综述与进展

染料敏化太阳电池:染料中稳定锚基团的研究进展

  • 田亚娟 ,
  • 蔡宁 ,
  • 陈亚通 ,
  • 钱赛男 ,
  • 霍延平
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  • a 广东工业大学轻工化工学院 广州 510006;
    b 中国科学院上海有机化学研究所 有机氟化学中国科学院重点实验室 上海 200032

收稿日期: 2017-09-08

  修回日期: 2017-11-16

  网络出版日期: 2017-12-08

基金资助

广东省自然科学基金(No.2017A030310039)、国家自然科学基金(Nos.61671162,21372051)、广东省科技计划(No.2016A010103031)资助项目.

Dye-Sensitized Solar Cells: Progress on Robust Anchor Groups in Dyes

  • Tian Yajuan ,
  • Cai Ning ,
  • Chen Yatong ,
  • Qian Sainan ,
  • Huo Yanping
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  • a School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006;
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Cheimstry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2017-09-08

  Revised date: 2017-11-16

  Online published: 2017-12-08

Supported by

Project supported by the Natural Science Foundation of Guangdong Province (No. 2017A030310039), the National Natural Science Foundation of China (Nos. 61671162, 21372051) and the Science and Technology Planning Project of Guangdong Province (No. 2016A010103031).

摘要

作为一种颇具潜力的光伏器件,染料敏化太阳电池(DSSCs)因其高性价比以及简单的制造工艺而备受关注.在这样的器件中,染料分子通过锚取代基与氧化物基底之间的化学键接枝在金属氧化物表面,从而实现光捕获以及光生电子的注入.一直以来,广泛应用于DSSCs的染料锚基团主要是羧酸基团,包括苯甲酸和氰基丙烯酸基团.但是,器件使用过程中染料从金属氧化物表面脱附以及由此带来的器件长期稳定性问题却不容忽视,因此,考虑到器件在实际应用中的耐久性要求,研究者们开发了多种在金属氧化物表面具有更好接枝能力的锚基团.主要综述了近年来所研发的几种稳定锚基团及其相应的光伏参数,并简单讨论了分子结构与器件性能之间的关系.同时,对锚基团在光催化水解制氢以及量子点敏化太阳电池的研究进行了简要阐述与展望.

本文引用格式

田亚娟 , 蔡宁 , 陈亚通 , 钱赛男 , 霍延平 . 染料敏化太阳电池:染料中稳定锚基团的研究进展[J]. 有机化学, 2018 , 38(5) : 1085 -1106 . DOI: 10.6023/cjoc201709014

Abstract

As a type of potential photovoltaic device, dye-sensitized solar cells (DSSCs) have attracted tremendous attention due to its high cost-effective and simple manufacturing process. In the device, dye molecules attach on the metal oxide surface via chemical bonds between anchor substituents and metal oxide substrate, realizing the light harvesting and photoelectron injection. Traditionally, carboxylic acids, such as benzoic acid and cyanoacrylic acid groups, have been widely utilized as the anchor groups in DSSCs. However, the detachment of dye molecules from metal oxide surface during device operation and consequent long-term stability issues cannot be ignored. Therefore, in view of durability of DSSCs in practical application, various anchor groups with a better ability to graft on the metal oxide have been explored. Several robust anchor groups in recent years and corresponding photovoltaic parameters are reviewed and the relationship between molecular structures and device performance is also discussed. The research progress of anchoring groups in photocatalytic hydrogen and quantum dot sensitized solar cells (QDSSCs) is also examined.

参考文献

[1] Sorensen, B. Renewable Energy, 1st ed, Academic Press, London, 1979.
[2] O'Regan, B.; Grätzel, M. Nature 1991, 353, 737.
[3] Yella, A.; Lee, H. W.; Tsao, H. N.; Yi, C.; Chandiran, A. K.; Nazeeruddin, M. K.; Diau, E. W. G.; Yeh, C. Y.; Zakeeruddin, S. M.; Grätzel, M. Science 2011, 334, 629.
[4] (a) Wang, Y.; Chen, B.; Wu, W.; Li, X.; Zhu, W.; Tian, H.; Xie, Y. Angew. Chem., Int. Ed. 2014, 53, 10779.
(b) Wei, T.; Sun, X.; Li, X.; Ågren, H.; Xie, Y. ACS Appl. Mater. Interfaces 2015, 39, 21956.
(c) Xie, Y.; Tang, Y.; Wu, W.; Wang, Y.; Liu, J.; Liu, X.; Tian, H.; Zhu, W. J. Am. Chem. Soc. 2015, 44. 14055.
(d) Tang, Y.; Wang, Y.; Li, X.; Ågren, H.; Zhu, W.; Xie, Y. ACS Appl. Mater. Interfaces 2015, 50, 27976.
(e) Song, H.; Li, X.; Ågren, H.; Xie, Y. Dyes Pigm. 2017, 137, 421.
[5] (a) Yang, H. W.; Guan, J. J.; Gao, F. X.; He, X. P.; Wang, A.; Sun, B. D.; Zhang, X. Q.; Zhang, B.; Feng, Y. Q. Chin. J. Org. Chem. 2015, 35, 2237(in Chinese). (杨贺玮, 官俊杰, 高峰贤, 何欣平, 王安, 孙宝德, 张学强, 张宝, 冯亚青, 有机化学, 2015, 35, 2237.)
(b) Zhou, D.; Cai, N.; Long, H.; Zhang, M.; Wang, Y.; Wang, P. J. Phys. Chem. C 2011, 115, 3163.
(c) Xu, M.; Zhou, D.; Cai, N.; Liu, J.; Li, R.; Wang, P. Energy Environ. Sci. 2011, 4, 4735.
(d) Li, R.; Liu, J.; Cai, N.; Zhang, M.; Wang, P. J. Phys. Chem. B 2010, 114, 4461.
(e) Cai, N.; Moon, S. J.; Cevey-Ha, L.; Moehl, T.; Humphry-Baker, R.; Wang, P.; Zakeeruddin, S. M.; Grätzel, M. Nano Lett. 2011, 11, 1452.
[6] (a) Cao, Y.; Cai, N.; Wang, Y.; Li, R.; Yuan, Y.; Wang, P. Phys. Chem. Chem. Phys. 2012, 14, 8282.
(b) Cai, N.; Zhang, J.; Xu, M.; Zhang, M.; Wang, P. Adv. Funct. Mater. 2013, 23, 3539.
(c) Cai, N.; Wang, Y.; Xu, M.; Fan, Y.; Li, R.; Zhang, M.; Wang, P. Adv. Funct. Mater. 2013, 23, 1846.
(d) Cai, N.; Li, R.; Wang, Y.; Zhang, M.; Wang, P. Energy Environ. Sci. 2013, 6, 139.
[7] Kalyanasundaram, K.; Grätzel, M. Coord. Chem. Rev. 1998, 177, 347.
[8] Mathew, S.; Yella, A.; Gao, P.; Humphry-Baker, R.; Curchod, B. F. E.; Ashari-Astani, N.; Tavernelli, I.; Rothlisberger, U.; Nazeeruddin, M. K.; Grätzel, M. Nat. Chem. 2014, 6, 242.
[9] Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595.
[10] Galoppini, E. Coord. Chem. Rev. 2004, 248, 1283.
[11] Péchy, P.; Rotzinger, F. P.; Nazeeruddin, M. K.; Kohle, O.; Zakeeruddin, S. M.; Humphry-Baker, R.; Grätzel, M. J. Chem. Soc. Chem. Commun. 1995, 65.
[12] Park, H.; Bae, E.; Lee, J. J.; Park, J.; Choi, W. J. Phys. Chem. B 2006, 110, 8740.
[13] Odobel, F.; Blart, E.; Lagree, M.; Villieras, M.; Boujtita, H.; EIMurr, N.; Caramori, S.; Alberto Bignozzi, C. J. Mater. Chem. 2003, 13, 502.
[14] Lopez-Duarte, I.; Wang, M.; Humphry-Baker, R.; Ince, M.; Martínez-Díaz, M. V.; Nazeeruddin, M. K.; Torres, T.; Grätzel, M. Angew. Chem., Int. Ed. 2012, 51, 1895.
[15] Mulhern, K. R.; Orchard, A.; Watson, D. F.; Detty, M. R. Langmuir 2012, 28, 7071.
[16] Brown, D. G.; Schauer, P. A.; Borau-Garcia, J.; Fancy, B. R.; Berlinguette, C. P. J. Am. Chem. Soc. 2013, 135, 1692.
[17] He, H.; Gurunga, A.; Si, L. Chem. Commun. 2012, 48, 5910.
[18] Si, L.; He, H.; Zhu, K. New J. Chem. 2014, 38, 1565.
[19] Mao, J.; He, N.; Ning, Z.; Zhang, Q.; Guo, F.; Chen, L.; Wu, W.; Hua, J.; Tian, H. Angew. Chem., Int. Ed. 2012, 51, 9873.
[20] Zhang, J.; Li, H.-B.; Zhang, J.-Z.; Wu, Y.; Geng, Y.; Fu, Q.; Su, Z.-M. J. Mater. Chem. A 2013, 1, 14000.
[21] Mao, J.; Zhang, X.; Liu, S.-H.; Shen, Z.; Li, X.; Wu, W.; Chou, P.-T.; Hua, J. Electrochim. Acta 2015, 179, 179.
[22] Matsui, M.; Tanaka, N.; Kubota, Y.; Funabiki, K.; Jin, J.; Higashijima, S.; Miura, H.; Manseki, K. RSC Adv. 2016, 6, 33111.
[23] Qian, X.; Yan, R.; Hang, Y.; Lv, Y.; Zheng, L.; Xu, C.; Hou, L. Dyes Pigm. 2017, 139, 274.
[24] Qian, X.; Lan, X.; Yan, R.; He, Y.; Huang, J.; Hou, L. Electrochim. Acta 2017, 232, 377.
[25] Yu, F.; Cui, S.-C.; Li, X.; Peng, Y.; Yu, Y.; Kang, Y.; Zhang, S.-C.; Li, J.; Liu, J.-G.; Hua, J. Dyes Pigm. 2017, 139, 7.
[26] Horiuchi, T.; Miuraa, H.; Uchida, S. Chem. Commun. 2003, 3036.
[27] Horiuchi, T.; Miura, H.; Uchida, S. J. Photochem. Photobiol., A Chem. 2004, 164, 29.
[28] Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S. J. Am. Chem. Soc. 2004, 126, 12218.
[29] Chen, Y.; Li, C.; Zeng, Z.; Wang, W.; Wang, X.; Zhang, B. Chem. Lett. 2005, 6, 762.
[30] Li, S.-L.; Jiang, K.-J.; Shao, K.-F.; Yang, L.-M. Chem. Commun. 2006, 2792.
[31] Tian, H.; Yang, X.; Chen, R.; Pan, Y.; Li, L.; Hagfeldt, A.; Sun, L. Chem. Commun. 2007, 3741.
[32] Liang, M.; Xu, W.; Cai, F.; Chen, P.; Peng, B.; Chen, J.; Li, Z. J. Phys. Chem. C 2007, 111, 4465.
[33] Tian, H.; Yang, X.; Pan, J.; Chen, R.; Liu, M.; Zhang, Q.; Hagfeldt, A.; Sun, L. Adv. Funct. Mater. 2008, 18, 3461.
[34] Ito, S.; Miura, H.; Uchida, S.; Takata, M.; Sumioka, K.; Liska, P.; Comte, P.; Péchy, P.; Grätzel, M. Chem. Commun. 2008, 5194.
[35] Zhang, X.-H.; Yao, Y.-S.; Li, C.; Wang, W.-B.; Cheng, X.-X.; Wang, X.-S.; Zhang, B.-W. Chin. J. Chem. 2008, 26, 929.
[36] Marinado, T.; Hagberg, D. P.; Hedlund, M.; Edvinsson, T.; Johansson, E. M. J.; Boschloo, G.; Rensmo, H.; Brinck, T.; Sun, L.; Hagfeldt, A. Phys. Chem. Chem. Phys. 2009, 11, 133.
[37] Pei, J.; Peng, S.; Shi, J.; Liang, Y.; Tao, Z.; Liang, J.; Chen, J. J. Power Sources 2009, 187, 620.
[38] Ahn, H. J.; Thogiti, S.; Cho, J. M.; Jang, B. Y.; Kim, J. H. Electron. Mater. Lett. 2015, 5, 882.
[39] Gupta, K. S. V.; Singh, S. P.; Islam, A.; Han, L.; Chandrasekharam, M. Electrochim. Acta 2015, 174, 581.
[40] Kathiravan, A.; Panneerselvam, M.; Sundaravel, K.; Pavithra, N.; Srinivasan, V.; Anandand, S.; Jaccob, M. Phys. Chem. Chem. Phys. 2016, 18, 13332.
[41] Kathiravan, A.; Srinivasan, V.; Khamrang, T.; Velusamy, M.; Jaccob, M.; Pavithra, N.; Anandane, S.; Velappan, K. Phys. Chem. Chem. Phys. 2017, 19, 3125.
[42] Hai, N. T.; Bao, L. Q.; Thogiti, S.; Cheruku, R.; Ahn, K.-S.; Kim, J. H. J. Nanosci. Nanotechnol. 2017, 5, 3181.
[43] Ooyama, Y.; Inoue, S.; Nagano, T.; Kushimoto, K.; Ohshita, J.; Imae, I.; Komaguchi, K.; Harima, Y. Angew. Chem., Int. Ed. 2011, 50, 7429.
[44] Ooyama, Y.; Nagano, T.; Inoue, S.; Imae, I.; Komaguchi, K.; Ohshita, J.; Harima, Y. Chem.-Eur. J. 2011, 17, 14837.
[45] Zhang, M.-D.; Xie, H.-X.; Ju, X.-H.; Qin, L.; Yang, Q.-X.; Zheng, H.-G.; Zhou, X.-F. Phys. Chem. Chem. Phys. 2013, 15, 634.
[46] Ooyama, Y.; Yamaguchi, N.; Imae, I.; Komaguchi, K.; Ohshita, J.; Harima, Y. Chem. Commun. 2013, 49, 2548.
[47] Wang, L.; Yang, X.; Li, S.; Cheng, M.; Sun, L. RSC Adv. 2013, 3, 13677.
[48] Wang, L.; Yang, X.; Zhao, J.; Zhang, F.; Wang, X.; Sun, L. ChemSusChem 2014, 7, 2640.
[49] Mao, J.; Wang, D.; Liu, S.-H.; Hang, Y.; Xu, Y.; Zhang, Q.; Wu, W.; Chou, P.-T.; Hua, J. Asian J. Org. Chem. 2014, 3, 153.
[50] (a) Cong, J.; Yang, X.; Liu, J.; Zhao, J.; Hao, Y.; Wang, Y.; Sun, L. Chem. Commun. 2012, 48, 6663.
(b) Ooyama, Y.; Hagiwara, Y.; Oda, Y.; Mizumo, T.; Harima, Y.; Ohshita, J. New J. Chem. 2013, 37, 2336.
[51] Massin, J.; Ducasse, L.; Toupance, T.; Olivier, C. J. Phys. Chem. C 2014, 118, 10677.
[52] Zhang, L.; Cole, J. M.; Dai, C. Appl. Mater. Interfaces 2014, 6, 7535.
[53] Daphnomili, D.; Landrou, G.; Prakash Singh, S.; Thomas, A.; Yesudas, K.; Bhanuprakash, K.; Sharma, G. D.; Coutsolelos, A. G. RSC Adv. 2012, 2, 12899.
[54] Daphnomili, D.; Sharma, G. D.; Biswas, S.; Justin Thomas, K. R.; Coutsolelos, A. G. J. Photochem. Photobiol., A:Chem. 2013, 253, 88.
[55] Mai, C.-L.; Moehl, T.; Hsieh, C.-H.; Decoppet, J. D.; Zakeeruddin, S. M.; Grätzel, M.; Yeh, C. Y. ACS Appl. Mater. Interfaces 2015, 7, 14975.
[56] Li, T.-Y.; Su, C.; Akula, S. B.; Sun, W.-G.; Chien, H.-M.; Li, W.-R. Org. Lett. 2016, 18, 3386.
[57] Asao, T.; Kikuchi, Y. Chem. Lett. 1972, 413.
[58] Barret, M. C.; Mahon, M. F.; Molloy, K. C.; Steed, J. W.; Wright, P. Inorg. Chem. 2001, 40, 4384.
[59] Nomiya, K.; Onodera, K.; Sukagoshi, K.; Shimada, K.; Yoshizawa, A.; Itoyanagi, T. A.; Sugie, A.; Tsuruta, S.; Sato, R.; Kasuga, N. C. Inorg. Chim. Acta 2009, 362, 43.
[60] Higashino, T.; Fujimori, Y.; Sugiura, K.; Tsuji, Y.;Ito, S.; Imahori, H. Angew. Chem., Int. Ed. 2015, 54, 9052.
[61] Cocozza, C.; Tsao, C. C. G.; Cheah, S. F.; Kraemer, S. M.; Raymond, K. N.; Miano, T. M.; Sposito, G. Geochim. Cosmochim. Acta 2002, 66, 431.
[62] Yang, J.; Bremer, P. J.; Lamont, I. L.; McQuillan, A. J. Langmuir 2006, 22, 10109.
[63] Upritchard, H. G.; Yang, J.; Bremer, P. J.; Lamont, I. L.; McQuillan, A. J. Langmuir 2007, 23, 7189.
[64] McNamara, W. R.; Snoeberger Ⅲ, R. C.; Li, G.; Richter, C.; Allen, L. J.; Milot, R. L.; Schmuttenmaer, C. A.; Crabtree, R. H.; Brudvig, G. W.; Batista, V. S. Energy Environ. Sci. 2009, 2, 1173.
[65] McNamara, W. R.; Milot, R. L.; Song, H.; Snoeberger, R. C.; Batista, V. S.; Schmuttenmaer, C. A.; Brudvig, G. W.; Crabtree, R. H. Energy Environ. Sci. 2010, 3, 917.
[66] Brewster, T. P.; Konezny, S. J.; Sheehan, S. W.; Martini, L. A.; Schmuttenmaer, C. A.; Batista, V. S.; Crabtree, R. H. Inorg. Chem. 2013, 52, 6752.
[67] Koenigsmann, C.; Ripolles, T. S.; Brennan, B. J.; Negre, C. F. A.; Koepf, M.; Durrell, A. C.; Milot, R. L.; Torre, J. A.; Crabtree, R. H.; Batista, V. S.; Brudvig, G.; Bisquert, J.; Schmuttenmaer, C. Phys. Chem. Chem. Phys. 2014, 16, 16629.
[68] Brennan, B. J.; Koenigsmann, C.; Materna, K. L.; Kim, P. M.; Koepf, M.; Crabtree, R. H.; Schmuttenmaer, C. A.; Brudvig, G. W. J. Phys. Chem. C 2016, 23, 12495.
[69] Bowman, D. N.; Mukherjee, S.; Barnes, L. J.; Jakubikova, E. J. Phys.:Condens. Matter. 2015, 27, 134205.
[70] Higashino, T.; Kurumisawa, Y.; Cai, N.; Fujimori, Y.; Tsuji, Y.; Nimura, S.; Packwood, D.; Jaehong Park, J.; Imahori, H. ChemSusChem 2017, 10, 3347.
[71] Politano, A.; Cattelan, M.; Boukhvalov, D. W.; Campi, D.; Cupolillo, A.; Agnoli, S.; Apostol, N. G.; Lacovig, P.; Lizzit, S.; Farías, D.; Chiarello, G.; Granozzi, G.; Larciprete, R. ACS Nano 2016, 10, 4543.
[72] Tsuji, K.; Tomita, O.; Higashi, M.; Abe, R. ChemSusChem 2016, 9, 2201.
[73] Zhang, Y.; Sun, Z.; Cheng, S.; Yan, F. ChemSusChem 2016, 9, 813.
[74] Kim, H. G.; Borse, P. H.; Choi, W.; Choi, W.; Lee, J. S. Angew. Chem., Int. Ed. 2005, 44, 4585.
[75] Zhang, X.; Peng, T.; Song, S. J. Mater. Chem. A 2016, 4, 2365.
[76] Fan, K.; Li, F. S.; Wang, L.; Daniel, Q.; Gabrielsson, E.; Sun, L. Phys. Chem. Chem. Phys. 2014, 16, 25234.
[77] Fan, K.; Li, F.; Wang, L.; Daniel, Q.; Gabrielsson, E.; Sun, L. J. Am. Chem. Soc. 2015, 137, 9153.
[78] Li, X.; Hu, Y.; Sanchez-Molina, I.; Zhou, Y.; Yu, F.; Haque, S. A.; Wu, W.; Hua, J.; Tian, H.; Robertson, N. J. Mater. Chem. A 2015, 3, 21733.
[79] Rao, C. N. R.; Lingampalli, S. R. Small 2016, 12, 16.
[80] Manfredi, N.; Cecconi, B.; Calabrese, V.; Minotti, A.; Peri, F.; Ruffo, R.; Monai, M.; Romero-Ocaña, I.; Montini, T.; Fornasiero, P.; Abbotto, A. Chem. Commun. 2016, 52, 6977.
[81] Maeda, K.; Eguchi, M.; Youngblood, W. J.; Mallouk, T. E. Chem Mater. 2008, 20, 6770.
[82] Bae, E. Y.; Choi, W.; Park, J.; Shin, H. S.; Kim, S. B.; Lee, J. S. J. Phys. Chem. B 2004, 108, 14093.
[83] Yu, F.; Cui, S.-C.; Li, X.; Peng, Y.; Yu, Y.; Yun, K.; Zhang, S.-C.; Li, J.; Liu, J.-G.; Hua, J. Dyes Pigm. 2017, 139, 7.
[84] Guerrero, G.; Alauzun, J. G.; Granier, M.; Laurencin, D.; Mutin, P. H. Dalton Trans. 2013, 42, 12569.
[85] Baker, D. R.; Kamat, P. V. Adv. Funct. Mater. 2009, 19, 805.
[86] Meng, Q. B. Acta Chim. Sinica 2015, 73, 161(in Chinese). (孟庆波, 化学学报, 2015, 73, 161.)
[87] Robel, I.; Subramanian, V.; Kuno, M.; Kamat, P. V. J. Am. Chem. Soc. 2006, 128, 2385.
[88] Ardalan, P.; Brennan, T. P.; Lee, H. B. R.; Bakke, J. R.; Ding, I. K.; McGehee, M. D.; Bent, S. F. ACS Nano 2011, 5, 1495.
[89] Yu, L.; Li, Z.; Song, H. J. Mater. Sci.:Mater. Electron. 2017, 28, 2867.
[90] Mora-Seró, I.; Giménez, S.; Moehl, T.; Fabregat-Santiago, F.; Lana-Villareal, T.; Gómez, R.; Bisquert, J. Nanotechnology 2008, 19, 424007.

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