4-Vinyl-, 4-vinyl-, and 4'-vinyl-2,2':6',2''-terpyridinyl ligands: their synthesis and the electrochemistry of their transition-metal coordination complexes
4'-Vinyl-2,2':6',2''-terpyridinyl was conveniently prepared from 2-acetylpyridine via -oxoketene dithioacetal methodology, the intermediate 4'-(methylthio)-2,2':6',2''-terpyridinyl being converted into the corresponding 4'-methyl derivative with methylmagnesium bromide and bis(triphenylphosphino)nickel(II) dichloride followed by generation of the methyl anion with lithium tetramethylpiperidide, reaction of the anion with chloromethyl methyl ether, and introduction of the vinyl group by treatment of the ether with potassium tert-butoxide/THF. Analogous reactions led to the 4-vinyl- and 6-vinyl isomers by using the appropriate methyl-substituted 2-acetylpyridine except that in these instances desulfurization of the 4'-methylthio group with nickel boride was an addition step. These vinyl-substituted ligands formed a variety of readily electropolymerizable simple and mixed-ligand complex monomers with cobalt, ruthenium, and iron with polymerization rates whose magnitude varied with position and number of vinyl substituents.
- Research Organization:
- Rensselaer Polytechnic Institute, Troy, NY
- OSTI ID:
- 6371713
- Journal Information:
- J. Am. Chem. Soc.; (United States), Vol. 109:13
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
14 SOLAR ENERGY
COBALT COMPLEXES
CHEMICAL PREPARATION
ELECTROCHEMISTRY
POLYMERIZATION
IRON COMPLEXES
PYRIDINES
RUTHENIUM COMPLEXES
VINYL MONOMERS
CHEMICAL REACTION KINETICS
CHEMICAL SHIFT
EXPERIMENTAL DATA
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
VOLTAMETRY
AZINES
CHEMICAL REACTIONS
CHEMISTRY
COMPLEXES
DATA
HETEROCYCLIC COMPOUNDS
INFORMATION
KINETICS
MAGNETIC RESONANCE
MONOMERS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
REACTION KINETICS
RESONANCE
SPECTRA
SYNTHESIS
TRANSITION ELEMENT COMPLEXES
400201* - Chemical & Physicochemical Properties
400400 - Electrochemistry
140505 - Solar Energy Conversion- Photochemical
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