注册 English

Effect of the position of substitution on the electronic properties of nitrophenyl derivatives of fulleropyrrolidines：Fundamental understanding toward raising LUMO energy of fullerene electron-acceptor

Xuan Zhang ,  Xu-Dong Li

downloadPDF
Citation:  Xuan Zhang, Xu-Dong Li. Effect of the position of substitution on the electronic properties of nitrophenyl derivatives of fulleropyrrolidines：Fundamental understanding toward raising LUMO energy of fullerene electron-acceptor[J]. Chinese Chemical Letters, 2014, 25(4): 501-504. doi: 10.1016/j.cclet.2013.11.050 shu

Effect of the position of substitution on the electronic properties of nitrophenyl derivatives of fulleropyrrolidines：Fundamental understanding toward raising LUMO energy of fullerene electron-acceptor

    • 通讯作者: Xuan Zhang,
  • 基金项目:

    This work was financially supported by Shanghai Pujiang Program (No. 11PJ1400200) (No. 11PJ1400200)

    Innovation Program of Shanghai Municipal Education Commission (No. 12ZZ067) (No. 12ZZ067)

摘要: A series of substituted para-, meta- and ortho-nitrophenyl derivatives of fulleropyrrolidine were synthesized to investigate the effects of the position of substitution on electronic properties by using steady-state absorption and fluorescence spectra, combined with DFT calculations. The results confirmed that the position of substitution has little effect on absorption and fluorescence spectra, whereas a significant effect was observed on their LUMO energy levels. The theoretical calculations revealed that the LUMO energy of the ortho-nitrophenyl substituted derivative was increased 0.1 eV above those of para- and meta-substitution. The prominent effect of ortho-substitution was attributed to the through-space orbital interaction between spatially closed electron-withdrawing nitro group and fullerene cage. These findings could provide fundamental insights in raising LUMO levels of C60-based electron acceptor materials and an alternative strategy to increase open circuit voltage Voc in polymer solar cells.

English

  • 

    1. [1] H.W. Kroto, J.R. Heath, S.C. O'Brien, R.F. Curl, R.E. Smalley, C60: Buckminsterfullerene, Nature 318 (1985) 162-163.[1] H.W. Kroto, J.R. Heath, S.C. O'Brien, R.F. Curl, R.E. Smalley, C60: Buckminsterfullerene, Nature 318 (1985) 162-163.

    2. [2] D.M. Guldi, Fullerenes: three dimensional electron acceptor materials, Chem. Commun. (2000) 321-327.[2] D.M. Guldi, Fullerenes: three dimensional electron acceptor materials, Chem. Commun. (2000) 321-327.

    3. [3] D.M. Guldi, B.M. Illescas, C.M. Atienza, M. Wielopolski, N. Martín, Fullerene for organic electronics, Chem. Soc. Rev. 38 (2009) 1587-1597.[3] D.M. Guldi, B.M. Illescas, C.M. Atienza, M. Wielopolski, N. Martín, Fullerene for organic electronics, Chem. Soc. Rev. 38 (2009) 1587-1597.

    4. [4] G. Li, R. Zhu, Y. Yang, Polymer solar cells, Nat. Photonics 6 (2012) 153-161.[4] G. Li, R. Zhu, Y. Yang, Polymer solar cells, Nat. Photonics 6 (2012) 153-161.

    5. [5] B.C. Thompson, J.M.J. Fréchet, Polymer-fullerene composite solar cells, Angew. Chem. Int. Ed. 47 (2008) 58-77.[5] B.C. Thompson, J.M.J. Fréchet, Polymer-fullerene composite solar cells, Angew. Chem. Int. Ed. 47 (2008) 58-77.

    6. [6] G. Dennler, M.C. Scharber, C.J. Brabec, Polymer-fullerene bulk-heterojunction solar cells, Adv. Mater. 21 (2009) 1323-1338.[6] G. Dennler, M.C. Scharber, C.J. Brabec, Polymer-fullerene bulk-heterojunction solar cells, Adv. Mater. 21 (2009) 1323-1338.

    7. [7] D. Jariwala, V.K. Sangwan, L.J. Lauhon, T.J. Marks, M.C. Hersam, Carbon nanomaterials for electronics, optoelectronics, photovoltaics, and sensing, Chem. Soc. Rev. 42 (2013) 2824-2860.[7] D. Jariwala, V.K. Sangwan, L.J. Lauhon, T.J. Marks, M.C. Hersam, Carbon nanomaterials for electronics, optoelectronics, photovoltaics, and sensing, Chem. Soc. Rev. 42 (2013) 2824-2860.

    8. [8] J.B. You, L.T. Dou, K. Yoshimura, et al., A polymer tandem solar cell with 10.6% power conversion efficiency, Nat. Commun. 4 (2013) 1446.[8] J.B. You, L.T. Dou, K. Yoshimura, et al., A polymer tandem solar cell with 10.6% power conversion efficiency, Nat. Commun. 4 (2013) 1446.

    9. [9] C.J. Brabec, A. Cravino, D. Meissner, et al., Origin of the open circuit voltage of plastic solar cells, Adv. Funct. Mater. 11 (2001) 374-380.[9] C.J. Brabec, A. Cravino, D. Meissner, et al., Origin of the open circuit voltage of plastic solar cells, Adv. Funct. Mater. 11 (2001) 374-380.

    10. [10] M.C. Scharber, D. Wühlbacher, M. Koppe, et al., Design rules for donors in bulkheterojunction solar cells - towards 10% energy-conversion efficiency, Adv. Mater. 18 (2006) 789-794.[10] M.C. Scharber, D. Wühlbacher, M. Koppe, et al., Design rules for donors in bulkheterojunction solar cells - towards 10% energy-conversion efficiency, Adv. Mater. 18 (2006) 789-794.

    11. [11] Y.F. Li, Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption, Acc. Chem. Res. 45 (2012) 723-733.[11] Y.F. Li, Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption, Acc. Chem. Res. 45 (2012) 723-733.

    12. [12] F.B. Kooistra, J. Knol, F. Kastenberg, et al., Increasing the open circuit voltage of bulk-heterojunction solar cells by raising the LUMO level of the acceptor, Org.[12] F.B. Kooistra, J. Knol, F. Kastenberg, et al., Increasing the open circuit voltage of bulk-heterojunction solar cells by raising the LUMO level of the acceptor, Org.

    13. [13] Y.J. He, H.Y. Chen, J.H. Hou, Y.F. Li, Indene-C60 bisadduct: a new acceptor for highperformance polymer solar cells, J. Am. Chem. Soc. 132 (2010) 1377-1382.[13] Y.J. He, H.Y. Chen, J.H. Hou, Y.F. Li, Indene-C60 bisadduct: a new acceptor for highperformance polymer solar cells, J. Am. Chem. Soc. 132 (2010) 1377-1382.

    14. [14] C.L. Chochos, N. Tagmatarchis, V.G. Gregoriou, Rational design on n-type organic materials for high performance organic photovoltaics, RSC Adv. 3 (2013) 7160-7181.[14] C.L. Chochos, N. Tagmatarchis, V.G. Gregoriou, Rational design on n-type organic materials for high performance organic photovoltaics, RSC Adv. 3 (2013) 7160-7181.

    15. [15] H.Y. Chen, J. Hou, S. Zhang, et al., Polymer solar cells with enhanced open-circuit voltage and efficiency, Nat. Photonics 3 (2009) 649-653.[15] H.Y. Chen, J. Hou, S. Zhang, et al., Polymer solar cells with enhanced open-circuit voltage and efficiency, Nat. Photonics 3 (2009) 649-653.

    16. [16] C. Liu, Y.J. Li, C.H. Li, et al., New methanofullerenes containing amide as electron acceptor for construction photovoltaic devices, J. Phys. Chem. C 113 (2009) 21970-21975.[16] C. Liu, Y.J. Li, C.H. Li, et al., New methanofullerenes containing amide as electron acceptor for construction photovoltaic devices, J. Phys. Chem. C 113 (2009) 21970-21975.

    17. [17] C. Liu, S.Q. Xiao, X.P. Shu, et al., Synthesis and photovoltaic properties of novel monoadducts and bisadducts based on amide methanofullerene, ACS Appl. Mater. Interfaces 4 (2012) 1065-1071.[17] C. Liu, S.Q. Xiao, X.P. Shu, et al., Synthesis and photovoltaic properties of novel monoadducts and bisadducts based on amide methanofullerene, ACS Appl. Mater. Interfaces 4 (2012) 1065-1071.

    18. [18] Y. Matsuo, Design concept for high-LUMO-level fullerene electron-acceptors for organic solar cells, Chem. Lett. 41 (2012) 754-759.[18] Y. Matsuo, Design concept for high-LUMO-level fullerene electron-acceptors for organic solar cells, Chem. Lett. 41 (2012) 754-759.

    19. [19] F. Matsumoto, T. Iwai, K. Moriwaki, et al., Design of fullerene derivatives for stabilizing LUMO energy using donor groups placed in spatial proximity to the C60 cage, J. Org. Chem. 77 (2012) 9038-9043.[19] F. Matsumoto, T. Iwai, K. Moriwaki, et al., Design of fullerene derivatives for stabilizing LUMO energy using donor groups placed in spatial proximity to the C60 cage, J. Org. Chem. 77 (2012) 9038-9043.

    20. [20] Y. Numata, Y. Tajima, J. Kawashima, The substituent effect to the reduction potentials of heterocycle-fused [60] fullerene derivatives, in: 214th ECS Meeting, 2008, Abstract #2719.[20] Y. Numata, Y. Tajima, J. Kawashima, The substituent effect to the reduction potentials of heterocycle-fused [60] fullerene derivatives, in: 214th ECS Meeting, 2008, Abstract #2719.

    21. [21] R.F. Peng, B. Jin, K. Cao, et al., Study on the synthetic technology of nitrofulleropyrrolidine, Chinese J. Org. Chem. 27 (2007) 276-278.[21] R.F. Peng, B. Jin, K. Cao, et al., Study on the synthetic technology of nitrofulleropyrrolidine, Chinese J. Org. Chem. 27 (2007) 276-278.

    22. [22] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT, 2010.[22] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT, 2010.

    23. [23] H. Wang, Y.J. He, Y.F. Li, et al., Photophysical and electronic properties of five PCBM-like C60 derivatives: spectral and quantum chemical view, J. Phys. Chem. A 116 (2012) 255-262.[23] H. Wang, Y.J. He, Y.F. Li, et al., Photophysical and electronic properties of five PCBM-like C60 derivatives: spectral and quantum chemical view, J. Phys. Chem. A 116 (2012) 255-262.

    24. [24] R. Koeppe, N.S. Sariciftci, Photoinduced charge and energy transfer involving fullerene derivatives, Photochem. Photobiol. Sci. 5 (2006) 1122-1131.[24] R. Koeppe, N.S. Sariciftci, Photoinduced charge and energy transfer involving fullerene derivatives, Photochem. Photobiol. Sci. 5 (2006) 1122-1131.

    25. [25] G.D. Han, W.R. Collins, T.L. Andrew, et al., Cyclobutadiene-C60 adducts: n-type materials for organic photovoltaic cells with high Voc, Adv. Funct. Mater. 23 (2013) 3061-3069.[25] G.D. Han, W.R. Collins, T.L. Andrew, et al., Cyclobutadiene-C60 adducts: n-type materials for organic photovoltaic cells with high Voc, Adv. Funct. Mater. 23 (2013) 3061-3069.

  • 加载中
WeChat 扫一扫看文章
计量
  • PDF下载量:  0
  • 文章访问数:  1487
  • HTML全文浏览量:  27
文章相关
  • 发布日期:  2013-12-01
  • 收稿日期:  2013-10-24
  • 网络出版日期:  2013-11-22
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章

All Rights Reserved by the Chinese Chemical Society   中国化学会 版权所有 京ICP备05002797号

本系统由北京仁和汇智信息技术有限公司开发    技术支持: info@rhhz.net