 3,4-Propylenedioxythiophene Oligomers in Neutral and Various Oxidation States Lin, Chuanwen; Endo, Takanori; Takase, Masayoshi Journal of the American Chemical Society, Vol. 133, Issue 29 https://doi.org/10.1021/ja2035442	journal	June 2011
Electrochemical Addressing of the Optical Properties of a Monolayer on a Transparent Conducting Substrate Shukla, Atindra D.; Das, Amitava; van der Boom, Milko E. Angewandte Chemie International Edition, Vol. 44, Issue 21 https://doi.org/10.1002/anie.200461958	journal	May 2005
The chemical and structural origin of efficient p-type doping in P3HT Duong, Duc T.; Wang, Chenchen; Antono, Erin Organic Electronics, Vol. 14, Issue 5 https://doi.org/10.1016/j.orgel.2013.02.028	journal	May 2013
Polar Side Chains Enhance Processability, Electrical Conductivity, and Thermal Stability of a Molecularly p-Doped Polythiophene Kroon, Renee; Kiefer, David; Stegerer, Dominik Advanced Materials, Vol. 29, Issue 24 https://doi.org/10.1002/adma.201700930	journal	April 2017
Anion-Dependent Doping and Charge Transport in Organic Electrochemical Transistors Flagg, Lucas Q.; Giridharagopal, Rajiv; Guo, Jiajie Chemistry of Materials, Vol. 30, Issue 15 https://doi.org/10.1021/acs.chemmater.8b02220	journal	July 2018
p-Type Doping of Poly(3-hexylthiophene) with the Strong Lewis Acid Tris(pentafluorophenyl)borane Pingel, Patrick; Arvind, Malavika; Kölln, Lisa Advanced Electronic Materials, Vol. 2, Issue 10 https://doi.org/10.1002/aelm.201600204	journal	September 2016
XPS studies on conducting polymers: polypyrrole films doped with perchlorate and polymeric anions Atanasoska, Ljiljana; Naoi, Katsuhiko; Smyrl, William H. Chemistry of Materials, Vol. 4, Issue 5 https://doi.org/10.1021/cm00023a012	journal	September 1992
Efficient molecular doping of polymeric semiconductors driven by anion exchange Yamashita, Yu; Tsurumi, Junto; Ohno, Masahiro Nature, Vol. 572, Issue 7771 https://doi.org/10.1038/s41586-019-1504-9	journal	August 2019

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Title: Curious Case of BiEDOT: MALDI-TOF Mass Spectrometry Reveals Unbalanced Monomer Incorporation with Direct (Hetero)arylation Polymerization

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