Elucidation of the Structure-Property Relationship of p-Type Organic Semiconductors through Rapid Library Construction via a One-Pot, Suzuki-Miyaura Coupling Reaction

被引：23
作者：
Fuse, Shinichiro [1 ]
Matsumura, Keisuke [1 ]
Wakamiya, Atsushi [2 ]
Masui, Hisashi [3 ]
Tanaka, Hiroshi [1 ]
Yoshikawa, Susumu [4 ]
Takahashi, Takashi [3 ]
机构：
[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan
[2] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan
[3] Yokohama Coll Pharm, Yokohama 2450066, Kanagawa, Japan
[4] Kyoto Univ, Inst Adv Energy, Kyoto 6110011, Japan
来源：
ACS COMBINATORIAL SCIENCE | 2014年 / 16卷 / 09期
关键词：
p-type semiconductor; structure-properly relationship; Suzuki-Miyaura coupling; one-pot; SOLAR-CELLS; COMBINATORIAL; DESIGN; ROUTE; DYES;
D O I：
10.1021/co500071x
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The elucidation of the structure property relationship is an important issue in the development of organic electronics. Combinatorial synthesis and the evaluation of systematically modified compounds is a powerful tool in the work of elucidating structure property relationships. In this manuscript, D-pi-A structure, 32 p-type organic semiconductors were rapidly synthesized via a one-pot, Suzuki-Miyaura coupling with subsequent Knoevenagel condensation. Evaluation of the solubility and photovoltaic properties of the prepared compounds revealed that the measured solubility was strongly correlated with the solubility parameter (SP), as reported by Fedors. In addition, the SPs were correlated with the J(sc), of thin-film organic solar cells prepared using synthesized compounds. Among the evaluated photovoltaic properties of the solar cells, J(sc) and V-oc had strong correlations with the photoconversion efficiency (PCE).
引用
收藏
页码：494 / 499
页数：6
相关论文
共 42 条
[1]   Vacuum-Deposited Small-Molecule Organic Solar Cells with High Power Conversion Efficiencies by Judicious Molecular Design and Device Optimization [J].
Chen, Yi-Hong ;
Lin, Li-Yen ;
Lu, Chih-Wei ;
Lin, Francis ;
Huang, Zheng-Yu ;
Lin, Hao-Wu ;
Wang, Po-Han ;
Liu, Yi-Hung ;
Wong, Ken-Tsung ;
Wen, Jianguo ;
Miller, Dean J. ;
Darling, Seth B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13616-13623
[2]   Synthesis of Conjugated Polymers for Organic Solar Cell Applications [J].
Cheng, Yen-Ju ;
Yang, Sheng-Hsiung ;
Hsu, Chain-Shu .
CHEMICAL REVIEWS, 2009, 109 (11) :5868-5923
[3]   Sequential palladium-catalyzed coupling reactions on solid-phase [J].
Doi, Takayuki ;
Inoue, Hitoshi ;
Tokita, Masatoshi ;
Watanabe, Junji ;
Takahashi, Takashi .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (01) :135-141
[4]   METHOD FOR ESTIMATING BOTH SOLUBILITY PARAMETERS AND MOLAR VOLUMES OF LIQUIDS [J].
FEDORS, RF .
POLYMER ENGINEERING AND SCIENCE, 1974, 14 (02) :147-154
[5]   D-π-A Sensitizers for Dye-Sensitized Solar Cells: Linear vs Branched Oligothiophenes [J].
Fischer, Markus K. R. ;
Wenger, Sophie ;
Wang, Mingkui ;
Mishra, Amaresh ;
Zakeeruddin, Shaik M. ;
Gratzel, Michael ;
Baeuerle, Peter .
CHEMISTRY OF MATERIALS, 2010, 22 (05) :1836-1845
[6]   Development of dual targeting inhibitors against aggregations of amyloid-β and tau protein [J].
Fuse, Shinichiro ;
Matsumura, Keisuke ;
Fujita, Yuki ;
Sugimoto, Hachiro ;
Takahashi, Takashi .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 :228-234
[7]   Elucidating the Structure-Property Relationships of Donor-π-Acceptor Dyes for Dye-Sensitized Solar Cells (DSSCs) through Rapid Library Synthesis by a One-Pot Procedure [J].
Fuse, Shinichiro ;
Sugiyama, Sakae ;
Maitani, Masato M. ;
Wada, Yuji ;
Ogomi, Yuhei ;
Hayase, Shuzi ;
Katoh, Ryuzi ;
Kaiho, Tatsuo ;
Takahashi, Takashi .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (34) :10685-10694
[8]   Design and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A [J].
Fuse, Shinichiro ;
Inaba, Kennichi ;
Takagi, Motoki ;
Tanaka, Masahiro ;
Hirokawa, Takatsugu ;
Johmoto, Kohei ;
Uekusa, Hidehiro ;
Shin-Ya, Kazuo ;
Takahashi, Takashi ;
Doi, Takayuki .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 66 :180-184
[9]   Sequential Coupling Approach to the Synthesis of Nickel(II) Complexes with N-aryl-2-amino Phenolates [J].
Fuse, Shinichiro ;
Tago, Hiroaki ;
Maitani, Masato M. ;
Wada, Yuji ;
Takahashi, Takashi .
ACS COMBINATORIAL SCIENCE, 2012, 14 (10) :545-550
[10]   An iterative approach to the synthesis of thiophene-based organic dyes [J].
Fuse, Shinichiro ;
Yoshida, Hayato ;
Takahashi, Takashi .
TETRAHEDRON LETTERS, 2012, 53 (26) :3288-3291
12345