A computational proof toward correlation between the theoretical chemical concept of electrophilicity index for the acceptors of C60 and C70 fullerene derivatives with the open-circuit voltage of polymer-fullerene solar cells

Solar Energy Materials and Solar Cells

Volumn 105, Issue , 2012, Pages 125-131

  Anafcheh, Maryam ^a   Ghafouri, Reza ^b   Hadipour, Nasser L ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

DFT; Electrophilicity; Fullerene; LUMO; Open circuit voltage; Organic solar cells

Indexed keywords

BACK TRANSFER; BULK HETEROJUNCTION SOLAR CELLS; C60 DERIVATIVE; C70 FULLERENES; CHEMICAL CONCEPTS; COMPUTATIONAL STUDIES; DFT; DONOR MOLECULES; ELECTRON ACCEPTOR; ELECTRON-RICH; ELECTROPHILICITY; ELECTROPHILICITY INDEX; FULLERENE DERIVATIVE; KEYPOINTS; LINEAR CORRELATION; LUMO; ORGANIC SOLAR CELL; PHOTOVOLTAIC DEVICES; POLYMER-FULLERENE; PROMINENT FEATURES; PROPIONIC ACIDS; QUANTUM CHEMICAL;

ELECTRONIC STRUCTURE; ELECTRONS; ESTERIFICATION; ESTERS; FULLERENES; HETEROJUNCTIONS; OPEN CIRCUIT VOLTAGE; QUANTUM CHEMISTRY;

SOLAR CELLS;

EID: 84862605832     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2012.05.015     Document Type: Article

References (56)

1. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, and A.J. Heeger Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions Science 270 1995 1789 1791
2. T.A. Skotheim, and J. Reynolds Handbook of Conducting Polymers 2007 CRC Press London
3. G. Yu, and A.J. Heeger Charge separation and photovoltaic conversion in polymer composites with internal donor/acceptor heterojunctions Journal of Applied Physics 78 1995 4510 4515
4. J.J.M. Halls, C.A. Walsh, N.C. Greenham, E.A. Marseglia, R.H. Friend, S.C. Moratti, and A.B. Holmes Efficient photodiodes from interpenetrating polymer networks Nature 376 1995 498 500
5. S. Günes, H. Neugebauer, and N.S. Sariciftci Conjugated polymer-based organic solar cells Chemical Reviews 107 2007 1324 1338
6. H. Spanggaard, and F.C. Krebs A brief history of the development of organic and polymeric photovoltaics Solar Energy Materials and Solar Cells 83 2004 125 146
7. F.C. Krebs, S.A. Gevorgyan, and J. Alstrup A roll-to-roll process to flexible polymer solar cells: model studies, manufacture and operational stability studies Journal of Materials Chemistry 19 2009 5442 5451
8. F.C. Krebs, T. Tromholt, and M. Jorgensen Upscaling of polymer solar cell fabricating using full roll-to-roll processing Nanoscale 2 2010 873 886
9. F.C. Krebs, J. Fyenbo, and M. Jorgensen Production integration of compact roll-to roll processed polymer solar cell modules: methods and manufacture using flexographic printing, slot-die coating and rotary screen printing Journal of Materials Chemistry 20 2010 8994 9001
10. J.C. Hummelen, B.W. Knight, F. LePeq, and F. Wudl Preparation and characterization of fulleroid and methanofullerene derivatives Journal of Organic Chemistry 60 1995 532 538
11. M.M. Wienk, J.M. Kroon, W.J.H. Verhees, J. Knol, J.C. Hummelen, P.A.V. Hal, and R.A.J. Janssen Efficient methano [70]fullerene/MDMO-PPV bulk heterojunction photovoltaic cells Angewandte Chemie-International Edition 42 2003 3371 3375
12. W.L. Ma, C.Y. Yang, X. Gong, K.H. Lee, A.J. Heeger, and Thermally Stable Efficient polymer solar cells with nanoscale control of the interpenetrating network morphology Advanced Functional Materials 15 2005 1617 1622
13. G. Li, V. Shrotriya, J.S. Huang, Y. Yao, T. Moriarty, K. Emery, and Y. Yang High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends Nature Materials 4 2005 864 868
14. Y. Zhao, Z.Y. Xie, Y. Qu, Y.H. Geng, and L.X Wang Solvent-vapor treatment induced performance enhancement of poly(3-hexylthiophene): methanofullerene bulk-heterojunction photovoltaic cells Applied Physics Letters 90 2007 043504-1 043504-3
15. A.J. Moule, and K. Meerholz Controlling morphology in polymer-fullerene mixtures Advanced Materials 20 2008 240 245
16. L.G. Li, G.H. Lu, and X.N. Yang Improving performance of polymer photovoltaic devices using an annealing-free approach via construction of ordered aggregates in solution Journal of Materials Chemistry 18 2008 1984 1990
17. L.P. Zheng, Q.M. Zhou, X.Y. Deng, M. Yuan, G. Yu, and Y. Cao Methanofullerenes used as electron acceptors in polymer photovoltaic devices Journal of Physical Chemistry B 108 2004 11921 11926
18. J.X. Li, N. Sun, Z.X. Guo, C.J. Li, Y.F. Li, L.M. Dai, D.B. Zhu, D.K. Sun, Y. Cao, and L.Z. Fan Photovoltaic devices with methanofullerenes as electron acceptors Journal of Physical Chemistry B 106 2002 11509 11514
19. C.H. Yang, Y.J. Li, J.H. Hou, C. He, Z.A. Tan, B.H. Fan, Y. Zhou, Q.J. Sun, Y.L. Li, Y.F. Li, and D.B. Zhu Thinner-film plastic photovoltaic cells based on different C60 derivatives Polymers for Advanced Technologies 17 2006 500 505
20. J.A. Renz, P.A. Troshin, G. Gobsch, V.F. Razumov, and H. Hoppe Fullerene solubility-current density relationship in polymer solar cells Physica Status Solidus (RRL) 2 2008 263 265
21. P.A. Troshin, E.A. Khakina, M. Egginger, A.E. Goryachev, S.I. Troyanov, A. Fuchsbauer, A.S. Peregudov, R.N. Lyubovskaya, V.F. Razumov, and N.S. Sariciftci Self-assembly of thiophene- and furan-appended methanofullerenes with poly(3-hexylthiophene) in organic solar cells ChemSusChem 3 2010 356 366
22. G.J. Zhao, Y.J. He, Z. Xu, J.H. Hou, M.J. Zhang, J. Min, H.Y. Chen, M.F. Ye, Z.R. Hong, Y. Yang, and Y.F. Li Effect of carbon chain length in the substituent of PCBM-like molecules on their photovoltaic properties Advanced Functional Materials 20 2010 1480 1487
23. M. Lenes, G.J.A.H. Wetzelaer, F.B. Kooist, S.C. Veenstra, J.C. Hummelen, and P.W.M. Blom Fullerene bisadducts for enhanced open-circuit voltages and efficiencies in polymer solar cells Advanced Materials 20 2008 2116 2119
24. C. Yang, J.Y. Kim, S. Cho, J.K. Lee, A.J. Heeger, and F. Wudl Functionalized methanofullerenes used as n-type materials in bulk-heterojunction polymer solar cells and in field-effect transistors Journal of the American Chemical Society 130 2008 6444 6450
25. P.A. Troshin, H Hoppe, A.S. Peregudov, M. Egginger, S. Shokhovets, G. Gobsch, N.S. Sariciftci, and V.F. Razumov [70]fullerene-based materials for organic solar cells ChemSusChem 4 2011 119 124
26. F.B. Kooistra, J. Knol, F. Kastenberg, L.M. Popescu, W.J.H. Verhees, J.M. Kroon, and J.C. Hummelen Increasing the open circuit voltage of bulk-heterojunction solar cells by raising the LUMO level of the acceptor Organic Letters 9 2007 551 554
27. P. Morvillo, and E. Bobeico Tuning the LUMO level of the acceptor to increase the open-circuit voltage of polymer-fullerene solar cells: a quantum chemical study Solar Energy Materials and Solar Cells 92 2008 1192 1198
28. M. Lenes, G.-J.A.H. Wetzelaer, F.B. Kooistra, S.C. Veenstra, K.J. Hummelen, and P.W.M. Blom Fullerene bisadducts for enhanced open-circuit voltages and efficiencies in polymer solar cells Advanced Materials 20 2008 2116 2119
29. M. Lenes, S.W. Shelton, A.B. Sieval, D.F. Kronholm, J.C.K. Hummelen, and P.W.M. Blom Electron trapping in higher adduct fullerene-based solar cells Advanced Functional Materials 19 2009 3002 3007
30. T. Niinomi, Y. Matsuo, M. Hashiguchi, Y. Sato, and E. Nakamura Penta(organo) [60]fullerenes as acceptors for organic photovoltaic cells Journal of Materials Chemistry 19 2009 5804 5811
31. Y. Matsuo, Y. Sato, T. Niinomi, I. Soga, H. Tanaka, and E. Nakamura Columnar structure in bulk heterojunction in solution-processable three-layered p-i-n organic photovoltaic devices using tetrabenzoporphyrin precursor and silylmethyl [60]fullerene Journal of the American Chemical Society 131 2009 16048 16050
32. R.B. Ross, C.M. Cardona, D.M. Guldi, S.G. Sankkaranarayanan, M.O. Reese, N. Kopidakis, J. Peet, B. Walker, G. Bazan, E.V. Keuren, B.C. Holloway, and M. Drees Endohedral fullerenes for organic photovoltaic devices Nature Materials 8 2009 208 212
33. J.A. Mikroyannidis, A.N. Kabanakis, S.S. Sharma, G.D. Sharma, A simple and effective modification of PCBM for use as an electron acceptor in efficient bulk heterojunction solar cells, Advanced Functional Materials 21 (2011) 746-755
34. Y.J. He, H.-Y. Chen, J.H. Hou, and Y.F. Li Journal of the American Chemical Society 132 2010 1377 1382
35. C.J. Brabec, A. Cravino, D. Meissner, N.S. Sariciftci, T. Fromherz, M.T. RispensL.Sanchez, J.C. Hummelen, Origin of the open circuit voltage of plastic solar cells, Advanced Functional Materials. 11 (2001) 374-380.
36. W. Ma, C. Yang, X. Gong, K. Lee, and A.J. Heeger Thermally stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology Advanced Functional Materials 15 2005 1617 1622
37. A. Troshin, H. Hoppe, J. Renz, M. Egginger, J.Y. Mayorova, A.E. Goryachev, A.S. Peregudov, R.N. Lyubovskaya, G Gobsch, N.S. Sariciftci, and V.F. Razumov Material solubility-photovoltaic performance relationship in the design of novel fullerene derivatives for bulk heterojunction solar cells Advanced Functional Materials 19 2009 779 788
38. Y. He, H.-Y. Chen, J. Hou, and Y. Li Indene-C60 bisadduct: a new acceptor for high-performance polymer solar cells Journal of the American Chemical Society 132 2010 1377 1382
39. Y. He, H.-Y. Chen, G. Zhao, J. Hou, and Y. Li Biindene-C60 adducts for the application as acceptor in polymer solar cells with higher open-circuit-voltage Solar Energy Materials and Solar Cells 95 2011 899 903
40. R.G. Parr, L.V. Szentpály, and S. Liu Electrophilicity index Journal of the American Chemical Society 121 1999 1922 1924
41. R.G. Parr, R.A. Donnelly, M. Levy, and W.E. Palke Electronegativity: the density functional viewpoint Journal of Chemical Physics 68 1978 3801 3807
42. P. Politzer, and J.S. Murry A link between the ionization energy ratios of an atom and its electronegativity and hardness Chemical Physics Letters 431 2006 195 198
43. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange Journal of Chemical Physics 98 1993 5648 5652
44. C. Lee, W. Yang, and R.G. Parr Development of the colle-salvetti correlation energy formula into a functional of the electron density Physical Review B 37 1988 785 789
45. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head- Gordon, E.S. Replogle, and J.A. Pople Gaussian 98 1998 Gaussian Inc. Pittsburgh PA
46. P.C. Hariharan, and J.A. Pople Accuracy of AHn equilibrium geometries by single determinant molecular orbital theory Molecular Physics 27 1974 209 214
47. G.E. Scuseria Ab initio theoretical predictions of the equilibrium geometries of C60, C60H60 and C60F60 Chemical Physics Letters 176 1991 423 427
48. M. Häser, J. Almlö f, and G.E. Scuseria The equilibrium geometry of C60 as predicted by second-order (MP2) perturbation theory Chemical Physics Letters 181 1991 497 500
49. K. Hedberg, L. Hedberg, D.S. Bethune, C.A. Brown, H.C. Dorn, R.D. Johnson, and M. Vries Bond lengths in free molecules of buckminsterfullerene, C60, from gas phase electron diffraction Science 254 1991 410 412
50. J.M. Hawkins, A. Meyer, T.A. Lewis, S.D. Loren, and F.J. Hollander Crystal structure of osmylated C60: confirmation of the soccer ball framework Science 252 1991 312 313
51. P. Morvillo Higher fullerenes as electron acceptors for polymer solar cells: a quantum chemical study Solar Energy Materials and Solar Cells 93 2009 1827 1832
52. A. Gadisa, M. Svensson, M.R. Andersson, and O. Inganäs Correlation between oxidation potential and open-circuit voltage of composite solar cells based on blends of polythiophenes/fullerene derivative Applied Physics Letters 84 2004 1609 1611
53. M.C. Scharber, M.C Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A.J. Heeger, and C.J. Brabec Design rules for donors in bulk-heterojunction solar cells - towards 10% energy-conversion efficiency Advanced Materials 18 2006 789 794
54. V.D. Mihailetchi, P.W.M Blom, J.C Hummelen, and M.T. Rispens Cathode dependence of the open-circuit voltage of polymer: fullerene bulk heterojunction solar cells Journal of Applied Physics 94 2003 6849 6854
55. L. Liu, Y. Shi, and Y. Yang Solvation-induced morphology effects on the performance of polymer-based photovoltaic devices Advanced Functional Materials 11 2001 420 424
56. H. Frohne, S.E. Shaheen, C.J. Brabec, D.C. Müller, N.S. Sariciftci, and K. Meerholz Influence of the anodic work function on the performance of organic solar cells ChemPhysChem 3 2002 795 799