Hierarchically structured microfibers of "single stack" perylene bisimide and quaterthiophene nanowires

ACS Nano

Volumn 7, Issue 10, 2013, Pages 8498-8508

  Marty, Roman ^a   Szilluweit, Ruth ^a   Sánchez Ferrer, Antoni ^b   Bolisetty, Sreenath ^b   Adamcik, Jozef ^b   Mezzenga, Raffaele ^b   Spitzner, Eike Christian ^c   Feifer, Martin ^c   Steinmann, Stephan N ^a   Corminboeuf, Clémence ^a   Frauenrath, Holger ^a  

^a EPFL   (Switzerland)

^b ETH ZURICH   (Switzerland)

^c CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

"single stack" nanofibrils; hierarchically structured microfibers; organic nanowires; perylene bisimides; quaterthiophenes; supramolecular self assembly

Indexed keywords

MICROFIBERS; NANO-FIBRILS; ORGANIC NANOWIRES; PERYLENE BISIMIDES; QUATERTHIOPHENES; SUPRAMOLECULAR SELF-ASSEMBLIES;

CHROMOPHORES; HYDROGEN BONDS; NANOWIRES; ORGANIC POLYMERS; POLYCYCLIC AROMATIC HYDROCARBONS; SELF ASSEMBLY; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

NANOFIBERS;

EID: 84887003607     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn402234t     Document Type: Article

References (48)

1. Zhao, Y. S.; Wu, J.; Huang, J. Vertical Organic Nanowire Arrays: Controlled Synthesis and Chemical Sensors J. Am. Chem. Soc. 2009, 131, 3158-3159
2. Che, Y.; Yang, X.; Loser, S.; Zang, L. Expedient Vapor Probing of Organic Amines Using Fluorescent Nanofibers Fabricated from an n-Type Organic Semiconductor Nano Lett. 2008, 8, 2219-2223
3. Che, Y.; Gross, D. E.; Huang, H.; Yang, D.; Yang, X.; Discekici, E.; Xue, Z.; Zhao, H.; Moore, J. S.; Zang, L. Diffusion-Controlled Detection of Trinitrotoluene: Interior Nanoporous Structure and Low Highest Occupied Molecular Orbital Level of Building Blocks Enhance Selectivity and Sensitivity J. Am. Chem. Soc. 2012, 134, 4978-4982
4. Wicklein, A.; Ghosh, S.; Sommer, M.; Würthner, F.; Thelakkat, M. Self-Assembly of Semiconductor Organogelator Nanowires for Photoinduced Charge Separation ACS Nano 2009, 3, 1107-1114
5. Xin, H.; Kim, F. S.; Jenekhe, S. A. Highly Efficient Solar Cells Based on Poly(3-butylthiophene) Nanowires J. Am. Chem. Soc. 2008, 130, 5424-5425
6. Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics Science 2001, 293, 1119-1122
7. Yamamoto, Y.; Fukushima, T.; Suna, Y.; Ishii, N.; Saeki, A.; Seki, S.; Tagawa, S.; Taniguchi, M.; Kawai, T.; Aida, T. Photoconductive Coaxial Nanotubes of Molecularly Connected Electron Donor and Acceptor Layers Science 2006, 314, 1761-1764
8. Briseno, A. L.; Mannsfeld, S. C. B.; Jenekhe, S. A.; Bao, Z.; Xia, Y. Introducing Organic Nanowire Transistors Mater. Today 2008, 11, 38-47
9. Xiao, S.; Tang, J.; Beetz, T.; Guo, X.; Tremblay, N.; Siegrist, T.; Zhu, Y.; Steigerwald, M.; Nuckolls, C. Transferring Self-Assembled, Nanoscale Cables into Electrical Devices J. Am. Chem. Soc. 2006, 128, 10700-10701
10. Grozema, F. C.; Siebbeles, L. D. A. Mechanism of Charge Transport in Self-Organizing Organic Materials Int. Rev. Phys. Chem. 2008, 27, 87-138
11. Aleshin, A. N.; Lee, H. J.; Park, Y. W.; Akagi, K. One-Dimensional Transport in Polymer Nanofibers Phys. Rev. Lett. 2004, 93, 196601
12. Kim, F. S.; Ren, G.; Jenekhe, S. A. One-Dimensional Nanostructures of π-Conjugated Molecular Systems: Assembly, Properties, and Applications from Photovoltaics, Sensors, and Nanophotonics to Nanoelectronics Chem. Mater. 2010, 23, 682-732
13. Faramarzi, V.; Niess, F.; Moulin, E.; Maaloum, M.; Dayen, J. F.; Beaufrand, J. B.; Zanettini, S.; Doudin, B.; Giuseppone, N. Light-Triggered Self-Construction of Supramolecular Organic Nanowires as Metallic Interconnects Nat. Chem. 2012, 4, 485-490
14. Kim, D. H.; Lee, D. Y.; Lee, H. S.; Lee, W. H.; Kim, Y. H.; Han, J. I.; Cho, K. High-Mobility Organic Transistors Based on Single-Crystalline Microribbons of Triisopropylsilylethynyl Pentacene via Solution-Phase Self-Assembly Adv. Mater. 2007, 19, 678-682
15. Briseno, A. L.; Mannsfeld, S. C. B.; Lu, X.; Xiong, Y.; Jenekhe, S. A.; Bao, Z.; Xia, Y. Fabrication of Field-Effect Transistors from Hexathiapentacene Single-Crystal Nanowires Nano Lett. 2007, 7, 668-675
16. Ahmed, E.; Earmme, T.; Ren, G.; Jenekhe, S. A. Novel n-Type Conjugated Ladder Heteroarenes: Synthesis, Self-Assembly of Nanowires, Electron Transport, and Electroluminescence of Bisindenoanthrazolines Chem. Mater. 2010, 22, 5786-5796
17. Balakrishnan, K.; Datar, A.; Oitker, R.; Chen, H.; Zuo, J.; Zang, L. Nanobelt Self-Assembly from an Organic n-Type Semiconductor: Propoxyethyl-PTCDI J. Am. Chem. Soc. 2005, 127, 10496-10497
18. Ajayaghosh, A.; George, S. J. First Phenylenevinylene Based Organogels: Self-Assembled Nanostructures via Cooperative Hydrogen Bonding and π-Stacking J. Am. Chem. Soc. 2001, 123, 5148-5149
19. Schwab, A. D.; Smith, D. E.; Bond-Watts, B.; Johnston, D. E.; Hone, J.; Johnson, A. T.; de Paula, J. C.; Smith, W. F. Photoconductivity of Self-Assembled Porphyrin Nanorods Nano Lett. 2004, 4, 1261-1265
20. Shao, H.; Parquette, J. R. A π-Conjugated Hydrogel Based on an Fmoc-Dipeptide Naphthalene Diimide Semiconductor Chem. Commun. 2010, 46, 4285-4287
21. Sun, Y.; Tan, L.; Jiang, S.; Qian, H.; Wang, Z.; Yan, D.; Di, C.; Wang, Y.; Wu, W.; Yu, G. High-Performance Transistor Based on Individual Single-Crystalline Micrometer Wire of Perylo[1,12-b,c,d]thiophene J. Am. Chem. Soc. 2007, 129, 1882-1883
22. Hong, D.-J.; Lee, E.; Lee, M. Nanofibers from Self-Assembly of an Aromatic Facial Amphiphile with Oligo(ethylene oxide) Dendrons Chem. Commun. 2007, 1801-1803
23. Lee, C. C.; Grenier, C.; Meijer, E. W.; Schenning, A. P. H. J. Preparation and Characterization of Helical Self-Assembled Nanofibers Chem. Soc. Rev. 2009, 38, 671-683
24. Balakrishnan, K.; Datar, A.; Zhang, W.; Yang, X.; Naddo, T.; Huang, J.; Zuo, J.; Yen, M.; Moore, J. S.; Zang, L. Nanofibril Self-Assembly of an Arylene Ethynylene Macrocycle J. Am. Chem. Soc. 2006, 128, 6576-6577
25. Hernando, J.; de Witte, P. A. J.; van Dijk, E. M. H. P.; Korterik, J.; Nolte, R. J. M.; Rowan, A. E.; García-Parajó, M. F.; van Hulst, N. F. Investigation of Perylene Photonic Wires by Combined Single-Molecule Fluorescence and Atomic Force Microscopy Angew. Chem., Int. Ed. 2004, 43, 4045-4049
26. Würthner, F.; Bauer, C.; Stepanenko, V.; Yagai, S. A Black Perylene Bisimide Super Gelator with an Unexpected J-Type Absorption Band Adv. Mater. 2008, 20, 1695-1698
27. Vadehra, G. S.; Wall, B. D.; Diegelmann, S. R.; Tovar, J. D. On-Resin Dimerization Incorporates a Diverse Array of pi-Conjugated Functionality within Aqueous Self-Assembling Peptide Backbones Chem. Commun. 2010, 46, 3947-3949
28. Yagai, S.; Seki, T.; Murayama, H.; Wakikawa, Y.; Ikoma, T.; Kikkawa, Y.; Karatsu, T.; Kitamura, A.; Honsho, Y.; Seki, S. Structural and Electronic Properties of Extremely Long Perylene Bisimide Nanofibers Formed through a Stoichiometrically Mismatched, Hydrogen-Bonded Complexation Small 2010, 6, 2731-2740
29. Wall, B. D.; Diegelmann, S. R.; Zhang, S.; Dawidczyk, T. J.; Wilson, W. L.; Katz, H. E.; Mao, H.-Q.; Tovar, J. D. Aligned Macroscopic Domains of Optoelectronic Nanostructures Prepared via Shear-Flow Assembly of Peptide Hydrogels Adv. Mater. 2011, 23, 5009-5014
30. Marcon, V.; Breiby, D. W.; Pisula, W.; Dahl, J.; Kirkpatrick, J.; Patwardhan, S.; Grozema, F.; Andrienko, D. Understanding Structure-Mobility Relations for Perylene Tetracarboxydiimide Derivatives J. Am. Chem. Soc. 2009, 131, 11426-11432
31. Pisula, W.; Tomovic, Z.; Simpson, C.; Kastler, M.; Pakula, T.; Müllen, K. Relationship between Core Size, Side Chain Length, and the Supramolecular Organization of Polycyclic Aromatic Hydrocarbons Chem. Mater. 2005, 17, 4296-4303
32. Brédas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Organic Semiconductors: A Theoretical Characterization of the Basic Parameters Governing Charge Transport Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5804-5809
33. Henson, Z. B.; Müllen, K.; Bazan, G. C. Design Strategies for Organic Semiconductors Beyond the Molecular Formula Nat. Chem. 2012, 4, 699-704
34. Tian, L.; Szilluweit, R.; Marty, R.; Bertschi, L.; Zerson, M.; Spitzner, E.-C.; Magerle, R.; Frauenrath, H. Development of a Robust Supramolecular Method to Prepare Well-Defined Nanofibrils from Conjugated Molecules Chem. Sci. 2012, 3, 1512-1521
35. Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L. D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Photoluminescence and Conductivity of Self-Assembled π-π Stacks of Perylene Bisimide Dyes Chem.-Eur. J. 2007, 13, 436-449
36. Thalacker, C.; Würthner, F. Chiral Perylene Bisimide-Melamine Assemblies: Hydrogen Bond-Directed Growth of Helically Stacked Dyes with Chiroptical Properties Adv. Funct. Mater. 2002, 12, 209-218
37. Dehm, V.; Chen, Z.; Baumeister, U.; Prins, P.; Siebbeles, L. D. A.; Würthner, F. Helical Growth of Semiconducting Columnar Dye Assemblies Based on Chiral Perylene Bisimides Org. Lett. 2007, 9, 1085-1088
38. Hu, J.; Wenfeng, K.; Deng, K.; Zou, W.; Huang, Y.; Wei, Z.; Faul, C. F. J. Self-Assembled Sugar-Substituted Perylene Diimide Nanostructures with Homochirality and High Gas Sensitivity Adv. Funct. Mater. 2012, 22, 4149-4158
39. Kawano, S.-I.; Fujita, N.; Shinkai, S. Quater-, Quinque-, and Sexithiophene Organogelators: Unique Thermochromism and Heating-Free Sol-Gel Phase Transition Chem.-Eur. J. 2005, 11, 4735-4742
40. Measey, T. J.; Schweitzer-Stenner, R. Vibrational Circular Dichroism as a Probe of Fibrillogenesis: The Origin of the Anomalous Intensity Enhancement of Amyloid-like Fibrils J. Am. Chem. Soc. 2011, 133, 1066-1076
41. Spitzner, E.-C.; Riesch, C.; Szilluweit, R.; Tian, L.; Frauenrath, H.; Magerle, R. Multi-Set Point Intermittent Contact (MUSIC) Mode Atomic Force Microscopy of Oligothiophene Fibrils ACS Macro Lett. 2012, 1, 380-383
42. Spitzner, E.-C.; Riesch, C.; Magerle, R. Subsurface Imaging of Soft Polymeric Materials with Nanoscale Resolution ACS Nano 2011, 5, 315-320
43. Tanaka, T.; Chatani, Y.; Tadokoro, H. Crystal Structure of Polyisobutylene J. Polym. Sci., Polym. Phys. Ed. 1974, 12, 515-531
44. Suter, U. W.; Saiz, E.; Flory, P. J. Conformational Characteristics of Polyisobutylene Macromolecules 1983, 16, 1317-1328
45. Zhao, H. M.; Pfister, J.; Settels, V.; Renz, M.; Kaupp, M.; Dehm, V. C.; Würthner, F.; Fink, R. F.; Engels, B. Understanding Ground-and Excited-State Properties of Perylene Tetracarboxylic Acid Bisimide Crystals by Means of Quantum Chemical Computations J. Am. Chem. Soc. 2009, 131, 15660-15668
46. Kayunkid, N.; Uttiya, S.; Brinkmann, M. Structural Model of Regioregular Poly(3-hexylthiophene) Obtained by Electron Diffraction Analysis Macromolecules 2010, 43, 4961-4967
47. Chai, J.-D.; Head-Gordon, M. Long-Range Corrected Hybrid Density Functionals With Damped Atom-Atom Dispersion Corrections Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
48. Weigend, F.; Ahlrichs, R. Balanced Basis Sets of Split Valence, Triple Zeta Valence and Quadruple Zeta Valence Quality for H to Rn: Design and Assessment of Accuracy Phys. Chem. Chem. Phys. 2005, 7, 3297-3305