ISSN 1000-6818CN 11-1892/O6CODEN WHXUEU
Acta Phys Chim Sin >> 2016,Vol.32>> Issue(12)>> 2968-2975     doi: 10.3866/PKU.WHXB201609194         中文摘要
Synthesis of a Novel D-π-A-π-A Organic Sensitizer and Its Application in a Dye-Sensitized Solar Cell and Dye-Sensitized Photocatalytic H2 Production
XIAO An1, LU Hui1, ZHAO Yang1, LUO Geng-Geng1,2
1 College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, Fujian Province, P. R. China;
2 State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. China
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A novel metal-free D-π-A-π-A-based organic sensitizer OD2 featuring a N,N'-dimethylaniline unit as the donor residue, acetylene and benzene groups as π-spacer units, and benzothiadiazole and cyanoacrylic acid residues as acceptor units, was designed and synthesized. After the spectra and electrochemistry of the organic dye were investigated, it was applied in the development of solar energy conversion, including dyesensitized solar cell (DSSC) and dye-sensitized photocatalytic H2 production. For a typical device based on OD2, a maximum power conversion efficiency (η) of 4.40% was obtained under simulated AM 1.5 irradiation (100 mW·cm-2) with Jsc=10.58 mA·cm-2, Voc=630 mV and FF=0.65. In comparison, the efficiency of photocatalytic H2 production by OD2 sensitized Pt/TiO2 is low with a TON (turnover number)=140 and quantum efficiency for H2 conversion of water (ΦH2)=0.42% under visible light irradiation for 10 h with a 300 W Xe-lamp light source and 10% (volume fraction) aqueous triethanolamine (TEOA) at pH 7.0. The above results showed that OD2 has greater potential in the light-to-electricity conversion than light-to-fuel conversion.

Keywords: Photoelectric property   Hydrogen production   Organic sensitizer   D-π-A-π-A configuration  
Received: 2016-08-22 Accepted: 2016-09-19 Publication Date (Web): 2016-09-19
Corresponding Authors: LUO Geng-Geng Email:

Fund: The project was supported by the National Natural Science Foundation of China (21201066), Natural Science Foundation of Fujian Province, China (2015J01053, 2011J01047), and Program for New Century Excellent Talents in Fujian Province Universities, China (Z1525081).

Cite this article: XIAO An, LU Hui, ZHAO Yang, LUO Geng-Geng. Synthesis of a Novel D-π-A-π-A Organic Sensitizer and Its Application in a Dye-Sensitized Solar Cell and Dye-Sensitized Photocatalytic H2 Production[J]. Acta Phys. -Chim. Sin., 2016,32 (12): 2968-2975.    doi: 10.3866/PKU.WHXB201609194

(1) Yu, Z.; Li, F.; Sun, L. Energy Environ. Sci. 2015, 8 (3), 760. doi: 10.1039/c4ee03565h
(2) Vos, J. G.; Kelly, J. M. Dalton Trans 2006, (41), 4869. doi: 10.1039/b606490f
(3) Zhang, X.; Veikko, U.; Mao, J.; Cai, P.; Peng, T. Chem. Eur. J. 2012, 18 (38), 12103. doi: 10.1002/chem.201200725
(4) Luo, H.; Song, W.; Hoertz, P. G.; Hanson, K.; Ghosh, R.; Rangan, S.; Brennaman, M. K.; Concepcion, J. J.; Binsteas, R.A.; Bartynski, R. A.; Lopez, R.; Mayer, T. J. Chem. Mater. 2013, 25 (2), 122. doi: 10.1021/cm3027972
(5) Kim, B. G.; Chung, K.; Kim, J. Chem. Eur. J. 2013, 19 (17), 5220. doi: 10.1002/chem.201204343
(6) Lee, S. H.; Park, Y.; Wee, K. R.; Son, H. J.; Cho, D.W.; Pac, C.; Choi, W.; Kang, S. O. Org. Lett. 2010, 12 (3), 460. doi: 10.1021/ol9026182
(7) Kloo, L. Chem. Commun. 2013, 49 (59), 6580. doi: 10.1039/c3cc42733a
(8) Watanabe, M.; Hagiwara, H.; Iribe, A.; Ogata, Y.; Shiomi, K.; Staykov, A.; Ida, S.; Tanaka, K.; Ishihara, T. J. Mater. Chem. A 2014, 2 (32), 12952. doi: 10.1039/c4ta02720e
(9) Cecconi, B.; Manfredi, N.; Ruffo, R.; Montini, T.; RomeroOcaña, I.; Fornasiero, P.; Abbotto, A. ChemSusChem 2015, 8 (24), 4216. doi: 10.1002/cssc.201501040
(10) Narayanaswamy, K.; Tiwari, A.; Mondal, K.; Pal, U.; Niveditha, S.; Bhanuprakash, K.; Singh, S. P. Phys. Chem. Chem. Phys. 2015, 17, 13710. doi: 10.1039/c5cp01777g
(11) Watanabe, M.; Hagiwara, H.; Ogata, Y.; Staykov, A.; Bishop, S.R.; Perry, N. H.; Chang, Y. J.; Ida, S.; Tanaka, K.; Ishihara, T. J. Mater. Chem. A 2015, 3 (43), 21713. doi: 10.1039/c5ta04991a
(12) Zhang, X.; Peng, T.; Song, S. J. Mater. Chem. A 2016, 4 (7), 2365. doi: 10.1039/c5ta08939e
(13) Hou, L. M.; Wen, Z.; Li, Y. X.; Hu, H. Y.; Kan, Y. H.; Su, Z. M.Acta Phys. -Chim. Sin. 2015, 31, 1504. [侯丽梅, 温智, 李银祥, 胡华友, 阚玉和, 苏忠民. 物理化学学报, 2015, 31, 1504.] doi: 10.38/PKU.WHXB201505211
(14) Wu, Y.; Zhu, W. Chem. Soc. Rev. 2013, 42 (5), 2039. doi: 10.1039/c2cs35346f
(15) Li, X.; Zheng, Z.; Jiang, W.; Wu, W.; Wang, Z.; Tian, H. Chem. Commun. 2015, 51 (17), 3590. doi: 10.1039/c4cc08539f
(16) Lan, T.; Lu, X.; Zhang, L.; Chen, Y.; Zhou, G.; Wang, Z. J. Mater. Chem. A 2015, 3 (38), 9869. doi: 10.1039/c5tc02070k
(17) Ying, W.; Yang, J.; Wielopolski, M.; Moehl, T.; Moser, J.; Comte, P.; Hua, J.; Zakeeruddin, S. M.; Tian, H.; Grätzel, M.Chem. Sci. 2014, 5 (1), 206. doi: 10.1039/c3sc51844b
(18) Liu, X.; Li, Y. X.; Peng, S. Q.; Lai, H. Acta Phys. -Chim. Sin.2015, 31, 612. [刘兴, 李越湘, 彭绍琴, 赖华. 物理化学学报, 2015, 31, 612.] doi: 10.38/PKU.WHXB201505211
(19) Li, X.; Cui, S.; Wang, D.; Zhou, Y.; Zhou, H.; Hu, Y.; Liu, J.; Long, Y.; Wu, W.; Hua, J.; Tian, H. ChemSusChem 2014, 7 (10), 2879. doi: 10.1002/cssc.201402414
(20) Das, S.; Jana, A.; Ramanathan, V.; Chakraborty, T.; Ghosh, S.; Das, P. K.; Bharadwaj, P. K. J. Organometal. Chem. 2006, 691 (11), 2512. doi: 10.1016/j.jorganchem.2006.01.043
(21) Luo, G. G.; Lu. H.; Wang, Y. H.; Dong, J.; Zhao, Y.; Wu, R. B.Dyes and Pigments 2016, 134, 498. doi: 10.1016/j.dyepig.2016.08.013
(22) Zhang, J.; Xu, Q.; Feng, Z.; Li, M.; Li. C. Angew. Chem. Int. Ed.2008, 47, 1766. doi: 10.1002/anie.200704788
(23) Luo, G. G.; Lu, H.; Zhang, X. L.; Dai, J. C.; Wu, J. H.; Wu, J. J.Phys. Chem. Chem. Phys. 2015, 17, 9716. doi: 10.1039/c5cp00732a
(24) Zhang, X.; Kitao, O.; Zhou, H.; Tamiaki, H.; Sasaki, S. J. Phys. Chem. C 2009, 113 (18), 7954. doi: 10.1021/jp900328u
(25) Rolczynski, B. S.; Szarko, J. M.; Son, H. J.; Liang, Y. Y.; Yu, L.P.; Chen, L. X. J. Am. Chem. Soc. 2012, 134 (9), 4142. doi: 10.1021/ja209003y
(26) Wang, P.; Zakeeruddin, S. M.; Moser, J. E.; Grätzel, M. J. Phys. Chem. B 2003, 107 (48), 13280. doi: 10.1021/jp0355399

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3. LIU Xing, LI Yue-Xiang, PENG Shao-Qin, LAI Hua.Progress in Visible-Light Photocatalytic Hydrogen Production by Dye Sensitization[J]. Acta Phys. -Chim. Sin., 2015,31(4): 612-626
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5. SHEN Wei, TIAN Wen-Wen, QI Zheng-Jian, SUN Yue-Ming.Photoelectric Properties of Novel Amide-Functionalized Ir(III) Complexes[J]. Acta Phys. -Chim. Sin., 2015,31(11): 2174-2182
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8. ZHAO Jian, ZHOU Wei, MA Jian-Xin.Effect of CO2 Pretreatment Operation Conditions on the Catalytic Performance and Structure of Ni-Co Bimetallic Catalyst[J]. Acta Phys. -Chim. Sin., 2014,30(7): 1325-1331
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12. ZHAO Jian, ZHOU Wei, XU Jun-Ke, MA Jian-Xin.Effect of Pretreatment Routes on the Performance and Structure of Ni-Co Bimetallic Catalysts[J]. Acta Phys. -Chim. Sin., 2013,29(04): 806-812
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17. LI Xiao-Ning, BAI Shou-Li, YANG Wen-Sheng, CHEN Ai-Fan, SUN Li-Na, LIN Yuan, ZHANG Jing-Bo.Electron Transport Properties of One-Dimensional Structural SnO2 Belts[J]. Acta Phys. -Chim. Sin., 2012,28(07): 1797-1802
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19. JIANG Li-Long, MA Yong-De, CAO Yan-Ning, YANG Yang, WEI Ke-Mei.Modified Bauxite Supported Ruthenium Catalysts for Hydrogen Evolution in the Water-Gas Shift Reaction[J]. Acta Phys. -Chim. Sin., 2012,28(03): 674-680
20. YAN Shi, HUANG Qin-Dong, LIN Jing-Dong, YUAN You-Zhu, LIAO Dai-Wei.Photocatalytic Activity of Cobalt Doped Titania for H2 Evolution[J]. Acta Phys. -Chim. Sin., 2011,27(10): 2406-2410
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