- Collection:
- Atlanta University and Clark Atlanta University Theses and Dissertations
- Title:
- Synthesis and polymerization of substituted imidazole chromophores, 1996
- Creator:
- Li, Haiying
- Date of Original:
- 1996-07-01
- Subject:
- Degrees, Academic
Dissertations, Academic - Location:
- United States, Georgia, Fulton County, Atlanta, 33.749, -84.38798
- Medium:
- theses
- Type:
- Text
- Format:
- application/pdf
- Description:
- Four new functionalized imidazole chromophores, l-(vinylbenzyl)-2-(4'-nitrophenyl)-4,5-bis(4'-methoxyphenyl)imidazole, l-( 1 '-oxo-2'-methylethenyl)-2-(4'-nitrophenyl)-4,5-bis-(4'-methoxyphenyl)imidazole, l-(2'-propenyl)-2-(4'-nitrophenyl)-4,5-bis(4'-methoxyphenyl)-imidazole, and l-(2'-hydroxylethyl)-2-(4'-nitrophenyl)-4,5-bis(4'-methoxyphenyl)imidazole were prepared from 2-(4'-nitrophenyl)-4,5-bis(4'-methoxyphenyl)imidazole by nucleophilic substitution at the 1-position. The new nonlinear optical (NLO) chromophore l-methyl-2-[2'-(5'-tricyanovinyl)thienyl]-4,5-bis(4'-methoxyphenyl)imidazole was prepared in three steps. Reaction of 4,4'-bimethoxybenzil, 2-thiophenecarboxaldehyde and ammonium acetate in glacial acetic acid gave 2-(2'-thienyl)-4,5-bis(4'-methoxyphenyl)imidazole, which upon treatment with iodomethane in the presence of potassium carbonate in N,N'-dimethylacetamide at 40 C gave l-methyl-2-(2'-thienyl)-4,5-bis(4'-methoxyphenyl)-imidazole. Treatment of l-methyl-2-(2'-thienyl)-4,5-bis(4'-methoxyphenyl)imidazole with n-butyllithium in THF followed by the addition of a tetracyanoethylene/THF solution gave, upon work up, l-methyl-2-[2'-(5'-tricyanovinyl)thienyl]-4,5-bis(4'-methoxyphenyl)imidazole. All new compounds were characterized by 'H NMR, 13C NMR, FT-IR, UV-vis and elemental analysis. Copolymerization of l-(vinylbenzyl)-2-(4'-nitrophenyl)-4,5-bis(4'-methoxyphenyl)-imidazole with methyl methacrylate (MMA) gave the corresponding polymer, poly(styrene-co-methyl methacrylate) with 2-(4'-nitrophenyl)-4,5-bis(4'-methoxyphenyl)imidazole side chains. Polyimides incorporating 2-(4' -nitrophenyl)-4,5-bis(4' -methoxyphenyl)imidazole chromophores were prepared by reacting l-(2'-hydroxylethyl)-2-(4'-nitrophenyl)-4,5-bis(4'-methoxyphenyI)imidazole with 3,3'-dihydroxy-4,4' -diaminobiphenyl-2,2' -bis(3,4-dicarboxy-phenyl)hexafluoropropane dianhydride polyimide in the presence of triphenyl-phosphine and diethyl azocarboxylate (DEAD) at 60 C. The incorporation of the NLO chromophores into the polymers was confirmed by 'H NMR, FT-IR, UV-vis.
- External Identifiers:
- Metadata URL:
- http://hdl.handle.net/20.500.12322/cau.td:1996_li_haiying
- Rights Holder:
- Clark Atlanta University
- Holding Institution:
- Atlanta University Center Robert W. Woodruff Library
- Rights:
-
