[en] To explore the effectiveness of monofluorinated isoindigo as an electron-deficient building block in push–pull conjugated polymers for organic solar cell applications, four low bandgap copolymers are effectively synthesized and characterized. The effects of fluorine introduction, thiophene spacer length and polymer molar mass on the general electro-optical polymer characteristics, thin film blend micro- structure and electronic performance are investigated. Isoindigo monofluorination effectively improves the power conversion efficiency from 2.8 up to 5.0% upon molar mass optimization, without using any processing additives or post-treatments.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Tomassetti, Mirco ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Ouhib, Farid ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Wislez, Arnaud ; University of Liège (ULg), Department of Chemistry, Nanochemistry and Molecular Systems (NANOCHEM)
Duwez, Anne-Sophie ; University of Liège (ULg), Department of Chemistry, Nanochemistry and Molecular Systems (NANOCHEM)
Penxten, Huguette; Hasselt University, Institute for Materials Research (IMO-IMOMEC), Design & Synthesis of Organic Semiconductors (DSOS)
Dierckx, Wouter; Hasselt University, Diepenbeek, Material Physics Division
Cardinaletti, Ilaria; Hasselt University, Diepenbeek, Material Physics Division
Bovee, Ralf A. A.; Eindhoven University of Technology, Institute for Complex Molecular Systems, Molecular Materials and Nanosystems, The Netherlands
van Pruissen, Gijs W. P.; Eindhoven University of Technology, Institute for Complex Molecular Systems, Molecular Materials and Nanosystems, The Netherlands
Jérôme, Christine ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Low bandgap copolymers based on monofluorinated isoindigo towards efficient polymer solar cells
Publication date :
07 September 2015
Journal title :
Polymer Chemistry
ISSN :
1759-9954
eISSN :
1759-9962
Publisher :
Royal Society Chemistry, Cambridge, United Kingdom
Volume :
6
Issue :
33
Pages :
6040-6049
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
The European Commission and the Walloon Region in the frame of the Interreg "Organext" project BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen
H. C. Liao C. C. Ho C. Y. Chang M. H. Jao S. B. Darling W. F. Su Mater. Today 2013 16 326
S. Lizin S. Van Passel E. De Schepper W. Maes L. Lutsen J. Manca D. Vanderzande Energy Environ. Sci. 2013 6 3136
A. J. Heeger Adv. Mater. 2014 26 10
N. Blouin A. Michaud M. Leclerc Adv. Mater. 2007 19 2295
H.-Y. Chen J. Hou S. Zhang Y. Liang G. Yang Y. Yang L. Yu Y. Wu G. Li Nat. Photonics 2009 3 649
Y. Liang Z. Xu J. Xia S.-T. Tsai Y. Wu G. Li C. Ray L. Yu Adv. Mater. 2010 22 E135
T. Chu J. Lu S. Beaupré Y. Zhang J.-R. Pouliot S. Wakim J. Zhou M. Leclerc Z. Li J. Ding Y. Tao J. Am. Chem. Soc. 2011 133 4250
D. Dang W. Chen S. Himmelberger Q. Tao A. Lundin R. Yang W. Zhu A. Salleo C. Müller E. Wang Adv. Energy Mater. 2014 4 1400680
E. Wang W. Mammo M. R. Andersson Adv. Mater. 2014 26 1801
L. Lu T. Xu W. Chen E. S. Landry L. Yu Nat. Photonics 2014 8 716
C. C. Chen W. H. Chang K. Yoshimura K. Ohya J. You J. Gao Z. Hong Y. Yang Adv. Mater. 2014 26 5670
Y. Liu J. Zhao Z. Li C. Mu W. Ma H. Hu K. Jiang H. Lin H. Ade H. Yan Nat. Commun. 2014 5 5293
A. R. B. M. Yusoff D. Kim H. P. Kim F. K. Shneider W. J. da Silva J. Jang Energy Environ. Sci. 2015 8 303
S.-H. Liao H.-J. Jhuo P.-N. Yeh Y.-S. Cheng Y.-L. Li Y.-H. Lee S. Sharma S.-A. Chen Sci. Rep. 2014 4 6813
J. Chen C. Cui Y. Li L. Zhou Q. Ou C. Li Y. Li J.-X. Tang Adv. Mater. 2014 27 1035
H. Zhou L. Yang W. You Macromolecules 2012 45 607
Z. Chen P. Cai J. Chen X. Liu L. Zhang L. Lan J. Peng Y. Ma Y. Cao Adv. Mater. 2014 26 2586
D. Dang W. Chen R. Yang W. Zhu W. Mammo E. Wang Chem. Commun. 2013 49 9335
M. Zhang X. Guo X. Wang H. Wang Y. Li Chem. Mater. 2011 23 4264
K.-H. Ong S.-L. Lim H.-S. Tan H.-K. Wong J. Li Z. Ma L. C. H. Moh S.-H. Lim J. C. de Mello Z.-K. Chen Adv. Mater. 2011 23 1409
I. Osaka M. Saito H. Mori T. Koganezawa K. Takimiya Adv. Mater. 2012 24 425
S. Van Mierloo A. Hadipour M.-J. Spijkman N. Van Den Brande B. Ruttens J. Kesters J. D'Haen G. Van Assche D. M. De Leeuw T. Aernouts J. Manca L. Lutsen D. J. Vanderzande W. Maes Chem. Mater. 2012 24 587
D. Bevk L. Marin L. Lutsen D. Vanderzande W. Maes RSC Adv. 2013 3 11418
P. Verstappen J. Kesters W. Vanormelingen G. H. L. Heintges J. Drijkoningen T. Vangerven L. Marin S. Koudjina B. Champagne J. Manca L. Lutsen D. Vanderzande W. Maes J. Mater. Chem. A 2015 3 2960
X. Guo R. P. Ortiz Y. Zheng M.-G. Kim S. Zhang Y. Hu G. Lu A. Facchetti T. J. Marks J. Am. Chem. Soc. 2011 133 13685
M. M. Wienk M. Turbiez J. Gilot R. A. J. Janssen Adv. Mater. 2008 20 2556
T. Lei Y. Cao Y. Fan C.-J. Liu S.-C. Yuan J. Pei J. Am. Chem. Soc. 2011 133 6099
R. Stalder J. Mei K. R. Graham L. A. Estrada J. R. Reynolds Chem. Mater. 2014 26 664
W. Zhuang M. Bolognesi M. Seri P. Henriksson D. Gedefaw R. Kroon M. Jarvid A. Lundin E. Wang M. Muccini M. R. Andersson Macromolecules 2013 46 8488
J. Mei K. R. Graham R. Stalder J. R. Reynolds Org. Lett. 2010 12 660
Z. Ma D. Dang Z. Tang D. Gedefaw J. Bergqvist W. Zhu W. Mammo M. R. Andersson O. Inganäs F. Zhang E. Wang Adv. Energy Mater. 2014 4 1301455
Y. Deng J. Liu J. Wang L. Liu W. Li H. Tian X. Zhang Z. Xie Y. Geng F. Wang Adv. Mater. 2014 26 471
I. Osaka M. Shimawaki H. Mori I. Doi E. Miyazaki T. Koganezawa K. Takimiya J. Am. Chem. Soc. 2012 134 3498
A. T. Yiu P. M. Beaujuge O. P. Lee C. H. Woo M. F. Toney J. M. J. Fréchet J. Am. Chem. Soc. 2012 134 2180
C. Liu K. Wang X. Hu Y. Yang C. Hsu W. Zhang S. Xiao X. Gong Y. Cao ACS Appl. Mater. Interfaces 2013 5 12163
J. J. Intemann K. Yao H. Yip Y. Xu Y. Li P. Liang F. Ding X. Li A. K.-Y. Jen Chem. Mater. 2013 25 3188
N. P. Holmes S. Ulum P. Sista K. B. Burke M. G. Wilson M. C. Stefan X. Zhou P. C. Dastoor W. J. Belcher Sol. Energy Mater. Sol. Cells 2014 128 369
X. He S. Mukherjee S. Watkins M. Chen T. Qin L. Thomsen H. Ade C. R. McNeill J. Phys. Chem. C 2014 118 9918
T. Vangerven P. Verstappen J. Drijkoningen W. Dierckx S. Himmelberger A. Salleo D. Vanderzande W. Maes J. V. Manca Chem. Mater. 2015 27 3726
S. Albrecht S. Janietz W. Schindler J. Frisch J. Kurpiers J. Kniepert S. Inal P. Pingel K. Fostiropoulos N. Koch D. Neher J. Am. Chem. Soc. 2012 134 14932
Y. Zhang J. Zou C. Cheuh H. Yip A. K. Jen Macromolecules 2012 45 5427
C. Gu M. Xiao X. Bao L. Han D. Zhu N. Wang S. Wen W. Zhu R. Yang Polym. Chem. 2014 5 6551
H. Wang X. Yu C. Yi H. Ren C. Liu Y. Yang S. Xiao J. Zheng A. Karim S. Z. D. Cheng X. Gong J. Phys. Chem. C 2013 117 4358
T. Lei J.-H. Dou Z.-J. Ma C.-H. Yao C.-J. Liu J.-Y. Wang J. Pei J. Am. Chem. Soc. 2012 134 20025
H. Zhou L. Yang A. C. Stuart S. C. Price S. Liu W. You Angew. Chem., Int. Ed. 2011 50 2995
Y. Yang R. Wu X. Wang X. Xu Z. Li K. Li Q. Peng Chem. Commun. 2014 50 439
Z. Ma W. Sun S. Himmelberger K. Vandewal Z. Tang J. Bergqvist A. Salleo J. W. Andreasen O. Inganäs M. R. Andersson C. Müller F. Zhang E. Wang Energy Environ. Sci. 2014 7 361
C.-C. Ho C.-A. Chen C.-Y. Chang S. B. Darling W.-F. Su J. Mater. Chem. A 2014 2 8026
A. J. Bard and L. R. Faulkner, Electrochemical methods: fundamentals and applications, Wiley, 2nd edn, 2001
S. Trasatti Pure Appl. Chem. 1986 58 955
M. M. M. Raposo A. M. C. Fonseca G. Kirsch Tetrahedron 2004 60 4071
T. Lei X. Xia J. Wang C. Liu J. Pei J. Am. Chem. Soc. 2014 136 2135
J. Kim T. M. Swager Nature 2001 411 1030
J. K. Lee W. L. Ma C. J. Brabec J. Yuen J. S. Moon J. Y. Kim K. Lee G. C. Bazan A. J. Heeger J. Am. Chem. Soc. 2008 130 3619
K. R. Graham C. Cabanetos J. P. Jahnke M. N. Idso A. El Labban G. O. Ngongang Ndjawa T. Heumueller K. Vandewal A. Salleo B. F. Chmelka A. Amassian P. M. Beaujuge M. D. McGehee J. Am. Chem. Soc. 2014 136 9608
T. M. Burke S. Sweetnam K. Vandewal M. D. McGehee Adv. Energy Mater. 2015 5 1500123
K. Vandewal W. D. Oosterbaan S. Bertho V. Vrindts A. Gadisa L. Lutsen D. Vanderzande J. V. Manca Appl. Phys. Lett. 2009 95 123303
D. Spoltore T. Vangerven P. Verstappen F. Piersimoni S. Bertho K. Vandewal N. Van den Brande B. Van Mele A. De Sio J. Parisi L. Lutsen D. Vanderzande W. Maes J. V. Manca Org. Electron. 2015 21 160
