Noncovalent functionalization of graphene attaching [6,6]-phenyl-C61- butyric acid methyl ester (PCBM) and application as electron extraction layer of polymer solar cells

ACS Nano

Volumn 7, Issue 5, 2013, Pages 4070-4081

  Qu, Shuxuan ^a   Li, Minghua ^a   Xie, Lixin ^a   Huang, Xiao ^a   Yang, Jinguo ^a   Wang, Nan ^a   Yang, Shangfeng ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

6,6 phenyl C61 butyric acid methyl ester (PCBM); electron extraction layer; graphene; polymer solar cells; pyrene

Indexed keywords

[6 ,6]-PHENYL-C61-BUTYRIC ACID METHYL ESTERS; ELECTRON EXTRACTION; ESTERIFICATION REACTIONS; GEOMETRIC CONFIGURATIONS; NON-COVALENT FUNCTIONALIZATION; POLYMER SOLAR CELLS; REDUCED GRAPHENE OXIDES (RGO); SPECTROSCOPIC CHARACTERIZATION;

BUTYRIC ACID; ELECTRONS; ESTERIFICATION; ESTERS; EXTRACTION; HETEROJUNCTIONS; POLYMERS; PYRENE; SOLAR CELLS;

GRAPHENE;

EID: 84878344341     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn4001963     Document Type: Article

References (64)

1. Geim, A. K.; Novoselov, K. S. The Rise of Graphene Nat. Mater. 2004, 6, 183-191
2. Novoselov, K. S.; Geim, A. K.; Morozov, S. V.; Jiang, D.; Zhang, Y.; Dubonos, S. V.; Grigorieva, I. V.; Firsov, A. A. Electric Field Effect in Atomically Thin Carbon Films Science 2004, 306, 666-669
3. Zhang, Y.; Tan, Y. W.; Stormer, H. L.; Kim, P. Experimental Observation of the Quantum Hall Effect and Berry's Phase in Graphene Nature 2005, 438, 201-204
4. Nair, R. R.; Blake, P.; Grigorenko, A. N.; Novoselov, K. S.; Booth, T. J.; Stauber, T.; Peres, N. M. R.; Geim, A. K. Fine Structure Constant Defines Visual Transparency of Graphene Science 2008, 320, 1308
5. Zhu, Y. W.; Murali, S.; Stoller, M. D.; Ganesh, K. J.; Cai, W. W.; Ferreira, P. J.; Pirkle, A.; Wallace, R. M.; Cychosz, K. A.; Thommes, M.; Su, D. et al. Carbon-Based Supercapacitors Produced by Activation of Graphene Science 2011, 332, 1537-1541
6. Lee, C.; Wei, X.; Kysar, J. W.; Hone, J. Measurement of the Elastic Properties and Intrinsic Strength of Monolayer Graphene Science 2008, 321, 385-388
7. Balandin, A. A.; Ghosh, S.; Bao, W.; Calizo, I.; Teweldebrhan, D.; Miao, F.; Lau, C. N. Superior Thermal Conductivity of Single-Layer Graphene Nano Lett. 2008, 8, 902-907
8. Wan, X.; Long, G.; Huang, L.; Chen, Y. Graphene-A Promising Material for Organic Photovoltaic Cells Adv. Mater. 2011, 23, 5342-5358
9. Guo, C. X.; Guai, G. H.; Li, C. M. Graphene Based Materials: Enhancing Solar Energy Harvesting Adv. Energy Mater. 2011, 1, 448-452
10. Meric, I.; Han, M. Y.; Young, A. F.; Ozyilmaz, B.; Kim, P.; Shepard, K. L. Current Saturation in Zero-Bandgap, Top-Gated Graphene Field-Effect Transistors Nat. Nanotechnol. 2008, 3, 654-659
11. Wan, X.; Hang, Y.; Chen, Y. Focusing on Energy and Optoelectronic Applications: A Journey for Graphene and Graphene Oxide at Large Scale Acc. Chem. Res. 2011, 45, 598-607
12. Dai, L. Functionalization of Graphene for Efficient Energy Conversion and Storage Acc. Chem. Res. 2013, 46, 31-42
13. Huang, X.; Zeng, Z.; Fan, Z.; Liu, J.; Zhang, H. Graphene-Based Electrodes Adv. Mater. 2012, 24, 5979-6004
14. Pang, S.; Hernandez, Y.; Feng, X.; Mullen, K. Graphene as Transparent Electrode Material for Organic Electronics Adv. Mater. 2011, 23, 2779-2795
15. Wang, Y.; Tong, S. W.; Xu, X. F.; Ozyilmaz, B.; Loh, K. P. Interface Engineering of Layer-by-Layer Stacked Graphene Anodes for High-Performance Organic Solar Cells Adv. Mater. 2011, 23, 1514-1518
16. Li, S.-S.; Tu, K.-H.; Lin, C.-C.; Chen, C.-W.; Chhowalla, M. Solution-Processable Graphene Oxide as an Efficient Hole Transport Layer in Polymer Solar Cells ACS Nano 2010, 4, 3169-3174
17. Liu, Z.; He, D.; Wang, Y.; Wu, H.; Wang, J. Solution-Processable Functionalized Graphene in Donor/Acceptor-Type Organic Photovoltaic Cells Sol. Energy Mater. Sol. Cells 2010, 94, 1196-1200
18. Liu, J.; Xue, Y.; Gao, Y.; Yu, D.; Durstock, M.; Dai, L. Hole and Electron Extraction Layers Based on Graphene Oxide Derivatives for High-Performance Bulk Heterojunction Solar Cells Adv. Mater. 2012, 24, 2228-2233
19. Huang, X.; Qi, X.; Boey, F.; Zhang, H. Graphene-Based Composites Chem. Soc. Rev. 2012, 41, 666-686
20. Ahmad, I.; Khan, U.; Gun'ko, Y. K. Graphene, Carbon Nanotube and Ionic Liquid Mixtures: Towards New Quasi-Solid State Electrolytes for Dye Sensitised Solar Cells J. Mater. Chem 2011, 21, 16990-16996
21. Stankovich, S.; Dikin, D. A.; Dommett, G. H.; Kohlhaas, K. M.; Zimney, E. J.; Stach, E. A.; Piner, R. D.; Nguyen, S. T.; Ruoff, R. S. Graphene-Based Composite Materials Nature 2006, 442, 282-286
22. 2 Composite Films for Supercapacitors Electrochim. Acta 2010, 55, 4170-4173
23. Su, Q.; Pang, S.; Alijani, V.; Li, C.; Feng, X.; Müllen, K. Composites of Graphene with Large Aromatic Molecules Adv. Mater. 2009, 21, 3191-3195
24. Tung, V. C.; Huang, J. H.; Tevis, I.; Kim, F.; Kim, J.; Chu, C. W.; Stupp, S. I.; Huang, J. X. Surfactant-Free Water-Processable Photoconductive All-Carbon Composite J. Am. Chem. Soc. 2011, 133, 4940-4947
25. Zhang, X.; Huang, Y.; Wang, Y.; Ma, Y.; Liu, Z.; Chen, Y. Synthesis and Characterization of a Graphene-C60 Hybrid Material Carbon 2009, 47, 334-337
26. Zhang, Y.; Ren, L.; Wang, S.; Marathe, A.; Chaudhuri, J.; Li, G. Functionalization of Graphene Sheets through Fullerene Attachment J. Mater. Chem 2011, 21, 5386-5398
27. Zhang, X.; Liu, Z.; Huang, Y.; Wan, X.; Tian, J.; Ma, Y.; Chen, Y. Synthesis, Characterization and Nonlinear Optical Property of Graphene-C60 Hybrid J. Nanosci. Nanotechnol. 2009, 9, 5752-5756
28. Tung, V. C.; Huang, J. H.; Kim, J.; Smith, A. J.; Chu, C. W.; Huang, J. X. Towards Solution Processed All-Carbon Solar Cells: A Perspective Energy Environ. Sci. 2012, 5, 7810-7818
29. Ramuz, M. P.; Vosgueritchian, M.; Wei, P.; Wang, C.; Gao, Y.; Wu, Y.; Chen, Y.; Bao, Z. Evaluation of Solution-Processable Carbon-Based Electrodes for All-Carbon Solar Cells ACS Nano 2012, 6, 10384-10395
30. Lohrman, J.; Kumar, P. V.; Kirkeminde, A.; Ferralis, N.; Grossman, J. C.; Ren, S. Nanocarbon-Based Photovoltaics ACS Nano 2012, 6, 8896-8903
31. Liu, Z. B.; Xu, Y. F.; Zhang, X. Y.; Zhang, X. L.; Chen, Y. S.; Tian, J. G. Porphyrin and Fullerene Covalently Functionalized Graphene Hybrid Materials with Large Nonlinear Optical Properties J. Phys. Chem. B 2009, 113, 9681-9686
32. Yu, D.; Park, K.; Durstock, M.; Dai, L. Fullerene-Grafted Graphene for Efficient Bulk Heterojunction Polymer Photovoltaic Devices J. Phys.Chem. Lett. 2011, 2, 1113-1118
33. Hummelen, J. C.; Knight, B. W.; LePeq, F.; Wudl, F.; Yao, J.; Wilkins, C. L. Preparation and Characterization of Fulleroid and Methanofullerene Derivatives J. Org. Chem. 1995, 60, 532-538
34. Chen, M.; Li, M.; Wang, H.; Qu, S.; Zhao, X.; Xie, L.; Yang, S. Side-Chain Substitution of Poly(3-hexylthiophene) (P3HT) by PCBM via Postpolymerization: An Intramolecular Hybrid Of Donor and Acceptor Polym. Chem. 2013, 4, 550-557
35. Chen, L.; Yao, K.; Chen, Y. Can Morphology Tailoring Based on Functionalized Fullerene Nanostructures Improve the Performance of Organic Solar Cells? J. Mater. Chem. 2012, 22, 18768-18771
36. Neises, B.; Steglich, W. Simple Method for the Esterification of Carboxylic Acids Angew. Chem., Int. Ed. Engl. 1978, 17, 522-524
37. Xu, Y.; Bai, H.; Lu, G.; Li, C.; Shi, G. Flexible Graphene Films via the Filtration of Water-Soluble Noncovalent Functionalized Graphene Sheets J. Am. Chem. Soc. 2008, 130, 5856-5857
38. Li, M.; Xu, P.; Yang, J.; Ying, H.; Haubner, K.; Dunsch, L.; Yang, S. Synthesis of Pyrene-Substituted Poly(3-hexylthiophene) via Postpolymerization and Its Noncovalent Interactions with Single-Walled Carbon Nanotubes J. Phys. Chem. C 2011, 115, 4584-4593
39. Hummers, W. S., Jr.; Offeman, R. E. Preparation of Graphitic Oxide J. Am. Chem. Soc. 1958, 80, 1339-1339
40. Li, D.; Muller, M. B.; Gilje, S.; Kaner, R. B.; Wallace, G. G. Processable Aqueous Dispersions of Graphene Nanosheets Nat. Nanotechnol. 2008, 3, 101-105
41. Chen, J. L.; Yan, X. P. A Dehydration and Stabilizer-Free Approach to Production of Stable Water Dispersions of Graphene Nanosheets J. Mater. Chem. 2010, 20, 4328-4332
42. Szabó, T.; Berkesi, O.; Forgó, P.; Josepovits, K.; Sanakis, Y.; Petridis, D.; Dékány, I. Evolution of Surface Functional Groups in a Series of Progressively Oxidized Graphite Oxides Chem. Mater. 2006, 18, 2740-2749
43. Chiang, T. C.; Seitz, F. Photoemission Spectroscopy in Solids Ann. Phys. 2001, 10, 61-74
44. Yang, D.; Velamakanni, A.; Bozoklu, G.; Park, S.; Stoller, M.; Piner, R. D.; Stankovich, S.; Jung, I.; Field, D. A.; Ventrice, C. A. et al. Chemical Analysis of Graphene Oxide Films after Heat and Chemical Treatments by X-ray Photoelectron and Micro-Raman Spectroscopy Carbon 2009, 47, 145-152
45. Kang, H.; Kulkarni, A.; Stankovich, S.; Ruoff, R. S.; Baik, S. Restoring Electrical Conductivity of Dielectrophoretically Assembled Graphite Oxide Sheets by Thermal and Chemical Reduction Techniques Carbon 2009, 47, 1520-1525
46. Ferrari, A. C.; Meyer, J. C.; Scardaci, V.; Casiraghi, C.; Lazzeri, M.; Mauri, F.; Piscanec, S.; Jiang, D.; Novoselov, K. S.; Roth, S. et al. Raman Spectrum of Graphene and Graphene Layers Phys. Rev. Lett. 2006, 97, 187401
47. Ferrari, A. C.; Robertson, J. Interpretation of Raman Spectra of Disordered and Amorphous Carbon Phys. Rev. B 2000, 61, 14095-14107
48. Parviz, D.; Das, S.; Ahmed, H. S. T.; Irin, F.; Bhattacharia, S.; Green, M. J. Dispersions of Non-Covalently Functionalized Graphene with Minimal Stabilizer ACS Nano 2012, 6, 8857-8867
49. Gómez-Navarro, C.; Weitz, R. T.; Bittner, A. M.; Scolari, M.; Mews, A.; Burghard, M.; Kern, K. Electronic Transport Properties of Individual Chemically Reduced Graphene Oxide Sheets Nano Lett. 2007, 7, 3499-3503
50. 4 Nanoparticles Induced Magnetic Field Effect on Efficiency Enhancement of P3HT:PCBM Bulk Heterojunction Polymer Solar Cells Sol. Energy Mater. Sol. Cells 2011, 95, 2880-2885
51. Zhang, W.; Wang, H.; Chen, B.; Bi, X.; Venkatesan, S.; Qiao, Q.; Yang, S. Oleamide as a Self-Assembled Cathode Buffer Layer for Polymer Solar Cells: The Role of the Terminal Group on the Function of the Surfactant J. Mater. Chem 2012, 22, 24067
52. Wang, H.; Zhang, W.; Xu, C.; Bi, X.; Chen, B.; Yang, S. Efficiency Enhancement of Polymer Solar Cells by Applying Poly(vinylpyrrolidone) as Cathode Buffer Layer via Spin-Coating or Self-Assembly ACS Appl. Mater. Inerfaces 2013, 5, 26-34
53. Wang, H.; Zhang, W.; Chen, B.; Yang, S. Enhancing Power Conversion Eficiency of Polymer Solar Cels via Treatment of PEDOT:PSS Anode Bufer Layer Using DMF Solvent J. Univ. Sci. Technol. China 2012, 42, 775-784
54. Dang, M. T.; Hirsch, L.; Wantz, G. P3HT:PCBM, Best Seller in Polymer Photovoltaic Research Adv. Mater. 2011, 23, 3597-3602
55. Rauh, D.; Wagenpfahl, A.; Deibel, C.; Dyakonov, V. Relation of Open Circuit Voltage to Charge Carrier Density in Organic Bulk Heterojunction Solar Cells Appl. Phys. Lett. 2011, 98, 133301
56. Mihailetchi, V. D.; Blom, P. W. M.; Hummelen, J. C.; Rispens, M. T. Cathode Dependence of the Open-Circuit Voltage of Polymer:Fullerene Bulk Heterojunction Solar Cells J. Appl. Phys. 2003, 94, 6849-6854
57. Jeon, Y. J.; Yun, J. M.; Kim, D. Y.; Na, S. I.; Kim, S. S. High-Performance Polymer Solar Cells with Moderately Reduced Graphene Oxide as an Efficient Hole Transporting Layer Sol. Energy Mater. Sol. Cells 2012, 105, 96-102
58. Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Conjugated Polymer-Based Organic Solar Cells Chem. Rev. 2007, 107, 1324-1338
59. Chen, L. M.; Xu, Z.; Hong, Z. R.; Yang, Y. Interface Investigation and Engineering-Achieving High Performance Polymer Photovoltaic Devices J. Mater. Chem. 2010, 20, 2575-2598
60. Po, R.; Carbonera, C.; Bernardi, A.; Camaioni, N. The Role of Buffer Layers in Polymer Solar Cells Energy Environ. Sci. 2011, 4, 285-310
61. Yip, H.-L.; Jen, A. K. Y. Recent Advances in Solution-Processed Interfacial Materials for Efficient and Stable Polymer Solar Cells Energy Environ. Sci. 2012, 5, 5994-6011
62. Palma, M.; Levin, J.; Lemaur, V.; Liscio, A.; Palermo, V.; Cornil, J.; Geerts, Y.; Lehmann, M.; Samorì, P. Self-Organization and Nanoscale Electronic Properties of Azatriphenylene-Based Architectures: A Scanning Probe Microscopy Study Adv. Mater. 2006, 18, 3313-3317
63. Wang, X.; Zhi, L.; Mullen, K. Transparent, Conductive Graphene Electrodes for Dye-Sensitized Solar Cells Nano Lett. 2008, 8, 323-327
64. Dang, M. T.; Wantz, G.; Bejbouji, H.; Urien, M.; Dautel, O. J.; Vignau, L.; Hirsch, L. Polymeric Solar Cells Based on P3HT:PCBM: Role of the Casting Solvent Sol. Energy Mater. Sol. Cells 2011, 95, 3408-3418