Segregated versus mixed interchain stacking in highly oriented films of naphthalene diimide bithiophene copolymers

ACS Nano

Volumn 6, Issue 11, 2012, Pages 10319-10326

  Brinkmann, Martin ^a   Gonthier, Eric ^a   Bogen, Stéfan ^a   Tremel, Kim ^b   Ludwigs, Sabine ^b   Hufnagel, Martin ^c   Sommer, Michael ^c,d  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF STUTTGART   (Germany)

^c Melville Laboratory for Polymer Synthesis   (United Kingdom)

^d UNIVERSITY OF FREIBURG   (Germany)

Author keywords

epitaxy; naphthalene diimide copolymers; orientation; polymorphism; semiconducting polymers

Indexed keywords

1 ,3 ,5-TRICHLOROBENZENE; BITHIOPHENES; CHARACTERISTIC SIGNATURE; CHARGE TRANSFER BANDS; ELECTRON ACCEPTING POLYMERS; EPITAXIAL CRYSTALLIZATION; HIGHLY ORIENTED FILMS; NAPHTHALENE DIIMIDE; SPIN-COATED FILMS; UV-VIS SPECTRA;

CHARGE TRANSFER; COPOLYMERS; CRYSTAL ORIENTATION; EPITAXIAL GROWTH; POLYMER FILMS; POLYMORPHISM; POLYTETRAFLUOROETHYLENES; SEMICONDUCTING POLYMERS; TRANSMISSION ELECTRON MICROSCOPY;

NAPHTHALENE;

IMIDE; NANOMATERIAL; NAPHTHALENE DERIVATIVE; NAPHTHALENEDIIMIDE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; MACROMOLECULE; MATERIALS TESTING; METHODOLOGY; PARTICLE SIZE; SURFACE PROPERTY; ULTRASTRUCTURE;

CRYSTALLIZATION; IMIDES; MACROMOLECULAR SUBSTANCES; MATERIALS TESTING; MOLECULAR CONFORMATION; NANOSTRUCTURES; NAPHTHALENES; PARTICLE SIZE; SURFACE PROPERTIES; THIOPHENES;

EID: 84870457933     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn304213h     Document Type: Article

References (50)

1. James, D. I., Smith, J., Heeney, M., Anthopoulos, T. D., Salleo, A.; McCulloch, I. Organic Semiconductor Materials for Transistors, in Organic Electronics II: More Materials and Applications, Wiley-VCH Verlag: Weinheim. Germany, 2012; pp 1-155.
2. Forrest, S. R. The Path to Ubiquitous and Low-Cost Organic Electronic Appliances on Plastic Nature 2004, 428, 911-918
3. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P. et al. Two-dimensional Charge Transport in Self-Organized, High-Mobility Conjugated Polymers Nature 1999, 401, 685-688
4. Ma, W.; Yang, C.; Gong, X.; Lee, K.; Heeger, A. J. Thermally Stable, Efficient Polymer Solar Cells with Nanoscale Control of the Interpenetrating Network Morphology Adv. Funct. Mater. 2005, 15, 1617-1622
5. McCulloch, I.; Heeney, M.; Bailey, C.; Genevicius, K.; MacDonald, I.; Shkunov, M.; Sparrowe, D.; Tierney, S.; Wagner, R.; Zhang, W. et al. Liquid-Crystalline Semiconducting Polymers with High Charge-Carrier Mobility Nat. Mater. 2006, 5, 328-333
6. Beaujuge, P. M.; Fréchet, J. M. J. Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications J. Am. Chem. Soc. 2011, 133, 20009-20029
7. Liang, Y.; Yu, L. A New Class of Semiconducting Polymers for Bulk Heterojunction Solar Cells with Exceptionally High Performance Acc. Chem. Res. 2010, 43, 1227-1236
8. Wang, E.; Hou, L.; Wang, Z.; Hellström, S.; Zhang, F.; Inganäs, O.; Andersson, M. R. An Easily Synthesized Blue Polymer for High-Performance Polymer Solar Cells Adv. Mater. 2010, 22, 5240-5244
9. Sonar, P.; Singh, S. P.; Li, Y.; Siang Soh, M.; Dodabalapur, A. A Low-Bandgap Diketopyrrolopyrrole-Benzothiadiazole-Based Copolymer for High-Mobility Ambipolar Organic Thin-Film Transistors Adv. Mater. 2010, 22, 5409-5413
10. Chen, Z.; Lee, M. J.; Ashraf, R. S.; Gu, Y.; Albert-Seifried, S.; Nielsen, M. M.; Schroeder, B.; Anthopoulos, T. D.; Heeney, M.; McCulloch, I. et al. High-Performance Ambipolar Diketopyrrolopyrrole-Thieno[3,2- b ]thiophene Copolymer Field-Effect Transistors with Balanced Hole and Electron Mobilities Adv. Mater. 2012, 24, 647-652
11. Kronemeijer, A. J.; Gili, E.; Shahid, M.; Rivnay, J.; Salleo, A.; Heeney, M.; Sirringhaus, H. A Selenophene-Based Low-Bandgap Donor-Acceptor Polymer Leading to Fast Ambipolar Logic Adv. Mater. 2012, 24, 1558-1565
12. Fan, J.; Yuen, J. D.; Wang, M.; Seifter, J.; Seo, J.-H.; Mohebbi, A. R.; Zakhidov, D.; Heeger, A.; Wudl, F. High-Performance Ambipolar Transistors and Inverters from an Ultralow Bandgap Polymer Adv. Mater. 2012, 24, 2186-2190
13. Bijleveld, J. C.; Zoombelt, A. P.; Mathijssen, S. G. J.; Wienk, M. M.; Turbiez, M.; de Leeuw, D. M.; Janssen, R. A. J. Poly(diketopyrrolopyrrole- terthiophene) for Ambipolar Logic and Photovoltaics J. Am. Chem. Soc. 2009, 131, 16616-16617
14. Li, W.; Roelofs, W. S. C.; Wienk, M. M.; Janssen, R. A. J. Enhancing the Photocurrent in Diketopyrrolopyrrole-Based Polymer Solar Cells via Energy Level Control J. Am. Chem. Soc. 2012, 134, 13787-13795
15. Zhang, M.; Tsao, H. N.; Pisula, W.; Yang, C.; Mishra, A. K.; Müllen, K. Field-Effect Transistors Based on a Benzothiadiazole-Cyclopentadithiophene Copolymer J. Am. Chem. Soc. 2007, 129, 3472-3473
16. Guo, J.; Liang, Y.; Szarko, J.; Lee, B.; Jung Son, H.; Rolczynski, B. S.; Yu, L.; Chen, L. X. Structure, Dynamics, and Power Conversion Efficiency Correlations in a New Low Bandgap Polymer: PCBM Solar Cell J. Phys. Chem. B 2010, 114, 742-748
17. Zhang, W.; Smith, J.; Watkins, S. E.; Gysel, R.; McGehee, M.; Salleo, A.; Kirkpatrick, J.; Ashraf, S.; Anthopoulos, T.; Heeney, M.; McCulloch, I. Indacenodithiophene Semiconducting Polymers for High-Performance, Air-Stable Transistors J. Am. Chem. Soc. 2010, 132, 11437-11439
18. Yiu, A. T.; Beaujuge, P. M.; Lee, O. P.; Woo, C. H.; Toney, M. F.; Fréchet, J. M. J. Side-Chain Tunability of Furan-Containing Low-Band-Gap Polymers Provides Control of Structural Order in Efficient Solar Cells J. Am. Chem. Soc. 2012, 134, 2180-2185
19. Piliego, C.; Holcombe, T. W.; Douglas, J. D.; Woo, C. H.; Beaujuge, P. M.; Fréchet, J. M. J. Synthetic Control of Structural Order in N -Alkylthieno[3,4- c ]pyrrole-4,6-dione-Based Polymers for Efficient Solar Cells J. Am. Chem. Soc. 2010, 132, 7595-7597
20. Zhang, X.; Richter, L. J.; DeLongchamp, D. M.; Kline, R. J.; Hammond, M. R.; McCulloch, I.; Heeney, M.; Ashraf, R. S.; Smith, J. N.; Anthopoulos, T. D. et al. Molecular Packing of High-Mobility Diketo Pyrrolo-Pyrrole Polymer Semiconductors with Branched Alkyl Side Chains J. Am. Chem. Soc. 2011, 133, 15073-15084
21. Guo, X.; Ortiz, R. P.; Zheng, Y.; Kim, M.-G.; Zhang, S.; Hu, Y.; Lu, G.; Facchetti, A.; Marks, T. J. Thieno[3,4- c ]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors J. Am. Chem. Soc. 2011, 133, 13685-13697
22. Tsao, H. N.; Cho, D. M.; Park, I.; Hansen, M. R.; Mavrinskiy, A.; Yoon, D. Y.; Graf, R.; Pisula, W.; Spiess, H. W.; Müllen, K. Ultrahigh Mobility in Polymer Field-Effect Transistors by Design J. Am. Chem. Soc. 2011, 133, 2605-2612
23. Zhan, X.; Tan, Z.; Domercq, B.; An, Z.; Zhang, X.; Barlow, S.; Li, Y.; Zhu, D.; Kippelen, B.; Marder, S. R. A High-Mobility Electron-Transport Polymer with Broad Absorption and Its Use in Field-Effect Transistors and All-Polymer Solar Cells J. Am. Chem. Soc. 2007, 129, 7246-7247
24. Chen, Z.; Zheng, Y.; Yan, H.; Facchetti, A. Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transistors J. Am. Chem. Soc. 2009, 131, 8-9
25. Yan, H.; Chen, Z.; Zheng, Y.; Newmann, C.; Quinn, J. R.; Dötz, F.; Kastler, M.; Facchetti, A. A High-Mobility Electron-Transporting Polymer for Printed Transistors Nature 2009, 457, 679-686
26. Guo, X.; Sunjoo Kim, F.; Seger, M. J.; Jenekhe, S. A.; Watson., M. D. Naphthalene Diimide-Based Polymer Semiconductors: Synthesis, Structure-Property Correlations, and n -Channel and Ambipolar Field-Effect Transistors Chem. Mater. 2012, 24, 1434-1442
27. Zhou, E.; Cong, J.; Zhao, M.; Zhang, L.; Hashimoto, K.; Tajima, K. Synthesis and Application of Poly(fluorene- alt -naphthalene diimide) as an n-Type Polymer for All-Polymer Solar Cells Chem. Commun. 2012, 48, 5283-5285
28. Zhou, E. J.; Cong, J. Z.; Wei, Q. S.; Tajima, K.; Yang, C. H.; Hashimoto, K. All-Polymer Solar Cells from Perylene Diimide Based Copolymers: Material Design and Phase Separation Control Angew. Chem., Int. Ed. 2011, 50, 2799-2803
29. Schubert, M.; Dolfen, D.; Frisch, J.; Roland, S.; Steyrleuthner, R.; Stiller, B.; Chen, Z.; Scherf, U.; Koch, N.; Facchetti, A. et al. Influence of Aggregation on the Performance of All-Polymer Solar Cells Containing Low-Bandgap Naphthalenediimide Copolymers Adv. Energy Mater. 2012, 2, 369-380
30. Rivnay, J.; Toney, M. F.; Zheng, Y.; Kauvar, I. V.; Chen, Z.; Wagner, V.; Facchetti, A.; Salleo, A. Unconventional Face-On Texture and Exceptional In-Plane Order of a High Mobility n-Type Polymer Adv. Mater. 2010, 22, 4359-4363
31. Rivnay, J.; Steyrleuthner, R.; Jimison, L. H.; Casadei, A.; Chen, Z.; Toney, M. F.; Facchetti, A.; Neher, D.; Salleo, A. Drastic Control of Texture in a High Performance n-Type Polymeric Semiconductor and Implications for Charge Transport Macromolecules 2011, 44, 5246-5255
32. Schuettfort, T.; Huettner, S.; Lilliu, S.; Macdonald, J. E.; Thomsen, L.; McNeill, C. R. Surface and Bulk Structural Characterization of a High-Mobility Electron-Transporting Polymer Macromolecules 2011, 44, 1530-1539
33. Wittmann, J.-C.; Smith, P. Highly Oriented Thin Films of Poly(tetrafluoroethylene) as a Substrate for Oriented Growth of Materials Nature 1991, 352, 414-417
34. Brinkmann, M.; Wittmann, J.-C. Orientation of Regioregular Poly(3-hexylthiophene) by Directional Solidification: A Simple Method to Reveal the Semicrystalline Structure of a Conjugated Polymer Adv. Mater. 2006, 18, 860-863
35. Brinkmann, M.; Rannou, P. Effect of Molecular Weight on the Structure and Morphology of Oriented Thin Films of Regioregular Poly(3-hexylthiophene) Grown by Directional Epitaxial Solidification Adv. Funct. Mater. 2007, 17, 101-108
36. Brinkmann, M. Directional Epitaxial Crystallization and Tentative Crystal Structure of Poly(9,9′-di- n -octyl-2,7-fluorene) Macromolecules 2007, 40, 7532-7541
37. Hartmann, L.; Tremel, K.; Uttiya, S.; Crossland, E.; Ludwigs, S.; Kayunkid, N.; Vergnat, C.; Brinkmann, M. 2D versus 3D Crystalline Order in Thin Films of Regioregular Poly(3-hexylthiophene) Oriented by Mechanical Rubbing and Epitaxy Adv. Funct. Mater. 2011, 21, 4047-4057
38. Jung Lee, M.; Gupta, D.; Zhao, N.; Heeney, M.; McCulloch, I.; Sirringhaus, H. Anisotropy of Charge Transport in a Uniaxially Aligned and Chain-Extended, High-Mobility, Conjugated Polymer Semiconductor Adv. Funct. Mater. 2011, 21, 932-940
39. Delongchamp, D. M.; Kline, R. J.; Jung, Y.; Germack, D. S.; Lin, E. K.; Moad, A. J.; Richter, L. J.; Toney, M. F.; Heeney, M.; McCullouch, I. Controlling the Orientation of Terraced Nanoscale "Ribbons" of a Poly(thiophene) Semiconductor ACS Nano 2009, 3, 780-787
40. Brinkmann, M.; Charoenthai, N.; Traiphol, R.; Piyakulawat, P.; Wlosnewski, J.; Asawapirom, U. Structure and Morphology in Highly Oriented Films of Poly(9,9-bis(n -octyl)fluorene-2,7-diyl) and Poly(9,9-bis(2-ethylhexyl) fluorene-2,7-diyl) Grown on Friction Transferred Poly(tetrafluoroethylene) Macromolecules 2009, 42, 8298-8306
41. Senkovskyy, V.; Tkachov, R.; Komber, H.; John, A.; Sommer, J.-U.; Kiriy, A. Mechanistic Insight into Catalyst-Transfer Polymerization of Unusual Anion-Radical Naphthalene Diimide Monomers: An Observation of Ni(0) Intermediates Macromolecules 2012, 45, 7770-7777
42. Brinkmann, M.; Rannou, P. Molecular Weight Dependence of Chain Packing and Semicrystalline Structure in Oriented Films of Regioregular Poly(3-hexylthiophene) Revealed by High-Resolution Transmission Electron Microscopy Macromolecules 2009, 42, 1125-1130
43. Salammal, T. S.; Mikayelyan, E.; Grigorian, S.; Pietsch, U.; Koenen, N.; Scherf, U.; Kayunkid, N.; Brinkmann, M. Impact of Thermal Annealing on the Semicrystalline Nanomorphology of Spin-Coated Thin Films of Regioregular Poly(3-alkylthiophene)s as Observed by High-Resolution Transmission Electron Microscopy and Grazing Incidence X-ray Diffraction Macromolecules 2012, 45, 5575-5585
44. Donley, C. L.; Zaumseil, J.; Andreasen, J. W.; Nielsen, M. M.; Sirringhaus, H.; Friend, R. H.; Kim, J.-S. Effects of Packing Structure on the Optoelectronic and Charge Transport Properties in Poly(9,9-di- n -octylfluorene- alt -benzothiadiazole) J. Am. Chem. Soc. 2005, 127, 12890-12899
45. Jespersen, K. G.; Beenken, W. J. D.; Zaushitsyn, Y.; Yartsev, A.; Andersson, M.; Pullerits, T.; Sundström, V. The Electronic States of Polyfluorene Copolymers with Alternating Donor-Acceptor Units J. Chem. Phys. 2004, 121, 12613-12617
46. )] J. Chem. Phys. 2009, 131, 035104
47. Fazzi, D.; Caironi, M.; Castiglioni, C. Quantum-Chemical Insights into the Prediction of Charge Transport Parameters for a Naphthalenetetracarboxydiimide-Based Copolymer with Enhanced Electron Mobility J. Am. Chem. Soc. 2011, 133, 19056-19059
48. Surin, M.; Sonar, P.; Grimsdale, A. C.; Müllen, K.; Lazzaroni, R.; Leclerc, P. Supramolecular Organization in Fluorene/Indenofluorene- Oligothiophene Alternating Conjugated Copolymers Adv. Funct. Mater. 2005, 15, 1426-1434
49. Guo, X.; Watson, M. D. Conjugated Polymers from Naphthalene Bisimide Org. Lett. 2008, 10, 5333-5336
50. Brinkmann, M.; Graff, S.; Wittmann, J.-C.; Chaumont, C.; Nuesch, F.; Anver, A.; Schaer, M.; Zuppiroli, L. Orienting Tetracene and Pentacene Thin Films onto Friction-Transferred Poly(tetrafluoroethylene) Substrate J. Phys. Chem. B 2003, 107, 10531-10539