Synthesis and characterization of new electron acceptor perylene diimide molecules for photovoltaic applications

被引:61
作者
Kozma, Erika [1 ]
Kotowski, Dariusz [1 ]
Catellani, Marinella [1 ]
Luzzati, Silvia [1 ]
Famulari, Antonino [2 ]
Bertini, Fabio [1 ]
机构
[1] CNR, Ist Studio Macromol, I-20133 Milan, Italy
[2] Politecn Milan, Dipartimento Chim Mat & Ingn Chim Giulio Natta, I-20131 Milan, Italy
关键词
Perylene diimides; Electron acceptor; Organic solar cell; DET calculations; HOMO and LUMO orbitals; n-type materials; GAUSSIAN-TYPE BASIS; ORGANIC SEMICONDUCTORS; ORBITAL METHODS; COPOLYMERS; POLYMER; ABSORPTION; MORPHOLOGY; INTERFACE; DESIGN; IMIDES;
D O I
10.1016/j.dyepig.2013.05.011
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Two new perylene diimide molecules, 1, 7-bis(1-naphtyl)-N,N'-bis-(10-nonadecyl)-perylene-3,4,9,10-bis (dicarboximide) PDI-2 and 1,7-bis(5-acenaphtenyl)-N,N'-bis-(10-nonadecyl)-perylene-3,4,9,10-bis(dicarboximide) PDI-3 have been synthesized and used as acceptor components in P3HT/PDI bulk heterojunction solar cells. The introduction of fused aromatic rings into the bay positions of the perylene core creates a stong steric hindrance, twisting the perylene plane with a direct consequence on the pi-pi intramolecular interactions between the adjacent PDIs. All these features contribute to the reduction of molecular aggregation in the solid state, with a strong influence on the performances of P3HT/PDI photovoltaic devices. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:329 / 338
页数:10
相关论文
共 47 条
[1]   Comparative analysis of the energy levels of planar and core-twisted perylene bisimides in solution and solid state by UV/VIS, CV, and UPS/IPES [J].
Arantes, C. ;
Scholz, M. ;
Schmidt, R. ;
Dehm, V. ;
Rocco, M. L. M. ;
Schoell, A. ;
Reinert, F. ;
Wuerthner, F. .
APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING, 2012, 108 (03) :629-637
[2]   Effect of side-chain substituents on self-assembly of perylene diimide molecules: Morphology control [J].
Balakrishnan, Kaushik ;
Datar, Aniket ;
Naddo, Tammene ;
Huang, Jialing ;
Oitker, Randy ;
Yen, Max ;
Zhao, Jincai ;
Zang, Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7390-7398
[3]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[4]   MacMolPlt: A graphical user interface for GAMESS [J].
Bode, BM ;
Gordon, MS .
JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 1998, 16 (03) :133-+
[5]   Effect of core twisting on self-assembly and optical properties of perylene bisimide dyes in solution and columnar liquid crystalline phases [J].
Chen, Zhijian ;
Baumeister, Ute ;
Tschierske, Carsten ;
Wuerthner, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) :450-465
[6]   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
[7]   Charge Photogeneration in Organic Solar Cells [J].
Clarke, Tracey M. ;
Durrant, James R. .
CHEMICAL REVIEWS, 2010, 110 (11) :6736-6767
[8]   Planarized star-shaped oligothiophenes as a new class of organic semiconductors for heterojunction solar cells [J].
de Bettignies, R ;
Nicolas, Y ;
Blanchard, P ;
Levillain, E ;
Nunzi, JM ;
Roncali, J .
ADVANCED MATERIALS, 2003, 15 (22) :1939-1943
[9]   Polymer-Fullerene Bulk-Heterojunction Solar Cells [J].
Dennler, Gilles ;
Scharber, Markus C. ;
Brabec, Christoph J. .
ADVANCED MATERIALS, 2009, 21 (13) :1323-1338
[10]   SELF-CONSISTENT MOLECULAR-ORBITAL METHODS .9. EXTENDED GAUSSIAN-TYPE BASIS FOR MOLECULAR-ORBITAL STUDIES OF ORGANIC MOLECULES [J].
DITCHFIELD, R ;
HEHRE, WJ ;
POPLE, JA .
JOURNAL OF CHEMICAL PHYSICS, 1971, 54 (02) :724-+