U.S. Department of EnergyOffice of Scientific and Technical Information
Strategic fluorination of polymers and fullerenes improves photostability of organic photovoltaic blends
Abstract
The photobleaching dynamics of a series of three organic photovoltaic (OPV) donor polymers and five different fullerenes are presented. The fullerenes studied include PC60BM and four perfluoroalkylfullerenes with relatively large electron affinities, namely C60(CF3)2, C60(i-C3F7)2, C60(CF3)4, and C60(CF3)8. The donor polymers were all based on cyclopentadithiophene (CPDT) and thienopyrrolodione (TPD), but the TPD side chains were designed to include alkyl, partially fluorinated alkyl, and fluorinated phenyl groups to improve miscibility of the active layer components. Exciton harvesting was probed with photoluminescence quenching measurements. Accelerated photodegradation studies of polymer:fullerene blends were then carried out under white light illumination at ~1.2 suns in air. A strong correlation was observed between the polymer donor photobleaching rate and the electron affinity of the fullerene. The most dramatic effect was observed for a blend of C60(CF3)8 with the donor containing fluorinated phenyl groups: the blend required 150 times the dosing of photons to bleach to 80% of its initial optical density than an analagous blend of PC60BM and non-fluorinated donor polymer. Furthermore, these results ultimately suggest that appropriate fluorination strategies applied to both the donor and acceptor can be a viable route toward a new paradigm of intrinsically photo- and phase-stable OPV active layers.
- Authors:
-
[2];
[2]
- Indian Inst. of Science, Bangalore (India)
- National Renewable Energy Lab. (NREL), Golden, CO (United States)
- Colorado State Univ., Fort Collins, CO (United States)
- Publication Date:
- Research Org.:
- National Renewable Energy Lab. (NREL), Golden, CO (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE), Renewable Power Office. Solar Energy Technologies Office
- OSTI Identifier:
- 1468736
- Alternate Identifier(s):
- OSTI ID: 1703027
- Report Number(s):
- NREL/JA-5900-71422
Journal ID: ISSN 1566-1199
- Grant/Contract Number:
- AC36-08GO28308
- Resource Type:
- Journal Article: Accepted Manuscript
- Journal Name:
- Organic Electronics
- Additional Journal Information:
- Journal Volume: 62; Journal ID: ISSN 1566-1199
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 14 SOLAR ENERGY; 36 MATERIALS SCIENCE; organic photovoltaics; photodegradation; photostability; photoluminescence quenching; perfluoroalkylated fullerenes
Citation Formats
Nellissery Viswanathan, Vinila, Ferguson, Andrew J., Pfeilsticker, Jason R., Larson, Bryon W., Garner, Logan E., Brook, Colin P., Strauss, Steven H., Boltalina, Olga V., Ramamurthy, Praveen C., and Braunecker, Wade A. Strategic fluorination of polymers and fullerenes improves photostability of organic photovoltaic blends. United States: N. p., 2018.
Web. doi:10.1016/j.orgel.2018.08.045.
Nellissery Viswanathan, Vinila, Ferguson, Andrew J., Pfeilsticker, Jason R., Larson, Bryon W., Garner, Logan E., Brook, Colin P., Strauss, Steven H., Boltalina, Olga V., Ramamurthy, Praveen C., & Braunecker, Wade A. Strategic fluorination of polymers and fullerenes improves photostability of organic photovoltaic blends. United States. https://doi.org/10.1016/j.orgel.2018.08.045
Nellissery Viswanathan, Vinila, Ferguson, Andrew J., Pfeilsticker, Jason R., Larson, Bryon W., Garner, Logan E., Brook, Colin P., Strauss, Steven H., Boltalina, Olga V., Ramamurthy, Praveen C., and Braunecker, Wade A. 2018.
"Strategic fluorination of polymers and fullerenes improves photostability of organic photovoltaic blends". United States. https://doi.org/10.1016/j.orgel.2018.08.045. https://www.osti.gov/servlets/purl/1468736.
@article{osti_1468736,
title = {Strategic fluorination of polymers and fullerenes improves photostability of organic photovoltaic blends},
author = {Nellissery Viswanathan, Vinila and Ferguson, Andrew J. and Pfeilsticker, Jason R. and Larson, Bryon W. and Garner, Logan E. and Brook, Colin P. and Strauss, Steven H. and Boltalina, Olga V. and Ramamurthy, Praveen C. and Braunecker, Wade A.},
abstractNote = {The photobleaching dynamics of a series of three organic photovoltaic (OPV) donor polymers and five different fullerenes are presented. The fullerenes studied include PC60BM and four perfluoroalkylfullerenes with relatively large electron affinities, namely C60(CF3)2, C60(i-C3F7)2, C60(CF3)4, and C60(CF3)8. The donor polymers were all based on cyclopentadithiophene (CPDT) and thienopyrrolodione (TPD), but the TPD side chains were designed to include alkyl, partially fluorinated alkyl, and fluorinated phenyl groups to improve miscibility of the active layer components. Exciton harvesting was probed with photoluminescence quenching measurements. Accelerated photodegradation studies of polymer:fullerene blends were then carried out under white light illumination at ~1.2 suns in air. A strong correlation was observed between the polymer donor photobleaching rate and the electron affinity of the fullerene. The most dramatic effect was observed for a blend of C60(CF3)8 with the donor containing fluorinated phenyl groups: the blend required 150 times the dosing of photons to bleach to 80% of its initial optical density than an analagous blend of PC60BM and non-fluorinated donor polymer. Furthermore, these results ultimately suggest that appropriate fluorination strategies applied to both the donor and acceptor can be a viable route toward a new paradigm of intrinsically photo- and phase-stable OPV active layers.},
doi = {10.1016/j.orgel.2018.08.045},
url = {https://www.osti.gov/biblio/1468736},
journal = {Organic Electronics},
issn = {1566-1199},
number = ,
volume = 62,
place = {United States},
year = {Tue Aug 28 00:00:00 EDT 2018},
month = {Tue Aug 28 00:00:00 EDT 2018}
}
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Works referenced in this record:
Recent advances in high performance donor-acceptor polymers for organic photovoltaics
journal, July 2017
- Holliday, Sarah; Li, Yilin; Luscombe, Christine K.
- Progress in Polymer Science, Vol. 70
A Wide Band Gap Polymer with a Deep Highest Occupied Molecular Orbital Level Enables 14.2% Efficiency in Polymer Solar Cells
journal, May 2018
- Li, Sunsun; Ye, Long; Zhao, Wenchao
- Journal of the American Chemical Society, Vol. 140, Issue 23
Printed metal back electrodes for R2R fabricated polymer solar cells studied using the LBIC technique
journal, May 2011
- Krebs, Frederik C.; Søndergaard, Roar; Jørgensen, Mikkel
- Solar Energy Materials and Solar Cells, Vol. 95, Issue 5
All solution roll-to-roll processed polymer solar cells free from indium-tin-oxide and vacuum coating steps
journal, August 2009
- Krebs, Frederik C.
- Organic Electronics, Vol. 10, Issue 5
OPV for mobile applications: an evaluation of roll-to-roll processed indium and silver free polymer solar cells through analysis of life cycle, cost and layer quality using inline optical and functional inspection tools
journal, January 2013
- Espinosa, Nieves; Lenzmann, Frank O.; Ryley, Stephen
- Journal of Materials Chemistry A, Vol. 1, Issue 24
Product integration of compact roll-to-roll processed polymer solar cell modules: methods and manufacture using flexographic printing, slot-die coating and rotary screen printing
journal, January 2010
- Krebs, Frederik C.; Fyenbo, Jan; Jørgensen, Mikkel
- Journal of Materials Chemistry, Vol. 20, Issue 41
Upscaling of polymer solar cell fabrication using full roll-to-roll processing
journal, January 2010
- Krebs, Frederik C.; Tromholt, Thomas; Jørgensen, Mikkel
- Nanoscale, Vol. 2, Issue 6
Stability of Polymer Solar Cells
journal, December 2011
- Jørgensen, Mikkel; Norrman, Kion; Gevorgyan, Suren A.
- Advanced Materials, Vol. 24, Issue 5
Degradation and stability of polymer-based solar cells
journal, January 2012
- Lee, Jea Uk; Jung, Jae Woong; Jo, Jea Woong
- Journal of Materials Chemistry, Vol. 22, Issue 46
Photooxidative degradation mechanism of model compounds of poly(p-phenylenevinylenes) [PPVs]
journal, December 2002
- Ma, Lichuan; Wang, Xuesong; Wang, Bojie
- Chemical Physics, Vol. 285, Issue 1
The mechanism of photo- and thermooxidation of poly(3-hexylthiophene) (P3HT) reconsidered
journal, June 2009
- Manceau, Matthieu; Rivaton, Agnès; Gardette, Jean-Luc
- Polymer Degradation and Stability, Vol. 94, Issue 6
The Role of Electron Affinity in Determining Whether Fullerenes Catalyze or Inhibit Photooxidation of Polymers for Solar Cells
journal, May 2012
- Hoke, Eric T.; Sachs-Quintana, I. T.; Lloyd, Matthew T.
- Advanced Energy Materials, Vol. 2, Issue 11
Photobleaching dynamics in small molecule vs. polymer organic photovoltaic blends with 1,7-bis-trifluoromethylfullerene
journal, January 2018
- Garner, Logan E.; Nellissery Viswanathan, Vinila; Arias, Dylan H.
- Journal of Materials Chemistry A, Vol. 6, Issue 11
A faux hawk fullerene with PCBM-like properties
journal, January 2015
- San, Long K.; Bukovsky, Eric V.; Larson, Bryon W.
- Chemical Science, Vol. 6, Issue 3
Electrochemical, Spectroscopic, and DFT Study of C 60 (CF 3 ) n Frontier Orbitals ( n = 2−18): The Link between Double Bonds in Pentagons and Reduction Potentials
journal, September 2007
- Popov, Alexey A.; Kareev, Ivan E.; Shustova, Natalia B.
- Journal of the American Chemical Society, Vol. 129, Issue 37
Perfluoroalkylfullerenes
journal, August 2014
- Boltalina, Olga V.; Popov, Alexey A.; Kuvychko, Igor V.
- Chemical Reviews, Vol. 115, Issue 2
The role of solvent vapor annealing in highly efficient air-processed small molecule solar cells
journal, January 2014
- Sun, Kuan; Xiao, Zeyun; Hanssen, Eric
- Journal of Materials Chemistry A, Vol. 2, Issue 24
The Effect of Processing Additives on Energetic Disorder in Highly Efficient Organic Photovoltaics: A Case Study on PBDTTT-C-T:PC 71 BM
journal, May 2015
- Gao, Feng; Himmelberger, Scott; Andersson, Mattias
- Advanced Materials, Vol. 27, Issue 26
Sequentially Different AB Diblock and ABA Triblock Copolymers as P3HT:PCBM Interfacial Compatibilizers for Bulk-Heterojunction Photovoltaics
journal, February 2016
- Fujita, Hiroyuki; Michinobu, Tsuyoshi; Fukuta, Seijiro
- ACS Applied Materials & Interfaces, Vol. 8, Issue 8
Promoting Morphology with a Favorable Density of States Using Diiodooctane to Improve Organic Photovoltaic Device Efficiency and Charge Carrier Lifetimes
journal, June 2017
- Garner, Logan E.; Bera, Abhijit; Larson, Bryon W.
- ACS Energy Letters, Vol. 2, Issue 7
Development of Highly Crystalline Donor–Acceptor-Type Random Polymers for High Performance Large-Area Organic Solar Cells
journal, September 2017
- Yun, Jae Hoon; Ahn, Hyungju; Lee, Phillip
- Macromolecules, Vol. 50, Issue 19
Improving the Performance of P3HT–Fullerene Solar Cells with Side-Chain-Functionalized Poly(thiophene) Additives: A New Paradigm for Polymer Design
journal, February 2012
- Lobez, Jose M.; Andrew, Trisha L.; Bulović, Vladimir
- ACS Nano, Vol. 6, Issue 4
Cyclopenta[c]thiophene-4,6-dione-Based Copolymers as Organic Photovoltaic Donor Materials
journal, April 2014
- Owczarczyk, Zbyslaw R.; Braunecker, Wade A.; Oosterhout, Stefan D.
- Advanced Energy Materials, Vol. 4, Issue 11
Alternating Copolymers of Cyclopenta[2,1-b;3,4-b′]dithiophene and Thieno[3,4-c]pyrrole-4,6-dione for High-Performance Polymer Solar Cells
journal, July 2011
- Li, Zhao; Tsang, Sai-Wing; Du, Xiaomei
- Advanced Functional Materials, Vol. 21, Issue 17
Direct Imide Formation from Thiophene Dicarboxylic Acids Gives Expanded Side-Chain Selection in Thienopyrrolediones
journal, February 2017
- Wolfe, Rylan M. W.; Reynolds, John R.
- Organic Letters, Vol. 19, Issue 5
Synthetic Control of Structural Order in N-Alkylthieno[3,4-c]pyrrole-4,6-dione-Based Polymers for Efficient Solar Cells
journal, June 2010
- Piliego, Claudia; Holcombe, Thomas W.; Douglas, Jessica D.
- Journal of the American Chemical Society, Vol. 132, Issue 22, p. 7595-7597
Electron Affinity of Phenyl–C 61 –Butyric Acid Methyl Ester (PCBM)
journal, July 2013
- Larson, Bryon W.; Whitaker, James B.; Wang, Xue-Bin
- The Journal of Physical Chemistry C, Vol. 117, Issue 29
Substituent effects in a series of 1,7-C60(RF)2 compounds (RF = CF3, C2F5, n-C3F7, i-C3F7, n-C4F9, s-C4F9, n-C8F17): electron affinities, reduction potentials and E(LUMO) values are not always correlated
journal, January 2012
- Kuvychko, Igor V.; Whitaker, James B.; Larson, Bryon W.
- Chemical Science, Vol. 3, Issue 5
Role of the Side Chain in the Phase Segregation of Polymer:Fullerene Bulk Heterojunction Composites
journal, July 2013
- Kim, Heejoo; Lee, Byoung Hoon; Lee, Kyu Cheol
- Advanced Energy Materials, Vol. 3, Issue 12
Removal of Residual Diiodooctane Improves Photostability of High-Performance Organic Solar Cell Polymers
journal, January 2016
- Tremolet de Villers, Bertrand J.; O’Hara, Kathryn A.; Ostrowski, David P.
- Chemistry of Materials, Vol. 28, Issue 3
Correlating triplet yield, singlet oxygen generation and photochemical stability in polymer/fullerene blend films
journal, January 2013
- Soon, Ying W.; Cho, Hoduk; Low, Jonathan
- Chemical Communications, Vol. 49, Issue 13
Materials and methods for encapsulation of OPV: A review
journal, November 2013
- Ahmad, Jakaria; Bazaka, Kateryna; Anderson, Liam J.
- Renewable and Sustainable Energy Reviews, Vol. 27
Determining the optimum morphology in high-performance polymer-fullerene organic photovoltaic cells
journal, December 2013
- Hedley, Gordon J.; Ward, Alexander J.; Alekseev, Alexander
- Nature Communications, Vol. 4, Issue 1
Photoinduced Carrier Generation and Decay Dynamics in Intercalated and Non-intercalated Polymer:Fullerene Bulk Heterojunctions
journal, June 2011
- Rance, William L.; Ferguson, Andrew J.; McCarthy-Ward, Thomas
- ACS Nano, Vol. 5, Issue 7
Controlling Exciton Diffusion and Fullerene Distribution in Photovoltaic Blends by Side Chain Modification
journal, July 2015
- Sajjad, Muhammad T.; Ward, Alexander J.; Kästner, Christian
- The Journal of Physical Chemistry Letters, Vol. 6, Issue 15
Contactless Determination of the Photoconductivity Action Spectrum, Exciton Diffusion Length, and Charge Separation Efficiency in Polythiophene-Sensitized TiO 2 Bilayers
journal, August 2003
- Kroeze, Jessica E.; Savenije, Tom J.; Vermeulen, Martien J. W.
- The Journal of Physical Chemistry B, Vol. 107, Issue 31
Photoinduced electron transfer in composites of conjugated polymers and dendrimers with branched colloidal nanoparticles
journal, January 2012
- Dayal, Smita; Kopidakis, Nikos; Rumbles, Garry
- Faraday Discuss., Vol. 155
Semi-random vs Well-Defined Alternating Donor–Acceptor Copolymers
journal, June 2014
- Braunecker, Wade A.; Oosterhout, Stefan D.; Owczarczyk, Zbyslaw R.
- ACS Macro Letters, Vol. 3, Issue 7
Dark Carriers, Trapping, and Activation Control of Carrier Recombination in Neat P3HT and P3HT:PCBM Blends
journal, October 2011
- Ferguson, Andrew J.; Kopidakis, Nikos; Shaheen, Sean E.
- The Journal of Physical Chemistry C, Vol. 115, Issue 46
Molecular engineering to improve carrier lifetimes for organic photovoltaic devices with thick active layers
journal, August 2017
- Oosterhout, Stefan D.; Braunecker, Wade A.; Owczarczyk, Zbyslaw R.
- Organic Electronics, Vol. 47
A Versatile Approach to Organic Photovoltaics Evaluation Using White Light Pulse and Microwave Conductivity
journal, November 2012
- Saeki, Akinori; Yoshikawa, Saya; Tsuji, Masashi
- Journal of the American Chemical Society, Vol. 134, Issue 46
Revealing the Dynamics of Charge Carriers in Polymer:Fullerene Blends Using Photoinduced Time-Resolved Microwave Conductivity
journal, October 2013
- Savenije, Tom J.; Ferguson, Andrew J.; Kopidakis, Nikos
- The Journal of Physical Chemistry C, Vol. 117, Issue 46
Quenching of Excitons by Holes in Poly(3-hexylthiophene) Films
journal, May 2008
- Ferguson, Andrew J.; Kopidakis, Nikos; Shaheen, Sean E.
- The Journal of Physical Chemistry C, Vol. 112, Issue 26
Pressure effect on heterogeneous trifluoromethylation of fullerenes and its application
journal, October 2011
- Kuvychko, Igor V.; Whitaker, James B.; Larson, Bryon W.
- Journal of Fluorine Chemistry, Vol. 132, Issue 10
Chemical tailoring of fullerene acceptors: synthesis, structures and electrochemical properties of perfluoroisopropylfullerenes
journal, January 2011
- Shustova, Natalia B.; Kuvychko, Igor V.; Peryshkov, Dmitry V.
- Chem. Commun., Vol. 47, Issue 3
Works referencing / citing this record:
Fluorous Fullerene Acceptors in Vacuum‐Deposited Photovoltaic Cells
journal, May 2019
- Reeves, Brian J.; Brook, Colin P.; Gerdes, Olga
- Solar RRL, Vol. 3, Issue 7
Stability of push–pull small molecule donors for organic photovoltaics: spectroscopic degradation of acceptor endcaps on benzo[1,2- b :4,5- b ′]dithiophene cores
journal, January 2019
- Watts, Kristen E.; Nguyen, Trung; Tremolet de Villers, Bertrand J.
- Journal of Materials Chemistry A, Vol. 7, Issue 34