First principles study of photo-oxidation degradation mechanisms in P3HT for organic solar cells

Sai, Na; Leung, Kevin; Zádor, Judit; Henkelman, Graeme

doi:10.1039/C4CP00146J

Title: First principles study of photo-oxidation degradation mechanisms in P3HT for organic solar cells

Journal Article · Wed Jan 01 00:00:00 EST 2014 · Physical Chemistry Chemical Physics. PCCP (Print)

DOI:https://doi.org/10.1039/C4CP00146J· OSTI ID:1383401

Sai, Na ^[1]; Leung, Kevin ^[2]; Zádor, Judit ^[3]; Henkelman, Graeme ^[4]

Energy Frontier Research Center (EFRC:CST) and Institute for Computational Engineering and Sciences; The University of Texas at Austin; Austin, USA; Department of Physics; The University of Texas at Austin
Sandia National Laboratory; Albuquerque, USA
Sandia National Laboratory; Livermore, USA
Energy Frontier Research Center (EFRC:CST) and Institute for Computational Engineering and Sciences; The University of Texas at Austin; Austin, USA

We present a theoretical study of degradation mechanisms for photoinduced oxidation in organic polymers in the condensed phase, using poly(3-hexylthiophene) (P3HT) as an example.

Cite

Export

Save

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Understanding Charge Separation and Transfer at Interfaces in Energy Materials (CST)

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

DOE Contract Number:: SC0001091

OSTI ID:: 1383401

Journal Information:: Physical Chemistry Chemical Physics. PCCP (Print), Vol. 16, Issue 17; Related Information: CST partners with University of Texas at Austin (lead); Sandia National Laboratories; ISSN 1463-9076

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (47)

Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Polymer-Fullerene Bulk-Heterojunction Solar Cells Brabec, Christoph J.; Gowrisanker, Srinivas; Halls, Jonathan J. M. Advanced Materials, Vol. 22, Issue 34 https://doi.org/10.1002/adma.200903697	journal	August 2010
Recent advances in solution-processed interfacial materials for efficient and stable polymer solar cells Yip, Hin-Lap; Jen, Alex K.-Y. Energy & Environmental Science, Vol. 5, Issue 3, p. 5994-6011 https://doi.org/10.1039/c2ee02806a	journal	January 2012
Oxygen doping-induced photogeneration loss in P3HT:PCBM solar cells Guerrero, Antonio; Boix, Pablo P.; Marchesi, Luís F. Solar Energy Materials and Solar Cells, Vol. 100 https://doi.org/10.1016/j.solmat.2012.01.012	journal	May 2012
Photodegradation of Polymers Rabek, Jan F. https://doi.org/10.1007/978-3-642-80090-0	book	January 1996
Two-electron reduction of ethylene carbonate: A quantum chemistry re-examination of mechanisms Leung, Kevin Chemical Physics Letters, Vol. 568-569 https://doi.org/10.1016/j.cplett.2012.08.022	journal	May 2013
Photochemical stability of π-conjugated polymers for polymer solar cells: a rule of thumb Manceau, Matthieu; Bundgaard, Eva; Carlé, Jon E. Journal of Materials Chemistry, Vol. 21, Issue 12 https://doi.org/10.1039/c0jm03105d	journal	January 2011
Stability of Polymer Solar Cells Jørgensen, Mikkel; Norrman, Kion; Gevorgyan, Suren A. Advanced Materials, Vol. 24, Issue 5 https://doi.org/10.1002/adma.201104187	journal	December 2011
Role of oxygen diffusion in polymer ageing: kinetic and mechanical aspects Audouin, L.; Langlois, V.; Verdu, J. Journal of Materials Science, Vol. 29, Issue 3 https://doi.org/10.1007/BF00445968	journal	February 1994
Further insights into the photodegradation of poly(3-hexylthiophene) by means of X-ray photoelectron spectroscopy Manceau, Matthieu; Gaume, Julien; Rivaton, Agnès Thin Solid Films, Vol. 518, Issue 23 https://doi.org/10.1016/j.tsf.2010.06.042	journal	September 2010
Photo-oxidation and ozonization of poly(3-hexylthiophene) thin films as studied by UV/VIS and photoelectron spectroscopy Hintz, H.; Egelhaaf, H. -J.; Peisert, H. Polymer Degradation and Stability, Vol. 95, Issue 5 https://doi.org/10.1016/j.polymdegradstab.2010.02.004	journal	May 2010
Radiation induced recombination centers in organic solar cells Street, R. A.; Northrup, J. E.; Krusor, B. S. Physical Review B, Vol. 85, Issue 20 https://doi.org/10.1103/PhysRevB.85.205211	journal	May 2012
Interaction of Oxygen with Conjugated Polymers: Charge Transfer Complex Formation with Poly(3-alkylthiophenes) Abdou, Mohamed S. A.; Orfino, Francesco P.; Son, Yongkeun Journal of the American Chemical Society, Vol. 119, Issue 19 https://doi.org/10.1021/ja964229j	journal	May 1997
Degradation and stability of polymer-based solar cells Lee, Jea Uk; Jung, Jae Woong; Jo, Jea Woong Journal of Materials Chemistry, Vol. 22, Issue 46 https://doi.org/10.1039/c2jm33645f	journal	January 2012
Mechanisms of photodegradation of poly(3-alkylthiophenes) in solution Abdou, Mohamed S. A.; Holdcroft, Steven Macromolecules, Vol. 26, Issue 11 https://doi.org/10.1021/ma00063a047	journal	May 1993
Reversible and Irreversible Light-Induced p-Doping of P3HT by Oxygen Studied by Photoelectron Spectroscopy (XPS/UPS) Hintz, H.; Peisert, H.; Egelhaaf, H. -J. The Journal of Physical Chemistry C, Vol. 115, Issue 27 https://doi.org/10.1021/jp2032737	journal	June 2011
Kinetics of elementary reactions in low-temperature autoignition chemistry Zádor, Judit; Taatjes, Craig A.; Fernandes, Ravi X. Progress in Energy and Combustion Science, Vol. 37, Issue 4 https://doi.org/10.1016/j.pecs.2010.06.006	journal	August 2011
Mechanisms for the Reaction of Thiophene and Methylthiophene with Singlet and Triplet Molecular Oxygen Song, Xinli; Fanelli, Matthew G.; Cook, Justin M. The Journal of Physical Chemistry A, Vol. 116, Issue 20 https://doi.org/10.1021/jp301919g	journal	May 2012
A dimer method for finding saddle points on high dimensional potential surfaces using only first derivatives Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 111, Issue 15 https://doi.org/10.1063/1.480097	journal	October 1999
High Efficiency Polymer Solar Cells with Long Operating Lifetimes Peters, Craig H.; Sachs-Quintana, I. T.; Kastrop, John P. Advanced Energy Materials, Vol. 1, Issue 4 https://doi.org/10.1002/aenm.201100138	journal	April 2011
A climbing image nudged elastic band method for finding saddle points and minimum energy paths Henkelman, Graeme; Uberuaga, Blas P.; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22, p. 9901-9904 https://doi.org/10.1063/1.1329672	journal	December 2000
Continuous surface charge polarizable continuum models of solvation. I. General formalism Scalmani, Giovanni; Frisch, Michael J. The Journal of Chemical Physics, Vol. 132, Issue 11 https://doi.org/10.1063/1.3359469	journal	March 2010
Investigation of the degradation mechanisms of a variety of organic photovoltaic devices by combination of imaging techniques—the ISOS-3 inter-laboratory collaboration Rösch, Roland; Tanenbaum, David M.; Jørgensen, Mikkel Energy & Environmental Science, Vol. 5, Issue 4 https://doi.org/10.1039/c2ee03508a	journal	January 2012
Reversible and Irreversible Interactions of Poly(3-hexylthiophene) with Oxygen Studied by Spin-Sensitive Methods Sperlich, Andreas; Kraus, Hannes; Deibel, Carsten The Journal of Physical Chemistry B, Vol. 115, Issue 46 https://doi.org/10.1021/jp2077215	journal	November 2011
Insights into Current Limitations of Density Functional Theory Cohen, A. J.; Mori-Sanchez, P.; Yang, W. Science, Vol. 321, Issue 5890 https://doi.org/10.1126/science.1158722	journal	August 2008
Degradation mechanisms in organic photovoltaic devices Grossiord, Nadia; Kroon, Jan M.; Andriessen, Ronn Organic Electronics, Vol. 13, Issue 3 https://doi.org/10.1016/j.orgel.2011.11.027	journal	March 2012
Impact of UV-Visible Light on the Morphological and Photochemical Behavior of a Low-Bandgap Poly(2,7-Carbazole) Derivative for Use in High-Performance Solar Cells Tournebize, Aurélien; Bussière, Pierre-Olivier; Wong-Wah-Chung, Pascal Advanced Energy Materials, Vol. 3, Issue 4 https://doi.org/10.1002/aenm.201200662	journal	November 2012
Effect of the damping function in dispersion corrected density functional theory Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars Journal of Computational Chemistry, Vol. 32, Issue 7 https://doi.org/10.1002/jcc.21759	journal	March 2011
Dimethyl Sulfide and Dimethyl Sulfoxide and Their Oxidation in the Atmosphere Barnes, Ian; Hjorth, Jens; Mihalopoulos, Nikos Chemical Reviews, Vol. 106, Issue 3 https://doi.org/10.1021/cr020529+	journal	February 2006
Solid-state photochemistry of π-conjugated poly(3-alkylthiophenes) Abdou, Mohamed S. A.; Holdcroft, Steven Canadian Journal of Chemistry, Vol. 73, Issue 11 https://doi.org/10.1139/v95-234	journal	November 1995
The mechanism of photo- and thermooxidation of poly(3-hexylthiophene) (P3HT) reconsidered Manceau, Matthieu; Rivaton, Agnès; Gardette, Jean-Luc Polymer Degradation and Stability, Vol. 94, Issue 6 https://doi.org/10.1016/j.polymdegradstab.2009.03.005	journal	June 2009
Photoinduced Degradation of Polymer and Polymer-Fullerene Active Layers: Experiment and Theory Reese, Matthew O.; Nardes, Alexandre M.; Rupert, Benjamin L. Advanced Functional Materials, Vol. 20, Issue 20 https://doi.org/10.1002/adfm.201001079	journal	August 2010
Challenges for Density Functional Theory Cohen, Aron J.; Mori-Sánchez, Paula; Yang, Weitao Chemical Reviews, Vol. 112, Issue 1 https://doi.org/10.1021/cr200107z	journal	December 2011
Degradation Patterns in Water and Oxygen of an Inverted Polymer Solar Cell Norrman, Kion; Madsen, Morten V.; Gevorgyan, Suren A. Journal of the American Chemical Society, Vol. 132, Issue 47 https://doi.org/10.1021/ja106299g	journal	December 2010
New Insights into the Mechanisms of Photodegradation/Stabilization of P3HT:PCBM Active Layers Using Poly(3-hexyl- d ₁₃ -Thiophene) Tournebize, Aurélien; Bussière, Pierre-Olivier; Rivaton, Agnès Chemistry of Materials, Vol. 25, Issue 22 https://doi.org/10.1021/cm402193y	journal	November 2013
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Involvement of Singlet Oxygen in the Solid-State Photochemistry of P3HT Manceau, Matthieu; Rivaton, Agnès; Gardette, Jean-Luc Macromolecular Rapid Communications, Vol. 29, Issue 22 https://doi.org/10.1002/marc.200800421	journal	November 2008
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
Photodegradation of P3HT−A Systematic Study of Environmental Factors Hintz, Holger; Egelhaaf, H. -J.; Lüer, Larry Chemistry of Materials, Vol. 23, Issue 2 https://doi.org/10.1021/cm102373k	journal	January 2011
Pathways for the degradation of organic photovoltaic P3HT:PCBM based devices Reese, Matthew O.; Morfa, Anthony J.; White, Matthew S. Solar Energy Materials and Solar Cells, Vol. 92, Issue 7 https://doi.org/10.1016/j.solmat.2008.01.020	journal	July 2008
Stability and Degradation of Organic and Polymer Solar Cells Krebs, Frederik C. John Wiley & Sons, Ltd https://doi.org/10.1002/9781119942436	book	April 2012
Ordered Stacking of Regioregular Head-to-Tail Polyalkylthiophenes: Insights from the Crystal Structure of Form I′ Poly(3-n-butylthiophene) Arosio, Paolo; Moreno, Margherita; Famulari, Antonino Chemistry of Materials, Vol. 21, Issue 1, p. 78-87 https://doi.org/10.1021/cm802168e	journal	January 2009
Stability/degradation of polymer solar cells Jørgensen, Mikkel; Norrman, Kion; Krebs, Frederik C. Solar Energy Materials and Solar Cells, Vol. 92, Issue 7, p. 686-714 https://doi.org/10.1016/j.solmat.2008.01.005	journal	July 2008
Reversible and irreversible degradation of organic solar cell performance by oxygen Seemann, Andrea; Sauermann, Tobias; Lungenschmied, Christoph Solar Energy, Vol. 85, Issue 6 https://doi.org/10.1016/j.solener.2010.09.007	journal	June 2011
Rationale for mixing exact exchange with density functional approximations Perdew, John P.; Ernzerhof, Matthias; Burke, Kieron The Journal of Chemical Physics, Vol. 105, Issue 22, p. 9982-9985 https://doi.org/10.1063/1.472933	journal	December 1996
The Role of Electron Affinity in Determining Whether Fullerenes Catalyze or Inhibit Photooxidation of Polymers for Solar Cells Hoke, Eric T.; Sachs-Quintana, I. T.; Lloyd, Matthew T. Advanced Energy Materials, Vol. 2, Issue 11 https://doi.org/10.1002/aenm.201200169	journal	May 2012
Importance of short-range versus long-range Hartree-Fock exchange for the performance of hybrid density functionals Vydrov, Oleg A.; Heyd, Jochen; Krukau, Aliaksandr V. The Journal of Chemical Physics, Vol. 125, Issue 7 https://doi.org/10.1063/1.2244560	journal	August 2006

Similar Records

First Principles Study of Photo-oxidation Degradation Mechanisms in P3HT for Organic Solar Cells

Journal Article · Wed Jan 01 00:00:00 EST 2014 · Phys. Chem. Chem. Phys. · OSTI ID:1383401

Sai, Na; Leung, Kevin; Zador, Judit; +1 more

Enhanced performance of P3HT/(PCBM:ZnO:TiO{sub 2}) blend based hybrid organic solar cells

Journal Article · Tue Mar 15 00:00:00 EDT 2016 · Materials Research Bulletin · OSTI ID:1383401

Murray, R.; Imran, M.; Ali, S.; +1 more

Optimalization activity of ZnO NR/TiO2 NR-P3HT as an active layer based on hybrid bulk heterojunction on dye sensitized solar cell (DSSC)

Journal Article · Tue Apr 19 00:00:00 EDT 2016 · AIP Conference Proceedings · OSTI ID:1383401

Ramelan, Ari Handono; Hanif, Qonita Awliya; Hasanah, Yesi Ihdina Fityatal; +2 more

Related Subjects

solar (photovoltaic)
phonons
energy storage (including batteries and capacitors)
defects
charge transport
materials and chemistry by design
synthesis (novel materials)
synthesis (self-assembly)

Title: First principles study of photo-oxidation degradation mechanisms in P3HT for organic solar cells

Citation Formats

References (47)

Similar Records

Related Subjects