Core-Extended Terrylene Tetracarboxdiimide: Synthesis and Chiroptical Characterization

被引:63
作者
Eversloh, Christian Luetke [1 ]
Liu, Zhihong [2 ]
Mueller, Beate [1 ]
Stangl, Michael [3 ]
Li, Chen [1 ]
Muellen, Klaus [1 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
[2] Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266101, Peoples R China
[3] Johannes Gutenberg Univ Mainz, Inst Pharm & Biochem, D-55128 Mainz, Germany
关键词
PERYLENE BISIMIDES; RESOLUTION;
D O I
10.1021/ol202254c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The novel 1,16:6,7:8,9:14,15-tetranaphthoterrylene tetracarboxdiimide was synthesized via a straightforward route, yielding optically active atropisomers with a high racemization barrier. Absorption, fluorescence, and circular dichroism measurements revealed high absorption coefficients and fluorescence quantum yields and enabled the stereochemical assignment in combination with quantum mechanical calculations.
引用
收藏
页码:5528 / 5531
页数:4
相关论文
共 25 条
[1]   Novel core-expanded rylenebis(dicarboximide) dyes bearing pentacene units:: Facile synthesis and photophysical properties [J].
Avlasevich, Yuri ;
Mueller, Sibylle ;
Erk, Peter ;
Muellen, Klaus .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (23) :6555-6561
[2]   Atroposelective synthesis of axially chiral biaryl compounds [J].
Bringmann, G ;
Mortimer, AJP ;
Keller, PA ;
Gresser, MJ ;
Garner, J ;
Breuning, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427
[3]   Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products [J].
Bringmann, Gerhard ;
Gulder, Tanja ;
Gulder, Tobias A. M. ;
Breuning, Matthias .
CHEMICAL REVIEWS, 2011, 111 (02) :563-639
[4]   SPECIFICATION OF MOLECULAR CHIRALITY [J].
CAHN, RS ;
INGOLD, C ;
PRELOG, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) :385-&
[5]   Atropochiral C,X- and C,C-Chelating Carbon Ligands [J].
Canac, Yves ;
Chauvin, Remi .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (16) :2325-2335
[6]   The Challenge of Atropisomerism in Drug Discovery [J].
Clayden, Jonathan ;
Moran, Wesley J. ;
Edwards, Paul J. ;
LaPlante, Steven R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) :6398-6401
[7]  
CROSS LC, 1976, PURE APPL CHEM, V45, P13
[8]  
Frisch M. J., 2003, Gaussian 03
[9]   Photophysical study of bay substituted perylenediimides [J].
Fron, Eduard ;
Schweitzer, Gerd ;
Osswald, Peter ;
Wuerthner, Frank ;
Marsal, Philippe ;
Beljonne, David ;
Muellen, Klaus ;
De Schryver, Frans C. ;
Van der Auweraer, Mark .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2008, 7 (12) :1509-1521
[10]   A Crystal-Engineered Hydrogen-Bonded Octachloroperylene Diimide with a Twisted Core: An n-Channel Organic Semiconductor [J].
Gsaenger, Marcel ;
Oh, Joon Hak ;
Koenemann, Martin ;
Hoeffken, Hans Wolfgang ;
Krause, Ana-Maria ;
Bao, Zhenan ;
Wuerthner, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) :740-743