Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides

被引:38
作者
Chen, Kew-Yu [1 ]
Fang, Tzu-Chien [1 ]
Chang, Ming-Jen [1 ]
机构
[1] Feng Chia Univ, Dept Chem Engn, Taichung 40724, Taiwan
关键词
1-Aminoperylene bisimides; Intramolecular charge transfer; Purple dyes; Self-assembly; SOLUBLE PERYLENE DERIVATIVES; SOLAR-CELLS; ORGANIC SEMICONDUCTORS; BUILDING-BLOCKS; ENERGY-TRANSFER; DIIMIDES; TRANSISTORS; ELECTRON; DYES; CHROMOPHORES;
D O I
10.1016/j.dyepig.2011.06.023
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
1-Aminoperylene bisimides (1a-1c) were synthesized under mild condition in high yields, and were characterized by FT-IR, (1)H NMR, UV-Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetric analyses. These compounds are stable up to 310 degrees C according to thermogravimetric analyses. They undergo two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Their spectroscopic properties in various conditions and complementary density functional theory (DFT) calculations are reported. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:517 / 523
页数:7
相关论文
共 39 条
[1]   Bis(n-octylamino)perylene-3,4:9,10-bis(dicarboximide)s and their radical cations:: Synthesis, electrochemistry, and ENDOR spectroscopy [J].
Ahrens, MJ ;
Tauber, MJ ;
Waslelewski, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2107-2114
[2]   Self-assembly of supramolecular light-harvesting arrays from covalent multi-chromophore peryiene-3,4:9,10-bis(dicarboximide) building blocks [J].
Ahrens, MJ ;
Sinks, LE ;
Rybtchinski, B ;
Liu, WH ;
Jones, BA ;
Giaimo, JM ;
Gusev, AV ;
Goshe, AJ ;
Tiede, DM ;
Wasielewski, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8284-8294
[3]   Synthesis and spectroscopic properties of highly water-soluble perylene derivatives [J].
Alvino, Antonello ;
Franceschin, Marco ;
Cefaro, Chiara ;
Borioni, Silvia ;
Ortaggi, Giancarlo ;
Bianco, Armandodoriano .
TETRAHEDRON, 2007, 63 (33) :7858-7865
[4]   Photophysical and electrochemical properties of 1,7-diaryl-substituted perylene diimides [J].
Chao, CC ;
Leung, MK ;
Su, YO ;
Chiu, KY ;
Lin, TH ;
Shieh, SJ ;
Lin, SC .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4323-4331
[5]   Air stable n-channel organic semiconductors for thin film transistors based on fluorinated derivatives of perylene diimides [J].
Chen, H. Z. ;
Ling, M. M. ;
Mo, X. ;
Shi, M. M. ;
Wang, M. ;
Bao, Z. .
CHEMISTRY OF MATERIALS, 2007, 19 (04) :816-824
[6]   Tuning excited-state electron transfer from an adiabatic to nonadiabatic type in donor-bridge-acceptor systems and the associated energy-transfer process [J].
Chen, Kew-Yu ;
Hsieh, Cheng-Chih ;
Cheng, Yi-Ming ;
Lai, Chin-Hung ;
Chou, Pi-Tai ;
Chow, Tahsin J. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (44) :12136-12144
[7]   1,7-Dinitroperylene bisimides: facile synthesis and characterization as n-type organic semiconductors [J].
Chen, Kew-Yu ;
Chow, Tahsin J. .
TETRAHEDRON LETTERS, 2010, 51 (45) :5959-5963
[8]   Application of 9-substituted 3,4-perylenedicarboxylic anhydrides as sensitizers for zinc oxide solar cell [J].
Dentani, Takuya ;
Funabiki, Kazumasa ;
Jin, Ji-Ye ;
Yoshida, Tsukasa ;
Minoura, Hideki ;
Matsui, Masaki .
DYES AND PIGMENTS, 2007, 72 (03) :303-307
[9]   Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes [J].
Dincalp, Haluk ;
Askar, Zuhal ;
Zafer, Ceylan ;
Icli, Siddik .
DYES AND PIGMENTS, 2011, 91 (02) :182-191
[10]   1,6-disubstituted perylene bisimides: concise synthesis and characterization as near-infrared fluorescent dyes [J].
Fan, LQ ;
Xu, YP ;
Tian, H .
TETRAHEDRON LETTERS, 2005, 46 (26) :4443-4447