A new family of liquid and solid guanidine-based n-type dopants for solution-processed perovskite solar cells

Nakayama, Hidenori; Schneider, Julia A.; Faust, Mina; Wang, Hengbin; Read de Alaniz, Javier; Chabinyc, Michael L.

doi:10.1039/D0QM00437E

Title: A new family of liquid and solid guanidine-based n-type dopants for solution-processed perovskite solar cells

Journal Article · Thu Nov 26 00:00:00 EST 2020 · Materials Chemistry Frontiers

DOI:https://doi.org/10.1039/D0QM00437E· OSTI ID:1646534

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^[2]; Faust, Mina ^[3];

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Electronics Materials and New Energy Laboratory, Mitsubishi Chemical Corporation, Yokohama R&D Center 1000, Yokohama 227-8502, Japan
Materials Department, University of California, Santa Barbara, USA, Mitsubishi Chemical Center for Advanced Materials
Materials Department, University of California, Santa Barbara, USA
Mitsubishi Chemical Center for Advanced Materials, University of California, Santa Barbara, USA

A new family of n-type dopants for organic semiconductors is reported. Changing the alkyl chain of these triazabicyclodecene (TBD) dopants alters their physical properties, including thermal stability, and influences their doping efficiency.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: DEAC02-05CH11231

OSTI ID:: 1646534

Journal Information:: Materials Chemistry Frontiers, Journal Name: Materials Chemistry Frontiers Vol. 4 Journal Issue: 12; ISSN 2052-1537

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (42)

High Conductivity in a Nonplanar n -Doped Ambipolar Semiconducting Polymer Perry, Erin E.; Chiu, Chien-Yang; Moudgil, Karttikay Chemistry of Materials, Vol. 29, Issue 22 https://doi.org/10.1021/acs.chemmater.7b03516	journal	November 2017
Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters Pratt, Russell C.; Lohmeijer, Bas G. G.; Long, David A. Journal of the American Chemical Society, Vol. 128, Issue 14 https://doi.org/10.1021/ja060662+	journal	March 2006
The coordination chemistry of guanidines and guanidinates Bailey, Philip J.; Pace, Stuart Coordination Chemistry Reviews, Vol. 214, Issue 1 https://doi.org/10.1016/S0010-8545(00)00389-1	journal	April 2001
Organic thermoelectric materials for energy harvesting and temperature control Russ, Boris; Glaudell, Anne; Urban, Jeffrey J. Nature Reviews Materials, Vol. 1, Issue 10 https://doi.org/10.1038/natrevmats.2016.50	journal	August 2016
Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics Bendikov, Michael; Wudl, Fred; Perepichka, Dmitrii F. Chemical Reviews, Vol. 104, Issue 11 https://doi.org/10.1021/cr030666m	journal	November 2004
Organic superbase-induced chemiluminescent decomposition of a hydroxyaryl-substituted dioxetane: Unique effect of a bifunctional guanidine base on the chemiluminescence profile of a bicyclic dioxetane bearing a 4-(benzoxazol-2-yl)-3,5-dihydroxyphenyl moiety Watanabe, Nobuko; Wakatsuki, Ayu; Ijuin, Hisako K. Tetrahedron Letters, Vol. 59, Issue 11 https://doi.org/10.1016/j.tetlet.2018.01.045	journal	March 2018
Mechanistic considerations of guanidine-catalyzed reactions Fu, Xiao; Tan, Choon-Hong Chemical Communications, Vol. 47, Issue 29 https://doi.org/10.1039/c0cc03691a	journal	January 2011
Molecular parameters responsible for thermally activated transport in doped organic semiconductors Schwarze, Martin; Gaul, Christopher; Scholz, Reinhard Nature Materials, Vol. 18, Issue 3 https://doi.org/10.1038/s41563-018-0277-0	journal	January 2019
Effective Solution- and Vacuum-Processed n-Doping by Dimers of Benzimidazoline Radicals Naab, Benjamin D.; Zhang, Siyuan; Vandewal, Koen Advanced Materials, Vol. 26, Issue 25 https://doi.org/10.1002/adma.201400668	journal	April 2014
Tetrakis(dimethylamino)ethylene as a Useful Reductant of Some Bromodifluoromethyl Heterocycles. Application to the Synthesis of New gem-Difluorinated Heteroarylated Compounds Burkholder, Conrad; Dolbier, William R.; Médebielle, Maurice The Journal of Organic Chemistry, Vol. 63, Issue 16 https://doi.org/10.1021/jo980201+	journal	July 1998
N-Type Surface Doping of MAPbI ₃ via Charge Transfer from Small Molecules Perry, Erin E.; Labram, John G.; Venkatesan, Naveen R. Advanced Electronic Materials, Vol. 4, Issue 7 https://doi.org/10.1002/aelm.201800087	journal	June 2018
Interface engineering of highly efficient perovskite solar cells Zhou, H.; Chen, Q.; Li, G. Science, Vol. 345, Issue 6196 https://doi.org/10.1126/science.1254050	journal	July 2014
n-Doping of Organic Electronic Materials using Air-Stable Organometallics Guo, Song; Kim, Sang Bok; Mohapatra, Swagat K. Advanced Materials, Vol. 24, Issue 5, p. 699-703 https://doi.org/10.1002/adma.201103238	journal	November 2011
An Amidine-Type n-Dopant for Solution-Processed Field-Effect Transistors and Perovskite Solar Cells Hu, Lin; Liu, Tiefeng; Duan, Jiashun Advanced Functional Materials, Vol. 27, Issue 41 https://doi.org/10.1002/adfm.201703254	journal	September 2017
A Universal Method to Produce Low-Work Function Electrodes for Organic Electronics Zhou, Y.; Fuentes-Hernandez, C.; Shim, J. Science, Vol. 336, Issue 6079, p. 327-332 https://doi.org/10.1126/science.1218829	journal	April 2012
Guanidine, trimethylenemethane, and "Y-delocalization." Can acyclic compounds have "aromatic" stability? Gund, Peter Journal of Chemical Education, Vol. 49, Issue 2 https://doi.org/10.1021/ed049p100	journal	February 1972
Measurements of the field-effect electron mobility of the acceptor ITIC Park, Youngrak; Fuentes-Hernandez, Canek; Jia, Xiaojia Organic Electronics, Vol. 58 https://doi.org/10.1016/j.orgel.2018.04.028	journal	July 2018
Relating open-circuit voltage losses to the active layer morphology and contact selectivity in organic solar cells Tang, Zheng; Wang, Jing; Melianas, Armantas Journal of Materials Chemistry A, Vol. 6, Issue 26 https://doi.org/10.1039/C8TA01195H	journal	January 2018
Leuco Crystal Violet as a Dopant for n-Doping of Organic Thin Films of Fullerene C ₆₀ Li, Fenghong; Werner, Ansgar; Pfeiffer, Martin The Journal of Physical Chemistry B, Vol. 108, Issue 44 https://doi.org/10.1021/jp0478615	journal	November 2004
Beating the thermodynamic limit with photo-activation of n-doping in organic semiconductors Lin, Xin; Wegner, Berthold; Lee, Kyung Min Nature Materials, Vol. 16, Issue 12 https://doi.org/10.1038/nmat5027	journal	November 2017
Thermoelectric Properties of Solution-Processed n-Doped Ladder-Type Conducting Polymers Wang, Suhao; Sun, Hengda; Ail, Ujwala Advanced Materials, Vol. 28, Issue 48 https://doi.org/10.1002/adma.201603731	journal	October 2016
Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions Yu, G.; Gao, J.; Hummelen, J. C. Science, Vol. 270, Issue 5243, p. 1789-1791 https://doi.org/10.1126/science.270.5243.1789	journal	December 1995
Moisture assisted perovskite film growth for high performance solar cells You, Jingbi; Yang, Yang (Michael); Hong, Ziruo Applied Physics Letters, Vol. 105, Issue 18 https://doi.org/10.1063/1.4901510	journal	November 2014
Doping of C60 with tertiary amines: TDAE, DBU, DBN. A comparative study Klos, H.; Rystau, I.; Schütz, W. Chemical Physics Letters, Vol. 224, Issue 3-4 https://doi.org/10.1016/0009-2614(94)00550-8	journal	July 1994
CO2 chemistry: task-specific ionic liquids for CO2 capture/activation and subsequent conversion Yang, Zhen-Zhen; Zhao, Ya-Nan; He, Liang-Nian RSC Advances, Vol. 1, Issue 4 https://doi.org/10.1039/c1ra00307k	journal	January 2011
A Guanidine-Based Superbase as Efficient Chemiluminescence Booster Geiselhart, Christina M.; Schmitt, Christian W.; Jöckle, Philipp Scientific Reports, Vol. 9, Issue 1 https://doi.org/10.1038/s41598-019-51105-z	journal	October 2019
Bis-1,3-dithiolium chloride: an unusually stable organic radical cation Wudl, F.; Smith, G. M.; Hufnagel, E. J. Journal of the Chemical Society D: Chemical Communications, Issue 21 https://doi.org/10.1039/c29700001453	journal	January 1970
Reducing Surface Recombination Velocities at the Electrical Contacts Will Improve Perovskite Photovoltaics Wang, Jian; Fu, Weifei; Jariwala, Sarthak ACS Energy Letters, Vol. 4, Issue 1 https://doi.org/10.1021/acsenergylett.8b02058	journal	December 2018
Solution doping of organic semiconductors using air-stable n-dopants Qi, Yabing; Mohapatra, Swagat K.; Bok Kim, Sang Applied Physics Letters, Vol. 100, Issue 8 https://doi.org/10.1063/1.3689760	journal	February 2012
High fill factor over 82% enabled by a biguanide doping electron transporting layer in planar perovskite solar cells Ge, Ru; Qin, Fei; Hu, Lin Frontiers of Optoelectronics, Vol. 11, Issue 4 https://doi.org/10.1007/s12200-018-0847-4	journal	November 2018
Doped Organic Transistors Lüssem, Björn; Keum, Chang-Min; Kasemann, Daniel Chemical Reviews, Vol. 116, Issue 22 https://doi.org/10.1021/acs.chemrev.6b00329	journal	October 2016
Interfacial charge-transfer doping of metal halide perovskites for high performance photovoltaics Noel, Nakita K.; Habisreutinger, Severin N.; Pellaroque, Alba Energy & Environmental Science, Vol. 12, Issue 10 https://doi.org/10.1039/C9EE01773A	journal	January 2019
Introducing a Nonvolatile N‐Type Dopant Drastically Improves Electron Transport in Polymer and Small‐Molecule Organic Transistors Panidi, Julianna; Kainth, Jaspreet; Paterson, Alexandra F. Advanced Functional Materials, Vol. 29, Issue 34 https://doi.org/10.1002/adfm.201902784	journal	June 2019
[DBU]C60. Spin pairing in a fullerene salt Skiebe, Andreas; Hirsch, Andreas; Klos, Holger Chemical Physics Letters, Vol. 220, Issue 1-2 https://doi.org/10.1016/0009-2614(94)00124-3	journal	March 1994
Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors Russ, Boris; Robb, Maxwell J.; Popere, Bhooshan C. Chemical Science, Vol. 7, Issue 3 https://doi.org/10.1039/C5SC04217H	journal	January 2016
Poly(ethylene imine) Impurities Induce n-doping Reaction in Organic (Semi)Conductors Fabiano, Simone; Braun, Slawomir; Liu, Xianjie Advanced Materials, Vol. 26, Issue 34 https://doi.org/10.1002/adma.201401986	journal	July 2014
Y-Aromaticity: Why Is the Trimethylenemethane Dication More Stable than the Butadienyl Dication? Dworkin, Amy; Naumann, Rachel; Seigfred, Christopher The Journal of Organic Chemistry, Vol. 70, Issue 19 https://doi.org/10.1021/jo0508090	journal	September 2005
Efficient Perovskite Solar Cells over a Broad Temperature Window: The Role of the Charge Carrier Extraction Shao, Shuyan; Liu, Jian; Fang, Hong-Hua Advanced Energy Materials, Vol. 7, Issue 22 https://doi.org/10.1002/aenm.201701305	journal	September 2017
An Isolated CO2 Adduct of a Nitrogen Base: Crystal and Electronic Structures Villiers, Claude; Dognon, Jean-Pierre; Pollet, Rodolphe Angewandte Chemie International Edition, Vol. 49, Issue 20 https://doi.org/10.1002/anie.201001035	journal	March 2010
Origin of Work Function Modification by Ionic and Amine-Based Interface Layers van Reenen, Stephan; Kouijzer, Sandra; Janssen, René A. J. Advanced Materials Interfaces, Vol. 1, Issue 8 https://doi.org/10.1002/admi.201400189	journal	August 2014
Solubility-Limited Extrinsic n-Type Doping of a High Electron Mobility Polymer for Thermoelectric Applications Schlitz, Ruth A.; Brunetti, Fulvio G.; Glaudell, Anne M. Advanced Materials, Vol. 26, Issue 18 https://doi.org/10.1002/adma.201304866	journal	January 2014
Amino-Functionalized Conjugated Polymer as an Efficient Electron Transport Layer for High-Performance Planar-Heterojunction Perovskite Solar Cells Sun, Chen; Wu, Zhihong; Yip, Hin-Lap Advanced Energy Materials, Vol. 6, Issue 5 https://doi.org/10.1002/aenm.201501534	journal	December 2015

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