The synthesis of novel core-substituted naphthalene diimides via Suzuki cross-coupling and their properties

被引:44
作者
Bhosale, Sheshanath V. [1 ]
Kalyankar, Mohan B. [2 ]
Bhosale, Sidhanath V. [2 ]
Langford, Steven J. [1 ]
Reid, Ellen F. [3 ]
Hogan, Conor F. [3 ]
机构
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
[2] N Maharashtra Univ, Dept Organ Chem, Jalgaon 425001, India
[3] La Trobe Univ, Dept Chem, Bundoora, Vic 3086, Australia
基金
澳大利亚研究理事会;
关键词
REDOX PROPERTIES; LIPID-BILAYERS; TRANSISTORS; BISIMIDES; DYES;
D O I
10.1039/b9nj00476a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper reports the efficient core-substitution of halogenated naphthalene diimides utilizing the Suzuki cross-coupling reaction to install various aryl substituents at the 2,6 positions. The UV-visible spectra of these compounds show a clear absorbance red shift and an enhanced fluorescence output, making them potential candidates for solar-cell dyes and electroactive elements for supramolecular materials.
引用
收藏
页码:2409 / 2413
页数:5
相关论文
共 23 条
[1]  
BHOSALE S, 2008, NAPHTHALENEDIIMIDES, P263
[2]   Synthetic functional π-stack architecture in lipid bilayers [J].
Bhosale, Sheshanath ;
Sisson, Adam L. ;
Sakai, Naomi ;
Matile, Stefan .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (16) :3031-3039
[3]   Photoproduction of proton gradients with π-stacked fluorophore scaffolds in lipid bilayers [J].
Bhosale, Sheshanath ;
Sisson, Adam L. ;
Talukdar, Pinaki ;
Fuerstenberg, Alexandre ;
Banerji, Natalie ;
Vauthey, Eric ;
Bollot, Guillaume ;
Mareda, Jiri ;
Roger, Cornelia ;
Wuerthner, Frank ;
Sakai, Naomi ;
Matile, Stefan .
SCIENCE, 2006, 313 (5783) :84-86
[4]   Chemistry of naphthalene diimides [J].
Bhosale, Sheshanath V. ;
Jani, Chintan H. ;
Langford, Steven J. .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :331-342
[5]   Very large acceleration of the photoinduced electron transfer in a Ru(bpy)3-naphthalene bisimide dyad bridged on the naphthyl core [J].
Chaignon, Frederique ;
Falkenstrom, Magnus ;
Karlsson, Susanne ;
Blart, Errol ;
Odobel, Fabrice ;
Hammarstrom, Leif .
CHEMICAL COMMUNICATIONS, 2007, (01) :64-66
[6]   Naphthalenedicarboximide- vs Perylenedicarboximide-Based Copolymers. Synthesis and Semiconducting Properties in Bottom-Gate N-Channel Organic Transistors [J].
Chen, Zhihua ;
Zheng, Yan ;
Yan, He ;
Facchetti, Antonio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) :8-+
[7]   Syntheses and properties of core-substituted naphthalene bisimides with aryl ethynyl or cyano groups [J].
Chopin, Stephanie ;
Chaignon, Frederique ;
Blart, Errol ;
Odobel, Fabrice .
JOURNAL OF MATERIALS CHEMISTRY, 2007, 17 (39) :4139-4146
[8]   Tri- and tetra-substituted naphthalene diimides as potent G-quadruplex ligands [J].
Cuenca, Francisco ;
Greciano, Olga ;
Gunaratnam, Mekala ;
Haider, Shozeb ;
Munnur, Deeksha ;
Nanjunda, Rupesh ;
Wilson, W. David ;
Neidle, Stephen .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (05) :1668-1673
[9]   Conjugated Polymers from Naphthalene Bisimide [J].
Guo, Xugang ;
Watson, Mark D. .
ORGANIC LETTERS, 2008, 10 (23) :5333-5336
[10]   Cyanonaphthalene diimide semiconductors for air-stable, flexible, and optically transparent n-channel field-effect transistors [J].
Jones, Brooks A. ;
Facchetti, Antonio ;
Marks, Tobin J. ;
Wasielewski, Michael R. .
CHEMISTRY OF MATERIALS, 2007, 19 (11) :2703-2705