Step-Economical Syntheses of Functional BODIPY-EDOT π-Conjugated Materials through Direct C-H Arylation

被引:33
作者
Chong, Hui [1 ]
Lin, Hsing-An [1 ]
Shen, Mo-Yuan [2 ]
Liu, Ching-Yuan [3 ]
Zhao, Haichao [1 ]
Yu, Hsiao-hua [1 ,2 ]
机构
[1] Respons Organ Mat Lab, Wako, Saitama 3510198, Japan
[2] Acad Sinica, Inst Chem, Taipei 11529, Taiwan
[3] Natl Cent Univ, Dept Chem & Mat Engn, Taoyuan 32001, Taiwan
关键词
ALTERNATING COPOLYMERS; EFFICIENT SYNTHESIS; COUPLING REACTIONS; FLUORESCENT-PROBE; DYES; POLYMERS; DERIVATIVES; THIOPHENE;
D O I
10.1021/acs.orglett.5b00875
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-Catalyzed direct C-H arylations of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) With 3,4-ethylenedioxythiophene (EDOT) derivatives at relatively low temperature (60 degrees C) provide moderate to good. yields (47%-72%) Of products having potential applications in fluorescent bioimaging and organic optoelectronics.
引用
收藏
页码:3198 / 3201
页数:4
相关论文
共 45 条
[11]   Manipulating non-innocent π-spacers: the challenges of using 2,6-disubstituted BODIPY cores within donor-acceptor light-harvesting motifs [J].
Bonnier, Catherine ;
Machin, Devin D. ;
Abdi, Omar ;
Koivisto, Bryan D. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (22) :3756-3760
[12]   Functionalization of Boron Dipyrrin (BODIPY) Dyes through Iridium and Rhodium Catalysis: A Complementary Approach to α- and β-Substituted BODIPYs [J].
Chen, Jinping ;
Mizumura, Masatoshi ;
Shinokubo, Hiroshi ;
Osuka, Atsuhiro .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (24) :5942-5949
[13]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[14]   Conjugated Polymer Nanoparticles for Light-Activated Anticancer and Antibacterial Activity with Imaging Capability [J].
Chong, Hui ;
Nie, Chenyao ;
Zhu, Chunlei ;
Yang, Qiong ;
Liu, Libing ;
Lv, Fengting ;
Wang, Shu .
LANGMUIR, 2012, 28 (04) :2091-2098
[15]   BODIPY-based conjugated polymers for broadband light sensing and harvesting applications [J].
Cortizo-Lacalle, Diego ;
Howells, Calvyn T. ;
Gambino, Salvatore ;
Vilela, Filipe ;
Vobecka, Zuzana ;
Findlay, Neil J. ;
Inigo, Anto R. ;
Thomson, Stuart A. J. ;
Skabara, Peter J. ;
Samuel, Ifor D. W. .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (28) :14119-14126
[16]   Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II) [J].
Coskun, Ali ;
Yilmaz, M. Deniz ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2007, 9 (04) :607-609
[17]  
Development and Management of Human Resources, 2008, DEV MANAGEMENT HUMAN, V10, P4
[18]   Synthesis of Thiophene- and Bithiophene-Based Alternating Copolymers via Pd-Catalyzed Direct C-H Arylation [J].
Fujinami, Yohei ;
Kuwabara, Junpei ;
Lu, Wei ;
Hayashi, Hideki ;
Kanbara, Takaki .
ACS MACRO LETTERS, 2012, 1 (01) :67-70
[19]   Predictable and Site-Selective Functionalization of Poly(hetero)arene Compounds by Palladium Catalysis [J].
Lapointe, David ;
Markiewicz, Thomas ;
Whipp, Christopher J. ;
Toderian, Amy ;
Fagnou, Keith .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (03) :749-759
[20]   A Photostable AIE Luminogen for Specific Mitochondrial Imaging and Tracking [J].
Leung, Chris Wai Tung ;
Hong, Yuning ;
Chen, Sijie ;
Zhao, Engui ;
Lam, Jacky Wing Yip ;
Tang, Ben Zhong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) :62-65