A synthetic approach towards interlocked π-conjugated macrocycles

被引:31
作者
Ammann, M
Rang, A
Schalley, CA
Bäuerle, P
机构
[1] Univ Ulm, Dept Organ Chem 2, D-89081 Ulm, Germany
[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
关键词
catenates; conjugated interlocked macrocycle; mass spectrometry; oligothiophene; phenanthroline; macrocycles;
D O I
10.1002/ejoc.200500938
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the synthesis of interlocked pi-conjugated macrocycles is described, Starting from 2,9-bis(oligothienyl)[1,10]phenanthrolines, (trimethylsilyl) acetylene groups were introduced at the terminal thiophene rings by selective iodination and subsequent Sonogashira-Hagihara coupling. Subsequently, we applied our recently developed metal-template approach to macrocyclization reactions by treating the deprotected acetylenes with cis-[Pt(dppp)Cl-2] to yield a platina-macrocycle. Based on this synthetic knowledge, by a
引用
收藏
页码:1940 / 1948
页数:9
相关论文
共 84 条
[81]   Catenanes and rotaxanes of the amide type [J].
Vogtle, F ;
Dunnwald, T ;
Schmidt, T .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (09) :451-460
[82]   ONE-STEP SYNTHESIS OF A FOURFOLD FUNCTIONALIZED CATENANE [J].
VOGTLE, F ;
MEIER, S ;
HOSS, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (12) :1619-1622
[83]   Relative binding affinities of molecular capsules investigated by ESI-mass spectrometry [J].
Zadmard, R ;
Kraft, A ;
Schrader, T ;
Linne, U .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (17) :4233-4239
[84]   Capsule-like assemblies in polar solvents [J].
Zadmard, R ;
Junkers, M ;
Schrader, T ;
Grawe, T ;
Kraft, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6511-6521