Functional Π-conjugated polymers based on maleimide for photovoltaic applications

• Authors: Ramona Gironda , Luciano Miozzo , Denis Tondelier , Marc Chaigneau , Jamal Ghabboun , Maryam Faroun , Antonio Papagni , Marco Matteo Salamone , Riccardo Ruffo , Abderrahim Yassar
• Languages of publication: EN

Abstracts

EN

A series of new bis-(2-thienyl) maleimide monomers
have been synthesized and characterized. The bis-(2-
thienyl)maleimide unit has been copolymerized with different
aromatic comonomers. Stille coupling polymerizations under
various conditions have been utilized. The copolymers were
then characterized by size-exclusion chromatography and
their optical and electronic properties were investigated by
UV-Vis absorption spectroscopy and cyclic voltammetry. All
maleimide based copolymers shared similar LUMO energy
levels, which are largely determined by the acceptor moiety,
and are close to that of PC61BM to be effective for charge
dissociation. These low band gap polymers have been tested
for photovoltaic applications and have shown moderate
photovoltaic performance. Interesting results were obtained
by adding the polymer to the P3HT:PC61BM mixture, as a
third component. The ternary blend BHJ solar cells showed
power conversion efficiencies of 35% exceeding those of the
corresponding binary blends.

Keywords

EN

Maleimide ; OPV ; ternary blends ; photovoltaic ; organic

Discipline

• 78.66.Sq: Composite materials
• 82.70.Uv: Surfactants, micellar solutions, vesicles, lamellae, amphiphilic systems, (hydrophilic and hydrophobic interactions)(see also 82.30.Rs Hydrogen bonding, hydrophilic effects in specific chemical reactions)
• 78.35.+c: Brillouin and Rayleigh scattering; other light scattering(for Raman scattering, see 78.30.-j; for time resolved light scattering spectroscopy, see 78.47.je)
• 81.07.Pr: Organic-inorganic hybrid nanostructures
• 88.40.jr: Organic photovoltaics

• Publisher: De Gruyter Open
• Journal: Organic Photonics and Photovoltaics
• Year: 2013
• Volume: 1
• Pages: 56-66

Dates

received

13 - 5 - 2013

accepted

25 - 9 - 2013

online

31 - 12 - 2013

Contributors

author

Ramona Gironda

• LPICM, UMR 7647 CNRS, Ecole polytechnique, route de Saclay,
  91128 Palaiseau Cedex, France
• Dipartimento di Scienza dei Materiali,
  Universit´r di Milano Bicocca, via R. Cozzi, 53, 20125, Milano, Italy

author

Luciano Miozzo

• LPICM, UMR 7647 CNRS, Ecole polytechnique, route de Saclay,
  91128 Palaiseau Cedex, France
• Dipartimento di Scienza dei Materiali,
  Universit´r di Milano Bicocca, via R. Cozzi, 53, 20125, Milano, Italy

author

Denis Tondelier

• LPICM, UMR 7647 CNRS, Ecole polytechnique, route de Saclay,
  91128 Palaiseau Cedex, France

author

Marc Chaigneau

• LPICM, UMR 7647 CNRS, Ecole polytechnique, route de Saclay,
  91128 Palaiseau Cedex, France

author

Jamal Ghabboun

• The Nanotechnology Research laboratory,
  Materials Engineering Department, Al-Quds University,
  East Jerusalem, Palestine
• Department of Physics, Bethlehem University,
  Bethlehem, Palestine

author

Maryam Faroun

• The Nanotechnology Research laboratory,
  Materials Engineering Department, Al-Quds University,
  East Jerusalem, Palestine

author

Antonio Papagni

• Dipartimento di Scienza dei Materiali,
  Universit´r di Milano Bicocca, via R. Cozzi, 53, 20125, Milano, Italy

author

Marco Matteo Salamone

• Dipartimento di Scienza dei Materiali,
  Universit´r di Milano Bicocca, via R. Cozzi, 53, 20125, Milano, Italy

author

Riccardo Ruffo

• Dipartimento di Scienza dei Materiali,
  Universit´r di Milano Bicocca, via R. Cozzi, 53, 20125, Milano, Italy

author

Abderrahim Yassar

• LPICM, UMR 7647 CNRS, Ecole polytechnique, route de Saclay,
  91128 Palaiseau Cedex, France

References

• [1] G. Yu, J. Gao, J. C. Hummelen, F. Wudl and A. J.Heeger, Science, 1995, 270,1789.
• [2] M. A. Green, K. Emery, Y. Hishikawa, W. Warta, E.D. Dunlop, Progress in Photovoltaics: Research andApplications, 2012, 20, 12.
• [3] H. Zhou, L. Yang ,W. You, Macromolecules, 2012, 45,607.
• [4] P. M. Beaujuge, J. M. J. Fréchet, Journal of the AmericanChemical Society, 2011, 133, 20009.[PubMed]
• [5] Y. Li, Accounts of Chemical Research, 2012, 45, 723.[PubMed]
• [6] E. Zhou, J. Cong, Q. Wei, K. Tajima, C. Yang, K.Hashimoto, Angewandte Chemie International Edition,2011, 50, 2799.
• [7] X. Zhan, A. Facchetti, S. Barlow, T. J. Marks, M. A.Ratner, M. R. Wasielewski, S. R. Marder, AdvancedMaterials, 2011, 23, 268.
• [8] X. Zha, X. Zhan, Chemical Society Reviews, 2011, 40,3728.
• [9] Y. Lin, Y. Li, X. Zhan, Chemical Society Reviews, 2012,41, 4245.[PubMed]
• [10] A. Pron, P. Berrouard , M. Leclerc, Macromol. Chem.Phys. 2013, 214, C. M. Amb. S. Chen, K R. Graham,J. Subbiah, C. E. Small, Franky So, J. R. Reynolds, J.Am. Chem Soc. 2011, 133, 10062; X. Guo, N. Zhou,S. J. Lou, J. W. Hennek, R. Ponce Ortiz, M. R. Butler,P.-Luc T. Boudreault, J. Strzalka, P.-Olivier Morin,M. Leclerc, J. T. López Navarrete, M. A. Ratner, L.X. Chen, R. P. H. Chang, A Facchetti, T. J. Marks J.Am. Chem Soc. 2012, 134, 18427; Ta-Ya Chu, J. Lu, S.Beaupré, Y. Zhang, J.-Rémi Pouliot, J. Zhou, A Najari,M. Leclerc, Y Tao, Adv. Func. Mater. 2012, 2345
• [11] H. Wang, Q. Shi, Y. Lin, H. Fan, P. Cheng, X. Zhan,Y. Li, D. Zhu, Macromolecules 2011, 44, 4213.
• [12] H. Xin, X. Guo, F. S. Kim, G. Ren, M. D. Watson andS. A. Jenekhe, Journal of Materials Chemistry, 2009,19, 5303.
• [13] T.-Z. Liu and Y. Chen, Polymer, 2005, 46, 10383.
• [14] L.-H. Chan, Y.-D. Lee, C.-T. Chen, Macromolecules,2006, 39, 3262.
• [15] R.-H. Lee, J.-Y. Syu, J.-L. Huang, Polymers for AdvancedTechnologies, 2011, 22, 2110.
• [16] L.-H. Chan, S.-Y. Juang, M.-C. Chen, Y.-J. Lin, Polymer,2012, 53, 2334.
• [17] H.-C. Yeh, W.-C. Wu, C.-T. Chen, Chemical Communications,2003, 404.
• [18] L.-H. Chan, Y.-D. Lee, C.-T. Chen, Tetrahedron, 2006,62, 9541.
• [19] H. Shih, R. J. Shih, D. A. Carson, Journal of HeterocyclicChemistry, 2011, 48, 1243.
• [20] D.-S. Choi, S. Huang, M. Huang, T. S. Barnard, R.D. Adams, J. M. Seminario, J. M. Tour, The Journal ofOrganic Chemistry, 1998, 63, 2646.[PubMed]
• [21] E. M. Beccalli, M. L. Gelmi, A. Marchesini, EuropeanJournal of Organic Chemistry, 1999, 1421.
• [22] A. Terpin, K. Polborn, W. Steglich, Tetrahedron, 1995,51, 9941.
• [23] E. K. Fields, S. J. Behrend, S. Meyerson, M. L. Winzenburg, B. R. Ortega and H. K. Hall, The Journalof Organic Chemistry, 1990, 55, 5165.
• [24] M. Dubernet, V. Caubert, J. Guillard, M.-C. Viaud-Massuard, Tetrahedron, 2005, 61, 4585.
• [25] H. Wang, Q. Shi, Y. Lin, H. Fan, P. Cheng, X. Zhan,Y. Li, D. Zhu, Macromolecules, 2011, 44, 4213.
• [26] P. S. Deore, N. P. Argade, The Journal of OrganicChemistry, 2011, 77, 739.[PubMed]
• [27] K. Onimura, M. Matsushima, M. Nakamura, T. Tominaga,K. Yamabuki, T. Oishi, Journal of Polymer SciencePart A: Polymer Chemistry, 2011, 49, 3550.
• [28] K. Onimura, M. Matsushima, K. Yamabuki, T. Oishi,Polym. J., 2010, 42, 290.
• [29] S. Shorunov, M. Krayushkin, F. Stoyanovich, M. Irie,Russian Journal of Organic Chemistry, 2006, 42,1490.
• [30] C. Marminon, A. Pierré, B. Pfeiffer, V. Pérez, S.Léonce, P. Renard, M. Prudhomme, Bioorganic &Medicinal Chemistry, 2003, 11, 679.[PubMed]
• [31] D. Waghray, W. Nulens, W. Dehaen, Organic Letters,2011, 13, 5516.[PubMed]
• [32] P. Frcre, J.-M. Raimundo, P. Blanchard, J. Delaunay,P. Richomme, J.-L. Sauvajol, J. Orduna, J. Garin, J.Roncali, The Journal of Organic Chemistry, 2003, 68,7254.
• [33] S. Sista, Y. Yao, Y. Yang, M. L. Tang, Z. Bao, AppliedPhysics Letters, 2007, 91, 223508.
• [34] E. Lim, S. Lee, K. K. Lee, Chemical Communications,2011, 47, 914.
• [35] J. Lee, M. H. Yun, J. Kim, J. Y. Kim, C. Yang, MacromolecularRapid Communications, 2012, 33, 140.
• [36] J.-H. Huang, M. Velusamy, K.-C. Ho, J.-T. Lin, C.-W.Chu, Journal of Materials Chemistry, 2010, 20, 2820.
• [37] M.C. Chen, D.J. Liaw, Y.C. Huang, H.Y. Wu, Y. Tai, SolarEnergy Materials & Solar Cells, 2011, 95, 2621.
• [38] Y.J. Cho, J. Yong, J.Y. Lee, B.D. Chin, S. R. Forrest,Organic Electronics, 2013, 14, 1081.

Identifiers

DOI

10.2478/oph-2013-0004