A "roller-wheel" Pt-containing small molecule that outperforms its polymer analogs in organic solar cells
Abstract
A novel Pt-bisacetylide small molecule (Pt-SM) featuring “roller-wheel” geometry was synthesized and characterized. When compared with conventional Pt-containing polymers and small molecules having “dumbbell” shaped structures, Pt-SM displays enhanced crystallinity and intermolecular π–π interactions, as well as favorable panchromatic absorption behaviors. Furthermore, organic solar cells (OSCs) employing Pt-SM achieve power conversion efficiencies (PCEs) up to 5.9%, the highest reported so far for Pt-containing polymers and small molecules.
- Authors:
-
- Univ. of New Mexico, Albuquerque, NM (United States)
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Kansas State Univ., Manhattan, KS (United States)
- Publication Date:
- Research Org.:
- Brookhaven National Laboratory (BNL), Upton, NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1255729
- Report Number(s):
- BNL-112247-2016-JA
Journal ID: ISSN 2041-6520; CSHCBM
- Grant/Contract Number:
- SC0012704
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemical Science
- Additional Journal Information:
- Journal Name: Chemical Science; Journal ID: ISSN 2041-6520
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
He, Wenhan, Wu, Qin, Livshits, Maksim Y., Dickie, Diane A., Yang, Jianzhong, Quinnett, Rachel, Rack, Jeffrey R., and Qin, Yang. A "roller-wheel" Pt-containing small molecule that outperforms its polymer analogs in organic solar cells. United States: N. p., 2016.
Web. doi:10.1039/C6SC00513F.
He, Wenhan, Wu, Qin, Livshits, Maksim Y., Dickie, Diane A., Yang, Jianzhong, Quinnett, Rachel, Rack, Jeffrey R., & Qin, Yang. A "roller-wheel" Pt-containing small molecule that outperforms its polymer analogs in organic solar cells. United States. https://doi.org/10.1039/C6SC00513F
He, Wenhan, Wu, Qin, Livshits, Maksim Y., Dickie, Diane A., Yang, Jianzhong, Quinnett, Rachel, Rack, Jeffrey R., and Qin, Yang. Mon .
"A "roller-wheel" Pt-containing small molecule that outperforms its polymer analogs in organic solar cells". United States. https://doi.org/10.1039/C6SC00513F. https://www.osti.gov/servlets/purl/1255729.
@article{osti_1255729,
title = {A "roller-wheel" Pt-containing small molecule that outperforms its polymer analogs in organic solar cells},
author = {He, Wenhan and Wu, Qin and Livshits, Maksim Y. and Dickie, Diane A. and Yang, Jianzhong and Quinnett, Rachel and Rack, Jeffrey R. and Qin, Yang},
abstractNote = {A novel Pt-bisacetylide small molecule (Pt-SM) featuring “roller-wheel” geometry was synthesized and characterized. When compared with conventional Pt-containing polymers and small molecules having “dumbbell” shaped structures, Pt-SM displays enhanced crystallinity and intermolecular π–π interactions, as well as favorable panchromatic absorption behaviors. Furthermore, organic solar cells (OSCs) employing Pt-SM achieve power conversion efficiencies (PCEs) up to 5.9%, the highest reported so far for Pt-containing polymers and small molecules.},
doi = {10.1039/C6SC00513F},
journal = {Chemical Science},
number = ,
volume = ,
place = {United States},
year = {Mon May 23 00:00:00 EDT 2016},
month = {Mon May 23 00:00:00 EDT 2016}
}
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Cited by: 19 works
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Figures / Tables:
Scheme 1.: Structures of Pt-Bisacetylide Materials.
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Works referenced in this record:
Tuning the Absorption, Charge Transport Properties, and Solar Cell Efficiency with the Number of Thienyl Rings in Platinum-Containing Poly(aryleneethynylene)s
journal, November 2007
- Wong, Wai-Yeung; Wang, Xing-Zhu; He, Ze
- Journal of the American Chemical Society, Vol. 129, Issue 46
Low-Band-Gap Platinum Acetylide Polymers as Active Materials for Organic Solar Cells
journal, January 2009
- Mei, Jianguo; Ogawa, Katsu; Kim, Young-Gi
- ACS Applied Materials & Interfaces, Vol. 1, Issue 1
Synthesis and Photovoltaic Properties of New Metalloporphyrin-Containing Polyplatinyne Polymers
journal, July 2011
- Zhan, Hongmei; Lamare, Simon; Ng, Annie
- Macromolecules, Vol. 44, Issue 13
Small Molecule Solution-Processed Bulk Heterojunction Solar Cells †
journal, February 2011
- Walker, Bright; Kim, Chunki; Nguyen, Thuc-Quyen
- Chemistry of Materials, Vol. 23, Issue 3
Interface investigation and engineering – achieving high performance polymer photovoltaic devices
journal, January 2010
- Chen, Li-Min; Xu, Zheng; Hong, Ziruo
- Journal of Materials Chemistry, Vol. 20, Issue 13, p. 2575-2598
What controls triplet exciton transfer in organic semiconductors?
journal, January 2011
- Köhler, Anna; Bässler, Heinz
- J. Mater. Chem., Vol. 21, Issue 12
Replacing Alkoxy Groups with Alkylthienyl Groups: A Feasible Approach To Improve the Properties of Photovoltaic Polymers
journal, August 2011
- Huo, Lijun; Zhang, Shaoqing; Guo, Xia
- Angewandte Chemie International Edition, Vol. 50, Issue 41
Platinum-segmented polydiacetylenes
journal, June 2014
- Hu, Keda; Pandres, Elena; Qin, Yang
- Journal of Polymer Science Part A: Polymer Chemistry, Vol. 52, Issue 18
Functionalized Acenes and Heteroacenes for Organic Electronics
journal, December 2006
- Anthony, John E.
- Chemical Reviews, Vol. 106, Issue 12
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals
journal, January 1985
- Hay, P. Jeffrey; Wadt, Willard R.
- The Journal of Chemical Physics, Vol. 82, Issue 1, p. 299-310
Conjugated Polymer–Small Molecule Alloy Leads to High Efficient Ternary Organic Solar Cells
journal, June 2015
- Zhang, Jianqi; Zhang, Yajie; Fang, Jin
- Journal of the American Chemical Society, Vol. 137, Issue 25
Organic Solar Cells Using a High-Molecular-Weight Benzodithiophene-Benzothiadiazole Copolymer with an Efficiency of 9.4%
journal, November 2014
- Subbiah, Jegadesan; Purushothaman, Balaji; Chen, Ming
- Advanced Materials, Vol. 27, Issue 4
Organometallic Photovoltaics: A New and Versatile Approach for Harvesting Solar Energy Using Conjugated Polymetallaynes
journal, September 2010
- Wong, Wai-Yeung; Ho, Cheuk-Lam
- Accounts of Chemical Research, Vol. 43, Issue 9
The Spectral Signatures of Frenkel Polarons in H- and J-Aggregates
journal, March 2010
- Spano, Frank C.
- Accounts of Chemical Research, Vol. 43, Issue 3
Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory
journal, July 1996
- Bauernschmitt, Rüdiger; Ahlrichs, Reinhart
- Chemical Physics Letters, Vol. 256, Issue 4-5
Polymer–Fullerene Composite Solar Cells
journal, January 2008
- Thompson, Barry C.; Fréchet, Jean M. J.
- Angewandte Chemie International Edition, Vol. 47, Issue 1, p. 58-77
Synthesis of Conjugated Polymers for Organic Solar Cell Applications
journal, November 2009
- Cheng, Yen-Ju; Yang, Sheng-Hsiung; Hsu, Chain-Shu
- Chemical Reviews, Vol. 109, Issue 11
Fulleropyrrolidine interlayers: Tailoring electrodes to raise organic solar cell efficiency
journal, September 2014
- Page, Zachariah A.; Liu, Yao; Duzhko, Volodimyr V.
- Science, Vol. 346, Issue 6208
Rational Design of High Performance Conjugated Polymers for Organic Solar Cells
journal, January 2012
- Zhou, Huaxing; Yang, Liqiang; You, Wei
- Macromolecules, Vol. 45, Issue 2
Triplet Excited State in Platinum−Acetylide Oligomers: Triplet Localization and Effects of Conformation
journal, February 2007
- Glusac, Ksenija; Köse, M. Erkan; Jiang, Hui
- The Journal of Physical Chemistry B, Vol. 111, Issue 5
Triplet energy transfer in conjugated polymers. III. An experimental assessment regarding the influence of disorder on polaronic transport
journal, April 2010
- Hoffmann, Sebastian T.; Scheler, Esther; Koenen, Jan-Moritz
- Physical Review B, Vol. 81, Issue 16
A fulleropyrrolidine end-capped platinum-acetylide triad: the mechanism of photoinduced charge transfer in organometallic photovoltaic cells
journal, January 2007
- Guo, Fengqi; Ogawa, Katsu; Kim, Young-Gi
- Physical Chemistry Chemical Physics, Vol. 9, Issue 21
Fluorine Substituted Conjugated Polymer of Medium Band Gap Yields 7% Efficiency in Polymer−Fullerene Solar Cells
journal, March 2011
- Price, Samuel C.; Stuart, Andrew C.; Yang, Liqiang
- Journal of the American Chemical Society, Vol. 133, Issue 12
Effect of Oligothienyl Chain Length on Tuning the Solar Cell Performance in Fluorene-Based Polyplatinynes
journal, September 2008
- Liu, Li; Ho, Cheuk-Lam; Wong, Wai-Yeung
- Advanced Functional Materials, Vol. 18, Issue 18
Conjugated Polymers Bearing Iridium Complexes for Triplet Photovoltaic Devices
journal, August 2008
- Schulz, Gisela L.; Holdcroft, Steven
- Chemistry of Materials, Vol. 20, Issue 16
Time-Dependent Density Functional Response Theory for Molecules
book, November 1995
- Casida, Mark E.
- Recent Advances in Density Functional Methods
Metallated conjugated polymers as a new avenue towards high-efficiency polymer solar cells
journal, May 2007
- Wong, Wai-Yeung; Wang, Xing-Zhu; He, Ze
- Nature Materials, Vol. 6, Issue 7
Platinum–acetylide polymer based solar cells: involvement of the triplet state for energy conversion
journal, January 2006
- Guo, Fengqi; Kim, Young-Gi; Reynolds, John R.
- Chem. Commun., Issue 17
Dramatic Enhancement of Power Conversion Efficiency in Polymer Solar Cells by Conjugating Very Low Ratio of Triplet Iridium Complexes to PTB7
journal, May 2015
- Qian, Min; Zhang, Ran; Hao, Jingyu
- Advanced Materials, Vol. 27, Issue 23
Quantum Mechanical Continuum Solvation Models
journal, August 2005
- Tomasi, Jacopo; Mennucci, Benedetta; Cammi, Roberto
- Chemical Reviews, Vol. 105, Issue 8
A polymer tandem solar cell with 10.6% power conversion efficiency
journal, February 2013
- You, Jingbi; Dou, Letian; Yoshimura, Ken
- Nature Communications, Vol. 4, Issue 1
Natural transition orbitals
journal, March 2003
- Martin, Richard L.
- The Journal of Chemical Physics, Vol. 118, Issue 11
Polymer Homo-Tandem Solar Cells with Best Efficiency of 11.3%
journal, January 2015
- Zhou, Huiqiong; Zhang, Yuan; Mai, Cheng-Kang
- Advanced Materials, Vol. 27, Issue 10
25th Anniversary Article: Rise to Power - OPV-Based Solar Parks
journal, October 2013
- Krebs, Frederik C.; Espinosa, Nieves; Hösel, Markus
- Advanced Materials, Vol. 26, Issue 1
H- and J-Aggregate Behavior in Polymeric Semiconductors
journal, April 2014
- Spano, Frank C.; Silva, Carlos
- Annual Review of Physical Chemistry, Vol. 65, Issue 1
Open-circuit voltage in organic solar cells
journal, January 2012
- Qi, Boyuan; Wang, Jizheng
- Journal of Materials Chemistry, Vol. 22, Issue 46
Functionalized Pentacene: Improved Electronic Properties from Control of Solid-State Order
journal, September 2001
- Anthony, John E.; Brooks, James S.; Eaton, David L.
- Journal of the American Chemical Society, Vol. 123, Issue 38
25th Anniversary Article: Bulk Heterojunction Solar Cells: Understanding the Mechanism of Operation
journal, December 2013
- Heeger, Alan J.
- Advanced Materials, Vol. 26, Issue 1
Efficient polymer solar cells employing a non-conjugated small-molecule electrolyte
journal, July 2015
- Ouyang, Xinhua; Peng, Ruixiang; Ai, Ling
- Nature Photonics, Vol. 9, Issue 8
Application of the energy gap law to the decay of charge transfer excited states, solvent effects
journal, September 1982
- Caspar, Jonathan V.; Sullivan, B. Patrick; Kober, Edward M.
- Chemical Physics Letters, Vol. 91, Issue 2
Triplet Energy Transport in Platinum-Acetylide Light Harvesting Arrays
journal, November 2014
- Chen, Zhuo; Hsu, Hsien-Yi; Arca, Mert
- The Journal of Physical Chemistry B, Vol. 119, Issue 24
Organometallic Donor−Acceptor Conjugated Polymer Semiconductors: Tunable Optical, Electrochemical, Charge Transport, and Photovoltaic Properties
journal, February 2009
- Wu, Pei-Tzu; Bull, Tricia; Kim, Felix S.
- Macromolecules, Vol. 42, Issue 3
Influence of blend microstructure on bulk heterojunction organic photovoltaic performance
journal, January 2011
- Brabec, Christoph J.; Heeney, Martin; McCulloch, Iain
- Chem. Soc. Rev., Vol. 40, Issue 3
Theory of space-charge-limited current enhanced by Frenkel effect
journal, February 1970
- Murgatroyd, P. N.
- Journal of Physics D: Applied Physics, Vol. 3, Issue 2
Failure of Time-Dependent Density Functional Theory for Long-Range Charge-Transfer Excited States: The Zincbacteriochlorin−Bacteriochlorin and Bacteriochlorophyll−Spheroidene Complexes
journal, March 2004
- Dreuw, Andreas; Head-Gordon, Martin
- Journal of the American Chemical Society, Vol. 126, Issue 12
Organic tandem solar cells: A review
journal, January 2009
- Ameri, Tayebeh; Dennler, Gilles; Lungenschmied, Christoph
- Energy & Environmental Science, Vol. 2, Issue 4
Finely Tuned Polymer Interlayers Enhance Solar Cell Efficiency
journal, July 2015
- Liu, Yao; Page, Zachariah A.; Russell, Thomas P.
- Angewandte Chemie International Edition, Vol. 54, Issue 39
Phenylene Vinylene Platinum(II) Acetylides with Prodigious Two-Photon Absorption
journal, November 2012
- Dubinina, Galyna G.; Price, Randi S.; Abboud, Khalil A.
- Journal of the American Chemical Society, Vol. 134, Issue 47
High Performance Amorphous Metallated π-Conjugated Polymers for Field-Effect Transistors and Polymer Solar Cells
journal, September 2008
- Baek, Nam Seob; Hau, Steven K.; Yip, Hin-Lap
- Chemistry of Materials, Vol. 20, Issue 18
Synthesis and photovoltaic properties of a low bandgap BODIPY–Pt conjugated polymer
journal, January 2014
- He, Wenhan; Jiang, Yingbing; Qin, Yang
- Polym. Chem., Vol. 5, Issue 4
Triplet energy transfer in conjugated polymers. I. Experimental investigation of a weakly disordered compound
journal, July 2008
- Sudha Devi, Lekshmi; Al-Suti, Mohammad K.; Dosche, Carsten
- Physical Review B, Vol. 78, Issue 4
Small-molecule solar cells with efficiency over 9%
journal, November 2014
- Zhang, Qian; Kan, Bin; Liu, Feng
- Nature Photonics, Vol. 9, Issue 1
Triplet energy transfer in conjugated polymers. II. A polaron theory description addressing the influence of disorder
journal, July 2008
- Fishchuk, Ivan I.; Kadashchuk, Andrey; Sudha Devi, Lekshmi
- Physical Review B, Vol. 78, Issue 4
A Selenium-Substituted Low-Bandgap Polymer with Versatile Photovoltaic Applications
journal, November 2012
- Dou, Letian; Chang, Wei-Hsuan; Gao, Jing
- Advanced Materials, Vol. 25, Issue 6
Triplet Exciton Diffusion in Platinum Polyyne Films
journal, October 2014
- Hsu, Hsien-Yi; Vella, Jarrett H.; Myers, Jason D.
- The Journal of Physical Chemistry C, Vol. 118, Issue 42
Solution-Processed Organic Solar Cells Based on Dialkylthiol-Substituted Benzodithiophene Unit with Efficiency near 10%
journal, October 2014
- Kan, Bin; Zhang, Qian; Li, Miaomiao
- Journal of the American Chemical Society, Vol. 136, Issue 44
A Series of Simple Oligomer-like Small Molecules Based on Oligothiophenes for Solution-Processed Solar Cells with High Efficiency
journal, March 2015
- Kan, Bin; Li, Miaomiao; Zhang, Qian
- Journal of the American Chemical Society, Vol. 137, Issue 11
Synthesis and Photovoltaic Effect in Dithieno[2,3- d :2′,3′- d ′]Benzo[1,2- b :4,5- b ′]dithiophene-Based Conjugated Polymers
journal, November 2012
- Son, Hae Jung; Lu, Luyao; Chen, Wei
- Advanced Materials, Vol. 25, Issue 6
Efficient Organic Heterojunction Photovoltaic Cells Based on Triplet Materials
journal, December 2005
- Shao, Y.; Yang, Y.
- Advanced Materials, Vol. 17, Issue 23
Metallopolyyne Polymers as New Functional Materials for Photovoltaic and Solar Cell Applications
journal, January 2008
- Wong, Wai-Yeung
- Macromolecular Chemistry and Physics, Vol. 209, Issue 1
Bulk Heterojunction Solar Cells: Morphology and Performance Relationships
journal, May 2014
- Huang, Ye; Kramer, Edward J.; Heeger, Alan J.
- Chemical Reviews, Vol. 114, Issue 14
Design and Synthesis of Molecular Donors for Solution-Processed High-Efficiency Organic Solar Cells
journal, August 2013
- Coughlin, Jessica E.; Henson, Zachary B.; Welch, Gregory C.
- Accounts of Chemical Research, Vol. 47, Issue 1
Replacing Alkoxy Groups with Alkylthienyl Groups: A Feasible Approach To Improve the Properties of Photovoltaic Polymers
journal, August 2011
- Huo, Lijun; Zhang, Shaoqing; Guo, Xia
- Angewandte Chemie, Vol. 123, Issue 41
Finely Tuned Polymer Interlayers Enhance Solar Cell Efficiency
journal, July 2015
- Liu, Yao; Page, Zachariah A.; Russell, Thomas P.
- Angewandte Chemie, Vol. 127, Issue 39
Quantum Mechanical Continuum Solvation Models
journal, October 2005
- Tomasi, Jacopo; Menucci, Benedetta; Cammi, Roberto
- ChemInform, Vol. 36, Issue 42
Functionalized Acenes and Heteroacenes for Organic Electronics
journal, May 2007
- Anthony, John E.
- ChemInform, Vol. 38, Issue 18
An Efficient Trap Passivator for Perovskite Solar Cells: Poly(propylene glycol) bis(2-aminopropyl ether)
journal, August 2020
- Chen, Ningli; Yi, Xiaohui; Zhuang, Jing
- Nano-Micro Letters, Vol. 12, Issue 1
Fluorine Substituted Conjugated Polymer of Medium Band Gap Yields 7% Efficiency in Polymer–Fullerene Solar Cells
journal, May 2011
- Price, Samuel C.; Stuart, Andrew C.; Yang, Liqiang
- Journal of the American Chemical Society, Vol. 133, Issue 20
Metallated conjugated polymers as a new avenue towards high-efficiency polymer solar cells
book, October 2010
- Wong, Wai-Yeung; Wang, Xing-Zhu; He, Ze
- Materials for Sustainable Energy
What controls triplet exciton transfer in organic semiconductors?
text, January 2011
- Köhler, Anna; Bässler, Heinz
- University of Bayreuth
Rational design of high performance conjugated polymers for organic solar cells
text, January 2012
- Liqiang, Yang,; Wei, You,; Huaxing, Zhou,
- American Chemical Society
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- Jin, Yingzhi; Zhang, Yanxin; Liu, Yanfeng
- Advanced Materials, Vol. 31, Issue 22
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journal, January 2018
- Marineau-Plante, Gabriel; Juvenal, Frank; Langlois, Adam
- Chemical Communications, Vol. 54, Issue 8
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journal, January 2018
- Chen, Yao; Wang, Gang; Yang, Lin
- Journal of Materials Chemistry C, Vol. 6, Issue 4
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journal, January 2019
- Montanaro, Stephanie; Gillett, Alexander J.; Feldmann, Sascha
- Physical Chemistry Chemical Physics, Vol. 21, Issue 20
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