Synthesis of Stereoregular Polymers as Precursors to Highly Conducting Carbon for Use in Applications in Micro- and Nanolithography

Gorman, Christopher B.; Vest, Ryan W.; Snover, Jonathan L.; Utz, T. L.; Serron, Scafford A.

doi:10.1021/bk-1998-0706.ch003

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“…Such tailing was also observed by Tang and co-workers for poly(phenylacetylene) derivatives . A similar absorption profile was observed by Gorman and co-workers for poly(cyanoacetylene) polymerized using TEA or palladium catalysts . In oligomers of 1-methyl-2-ethynyl-4,5-dicyanoimidazole ( 11 ), absorption at longer wavelengths clearly represents transitions due to the conjugated backbone.…”

Section: Resultssupporting

confidence: 80%

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New Acetylenic Monomers and Polymers from 4,5-Dicyanoimidazole

Densmore

Rasmussen

2004

Macromolecules

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An efficient synthesis of 1-methyl-2-ethynyl-4,5-dicyanoimidazole via Sonogashira coupling is described. Our optimized method generates 1-methyl-2-ethynyl-4,5-dicyanoimidazole in almost 80% yield from 1-methyl-2-bromo-4,5-dicyanoimidazole. Syntheses of the ethyl, propyl, and p-methoxybenzyl derivatives of 2-ethynyl-4,5-dicyanoimidazole are also reported. The polymerization of 1-methyl-2-ethynyl-4,5-dicyanoimidazole with transition-metal catalysts and triethylamine is described. Variation of catalyst concentration, reaction time, and temperature is also described. A more complete mechanistic picture of acetylene polymerizations, especially those with electron-withdrawing substituents, is presented. Solid samples of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers are EPR-active, and the number of free spins was quantified. Cyclic voltammetry was used to investigate the reduction of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers and other dicyanoimidazole derivatives.

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Section: Resultssupporting

confidence: 80%

“…Mechanistic Aspects. As noted above, the anionic polymerization of cyanoacetylene with butyllithium and triethylamine was reported by Gorman and co-workers . In our work, we observed that 1-methyl-2-ethynyl-4,5-dicyanoimidazole ( 8 ) could be polymerized using triethylamine (TEA).…”

Section: Resultssupporting

confidence: 73%

New Acetylenic Monomers and Polymers from 4,5-Dicyanoimidazole

Densmore

Rasmussen

2004

Macromolecules

View full text Add to dashboard Cite

show abstract

Synthesis of Stereoregular Polymers as Precursors to Highly Conducting Carbon for Use in Applications in Micro- and Nanolithography

Cited by 1 publication

References 0 publications

New Acetylenic Monomers and Polymers from 4,5-Dicyanoimidazole

New Acetylenic Monomers and Polymers from 4,5-Dicyanoimidazole

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