Abstract
Multi-walled carbon nanotubes (MWCNTs) functionalized with poly[2-methoxy-5-(2′-ethylhexyloxy)-1,4-phenylenevinylene] (MWCNT-f-MEH-PPV) nanocomposites were successfully prepared by employing a “grafting from” approach. The content of the functionalizing MEH-PPV in the composites was observed as 76 wt.%. Compared with pristine MWCNTs (p-MWCNT), the aqueous solubility and thermal stability of the former are significantly enhanced. The effect of covalently and non-covalently functionalized nanotubes on dye-sensitized solar cell performance was also studied. Solar cells were successfully fabricated from isolated MEH-PPV, p-MWCNT/MEH-PPV, and MWCNT-f-MEH-PPV/MEH-PPV counter electrodes. The devices based on a MWCNT-f-MEH-PPV/MEH-PPV counter electrode demonstrated the best photovoltaic performance as observed by higher J SC, V OC, and fill factor (FF) values. The experimental phenomena can be explained by quantum-chemical calculations: Charge transfer from MEH-PPV oligomers to nanotubes is greater when covalently functionalized compared with non-covalently functionalized. This suggests that the improvement in the photovoltaic parameters of the cells containing covalently functionalized nanotubes results not only from the higher concentration present in the nanotube films of the counter electrode, but also from the greater electron delocalization between the oligomers and nanotubes.
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Iijima S (1991) Nature 354:56
Saito R, Fujita M, Dresselhaus G, Dresselhaus MS (1992) Phys Rev B 46:1804
Wilder JWG, Venema LC, Rinzler AG, Smalley RE, Dekker C (1998) Nature 391:59
Hu LB, Hecht DS, Gruner G (2010) Chem Rev 110:5790
Yakobson BI, Brabec CJ, Bernholc J (1996) Phys Rev Lett 76:2511
Yu MF, Lourie O, Dyer MJ, Moloni K, Kelly TF, Ruoff RS (2000) Science 287:637
Byrne MT, Gun’ko YK (2010) Adv Mater 22:1672
Lee WJ, Ramasamy E, Lee DY, Song JS (2009) ACS Appl Mater Interfaces 1:1145
Vacca P, Nenna G, Miscioscia R, Palumbo D, Minarini C, Sala DD (2009) J Phys Chem C 113:5777
Coleman JN, Khan U, Gun’ko YK (2006) Adv Mater 18:689
Ferrer-Anglada N, Gomis V, El-Hachemi Z, Weglikovska UD, Kaempgen M, Roth S (2006) Phys Status Solidi A 203:1082
Dillon AC (2010) Chem Rev 110:6856
Rowell MW, Topinka MA, McGehee MD, Prall HJ, Dennler G, Sariciftci NS, Hu LB, Gruner G (2006) Appl Phys Lett 88:233506
Karousis N, Tagmatarchis N, Tasis D (2010) Chem Rev 110:5366
Hong CY, You YZ, Wu D, Liu Y, Pan CY (2005) Macromolecules 38:2606
Gao Y, Song G, Adronov A, Li H (2010) J Phys Chem C 114:16242
Kalinina I, Worsley K, Lugo C, Mandal S, Bekyarova E, Haddon RC (2011) Chem Mater 23:1246
Yoon JT, Jeong YG, Lee SC, Min BG (2009) Polym Adv Tech 20:631
De S, Lyons PE, Sorel S, Doherty EM, King PJ, Blau WJ, Nirmalraj PN, Boland JJ, Scardaci V, Joimel J, Coleman JN (2009) ACS Nano 3:714
Yun DJ, Hong K, Kim SH, Yun WM, Jang JY, Kwon WS, Park CE, Rhee SW (2011) ACS Appl Mater Interfaces 3:43
O’Connell MJ, Boul P, Ericson LM, Huffman C, Wang Y, Haroz E, Kuper C, Tour J, Ausman KD, Smalley RE (2001) Chem Phys Lett 342:265
Tasis D, Tagmatarchis N, Bianco A, Prato M (2006) Chem Rev 106:1105
Wang L, Liu Y, Jiang X, Qin D, Cao Y (2007) J Phys Chem C 111:9538
Verma D, Ranga Rao A, Dutta V (2009) Sol Energy Mater Sol Cells 93:1482
Inpor K, Meeyoo V, Thanachayanont C (2011) Curr Appl Phys 11:S171
Nan YX, Chen F, Yang LG, Jiang XX, Zuo LJ, Zhang JL, Yan QX, Shi MM, Chen HZ (2011) Sol Energy Mater Sol Cells 95:3233
Alam MM, Jenekhe SA (2004) Chem Mater 16:4647
Collison CJ, Pellizzeri S, Ambrosio F (2009) J Phys Chem B 113:5809
Lin CS, Zhang RQ, Niehaus TA, Frauenheim T (2007) J Phys Chem C 111:4069
Lu J, Nagase S, Zhang XW, Wang D, Ni M, Maeda Y, Wakahara T, Nakahodo T, Tsuchiya T, Akasaka T, Gao ZX, Yu DP, Ye HQ, Mei WN, Zhou YS (2006) J Am Chem Soc 128:5114
Zhao JX, Ding YH (2008) J Phys Chem C 112:13141
Neef CJ, Ferraris JP (2004) Macromolecules 37:2671
Saito R, Dresselhaus G, Dresselhaus MS (2000) Phys Rev B 61:2981
Martin SJ, Mellor H, Bradley DDC, Burn PL (1998) Opt Mater 9:88
Chou HL, Lin KF, Wang DC (2006) J Polym Res 13:79
O’Connell MJ, Bachilo SM, Huffman CB, Moore VC, Strano MS, Haroz EH, Rialon KL, Boul PJ, Noon WH, Kittrell C, Ma J, Hauge RH, Weisman RB, Smalley RE (2002) Science 297:593
Kashiwagi T, Grulke E, Hilding J, Harris R, Awad W, Douglas J (2002) Macromol Rapid Commun 23:761
Huang Z, Liu X, Li K, Li D, Luo Y, Li H, Song W, Chen L, Meng Q (2007) Electrochem Commun 9:596
Kong J, Cassell AM, Dai H (1998) Chem Phys Lett 292:567
Li Z, Ye B, Hu X, Ma X, Zhang X, Deng Y (2009) Electrochem Commun 11:1768
Liu MH, Zhu T, Li ZC, Liu ZF (2009) J Phys Chem C 113:9670
Eitan A, Jiang KY, Dukes D, Andrews R, Schadler LS (2003) Chem Mater 15:3198
Mitsuke K, Bashyal D, Nakajima K (2011) In: Pattanprateeb P (ed) Proceedings of the pure and applied chemistry international conference (PACCON), Srinakharinwirot University, Bangkok, Thailand, p 457
Delley B (1990) J Chem Phys 92:508
Delley B (1996) J Phys Chem 100:6107
Delley B (2000) J Chem Phys 113:7756
Perdew JP, Burke K, Ernzerhof M (1996) Phys Rev Lett 77:3865
Inada Y, Orita H (2008) J Comput Chem 29:225
Monkhorst HJ, Pack JD (1976) Phys Rev B 13:5188
Acknowledgments
This work was supported by the Thailand Research Fund (TRF) through a Senior Research Scholar (RTA5380010). P.P. is grateful to the Development and Promotion of Science and Technology Talents (DPST) project for a scholarship and S.S. to the Thailand Research Fund (MRG5480273) for financial support. We also acknowledge the Laboratory for Computational and Applied Chemistry (LCAC) at Kasetsart University (KU), Kasetsart University Research and Development Institute (KURDI), Large Simulations Research Laboratory (NECTEC), and National Nanotechnology Center (NANOTEC) for software and research facilities. A part of this work was conducted under projects of the National Research University (NRU) and National Center of Excellence for Petroleum, Petrochemicals, and Advanced Materials (NCEPPAM) promoted by the Commission on Higher Education, Ministry of Education, Thailand. We are grateful to Prof. Toshi Nagata (Institute for Molecular Science, Okazaki, Japan) for his permission to use the cyclic voltammetry (CV) instrument and valuable discussion on the CV results.
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Prajongtat, P., Suramitr, S., Gleeson, M.P. et al. Enhancement of the solubility, thermal stability, and electronic properties of carbon nanotubes functionalized with MEH-PPV: a combined experimental and computational study. Monatsh Chem 144, 925–935 (2013). https://doi.org/10.1007/s00706-013-0963-1
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DOI: https://doi.org/10.1007/s00706-013-0963-1