2,5,8,11-Tetraboronic Ester Perylenediimides: A Next Generation Building Block for Dye-Stuff Synthesis

被引:97
作者
Battagliarin, Glauco [1 ]
Li, Chen [1 ]
Enkelmann, Volker [1 ]
Muellen, Klaus [1 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
关键词
RUTHENIUM-CATALYZED CONVERSION; TRANSFER HYDROGENATION; BOND; TRANSISTORS; BISIMIDES; ALCOHOLS; KETONES; IMIDE; OXIME;
D O I
10.1021/ol2008457
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Via an unprecedentedly reported ruthenium catalyzed reaction, an efficient and straightforward method was developed for the synthesis of 2,5,8,11-tetraboronate perylenediimide derivatives. A possible reaction mechanism is proposed. The synthesis of 2,5,8,11-tetra-lodo and totra-amino perylenedilmides derivatives is also reported.
引用
收藏
页码:3012 / 3015
页数:4
相关论文
共 40 条
[1]   Ruthenium-catalysed conversion of oxime ethers into nitriles [J].
Anand, Naveen ;
Owston, Nathan A. ;
Parker, Alexandra J. ;
Slatford, Paul A. ;
Williams, Jonathan M. J. .
TETRAHEDRON LETTERS, 2007, 48 (44) :7761-7763
[2]  
[Anonymous], 2011, ADV ENERGY MAT, DOI DOI 10.1002/AENM.201190005
[3]  
[Anonymous], 2007, ANGEW CHEM-GER EDIT
[4]   Synthesis and applications of core-enlarged perylene dyes [J].
Avlasevich, Yuri ;
Li, Chen ;
Muellen, Klaus .
JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (19) :3814-3826
[5]   Photophysics and Redox Properties of Rylene Imide and Diimide Dyes Alkylated Ortho to the Imide Groups [J].
Bullock, Joseph E. ;
Vagnini, Michael T. ;
Ramanan, Charusheela ;
Co, Dick T. ;
Wilson, Thea M. ;
Dicke, Jay W. ;
Marks, Tobin J. ;
Wasielewski, Michael R. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (05) :1794-1802
[6]   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
[7]   Ruthenium-Catalyzed Tertiary Amine Formation from Nitroarenes and Alcohols [J].
Feng, Chao ;
Liu, Yong ;
Peng, Shengming ;
Shuai, Qi ;
Deng, Guojun ;
Li, Chao-Jun .
ORGANIC LETTERS, 2010, 12 (21) :4888-4891
[8]  
GEISSLER G, 1959, Patent No. 1130099
[9]   Alkenes from alcohols by tandem hydrogen transfer and condensation [J].
Hall, Michael I. ;
Pridmore, Simon J. ;
Williams, Jonathan M. J. .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (13) :1975-1978
[10]   Direct Ruthenium-Catalyzed C-C Coupling of Ethanol: Diene Hydro-hydroxyethylation To Form All-Carbon Quaternary Centers [J].
Han, Hoon ;
Krische, Michael J. .
ORGANIC LETTERS, 2010, 12 (12) :2844-2846