"Click-chemistry" approach in the design of 1,2,3-triazolyl-pyridine ligands and their Ru(II)-complexes for dye-sensitized solar cells

被引:66
作者
Stengel, Ilona [2 ]
Mishra, Amaresh [2 ]
Pootrakulchote, Nuttapol [1 ]
Moon, Soo-Jin [1 ]
Zakeeruddin, Shaik M. [1 ]
Graetzel, Michael [1 ]
Baeuerle, Peter [2 ]
机构
[1] Swiss Fed Inst Technol, Sch Basic Sci, Inst Chem Sci & Engn, Lab Photon & Interfaces, CH-1015 Lausanne, Switzerland
[2] Univ Ulm, Inst Organ Chem & Adv Mat 2, D-89081 Ulm, Germany
基金
瑞士国家科学基金会;
关键词
ENERGY-CONVERSION; 1,3-DIPOLAR CYCLOADDITIONS; EFFICIENT SYNTHESIS; COMPLEXES; PERFORMANCE; ALKYNES; FAMILY; AZIDES; LIGHT;
D O I
10.1039/c0jm03750h
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The synthesis of new 1,2,3-triazolyl-pyridine ligands via "click-chemistry" and their corresponding Ru(L)(2,2'-bipyridyl-4,4'-dicarboxylic acid)(NCS)(2) complexes (L = 1,2,3-triazolyl-pyridine) are presented. The complexes have been photophysically and electrochemically characterized and have been used as sensitizers in dye-sensitized solar cells (DSSC). In DSSCs with an acetonitrile-based electrolyte the cells comprising of Ru(2-(1-(4-hexylphenyl)-1H-1,2,3-triazol-4-yl)pyridine)(2,2'-bipyridyl- 4,4'-dicarboxylic acid)(NCS)(2) TBA salt 1 showed an overall power conversion efficiency of 7.8% under full sunlight intensity, and Ru(2-(4-(4-hexylphenyl)-1H-1,2,3-triazol-1-yl)pyridine)(2,2'-bipyridyl- 4,4'-dicarboxylic acid)(NCS)(2) TBA salt 2 an efficiency of 4.7%. Transient photovoltage and photocurrent decay measurements showed an enhanced performance for dye 1 due to faster electron transport into the TiO2 film and lower recombination rate in comparison to dye 2 sensitized devices. Additionally, solid-state devices were prepared with 2 mm thick TiO2 films using spiro-OMeTAD as a hole-transport material. The solid-state dye-sensitized solar cells showed power conversion efficiencies of 1.92% and 0.38% for sensitizer 1 and 2, respectively.
引用
收藏
页码:3726 / 3734
页数:9
相关论文
共 43 条
[1]   Rapid synthesis of aryl azides from aryl halides under mild conditions [J].
Andersen, J ;
Madsen, U ;
Björkling, F ;
Liang, XF .
SYNLETT, 2005, (14) :2209-2213
[2]   High-performance dye-sensitized solar cells based on solvent-free electrolytes produced from eutectic melts [J].
Bai, Yu ;
Cao, Yiming ;
Zhang, Jing ;
Wang, Mingkui ;
Li, Renzhi ;
Wang, Peng ;
Zakeeruddin, Shaik M. ;
Graetzel, Michael .
NATURE MATERIALS, 2008, 7 (08) :626-630
[3]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[4]   Highly Efficient Light-Harvesting Ruthenium Sensitizer for Thin-Film Dye-Sensitized Solar Cells [J].
Chen, Chia-Yuan ;
Wang, Mingkui ;
Li, Jheng-Ying ;
Pootrakulchote, Nuttapol ;
Alibabaei, Leila ;
Ngoc-le, Cevey-ha ;
Decoppet, Jean-David ;
Tsai, Jia-Hung ;
Graetzel, Carole ;
Wu, Chun-Guey ;
Zakeeruddin, Shaik M. ;
Graetzel, Michael .
ACS NANO, 2009, 3 (10) :3103-3109
[5]   New family of ruthenium-dye-sensitized nanocrystalline TiO2 solar cells with a high solar-energy-conversion efficiency [J].
Chen, Kung-Shih ;
Liu, Wei-Hsin ;
Wang, Yu-Hsiu ;
Lai, Chin-Hung ;
Chou, Pi-Tai ;
Lee, Gene-Hsiang ;
Chen, Kellen ;
Chen, Hsing-Yi ;
Chi, Yun ;
Tung, Fu-Ching .
ADVANCED FUNCTIONAL MATERIALS, 2007, 17 (15) :2964-2974
[6]   Excited-state properties of ruthenium(II) polypyridyl complexes containing asymmetric triazole ligands [J].
Fanni, S ;
Keyes, TE ;
O'Connor, CM ;
Hughes, H ;
Wang, RY ;
Vos, JG .
COORDINATION CHEMISTRY REVIEWS, 2000, 208 :77-86
[7]   Synthesis, X-ray crystal structures, spectroscopy and electrochemistry of ruthenium(II) complexes of two chelating ligands containing [1,2,3]triazolo[1,5-a]pyridine subunits [J].
Fitchett, Christopher M. ;
Keene, F. Richard ;
Richardson, Chris ;
Steel, Peter J. .
INORGANIC CHEMISTRY COMMUNICATIONS, 2008, 11 (06) :595-598
[8]   Multidentate 1,2,3-Triazole-Containing Chelators from Tandem Deprotection/Click Reactions of (Trimethylsilyl)alkynes and Comparison of Their Ruthenium(II) Complexes [J].
Fletcher, James T. ;
Bumgarner, Benjamin J. ;
Engels, Nicole D. ;
Skoglund, David A. .
ORGANOMETALLICS, 2008, 27 (21) :5430-5433
[9]   Conjugation of Selenophene with Bipyridine for a High Molar Extinction Coefficient Sensitizer in Dye-Sensitized Solar Cells [J].
Gao, Feifei ;
Cheng, Yueming ;
Yu, Qingjiang ;
Liu, Shi ;
Shi, Dong ;
Li, Yunhui ;
Wang, Peng .
INORGANIC CHEMISTRY, 2009, 48 (06) :2664-2669
[10]   Recent Advances in Sensitized Mesoscopic Solar Cells [J].
Graetzel, Michael .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (11) :1788-1798