Modular synthesis of asymmetric rylene derivatives
作者： Caitlin S. Sample , Eisuke Goto , Nisha V. Handa , Zachariah A. Page , Yingdong Luo
DOI: 10.1039/C6TC05139A
关键词: Modular design 、 Naphthalic anhydride 、 Coupling (computer programming) 、 Materials science 、 Combinatorial chemistry
摘要: The modular synthesis of asymmetric rylenes from naphthalic anhydride derivatives is presented. Imidization, Suzuki–Miyaura coupling and cyclodehydrogenation reactions are utilized for the generation novel functional with these three core transformations providing significant flexibility over final structure. combination simple purification high yields enables access to handles at imide-position site-specific incorporation bay position substituents. resulting library perylenes bisnapthalimide-anthracene showcase presented methodology ability tune optoelectronic electrochemical properties.
rsc.org
uq.edu.au参考文章(29)
William E. Ford, Prashant V. Kamat, Photochemistry of 3,4,9,10-perylenetetracarboxylic dianhydride dyes. 3. Singlet and triplet excited-state properties of the bis(2,5-di-tert-butylphenyl)imide derivative The Journal of Physical Chemistry. ,vol. 91, pp. 6373- 6380 ,(1987) , 10.1021/J100309A012
Yukinori Nagao, Narumi Ishikawa, Yoriko Tanabe, Takahisa Misono, SYNTHESIS OF UNSYMMETRICAL PERYLENEBIS(DICARBOXIMIDE) DERIVATIVES Chemistry Letters. ,vol. 8, pp. 151- 154 ,(1979) , 10.1246/CL.1979.151
Michael J. Ahrens, Michael J. Fuller, Michael R. Wasielewski, Cyanated perylene-3,4-dicarboximides and perylene-3,4:9,10-bis(dicarboximide): Facile chromophoric oxidants for organic photonics and electronics Chemistry of Materials. ,vol. 15, pp. 2684- 2686 ,(2003) , 10.1021/CM034140U
Takaaki Sakamoto, Chyongjin Pac, A "green" route to perylene dyes: direct coupling reactions of 1,8-naphthalimide and related compounds under mild conditions using a "new" base complex reagent, t-BuOK/DBN. Journal of Organic Chemistry. ,vol. 66, pp. 94- 98 ,(2001) , 10.1021/JO0010835
Mahin Sadrai, George R. Bird, A new laser dye with potential for high stability and a broad band of lasing action: Perylene-3,4,9,10-tetracarboxylic acid-bis-N,N′(2′,6′ xylidyl)diimide Optics Communications. ,vol. 51, pp. 62- 64 ,(1984) , 10.1016/0030-4018(84)90285-2
Y Nagao, Synthesis and properties of N,N'-unsymmetrical dialkyl-3,4:9,10-perylenebis(dicarboximide)s Dyes and Pigments. ,vol. 6, pp. 303- 311 ,(1985) , 10.1016/0143-7208(85)87006-6
Xiaowei Zhan, Zhan'ao Tan, Benoit Domercq, Zesheng An, Xuan Zhang, Stephen Barlow, Yongfang Li, Daoben Zhu, Bernard Kippelen, Seth R. Marder, A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. Journal of the American Chemical Society. ,vol. 129, pp. 7246- 7247 ,(2007) , 10.1021/JA071760D
Frank Würthner, Vladimir Stepanenko, Zhijian Chen, Chantu R. Saha-Möller, Nikolaus Kocher, Dietmar Stalke, Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes Journal of Organic Chemistry. ,vol. 69, pp. 7933- 7939 ,(2004) , 10.1021/JO048880D
Sven Hüttner, Michael Sommer, Mukundan Thelakkat, n-type organic field effect transistors from perylene bisimide block copolymers and homopolymers Applied Physics Letters. ,vol. 92, pp. 093302- ,(2008) , 10.1063/1.2885712
A. Yakimov, S. R. Forrest, High photovoltage multiple-heterojunction organic solar cells incorporating interfacial metallic nanoclusters Applied Physics Letters. ,vol. 80, pp. 1667- 1669 ,(2002) , 10.1063/1.1457531