Grooved nanowires from self-assembling hairpin molecules for solar cells

ACS Nano

Volumn 6, Issue 3, 2012, Pages 2032-2040

  Tevis, Ian D ^a   Tsai, Wei Wen ^a   Palmer, Liam C ^a   Aytun, Taner ^b   Stupp, Samuel I ^a,b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b Northwestern University   (United States)

Author keywords

morphology; nanowire; organogelator; photovoltaic; self assembly; sexithiophene

Indexed keywords

BULK HETEROJUNCTION ORGANIC SOLAR CELLS; BULK HETEROJUNCTION SOLAR CELLS; DEVICE EFFICIENCY; DOMAIN GROWTH; MIXED-DONORS; ONE-DIMENSIONAL STRUCTURE; ORGANO-GELATOR; PERCOLATING NETWORKS; PHOTOVOLTAIC; PHOTOVOLTAIC DEVICES; POWER CONVERSION EFFICIENCIES; RECEPTOR LIGANDS; SELF-ASSEMBLED NANOWIRES; SELF-ASSEMBLING; SEXITHIOPHENES; SOLVENT EVAPORATION; THERMAL-ANNEALING; TWO DOMAINS;

CONVERSION EFFICIENCY; FULLERENES; HETEROJUNCTIONS; MOLECULES; MORPHOLOGY; PERCOLATION (COMPUTER STORAGE); PHASE SEPARATION; PHOTOVOLTAIC EFFECTS; SELF ASSEMBLY;

NANOWIRES;

NANOWIRE; THIOPHENE DERIVATIVE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMISTRY; ELECTRIC CONDUCTIVITY; POWER SUPPLY; SOLAR ENERGY;

ELECTRIC CONDUCTIVITY; ELECTRIC POWER SUPPLIES; MICROSCOPY, ATOMIC FORCE; NANOWIRES; SOLAR ENERGY; THIOPHENES;

EID: 84859119905     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn203328n     Document Type: Article

References (60)

1. Peet, J.; Heeger, A. J.; Bazan, G. C. "Plastic" Solar Cells: Self-Assembly of Bulk Heterojunction Nanomaterials by Spontaneous Phase Separation Acc. Chem. Res. 2009, 42, 1700-1708
2. Li, G.; Shrotriya, V.; Huang, J. S.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. High-Efficiency Solution Processable Polymer Photovoltaic Cells by Self-Organization of Polymer Blends Nat. Mater. 2005, 4, 864-868
3. Chen, H. Y.; Hou, J. H.; Zhang, S. Q.; Liang, Y. Y.; Yang, G. W.; Yang, Y.; Yu, L. P.; Wu, Y.; Li, G. Polymer Solar Cells with Enhanced Open-Circuit Voltage and Efficiency Nat. Photonics 2009, 3, 649-653
4. Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J. Bulk Heterojunction Solar Cells with Internal Quantum Efficiency Approaching 100% Nat. Photonics 2009, 3, 297-302
5. Janssen, R. A. J.; Hummelen, J. C.; Saricifti, N. S. Polymer-Fullerene Bulk Heterojunction Solar Cells MRS Bull. 2005, 30, 33-36
6. Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated Polymer-Based Organic Solar Cells Chem. Rev. 2007, 107, 1324-1338
7. Sirringhaus, H. Device Physics of Solution-Processed Organic Field-Effect Transistors Adv. Mater. 2005, 17, 2411-2425
8. Kim, Y.; Nelson, J.; Zhang, T.; Cook, S.; Durrant, J. R.; Kim, H.; Park, J.; Shin, M.; Nam, S.; Heeney, M.; McCulloch, I.; Ha, C. S.; Bradley, D. D. C. Distorted Asymmetric Cubic Nanostructure of Soluble Fullerene Crystals in Efficient Polymer: Fullerene Solar Cells ACS Nano 2009, 3, 2557-2562
9. Keawprajak, A.; Piyakulawat, P.; Klamchuen, A.; Iamraksa, P.; Asawapirom, U. Influence of Crystallizable Solvent on the Morphology and Performance of P3HT:PCBM Bulk-Heterojunction Solar Cells Sol. Energy Mater. Sol. Cells 2010, 94, 531-536
10. Zhao, J.; Swinnen, A.; Van Assche, G.; Manca, J.; Vanderzande, D.; Van Mele, B. Phase Diagram of P3HT/PCBM Blends and Its Implication for the Stability of Morphology J. Phys. Chem. B 2009, 113, 1587-1591
11. Miller, S.; Fanchini, G.; Lin, Y. Y.; Li, C.; Chen, C. W.; Su, W. F.; Chhowalla, M. Investigation of Nanoscale Morphological Changes in Organic Photovoltaics during Solvent Vapor Annealing J. Mater. Chem. 2008, 18, 306-312
12. Li, G.; Yao, Y.; Yang, H.; Shrotriya, V.; Yang, G.; Yang, Y. "Solvent Annealing" Effect in Polymer Solar Cells Based on Poly(3-hexylthiophene) and Methanofullerenes Adv. Funct. Mater. 2007, 17, 1636-1644
13. Walker, B.; Tomayo, A. B.; Dang, X. D.; Zalar, P.; Seo, J. H.; Garcia, A.; Tantiwiwat, M.; Nguyen, T. Q. Nanoscale Phase Separation and High Photovoltaic Efficiency in Solution-Processed, Small-Molecule Bulk Heterojunction Solar Cells Adv. Funct. Mater. 2009, 19, 3063-3069
14. Mayerhoffer, U.; Deing, K.; Gruss, K.; Braunschweig, H.; Meerholz, K.; Wurthner, F. Outstanding Short-Circuit Currents in BHJ Solar Cells Based on NIR-Absorbing Acceptor-Substituted Squaraines Angew. Chem., Int. Ed. 2009, 48, 8776-8779
15. Burckstummer, H.; Kronenberg, N. M.; Gsanger, M.; Stolte, M.; Meerholz, K.; Wurthner, F. Tailored Merocyanine Dyes for Solution-Processed BHJ Solar Cells J. Mater. Chem. 2010, 20, 240-243
16. Tamayo, A. B.; Walker, B.; Nguyen, T. Q. A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells J. Phys. Chem. C 2008, 112, 11545-11551
17. Ma, B. W.; Woo, C. H.; Miyamoto, Y.; Frechet, J. M. J. Solution Processing of a Small Molecule, Subnaphthalocyanine, for Efficient Organic Photovoltaic Cells Chem. Mater. 2009, 21, 1413-1417
18. Loser, S.; Bruns, C. J.; Miyauchi, H.; Ortiz, R. P.; Facchetti, A.; Stupp, S. I.; Marks, T. J. A Naphthodithiophene-Diketopyrrolopyrrole Donor Molecule for Efficient Solution-Processed Solar Cells J. Am. Chem. Soc. 2011, 133, 8142-8145
19. Palmer, L. C.; Stupp, S. I. Molecular Self-Assembly into One-Dimensional Nanostructures Acc. Chem. Res. 2008, 41, 1674-1684
20. Hulvat, J. F.; Sofos, M.; Tajima, K.; Stupp, S. I. Self-Assembly and Luminescence of Oligo(p -phenylene vinylene) Amphiphiles J. Am. Chem. Soc. 2005, 127, 366-372
21. Messmore, B. W.; Hulvat, J. F.; Sone, E. D.; Stupp, S. I. Synthesis, Self-Assembly, and Characterization of Supramolecular Polymers from Electroactive Dendron Rodcoil Molecules J. Am. Chem. Soc. 2004, 126, 14452-14458
22. Stone, D. A.; Hsu, L.; Stupp, S. I. Self-Assembling Quinquethiophene- Oligopeptide Hydrogelators Soft Matter 2009, 5, 1990-1993
23. Tsai, W. W.; Li, L. S.; Cui, H. G.; Jiang, H. Z.; Stupp, S. I. Self-Assembly of Amphiphiles with Terthiophene and Tripeptide Segments into Helical Nanostructures Tetrahedron 2008, 64, 8504-8514
24. Stone, D. A.; Tayi, A. S.; Goldberger, J. E.; Palmer, L. C.; Stupp, S. I. Self-Assembly and Conductivity of Hydrogen-Bonded Oligothiophene Nanofiber Networks Chem. Commun. 2011, 47, 5702-5704
25. Pratihar, P.; Ghosh, S.; Stepanenko, V.; Patwardhan, S.; Grozema, F. C.; Siebbeles, L. D. A.; Wurthner, F. Self-Assembly and Semiconductivity of an Oligothiophene Supergelator Beilstein J. Org. Chem. 2010, 6, 1070-1078
26. Puigmarti-Luis, J.; Laukhin, V.; del Pino, A. P.; Vidal-Gancedo, J.; Rovira, C.; Laukhina, E.; Amabilino, D. B. Supramolecular Conducting Nanowires from Organogels Angew. Chem., Int. Ed. 2007, 46, 238-241
27. Sofos, M.; Stone, D. A.; Goswami, D. K.; Okasinski, J. S.; Jin, H.; Bedzyk, M. J.; Stupp, S. I. Nanoscale Structure of Self-Assembling Hybrid Materials of Inorganic and Electronically Active Organic Phases J. Phys. Chem. C 2008, 112, 2881-2887
28. Tajima, K.; Li, L. S.; Stupp, S. I. Nanostructured Oligo(p -phenylene vinylene)/Silicate Hybrid Films: One-Step Fabrication and Energy Transfer Studies J. Am. Chem. Soc. 2006, 128, 5488-5495
29. Xue, P. C.; Lu, R.; Zhao, L.; Xu, D. F.; Zhang, X. F.; Li, K. C.; Song, Z. G.; Yang, X. C.; Takafuji, M.; Ihara, H. Hybrid Self-Assembly of a π Gelator and Fullerene Derivative with Photoinduced Electron Transfer for Photocurrent Generation Langmuir 2010, 26, 6669-6675
30. Amabilino, D. B.; Puigmarti-Luis, J. Gels as a Soft Matter Route to Conducting Nanostructured Organic and Composite Materials Soft Matter 2010, 6, 1605-1612
31. Bushey, M. L.; Nguyen, T. Q.; Zhang, W.; Horoszewski, D.; Nuckolls, C. Using Hydrogen Bonds To Direct the Assembly of Crowded Aromatics Angew. Chem., Int. Ed. 2004, 43, 5446-5453
32. Canas-Ventura, M. E.; Xiao, W.; Wasserfallen, D.; Mullen, K.; Brune, H.; Barth, J. V.; Fasel, R. Self-Assembly of Periodic Bicomponent Wires and Ribbons Angew. Chem., Int. Ed. 2007, 46, 1814-1818
33. Schenning, A.; Meijer, E. W. Supramolecular Electronics; Nanowires from Self-Assembled π-Conjugated Systems Chem. Commun. 2005, 3245-3258
34. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. About Supramolecular Assemblies of π-Conjugated Systems Chem. Rev. 2005, 105, 1491-1546
35. Schenning, A.; Jonkheijm, P.; Peeters, E.; Meijer, E. W. Hierarchical Order in Supramolecular Assemblies of Hydrogen-Bonded Oligo(p -phenylene vinylene)s J. Am. Chem. Soc. 2001, 123, 409-416
36. Yamaguchi, T.; Ishii, N.; Tashiro, K.; Aida, T. Supramolecular Peapods Composed of a Metalloporphyrin Nanotube and Fullerenes J. Am. Chem. Soc. 2003, 125, 13934-13935
37. Jang, W. D.; Jiang, D. L.; Aida, T. Dendritic Physical Gel: Hierarchical Self-Organization of a Peptide-Core Dendrimer To Form a Micrometer-Scale Fibrous Assembly J. Am. Chem. Soc. 2000, 122, 3232-3233
38. Schillinger, E. K.; Mena-Osteritz, E.; Hentschel, J.; Borner, H. G.; Bauerle, P. Oligothiophene versus β-Sheet Peptide: Synthesis and Self-Assembly of an Organic Semiconductor-Peptide Hybrid Adv. Mater. 2009, 21, 1562-1567
39. Ajayaghosh, A.; Praveen, V. K. π-Organogels of Self-Assembled p -Phenylenevinylenes: Soft Materials with Distinct Size, Shape, and Functions Acc. Chem. Res. 2007, 40, 644-656
40. Ghosh, S.; Li, X. Q.; Stepanenko, V.; Wurthner, F. Control of H- and J-Type π Stacking by Peripheral Alkyl Chains and Self-Sorting Phenomena in Perylene Bisimide Homo- and Heteroaggregates Chem.-Eur. J. 2008, 14, 11343-11357
41. Schoonbeek, F. S.; van Esch, J. H.; Wegewijs, B.; Rep, D. B. A.; de Haas, M. P.; Klapwijk, T. M.; Kellogg, R. M.; Feringa, B. L. Efficient Intermolecular Charge Transport in Self-Assembled Fibers of Mono- and Bithiophene Bisurea Compounds Angew. Chem., Int. Ed. 1999, 38, 1393-1397
42. Yagai, S.; Kinoshita, T.; Kikkawa, Y.; Karatsu, T.; Kitamura, A.; Honsho, Y.; Seki, S. Interconvertible Oligothiophene Nanorods and Nanotapes with High Charge-Carrier Mobilities Chem.-Eur. J. 2009, 15, 9320-9324
43. van Herrikhuyzen, J.; Syamakumari, A.; Schenning, A. P. H. J.; Meijer, E. W. Synthesis of n-Type Perylene Bisimide Derivatives and Their Orthogonal Self-Assembly with p-Type Oligo(p -phenylene vinylene)s J. Am. Chem. Soc. 2004, 126, 10021-10027
44. Ajayaghosh, A.; George, S. J.; Schenning, A. P. H. J. Hydrogen-Bonded Assemblies of Dyes and Extended π-Conjugated Systems Top. Curr. Chem. 2005, 258, 83-118
45. Gesquiere, A.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Supramolecular π-Stacked Assemblies of Bis(urea)-Substituted Thiophene Derivatives and Their Electronic Properties Probed with Scanning Tunneling Microscopy and Scanning Tunneling Spectroscopy Nano Lett. 2001, 1, 201-206
46. Li, Y.; Li, G. T.; Wang, X. Y.; Li, W. N.; Su, Z. X.; Zhang, Y. H.; Ju, Y. Unique Twisted Ribbons Generated by Self-Assembly of Oligo(p -phenylene ethylene) Bearing Dimeric Bile Acid Pendant Groups Chem.-Eur. J. 2009, 15, 6399-6407
47. Prasanthkumar, S.; Gopal, A.; Ajayaghosh, A. Self-Assembly of Thienylenevinylene Molecular Wires to Semiconducting Gels with Doped Metallic Conductivity J. Am. Chem. Soc. 2010, 132, 13206-13207
48. Prasanthkumar, S.; Saeki, A.; Seki, S.; Ajayaghosh, A. Solution Phase Epitaxial Self-Assembly and High Charge-Carrier Mobility Nanofibers of Semiconducting Molecular Gelators J. Am. Chem. Soc. 2010, 132, 8866-8867
49. Wicklein, A.; Ghosh, S.; Sommer, M.; Wurthner, F.; Thelakkat, M. Self-Assembly of Semiconductor Organogelator Nanowires for Photoinduced Charge Separation ACS Nano 2009, 3, 1107-1114
50. Messmore, B. W.; Stupp, S. I. Mirror Image Nanostructures J. Am. Chem. Soc. 2005, 127, 7992-7993
51. Tsai, W.-W.; Tevis, I. D.; Tayi, A. S.; Cui, H.; Stupp, S. I. Semiconducting Nanowires from Hairpin-Shaped Self-Assembling Sexithiophenes J. Phys. Chem. B 2010, 114, 14778-14786
52. Coropceanu, V.; Cornil, J.; da Silva, D. A.; Olivier, Y.; Silbey, R.; Bredas, J. L. Charge Transport in Organic Semiconductors Chem. Rev. 2007, 107, 926-952
53. Yang, X. N.; Loos, J.; Veenstra, S. C.; Verhees, W. J. H.; Wienk, M. M.; Kroon, J. M.; Michels, M. A. J.; Janssen, R. A. J. Nanoscale Morphology of High-Performance Polymer Solar Cells Nano Lett. 2005, 5, 579-583
54. Padinger, F.; Rittberger, R. S.; Sariciftci, N. S. Effects of Postproduction Treatment on Plastic Solar Cells Adv. Funct. Mater. 2003, 13, 85-88
55. Kim, H. J.; Park, J. H.; Lee, H. H.; Lee, D. R.; Kim, J. J. The Effect of Al Electrodes on the Nanostructure of Poly(3-hexylthiophene): Fullerene Solar Cell Blends during Thermal Annealing Org. Electron. 2009, 10, 1505-1510
56. Clarke, T. M.; Ballantyne, A. M.; Nelson, J.; Bradley, D. D. C.; Durrant, J. R. Free Energy Control of Charge Photogeneration in Polythiophene/Fullerene Solar Cells: The Influence of Thermal Annealing on P3HT/PCBM Blends Adv. Funct. Mater. 2008, 18, 4029-4035
57. Mihailetchi, V. D.; Xie, H.; de Boer, B.; Koster, L. J. A.; Blom, P. W. M. Charge Transport and Photocurrent Generation in Poly(3-hexylthiophene): Methanofullerene Bulk-Heterojunction Solar Cells Adv. Funct. Mater. 2006, 16, 699-708
58. Muller, C.; Ferenczi, T. A. M.; Campoy-Quiles, M.; Frost, J. M.; Bradley, D. D. C.; Smith, P.; Stingelin-Stutzmann, N.; Nelson, J. Binary Organic Photovoltaic Blends: A Simple Rationale for Optimum Compositions Adv. Mater. 2008, 20, 3510-3515
59. 70 Phys. Chem. Chem. Phys. 2010, 12, 7091-7097
60. Perez, E. M.; Martin, N. Molecular Tweezers for Fullerenes Pure Appl. Chem. 2010, 82, 523-533