Increased Exciton Dipole Moment Translates into Charge-Transfer Excitons in Thiophene-Fluorinated Low-Bandgap Polymers for Organic Photovoltaic Applications

Collado-Fregoso, Elisa; Boufflet, Pierre; Fei, Zhuping; Gann, Eliot; Ashraf, Shahid; Li, Zhe; McNeill, Christopher R.; Durrant, James R.; Heeney, Martin

doi:10.1021/acs.chemmater.5b02948

Title: Increased Exciton Dipole Moment Translates into Charge-Transfer Excitons in Thiophene-Fluorinated Low-Bandgap Polymers for Organic Photovoltaic Applications

Journal Article · Mon Nov 23 00:00:00 EST 2015 · Chemistry of Materials

DOI:https://doi.org/10.1021/acs.chemmater.5b02948· OSTI ID:1234034

Collado-Fregoso, Elisa ^[1]; Boufflet, Pierre ^[1]; Fei, Zhuping ^[1]; Gann, Eliot ^[2]; Ashraf, Shahid ^[1]; Li, Zhe ^[3]; McNeill, Christopher R. ^[4]; Durrant, James R. ^[3]; Heeney, Martin ^[1]

Centre for Plastic Electronics, Department of Chemistry, Imperial College London, Exhibition Road, London SW7 2AZ, United Kingdom
Australian Synchrotron, 800 Blackburn Road, Clayton, Victoria 3169, Australia, Materials Science and Engineering, Monash University, Wellington Road, Clayton, Victoria 3800, Australia
Centre for Plastic Electronics, Department of Chemistry, Imperial College London, Exhibition Road, London SW7 2AZ, United Kingdom, SPECIFIC IKC, College of Engineering, Swansea University, Central Avenue, Baglan, Port Talbot SA12 7AX, United Kingdom
Materials Science and Engineering, Monash University, Wellington Road, Clayton, Victoria 3800, Australia

View Journal Article

Cite

Export

Save

Sponsoring Organization:: USDOE

OSTI ID:: 1234034

Journal Information:: Chemistry of Materials, Journal Name: Chemistry of Materials Vol. 27 Journal Issue: 23; ISSN 0897-4756

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 39 works

Citation information provided by
Web of Science

References (59)

Optical Oxygen Pressure Sensing Based on Triplet–Triplet Quenching of Fullerene–Polystyrene Film Using Laser Flash Photolysis: Soccerballene C ₆₀ Versus Rugbyballene C ₇₀ Amao, Yutaka; Asai, Keisuke; Okura, Ichiro Bulletin of the Chemical Society of Japan, Vol. 72, Issue 10 https://doi.org/10.1246/bcsj.72.2223	journal	October 1999
Highly Efficient 2D-Conjugated Benzodithiophene-Based Photovoltaic Polymer with Linear Alkylthio Side Chain Ye, Long; Zhang, Shaoqing; Zhao, Wenchao Chemistry of Materials, Vol. 26, Issue 12 https://doi.org/10.1021/cm501513n	journal	June 2014
Crystallization-Induced 10-nm Structure Formation in P3HT/PCBM Blends Kohn, Peter; Rong, Zhuxia; Scherer, Kai H. Macromolecules, Vol. 46, Issue 10 https://doi.org/10.1021/ma400403c	journal	April 2013
Charge Carrier Formation in Polythiophene/Fullerene Blend Films Studied by Transient Absorption Spectroscopy Ohkita, Hideo; Cook, Steffan; Astuti, Yeni Journal of the American Chemical Society, Vol. 130, Issue 10 https://doi.org/10.1021/ja076568q	journal	March 2008
Single-Junction Polymer Solar Cells with Over 10% Efficiency by a Novel Two-Dimensional Donor–Acceptor Conjugated Copolymer Liu, Chang; Yi, Chao; Wang, Kai ACS Applied Materials & Interfaces, Vol. 7, Issue 8 https://doi.org/10.1021/am509047g	journal	February 2015
Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions Jackson, Nicholas E.; Savoie, Brett M.; Kohlstedt, Kevin L. Journal of the American Chemical Society, Vol. 135, Issue 28 https://doi.org/10.1021/ja403667s	journal	May 2013
Efficiency limitations in a low band-gap diketopyrrolopyrrole-based polymer solar cell Albert-Seifried, Sebastian; Ko, Doo-Hyun; Hüttner, Sven Phys. Chem. Chem. Phys., Vol. 16, Issue 14 https://doi.org/10.1039/c4cp00485j	journal	January 2014
Fluorine Substituents Reduce Charge Recombination and Drive Structure and Morphology Development in Polymer Solar Cells Stuart, Andrew C.; Tumbleston, John R.; Zhou, Huaxing Journal of the American Chemical Society, Vol. 135, Issue 5 https://doi.org/10.1021/ja309289u	journal	January 2013
Synthesis, Characterization, and Transistor and Solar Cell Applications of a Naphthobisthiadiazole-Based Semiconducting Polymer Osaka, Itaru; Shimawaki, Masafumi; Mori, Hiroki Journal of the American Chemical Society, Vol. 134, Issue 11 https://doi.org/10.1021/ja3015346	journal	March 2012
Charge Photogeneration in Low Band Gap Polyselenophene/Fullerene Blend Films Clarke, Tracey M.; Ballantyne, Amy M.; Tierney, Steve The Journal of Physical Chemistry C, Vol. 114, Issue 17 https://doi.org/10.1021/jp9120782	journal	April 2010
Soft x-ray scattering facility at the Advanced Light Source with real-time data processing and analysis Gann, E.; Young, A. T.; Collins, B. A. Review of Scientific Instruments, Vol. 83, Issue 4 https://doi.org/10.1063/1.3701831	journal	April 2012
Exciton diffusion length in narrow bandgap polymers Mikhnenko, Oleksandr V.; Azimi, Hamed; Scharber, Markus Energy & Environmental Science, Vol. 5, Issue 5 https://doi.org/10.1039/c2ee03466b	journal	January 2012
Charge Recombination in Conjugated Polymer/Fullerene Blended Films Studied by Transient Absorption Spectroscopy Nogueira, Ana F.; Montanari, Ivan; Nelson, Jenny The Journal of Physical Chemistry B, Vol. 107, Issue 7 https://doi.org/10.1021/jp027101z	journal	February 2003
Determining the Exciton Diffusion Length in a Polyfluorene from Ultrafast Fluorescence Measurements of Polymer/Fullerene Blend Films Bruno, A.; Reynolds, L. X.; Dyer-Smith, C. The Journal of Physical Chemistry C, Vol. 117, Issue 39 https://doi.org/10.1021/jp404985q	journal	September 2013
A low-background-intensity focusing small-angle X-ray scattering undulator beamline Kirby, Nigel M.; Mudie, Stephen T.; Hawley, Adrian M. Journal of Applied Crystallography, Vol. 46, Issue 6 https://doi.org/10.1107/S002188981302774X	journal	November 2013
Diffusion-limited recombination in polymer-fullerene blends and its influence on photocurrent collection Nelson, Jenny Physical Review B, Vol. 67, Issue 15 https://doi.org/10.1103/PhysRevB.67.155209	journal	April 2003
Photophysical properties of novel water soluble fullerene derivatives Foley, Sarah; Bosi, Susanna; Larroque, Christain Chemical Physics Letters, Vol. 350, Issue 3-4 https://doi.org/10.1016/S0009-2614(01)01285-4	journal	December 2001
Silaindacenodithiophene-Based Low Band Gap Polymers - The Effect of Fluorine Substitution on Device Performances and Film Morphologies Schroeder, Bob C.; Huang, Zhenggang; Ashraf, Raja Shahid Advanced Functional Materials, Vol. 22, Issue 8 https://doi.org/10.1002/adfm.201102941	journal	February 2012
Fluorinated conjugated polymers in organic bulk heterojunction photovoltaic solar cells Meyer, Franck Progress in Polymer Science, Vol. 47 https://doi.org/10.1016/j.progpolymsci.2015.04.007	journal	August 2015
Ultrafast relaxation of charge-transfer excitons in low-bandgap conjugated copolymers Hwang, Inchan; Beaupré, Serge; Leclerc, Mario Chemical Science, Vol. 3, Issue 7 https://doi.org/10.1039/c2sc20078c	journal	January 2012
The influence of molecular orientation on organic bulk heterojunction solar cells Tumbleston, John R.; Collins, Brian A.; Yang, Liqiang Nature Photonics, Vol. 8, Issue 5 https://doi.org/10.1038/nphoton.2014.55	journal	April 2014
Semi-crystalline photovoltaic polymers with efficiency exceeding 9% in a ∼300 nm thick conventional single-cell device Nguyen, T. L.; Choi, H.; Ko, S. -J. Energy Environ. Sci., Vol. 7, Issue 9 https://doi.org/10.1039/C4EE01529K	journal	January 2014
Fluorine Substituted Conjugated Polymer of Medium Band Gap Yields 7% Efficiency in Polymer−Fullerene Solar Cells Price, Samuel C.; Stuart, Andrew C.; Yang, Liqiang Journal of the American Chemical Society, Vol. 133, Issue 12 https://doi.org/10.1021/ja1112595	journal	March 2011
Transient Absorption Studies of Bimolecular Recombination Dynamics in Polythiophene/Fullerene Blend Films Clarke, Tracey M.; Jamieson, Fiona C.; Durrant, James R. The Journal of Physical Chemistry C, Vol. 113, Issue 49 https://doi.org/10.1021/jp909442s	journal	August 2009
Accurate description of torsion potentials in conjugated polymers using density functionals with reduced self-interaction error Sutton, Christopher; Körzdörfer, Thomas; Gray, Matthew T. The Journal of Chemical Physics, Vol. 140, Issue 5 https://doi.org/10.1063/1.4863218	journal	February 2014
Material Crystallinity as a Determinant of Triplet Dynamics and Oxygen Quenching in Donor Polymers for Organic Photovoltaic Devices Soon, Ying W.; Shoaee, Safa; Ashraf, Raja Shahid Advanced Functional Materials, Vol. 24, Issue 10 https://doi.org/10.1002/adfm.201302612	journal	October 2013
Synthesis of Fluorinated Polythienothiophene- co -benzodithiophenes and Effect of Fluorination on the Photovoltaic Properties Son, Hae Jung; Wang, Wei; Xu, Tao Journal of the American Chemical Society, Vol. 133, Issue 6 https://doi.org/10.1021/ja108601g	journal	February 2011
Small Bandgap Polymers for Organic Solar Cells (Polymer Material Development in the Last 5 Years) Kroon, Renee; Lenes, Martijn; Hummelen, Jan C. Polymer Reviews, Vol. 48, Issue 3 https://doi.org/10.1080/15583720802231833	journal	August 2008
Polaron pair mediated triplet generation in polymer/fullerene blends Dimitrov, Stoichko D.; Wheeler, Scot; Niedzialek, Dorota Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms7501	journal	March 2015
Mobility-Controlled Performance of Thick Solar Cells Based on Fluorinated Copolymers Li, Wentao; Albrecht, Steve; Yang, Liqiang Journal of the American Chemical Society, Vol. 136, Issue 44 https://doi.org/10.1021/ja5067724	journal	October 2014
Electron Transfer Dynamics in Dye-Sensitized Solar Cells Listorti, Andrea; O’Regan, Brian; Durrant, James R. Chemistry of Materials, Vol. 23, Issue 15 https://doi.org/10.1021/cm200651e	journal	August 2011
Thieno[3,4- b ]thiophene Acceptors with Alkyl, Aryl, Perfluoroalkyl, and Perfluorophenyl Pendants for Donor–Acceptor Low Bandgap Polymers Homyak, Patrick D.; Tinkham, Jonathan; Lahti, Paul M. Macromolecules, Vol. 46, Issue 22 https://doi.org/10.1021/ma4019476	journal	November 2013
Fine-Tuning of Fluorinated Thieno[3,4-b]thiophene Copolymer for Efficient Polymer Solar Cells Wang, Hangxing; Yu, Xinfei; Yi, Chao The Journal of Physical Chemistry C, Vol. 117, Issue 9 https://doi.org/10.1021/jp311031s	journal	February 2013
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes Fei, Zhuping; Boufflet, Pierre; Wood, Sebastian Journal of the American Chemical Society, Vol. 137, Issue 21 https://doi.org/10.1021/jacs.5b02785	journal	May 2015
Effect of Fluorination of 2,1,3-Benzothiadiazole Nielsen, Christian B.; White, Andrew J. P.; McCulloch, Iain The Journal of Organic Chemistry, Vol. 80, Issue 10 https://doi.org/10.1021/acs.joc.5b00430	journal	May 2015
Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells Liu, Yuhang; Zhao, Jingbo; Li, Zhengke Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6293	journal	November 2014
Effect of Pendant Functionality in Thieno[3,4- b ]thiophene- alt -benzodithiophene Polymers for OPVs Homyak, Patrick; Liu, Yao; Ferdous, Sunzida Chemistry of Materials, Vol. 27, Issue 2 https://doi.org/10.1021/cm503334h	journal	January 2015
Polymer:fullerene solar cells: materials, processing issues, and cell layouts to reach power conversion efficiency over 10%, a review Etxebarria, Ikerne; Ajuria, Jon; Pacios, Roberto Journal of Photonics for Energy, Vol. 5, Issue 1 https://doi.org/10.1117/1.JPE.5.057214	journal	January 2015
Ultrafast Exciton Dissociation Followed by Nongeminate Charge Recombination in PCDTBT:PCBM Photovoltaic Blends Etzold, Fabian; Howard, Ian A.; Mauer, Ralf Journal of the American Chemical Society, Vol. 133, Issue 24 https://doi.org/10.1021/ja201837e	journal	June 2011
Disentangling the impact of side chains and fluorine substituents of conjugated donor polymers on the performance of photovoltaic blends Yang, Liqiang; Tumbleston, John R.; Zhou, Huaxing Energy Environ. Sci., Vol. 6, Issue 1 https://doi.org/10.1039/C2EE23235A	journal	January 2013
Influence of Fluorination and Molecular Weight on the Morphology and Performance of PTB7:PC ₇₁ BM Solar Cells He, Xiaoxi; Mukherjee, Subhrangsu; Watkins, Scott The Journal of Physical Chemistry C, Vol. 118, Issue 19 https://doi.org/10.1021/jp501222w	journal	May 2014
Fluorination of Polythiophene Derivatives for High Performance Organic Photovoltaics Jo, Jea Woong; Jung, Jae Woong; Wang, Hsin-Wei Chemistry of Materials, Vol. 26, Issue 14 https://doi.org/10.1021/cm502229k	journal	July 2014
Quinoxaline-Based Semiconducting Polymers: Effect of Fluorination on the Photophysical, Thermal, and Charge Transport Properties Iyer, Akila; Bjorgaard, Josiah; Anderson, Trent Macromolecules, Vol. 45, Issue 16 https://doi.org/10.1021/ma3009788	journal	July 2012
Fluorinated Copolymer PCPDTBT with Enhanced Open-Circuit Voltage and Reduced Recombination for Highly Efficient Polymer Solar Cells Albrecht, Steve; Janietz, Silvia; Schindler, Wolfram Journal of the American Chemical Society, Vol. 134, Issue 36 https://doi.org/10.1021/ja305039j	journal	August 2012
Charge Photogeneration for a Series of Thiazolo-Thiazole Donor Polymers Blended with the Fullerene Electron Acceptors PCBM and ICBA Shoaee, Safa; Subramaniyan, Selvam; Xin, Hao Advanced Functional Materials, Vol. 23, Issue 26 https://doi.org/10.1002/adfm.201203148	journal	February 2013
Absolute Measurement of Domain Composition and Nanoscale Size Distribution Explains Performance in PTB7:PC ₇₁ BM Solar Cells Collins, Brian A.; Li, Zhe; Tumbleston, John R. Advanced Energy Materials, Vol. 3, Issue 1 https://doi.org/10.1002/aenm.201200377	journal	October 2012
Mediating Solar Cell Performance by Controlling the Internal Dipole Change in Organic Photovoltaic Polymers Carsten, Bridget; Szarko, Jodi M.; Lu, Luyao Macromolecules, Vol. 45, Issue 16 https://doi.org/10.1021/ma3011119	journal	July 2012
Hot exciton dissociation in polymer solar cells Grancini, G.; Maiuri, M.; Fazzi, D. Nature Materials, Vol. 12, Issue 1 https://doi.org/10.1038/nmat3502	journal	December 2012
Estimate of singlet diffusion lengths in PCBM films by time-resolved emission studies Cook, Steffan; Furube, Akihiro; Katoh, Ryuzi Chemical Physics Letters, Vol. 478, Issue 1-3 https://doi.org/10.1016/j.cplett.2009.06.091	journal	August 2009
Role of Interfacial Charge Transfer State in Charge Generation and Recombination in Low-Bandgap Polymer Solar Cell Yamamoto, Shunsuke; Ohkita, Hideo; Benten, Hiroaki The Journal of Physical Chemistry C, Vol. 116, Issue 28 https://doi.org/10.1021/jp303284r	journal	July 2012
Tuning the Polarizability in Donor Polymers with a Thiophenesaccharin Unit for Organic Photovoltaic Applications Xu, Tao; Lu, Luyao; Zheng, Tianyue Advanced Functional Materials, Vol. 24, Issue 22 https://doi.org/10.1002/adfm.201303688	journal	February 2014
Thiophene fluorination to enhance photovoltaic performance in low band gap donor–acceptor polymers Fei, Zhuping; Shahid, Munazza; Yaacobi-Gross, Nir Chemical Communications, Vol. 48, Issue 90 https://doi.org/10.1039/c2cc35079c	journal	January 2012
Charge transfer relaxation in donor–acceptor type conjugated materials Scarongella, Mariateresa; Laktionov, Andrey; Rothlisberger, Ursula Journal of Materials Chemistry C, Vol. 1, Issue 12 https://doi.org/10.1039/c3tc00829k	journal	January 2013
Fullerenecrystallisation as a key driver of charge separation in polymer/fullerene bulk heterojunction solar cells Jamieson, Fiona C.; Domingo, Ester Buchaca; McCarthy-Ward, Thomas Chem. Sci., Vol. 3, Issue 2, p. 485-492 https://doi.org/10.1039/C1SC00674F	journal	January 2012
Examining the Effect of the Dipole Moment on Charge Separation in Donor–Acceptor Polymers for Organic Photovoltaic Applications Carsten, Bridget; Szarko, Jodi M.; Son, Hae Jung Journal of the American Chemical Society, Vol. 133, Issue 50 https://doi.org/10.1021/ja208642b	journal	December 2011
Ultrafast Intramolecular Exciton Splitting Dynamics in Isolated Low-Band-Gap Polymers and Their Implications in Photovoltaic Materials Design Rolczynski, Brian S.; Szarko, Jodi M.; Son, Hae Jung Journal of the American Chemical Society, Vol. 134, Issue 9 https://doi.org/10.1021/ja209003y	journal	February 2012
Towards optimisation of photocurrent from fullerene excitons in organic solar cells Dimitrov, Stoichko D.; Huang, Zhenggang; Deledalle, Florent Energy & Environmental Science, Vol. 7, Issue 3 https://doi.org/10.1039/c3ee42607f	journal	January 2014
Effect of Fluorination on the Properties of a Donor–Acceptor Copolymer for Use in Photovoltaic Cells and Transistors Bronstein, Hugo; Frost, Jarvist M.; Hadipour, Afshin Chemistry of Materials, Vol. 25, Issue 3 https://doi.org/10.1021/cm301910t	journal	January 2013

Similar Records

Examining the Effect of the Dipole Moment on Charge Delocalization in Donor-Acceptor Polymers for Organic Photovoltaic Applications

Journal Article · Sat Jan 01 00:00:00 EST 2011 · Journal of the American Chemical Society · OSTI ID:1234034

Carsten, B.; Szarko, J. M.; Son, H. J.; +6 more

Examining the Effect of the Dipole Moment on Charge Separation in Donor–Acceptor Polymers for Organic Photovoltaic Applications

Journal Article · Wed Dec 21 00:00:00 EST 2011 · Journal of the American Chemical Society · OSTI ID:1234034

Carsten, Bridget; Szarko, Jodi M.; Son, Hae Jung; +7 more

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

Journal Article · Tue Oct 13 00:00:00 EDT 2015 · Macromolecules · OSTI ID:1234034

Homyak, Patrick; Liu, Yao; Liu, Feng; +2 more

Title: Increased Exciton Dipole Moment Translates into Charge-Transfer Excitons in Thiophene-Fluorinated Low-Bandgap Polymers for Organic Photovoltaic Applications

Citation Formats

References (59)

Similar Records

Related Subjects