Apr 26, 2013
Synthesis of 2-azulenyl-1,1,4,4-tetracyano-3-ferrocenyl-1,3-butadienes by [2+2] cycloaddition of (ferrocenylethynyl)azulenes with tetracyanoethylene.
Chemistry (Weinheim an der Bergstrasse, Germany)
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- Volume
- 19
- Number
- 18
- First page
- 5721
- Last page
- 30
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1002/chem.201202257
1-, 2-, and 6-(Ferrocenylethynyl)azulene derivatives 10-16 have been prepared by palladium-catalyzed alkynylation of ethynylferrocene with the corresponding haloazulenes under Sonogashira-Hagihara conditions. Compounds 10-16 reacted with tetracyanoethylene (TCNE) in a [2+2] cycloaddition-cycloreversion reaction to afford the corresponding 2-azulenyl-1,1,4,4,-tetracyano-3-ferrocenyl-1,3-butadiene chromophores 17-23 in excellent yields. The redox behavior of the novel azulene chromophores 17-23 was examined by using cyclic voltammetry (CV) and differential pulse voltammetry (DPV), which revealed their multistep electrochemical reduction properties. Moreover, a significant color change was observed by visible spectroscopy under electrochemical reduction conditions.
- Link information
- ID information
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- DOI : 10.1002/chem.201202257
- ISSN : 0947-6539
- Pubmed ID : 23447514
- SCOPUS ID : 84876940685