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
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页码:1940 / 1948
页数:9
相关论文
共 84 条
[1]   [2]CATENANE OR NOT [2]CATENANE [J].
ADAMS, H ;
CARVER, FJ ;
HUNTER, CA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (08) :809-810
[2]   Interlocked and intertwined structures and superstructures [J].
Amabilino, DB ;
Stoddart, JF .
CHEMICAL REVIEWS, 1995, 95 (08) :2725-2828
[3]   Synthesis and electronic properties of series of oligothiophene-[1,10]phenanthrolines [J].
Ammann, M ;
Bäuerle, P .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (22) :4143-4152
[4]   EXPANDING ROLES FOR TEMPLATES IN SYNTHESIS [J].
ANDERSON, S ;
ANDERSON, HL ;
SANDERS, JKM .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (09) :469-475
[5]   EFFECT OF CHELATE-RING SIZE ON SPECTROSCOPIC AND CHEMICAL PROPERTIES OF METHYLPLATINUM(II) COMPLEXES OF DITERTIARY PHOSPHINES PH-2P-[CH-2]-NPPH-2(N=1,2, OR 3) [J].
APPLETON, TG ;
BENNETT, MA ;
TOMKINS, IB .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1976, (05) :439-446
[6]  
Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO
[7]  
2-X
[8]  
Balzani V., 2003, Molecular Devices and Machines, a Journey into the Nanoworld
[9]  
Bauerle P., 1998, ELECT MAT OLIGOMERIC
[10]   Optical absorption spectra of linear and cyclic thiophenes-selection rules manifestation [J].
Bednarz, M ;
Reineker, P ;
Mena-Osteritz, E ;
Bäuerle, P .
JOURNAL OF LUMINESCENCE, 2004, 110 (04) :225-231