Growth of polythiophene/perylene tetracarboxydiimide donor/acceptor shish-kebab nanostructures by coupled crystal modification

ACS Nano

Volumn 6, Issue 12, 2012, Pages 10924-10929

  Bu, Laju ^a   Pentzer, Emily ^a   Bokel, Felicia A ^a   Emrick, Todd ^a   Hayward, Ryan C ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

coupled crystallization; donor acceptor; heterogeneous nucleation; perylene tetracaboxydiimide; poly(3 hexyl thiophene) (P3HT); shish kebab cystals

Indexed keywords

DONOR/ACCEPTOR; HETEROGENEOUS NUCLEATION; PERYLENES; POLY(3-HEXYL THIOPHENE) (P3HT); SHISH-KEBABS;

CRYSTALLINE MATERIALS; NANOWIRES; NUCLEATION; POLYCYCLIC AROMATIC HYDROCARBONS; THIOPHENE;

SOLVENTS;

DRUG DERIVATIVE; IMIDE; NANOMATERIAL; PERYLENE; POLY(3 HEXYLTHIOPHENE); POLY(3-HEXYLTHIOPHENE); SOLVENT; THIOPHENE DERIVATIVE;

ARTICLE; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; IMIDES; NANOSTRUCTURES; PERYLENE; SOLVENTS; THIOPHENES;

EID: 84871564125     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn3043836     Document Type: Article

References (43)

1. Günes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated Polymer-Based Organic Solar Cells Chem. Rev. 2007, 107, 1324-1338
2. Peet, J.; Heeger, A. J.; Bazan, G. C. The Role of Processing in the Fabrication and Optimization of Plastic Solar Cells Acc. Chem. Res. 2009, 42, 1700-1708
3. Brady, M. A.; Su, G. M.; Chabinyc, M. L. Recent Progress in the Morphology of Bulk Heterojunction Photovoltaics Soft Matter 2011, 7, 11065-11077
4. Buxton, G. A.; Clarke, N. Predicting Structure and Property Relations in Polymeric Photovoltaic Devices Phys. Rev. B 2006, 74, 085207
5. Slota, J. E.; He, X. M.; Huck, W. T. S. Controlling Nanoscale Morphology in Polymer Photovoltaic Devices Nano Today 2010, 5, 231-242
6. Peet, J.; Senatore, M. L.; Heeger, A. J.; Bazan, G. C. The Role of Processing in the Fabrication and Optimization of Plastic Solar Cells Adv. Mater. 2009, 21, 1521-1527
7. Thompson, B. C.; Fréchet, J. M. J. Polymer-Fullerene Composite Solar Cells Angew. Chem.-Int. Ed. 2008, 47, 58-77
8. Topham, P. D.; Parnell, A. J.; Hiorns, R. C. Block Copolymer Strategies for Solar Cell Technology J. Polym. Sci. Pt. B 2011, 49, 1131-1156
9. Liang, Y. Y.; Wang, H. B.; Yuan, S. W.; Lee, Y. G.; Gan, L.; Yu, L. P. Conjugated Block Copolymers and Co-Oligomers: From Supramolecular Assembly to Molecular Electronics J. Mater. Chem. 2007, 17, 2183-2194
10. Bu, L. J.; Guo, X. Y.; Yu, B.; Qu, Y.; Xie, Z. Y.; Yan, D. H.; Geng, Y. H.; Wang, F. S. Monodisperse Co-oligomer Approach toward Nanostructured Films with Alternating Donor-Acceptor Lamellae J. Am. Chem. Soc. 2009, 131, 13242-13243
11. Bassani, D. M.; Jonusauskaite, L.; Lavie-Cambot, A.; McClenaghan, N. D.; Pozzo, J. L.; Ray, D.; Vives, G. Harnessing Supramolecular Interactions in Organic Solid-State Devices: Current Status and Future Potential Coord. Chem. Rev. 2010, 254, 2429-2445
12. González-Rodríguez, D.; Schenning, A. P. H. J. Hydrogen-Bonded Supramolecular pi-Functional Materials Chem. Mater. 2011, 23, 310-325
13. Würthner, F.; Chen, Z. J.; Hoeben, F. J. M.; Osswald, P.; You, C. C.; Jonkheijm, P.; von Herrikhuyzen, J.; Schenning, A.; van der Schoot, P.; Meijer, E. W. et al. Supramolecular p-n-Heterojunctions by Co-Self-Organization of Oligo(p -phenylene vinylene) and Perylene Bisimide Dyes J. Am. Chem. Soc. 2004, 126, 10611-10618
14. Sugiyasu, K.; Kawano, S. I.; Fujita, N.; Shinkai, S. Self-Sorting Organogels with p-n Heterojunction Points Chem. Mater. 2008, 20, 2863-2865
15. Grünbaum, E.; Matthews, J. W. Epitaxial Growth; Academic Press, Harcourt Brace Jovanovich: New York, 1975; Vol. 2.
16. Schmelzer, J. Nucleation Theory and Application; Wiley-VCH: Weinheim, Germany, 2005.
17. Ayers, J. E. Heteroepitaxy of Semiconductors; Theory, Growth, and Characterization; Taylor & Francis Group: LLC, 2007.
18. Santiso, J.; Burriel, M. Deposition and Characterisation of Epitaxial Oxide Thin Films for SOFCs J. Solid State Electrochem. 2011, 15, 985-1006
19. Hinderhofer, A.; Schreiber, F. Organic-Organic Heterostructures: Concepts and Applications Chemphyschem 2012, 13, 628-643
20. Zhang, Y. J.; Dong, H. L.; Tang, Q. X.; Ferdous, S.; Liu, F.; Mannsfeld, S. C. B.; Hu, W. P.; Briseno, A. L. Organic Single-Crystalline p-n Junction Nanoribbons J. Am. Chem. Soc. 2010, 132, 11580-11584
21. Brinkmann, M. Structure and Morphology Control in Thin Films of Regioregular Poly(3-hexylthiophene) J. Polym. Sci., Part B 2011, 49, 1218-1233
22. Liu, J. H.; Zou, J. H.; Zhai, L. Bottom-up Assembly of Poly(3-hexylthiophene) on Carbon Nanotubes: 2D Building Blocks for Nanoscale Circuits Macromol. Rapid Commun. 2009, 30, 1387-1391
23. Chunder, A.; Liu, J. H.; Zhai, L. Reduced Graphene Oxide/Poly(3- hexylthiophene) Supramolecular Composites Macromol. Rapid Commun. 2010, 31, 380-384
24. Zhou, X.; Yang, X. N. Improved Dispersibility of Graphene Oxide in o -Dichlorobenzene by Adding a Poly(3-alkylthiophene) Carbon 2012, 50, 4566-4572
25. Brinkmann, M.; Chandezon, F.; Pansu, R. B.; Julien-Rabant, C. Epitaxial Growth of Highly Oriented Fibers of Semiconducting Polymers with a Shish-Kebab-like Superstructure Adv. Funct. Mater. 2009, 19, 2759-2766
26. Brinkmann, M.; Contal, C.; Kayunkid, N.; Djuric, T.; Resel, R. Highly Oriented and Nanotextured Films of Regioregular Poly(3-hexylthiophene) Grown by Epitaxy on the Nanostructured Surface of an Aromatic Substrate Macromolecules 2010, 43, 7604-7610
27. Yan, H.; Yan, Y.; Yu, Z.; Wei, Z. X. Self-Assembling Branched and Hyperbranched Nanostructures of Poly(3-hexylthiophene) by a Solution Process J Phys. Chem. C 2011, 115, 3257-3262
28. Patra, S. K.; Ahmed, R.; Whittell, G. R.; Lunn, D. J.; Dunphy, E. L.; Winnik, M. A.; Manners, I. Cylindrical Micelles of Controlled Length with a π-Conjugated Polythiophene Core via Crystallization-Driven Self-Assembly J. Am. Chem. Soc. 2011, 133, 8842-8845
29. Kamps, A. C.; Fryd, M.; Park, S. J. Hierarchical Self-Assembly of Amphiphilic Semiconducting Polymers into Isolated, Bundled, and Branched Nanofibers ACS Nano 2012, 6, 2844-2852
30. Li, C.; Wonneberger, H. Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow Adv. Mater. 2012, 24, 613-636
31. Dittmer, J. J.; Marseglia, E. A.; Friend, R. H. Electron Trapping in Dye/Polymer Blend Photovoltaic Cells Adv. Mater. 2000, 12, 1270-1274
32. Guo, X. Y.; Bu, L. J.; Zhao, Y.; Xie, Z. Y.; Geng, Y. H.; Wang, L. X. Controlled Phase Separation for Efficient Energy Conversion in Dye/Polymer Blend Bulk Heterojunction Photovoltaic Cells Thin Solid Films 2009, 517, 4654-4657
33. Kamm, V.; Battagliarin, G.; Howard, I. A.; Pisula, W.; Mavrinskiy, A.; Li, C.; Mullen, K.; Laquai, F. Polythiophene:Perylene Diimide Solar Cells-The Impact of Alkyl-Substitution on the Photovoltaic Performance Adv. Energy Mater. 2011, 1, 297-302
34. Sommer, M.; Huttner, S.; Steiner, U.; Thelakkat, M. Influence of Molecular Weight on the Solar Cell Performance of Double-Crystalline Donor-Acceptor Block Copolymers Appl. Phys. Lett. 2009, 95, 183308
35. Zhang, Q. L.; Cirpan, A.; Russell, T. P.; Emrick, T. Donor-Acceptor Poly(thiophene-block-perylene diimide) Copolymers: Synthesis and Solar Cell Fabrication Macromolecules 2009, 42, 1079-1082
36. Tao, Y. F.; McCulloch, B.; Kim, S.; Segalman, R. A. The Relationship between Morphology and Performance of Donor-Acceptor Rod-Coil Block Copolymer Solar Cells Soft Mater. 2009, 5, 4219-4230
37. Rajaram, S.; Armstrong, P. B.; Kim, B. J.; Fréchet, J. M. J. Effect of Addition of a Diblock Copolymer on Blend Morphology and Performance of Poly(3-hexylthiophene):Perylene Diimide Solar Cells Chem. Mater. 2009, 21, 1775-1777
38. Briseno, A. L.; Mannsfeld, S. C. B.; Reese, C.; Hancock, J. M.; Xiong, Y.; Jenekhe, S. A.; Bao, Z.; Xia, Y. N. Perylenediimide Nanowires and Their Use in Fabricating Field-Effect Transistors and Complementary Inverters Nano Lett. 2007, 7, 2847-2853
39. Liu, J.; Arif, M.; Zou, J.; Khondaker, S. I.; Zhai, L. Controlling Poly(3-hexylthiophene) Crystal Dimension: Nanowhiskers and Nanoribbons Macromolecules 2009, 42, 9390-9393
40. Song, R. Q.; Cölfen, H. Additive Controlled Crystallization CrystEngComm 2011, 13, 1249-1276
41. Balakrishnan, K.; Datar, A.; Naddo, T.; Huang, J. L.; Oitker, R.; Yen, M.; Zhao, J. C.; Zang, L. Effect of Side-Chain Substituents on Self-Assembly of Perylene Diimide Molecules: Morphology Control J. Am. Chem. Soc. 2006, 128, 7390-7398
42. Demming, S.; Langhals, H. Very Soluble and Photostable Perylene Fluorescent Dyes Chem. Ber. 1998, 121, 225-230
43. Loewe, R. S.; Ewbank, P. C.; Liu, J. S.; Zhai, L.; McCullough, R. D. Regioregular, Head-to-Tail Coupled Poly(3-alkylthiophenes) Made Easy by the GRIM Method: Investigation of the Reaction and the Origin of Regioselectivity Macromolecules 2001, 34, 4324-4333