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A Synthetic Approach Towards Interlocked π‐Conjugated Macrocycles
Author(s) -
Ammann Martin,
Rang Alexander,
Schalley Christoph A.,
Bäuerle Peter
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500938
Subject(s) - chemistry , sonogashira coupling , diacetylene , conjugated system , trimethylsilyl , thiophene , combinatorial chemistry , tandem , halogenation , stereochemistry , acetylene , organic chemistry , palladium , catalysis , polymer , monomer , materials science , composite material
A method for the synthesis of interlocked π‐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 multiple transition‐metal‐template protocol we accomplished the synthesis of a copper( I )–catenate consisting of two interlocked π‐conjugated macrocycles which contain oligothiophene, diacetylene and phenanthroline units. Conclusive evidence for the new structures came from a detailed characterization of the platina‐macrocycles and catenates by ESI‐FT‐ICR and tandem mass spectrometry experiments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)