Conjugated Macrocycles: Concepts and Applications

被引:458
作者
Iyoda, Masahiko [1 ]
Yamakawa, Jun [1 ]
Rahman, M. Jalilur [1 ]
机构
[1] Tokyo Metropolitan Univ, Dept Chem, Grad Sch Sci & Engn, Tokyo 1920397, Japan
基金
日本科学技术振兴机构;
关键词
conjugated rings; macrocycles; supramolecular chemistry; SHAPE-PERSISTENT MACROCYCLES; ELECTRON-TRANSFER OXIDATION; X-RAY-STRUCTURE; ARYLENE-ETHYNYLENE MACROCYCLES; LIGHT-EMITTING CHARACTERISTICS; ONE-POT SYNTHESIS; FACE-TO-FACE; 2-PHOTON ABSORPTION; PHOTOPHYSICAL PROPERTIES; EXPANDED PORPHYRINS;
D O I
10.1002/anie.201006198
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
One of the most important objectives in materials, chemical, and physical sciences is the creation of large conjugated macrocycles with well-defined shapes, since such molecules are not only theoretically and experimentally interesting but also have potential applications in nanotechnology. Fully unsaturated macrocycles are regarded as models for infinitely conjugated π systems with inner cavities, and exhibit unusual optical and magnetic behavior. Macrocycles have interior and exterior sites, and site-specific substitution at both or either site can afford attractive structures, such as 1D, 2D, and 3D supramolecular nanostructures. These nanostructures could be controlled through the use of π-extended large macrocycles by a bottom-up strategy. Numerous shape-persistent π-conjugated macrocycles have been synthesized, but only a few are on the nanoscale. This Review focuses on nanosized π-conjugated macrocycles (>1 nm diameter) and giant macrocycles (>2 nm diameter), and summarizes their syntheses and properties. Going in giant circles: Fully unsaturated macrocycles exhibit unusual optical and magnetic behavior because of their effective cyclic conjugation. In particular, site-specific substitution at interior and exterior sites can afford attractive structures for a wide range of research fields such as organic chemistry, polymer and materials science, and supramolecular chemistry. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10522 / 10553
页数:32
相关论文
共 383 条
[1]   Synthesis of a Mobius aromatic hydrocarbon [J].
Ajami, D ;
Oeckler, O ;
Simon, A ;
Herges, R .
NATURE, 2003, 426 (6968) :819-821
[2]   Chiral (2,5)Pyrido[74]allenoacetylenic Cyclophanes: Synthesis and Characterization [J].
Alonso-Gomez, Jose Lorenzo ;
Navarro-Vazquez, Armando ;
Cid, M. Magdalena .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (26) :6495-6503
[3]   An Enantiomerically Pure Alleno-Acetylenic Macrocycle: Synthesis and Rationalization of Its Outstanding Chiroptical Response [J].
Alonso-Gomez, Jose Lorenzo ;
Rivera-Fuentes, Pablo ;
Harada, Nobuyuki ;
Berova, Nina ;
Diederich, Francois .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (30) :5545-5548
[4]   Synthesis and characteristics of a nonaggregating tris(tetrathiafulvaleno)dodecadehydro[18]annulene [J].
Andersson, Asbjorn Sune ;
Kilsa, Kristine ;
Hassenkam, Tue ;
Gisselbrecht, Jean-Paul ;
Boudon, Corinne ;
Gross, Maurice ;
Nielsen, Mogens Brondsted ;
Diederich, Francois .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (33) :8451-8459
[5]  
[Anonymous], 2008, ANGEW CHEM
[6]  
[Anonymous], ANNULENES BENZO HETE
[7]  
[Anonymous], 2009, ANGEW CHEM
[8]  
[Anonymous], 2006, ANGEW CHEM-GER EDIT
[9]  
[Anonymous], 1996, ANGEW CHEM
[10]  
[Anonymous], 2000, ANGEW CHEM