Tailoring ultrasound-induced growth of perylene diimide nanowire crystals from solution by modification with poly(3-hexyl thiophene)

ACS Nano

Volumn 9, Issue 2, 2015, Pages 1878-1885

  Bu, Laju ^a,b   Dawson, Trenton J ^a   Hayward, Ryan C ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

living crystallization; organic nanocrystals; seeded crystallization; selective adsorption; soluble additive; sonocrystallization

Indexed keywords

ADDITIVES; BIOMINERALIZATION; CRYSTAL GROWTH; CRYSTALLIZATION; NANOCRYSTALLINE MATERIALS; NANOCRYSTALS; NANOWIRES; ORGANIC SEMICONDUCTOR MATERIALS; POLYCYCLIC AROMATIC HYDROCARBONS; SOLS; SUSPENSIONS (FLUIDS); THIOPHENE; ULTRASONICS;

ORGANIC NANOCRYSTALS; SEEDED CRYSTALLIZATION; SELECTIVE ADSORPTION; SOLUBLE ADDITIVES; SONOCRYSTALLIZATION;

GROWTH RATE;

IMIDE; NANOWIRE; PERYLENE; PERYLENEDIIMIDE; POLY(3-HEXYLTHIOPHENE); SOLUTION AND SOLUBILITY; THIOPHENE DERIVATIVE;

ANALOGS AND DERIVATIVES; CHEMISTRY; NANOTECHNOLOGY; PROCEDURES; SOLUTION AND SOLUBILITY; TEMPERATURE; ULTRASOUND;

IMIDES; NANOTECHNOLOGY; NANOWIRES; PERYLENE; SOLUTIONS; SONICATION; TEMPERATURE; THIOPHENES; ULTRASONIC WAVES;

EID: 84923435468     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn506795q     Document Type: Article

References (47)

1. Heeger, A. J. 25th Anniversary Article: Bulk Heterojunction Solar Cells: Understanding the Mechanism of Operation Adv. Mater. 2013, 26, 10-28
2. Noriega, R.; Rivnay, J.; Vandewal, K.; Koch, F. P. V.; Stingelin, N.; Smith, P.; Toney, M. F.; Salleo, A. A General Relationship between Disorder, Aggregation and Charge Transport in Conjugated Polymers Nat. Mater. 2013, 12, 1037-1043
3. Li, R. J.; Hu, W. P.; Liu, Y. Q.; Zhu, D. B. Micro- and Nanocrystals of Organic Semiconductors Acc. Chem. Res. 2010, 43, 529-540
4. Liu, F.; Gu, Y.; Jung, J. W.; Jo, W. H.; Russell, T. P. On the Morphology of Polymer-Based Photovoltaics J. Polym. Sci., Part B: Polym. Phys. 2012, 50, 1018-1044
5. Liao, H. C.; Ho, C. C.; Chang, C. Y.; Jao, M. H.; Darling, S. B.; Su, W. F. Additives for Morphology Control in High-Efficiency Organic Solar Cells Mater. Today 2013, 16, 326-336
6. He, M.; Wang, M. Y.; Lin, C. J.; Lin, Z. Q. Optimization of Molecular Organization and Nanoscale Morphology for High Performance Low Bandgap Polymer Solar Cells Nanoscale 2014, 6, 3984-3994
7. Dang, M. T.; Hirsch, L.; Wantz, G.; Wuest, J. D. Controlling the Morphology and Performance of Bulk Heterojunctions in Solar Cells. Lessons Learned from the Benchmark Poly(3-hexylthiophene): 6,6-Phenyl-C-61-butyric Acid Methyl Ester System Chem. Rev. 2013, 113, 3734-3765
8. Arias, A. C.; MacKenzie, J. D.; McCulloch, I.; Rivnay, J.; Salleo, A. Materials and Applications for Large Area Electronics: Solution-Based Approaches Chem. Rev. 2010, 110, 3-24
9. Samitsu, S.; Shimomura, T.; Ito, K. Nanofiber Preparation by Whisker Method Using Solvent-Soluble Conducting Polymers Thin Solid Films 2008, 516, 2478-2486
10. Kim, F. S.; Ren, G. Q.; Jenekhe, S. A. One-Dimensional Nanostructures of π-Conjugated Molecular Systems: Assembly, Properties, and Applications from Photovoltaics, Sensors, and Nanophotonics to Nanoelectronics Chem. Mater. 2011, 23, 682-732
11. Berson, S.; De Bettignies, R.; Bailly, S.; Guillerez, S. Poly(3-hexylthiophene) Fibers for Photovoltaic Applications Adv. Funct. Mater. 2007, 17, 1377-1384
12. 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
13. Li, L. G.; Lu, G. H.; Yang, X. N. Improving Performance of Polymer Photovoltaic Devices Using an Annealing-Free Approach via Construction of Ordered Aggregates in Solution J. Mater. Chem. 2008, 18, 1984-1990
14. Yu, W.; Yang, D.; Zhu, X. G.; Wang, X. L.; Tu, G. L.; Fan, D. Y.; Zhang, J.; Li, C. Control of Nanomorphology in All-Polymer Solar Cells via Assembling Nanoaggregation in a Mixed Solution ACS Appl. Mater. Interfaces 2014, 6, 2348-2353
15. Bag, M.; Gehan, T. S.; Algaier, D. D.; Liu, F.; Nagarjuna, G.; Lahti, P. M.; Russell, T. P.; Venkataraman, D. Efficient Charge Transport in Assemblies of Surfactant-Stabilized Semiconducting Nanoparticles Adv. Mater. 2013, 25, 6411-6415
16. Nagarjuna, G.; Baghgar, M.; Labastide, J. A.; Algaier, D. D.; Barnes, M. D.; Venkataraman, D. Tuning Aggregation of Poly(3-hexylthiophene) within Nanoparticles ACS Nano 2012, 6, 10750-10758
17. Liu, J. S.; Sheina, E.; Kowalewski, T.; McCullough, R. D. Tuning the Electrical Conductivity and Self-Assembly of Regioregular Polythiophene by Block Copolymerization: Nanowire Morphologies in New Di- and Triblock Copolymers Angew. Chem., Int. Ed. 2002, 41, 329-332
18. Wang, H. W.; Pentzer, E.; Emrick, T.; Russell, T. P. Preparation of Low Band Gap Fibrillar Structures by Solvent-Induced Crystallization ACS Macro Lett. 2014, 3, 30-34
19. Hahm, S. G.; Rho, Y.; Jung, J.; Kim, S. H.; Sajoto, T.; Kim, F. S.; Barlow, S.; Park, C. E.; Jenekhe, S. A.; Marder, S. R. High-Performance n-Channel Thin-Film Field-Effect Transistors Based on a Nanowire-Forming Polymer Adv. Funct. Mater. 2013, 23, 2060-2071
20. Ren, G. Q.; Ahmed, E.; Jenekhe, S. A. Nanowires of Oligothiophene-Functionalized Naphthalene Diimides: Self Assembly, Morphology, and All-Nanowire Bulk Heterojunction Solar Cells J. Mater. Chem. 2012, 22, 24373-24379
21. 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
22. Zang, L.; Che, Y. K.; Moore, J. S. One-Dimensional Self-Assembly of Planar pi-Conjugated Molecules: Adaptable Building Blocks for Organic Nanodevices Acc. Chem. Res. 2008, 41, 1596-1608
23. Lim, J. A.; Lee, H. S.; Lee, W. H.; Cho, K. Control of the Morphology and Structural Development of Solution-Processed Functionalized Acenes for High-Performance Organic Transistors Adv. Funct. Mater. 2009, 19, 1515-1525
24. Cao, X. Q.; Wu, Y. S.; Fu, H. B.; Yao, J. N. Self-Assembly of Perylenediimide Nanobelts and Their Size-Tunable Exciton Dynamic Properties J. Phys. Chem. Lett. 2011, 2, 2163-2167
25. Hartnett, P. E.; Timalsina, A.; Matte, H. S. S. R.; Zhou, N.; Guo, X.; Zhao, W.; Facchetti, A.; Chang, R. P. H.; Hersam, M. C.; Wasielewski, M. R. Slip-Stacked Perylenediimides as an Alternative Strategy for High Efficiency Nonfullerene Acceptors in Organic Photovoltaics J. Am. Chem. Soc. 2014, 136, 16345-16356
26. Bu, L. J.; Pentzer, E.; Bokel, F. A.; Emrick, T.; Hayward, R. C. Growth of Polythiophene/Perylene Tetracarboxydiimide Donor/Acceptor Shish-Kebab Nanostructures by Coupled Crystal Modification ACS Nano 2012, 6, 10924-10929
27. Li, L.; Jacobs, D. L.; Bunes, B. R.; Huang, H.; Yang, X.; Zang, L. Anomalous High Photovoltages Observed in Shish Kebab-like Organic p-n Junction Nanostructures Polym. Chem. 2014, 5, 309-313
28. Chen, J. H.; Shao, M.; Xiao, K.; He, Z. R.; Li, D. W.; Lokitz, B. S.; Hensley, D. K.; Kilbey, S. M.; Anthony, J. E.; Keum, J. K. Conjugated Polymer-Mediated Polymorphism of a High Performance, Small-Molecule Organic Semiconductor with Tuned Intermolecular Interactions, Enhanced Long-Range Order, and Charge Transport Chem. Mater. 2013, 25, 4378-4386
29. Suzuki, T.; Okamoto, T.; Saeki, A.; Seki, S.; Sato, H.; Matsuo, Y. Formation of Photoconductive Nanowires of Tetracene Derivative in Composite Thin Film ACS Appl. Mater. Interfaces 2013, 5, 1937-1942
30. Song, R. Q.; Cölfen, H. Additive Controlled Crystallization CrystEngComm 2011, 13, 1249-1276
31. Ruecroft, G.; Hipkiss, D.; Ly, T.; Maxted, N.; Cains, P. W. Sonocrystallization: The Use of Ultrasound for Improved Industrial Crystallization Org. Process Res. Dev. 2005, 9, 923-932
32. Li, H.; Wang, J. K.; Bao, Y.; Guo, Z. C.; Zhang, M. Y. Rapid Sonocrystallization in the Salting-out Process J. Cryst. Growth 2003, 247, 192-198
33. Kang, P.; Chen, C. N.; Hao, L. Y.; Zhu, C. L.; Hu, Y.; Chen, Z. Y. A Novel Sonication Route To Prepare Anthracene Nanoparticles Mater. Res. Bull. 2004, 39, 545-551
34. Zhao, K.; Xue, L. J.; Liu, J. G.; Gao, X.; Wu, S. P.; Han, Y. C.; Geng, Y. H. A New Method To Improve Poly(3-hexyl thiophene) (P3HT) Crystalline Behavior: Decreasing Chains Entanglement To Promote Order-Disorder Transformation in Solution Langmuir 2010, 26, 471-477
35. Kim, B. G.; Kim, M. S.; Kim, J. Ultrasonic-Assisted Nanodimensional Self-Assembly of Poly-3-hexylthiophene for Organic Photovoltaic Cells ACS Nano 2010, 4, 2160-2166
36. Aiyar, A. R.; Hong, J. I.; Izumi, J.; Choi, D.; Kleinhenz, N.; Reichmanis, E. Ultrasound-Induced Ordering in Poly(3-hexylthiophene): Role of Molecular and Process Parameters on Morphology and Charge Transport ACS Appl. Mater. Interfaces 2013, 5, 2368-2377
37. Sehgal, C.; Steer, R. P.; Sutherland, R. G.; Verrall, R. E. Sonoluminescence of Argon Saturated Alkali-Metal Salt-Solutions as a Probe of Acoustic Cavitation J. Chem. Phys. 1979, 70, 2242-2248
38. de Castro, M. D. L.; Priego-Capote, F. Ultrasound-Assisted Crystallization (Sonocrystallization) Ultrason. Sonochem. 2007, 14, 717-724
39. Cravotto, G.; Gaudino, E. C.; Cintas, P. On the Mechanochemical Activation by Ultrasound Chem. Soc. Rev. 2013, 42, 7521-7534
40. Balakrishnan, K.; Datar, A.; Oitker, R.; Chen, H.; Zuo, J. M.; Zang, L. Nanobelt Self-Assembly from an Organic n-Type Semiconductor: Propoxyethyl-PTCDI J. Am. Chem. Soc. 2005, 127, 10496-10497
41. Usowicz, M. T.; Kelley, M. J.; Singer, K. D.; Duzhko, V. V. Tailored One- and Two-Dimensional Self-Assembly of a Perylene Diimide Derivative in Organic Solvents J. Phys. Chem. B 2011, 115, 9703-9709
42. Van Hook, A. Crystallization: Theory and Practice; Reinhold Pub. Corp.: New York, 1961.
43. Hulett, G. A. The Solubility of Gypsum As Affected by Size of Particles and by Different Crystallographic Surfaces J. Am. Chem. Soc. 1905, 27, 49-56
44. Brinkmann, M. Structure and Morphology Control in Thin Films of Regioregular Poly(3-hexylthiophene) J. Polym. Sci., Part B: Polym. Phys. 2011, 49, 1218-1233
45. Gädt, T.; Ieong, N. S.; Cambridge, G.; Winnik, M. A.; Manners, I. Complex and Hierarchical Micelle Architectures from Diblock Copolymers Using Living, Crystallization-Driven Polymerizations Nat. Mater. 2009, 8, 144-150
46. Gwyther, J.; Gilroy, J. B.; Rupar, P. A.; Lunn, D. J.; Kynaston, E.; Patra, S. K.; Whittell, G. R.; Winnik, M. A.; Manners, I. Dimensional Control of Block Copolymer Nanofibers with a Conjugated Core: Crystallization-Driven Solution Self-Assembly of Amphiphilic Poly(3-hexylthiophene)-b-poly(2-vinylpyridine) Chem.-Eur. J. 2013, 19, 9186-9197
47. 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