Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

被引:35
作者
Rocard, Lou [1 ]
Goujon, Antoine [1 ]
Hudhomme, Pietrick [1 ]
机构
[1] Univ Angers, SFR MATRIX, Lab MOLTECH Anjou, CNRS,UMR 6200, 2 Bd Lavoisier, Angers 49045, France
关键词
perylenediimide; nitro group; organic materials; SOLAR-CELLS; PHYSICAL-PROPERTIES; BISIMIDES SYNTHESIS; DIIMIDES SYNTHESIS; OPTICAL-PROPERTIES; ENERGY; PERFORMANCE; DERIVATIVES; ACCEPTORS; DYADS;
D O I
10.3390/molecules25061402
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Perylenediimide (PDI) is one of the most important classes of dyes and is intensively explored in the field of functional organic materials. The functionalization of this electron-deficient aromatic core is well-known to tune the outstanding optoelectronic properties of PDI derivatives. In this respect, the functionalization has been mostly addressed in bay-positions to halogenated derivatives through nucleophilic substitutions or metal-catalyzed coupling reactions. Being aware of the synthetic difficulties of obtaining the key intermediate 1-bromoPDI, we will present as an alternative in this review the potential of 1-nitroPDI: a powerful building block to access a large variety of PDI-based materials.
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页数:17
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共 74 条
[1]   Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules [J].
Aivali, Stefania ;
Tsimpouki, Loukia ;
Anastasopoulos, Charalampos ;
Kallitsis, Joannis K. .
MOLECULES, 2019, 24 (23)
[2]   Synthesis and Photophysical Properties of Donor- and Acceptor-Substituted 1,7-Bis(arylalkynyl)perylene-3,4:9,10-bis(dicarboximide)s [J].
An, Zesheng ;
Odom, Susan A. ;
Kelley, Richard F. ;
Huang, Chun ;
Zhang, Xuan ;
Barlow, Stephen ;
Padilha, Lazaro A. ;
Fu, Jie ;
Webster, Scott ;
Hagan, David J. ;
Van Stryland, Eric W. ;
Wasielewski, Michael R. ;
Marder, Seth R. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (19) :5585-5593
[3]   Small-Molecule, Nonfullerene Acceptors for Polymer Bulk Heterojunction Organic Photovoltaics [J].
Anthony, John E. .
CHEMISTRY OF MATERIALS, 2011, 23 (03) :583-590
[4]   Synthesis of Molecular Dyads and Triads Based Upon N-Annulated Perylene Diimide Monomers and Dimers [J].
Cann, Jonathan R. ;
Cabanetos, Clement ;
Welch, Gregory C. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (48) :6933-6943
[5]   Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties [J].
Chen, Kew-Yu ;
Chang, Che-Wei .
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2014, 15 (12) :22642-22660
[6]   Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides [J].
Chen, Kew-Yu ;
Fang, Tzu-Chien ;
Chang, Ming-Jen .
DYES AND PIGMENTS, 2012, 92 (01) :517-523
[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]   Catalyst-Free One-Pot Synthesis of Unsymmetrical Five- and Six-Membered Sulfur-Annulated Heterocyclic Perylene Diimides for Electron-Transporting Property [J].
Chen, Lingcheng ;
Xia, Pengjie ;
Du, Tian ;
Deng, Yunfeng ;
Xiao, Yi .
ORGANIC LETTERS, 2019, 21 (14) :5529-5532
[9]   Colorimetric and ratiometric fluorescent chemosensor for fluoride ion based on perylene diimide derivatives [J].
Chen, Zhi Jun ;
Wang, Li Min ;
Zou, Gang ;
Zhang, Liang ;
Zhang, Guan Jun ;
Cai, Xiao Fei ;
Teng, Ming Shuang .
DYES AND PIGMENTS, 2012, 94 (03) :410-415
[10]   Perylenecarboxydiimide-gold(I) organometallic dyes. Optical properties and Langmuir films [J].
Dominguez, Cristina ;
Jesus Baena, Maria ;
Coco, Silverio ;
Espinet, Pablo .
DYES AND PIGMENTS, 2017, 140 :375-383