Synthesis of polyamines with pendant cyanoimidazole units and their electrochemical properties

Abstract

The 2‐(1‐methyl‐4,5‐dicyanoimidazolyl) group was attached to poly(diallylamine) and polyethylenimine, affording polymers containing an electron‐withdrawing pendant group. The key to their preparation is high reactivity of 1‐methyl‐2‐fluoro‐4,5‐dicyanoimidazole (1) toward nucleophilic aromatic substitution (NAS) reactions with aliphatic amines. Cyclic voltammograms of these polymers show reduction waves at −2.6 to −2.7 V vs. Ag/Ag+ but no reoxidation waves, unlike those of monomeric and oligomeric model compounds, which are quasi‐reversible. The cyclic voltammetry studies of oligomeric model compounds with different alkyl spacers show that the degree of quasi‐reversibility decreases as dicyanoimidazoles are crowded together in a molecule, suggesting that a certain degree of chemical reaction occurs between reduced dicyanoimidazole groups. © 1998 John Wiley & Sons, Inc. J. Polym. Sci. A Polym. Chem. 36: 2619–2629, 1998

The Novel Phosphate and Bile Acid Sequestrant Polymer SAR442357 Delays Disease Progression in a Rat Model of Diabetic Nephropathy

“…Poly(allylamine hydrochloride) (PAA.HCl) and poly(diallylamine hydrochloride) (PDA.HCl) were synthesized by free radical polymerization of allylamine and diallylamine respectively, in the forms of their hydrochloride salts by following reported procedures (Harada and Hasegawa, 1984;Jang and Rasmussen, 1998). The crosslinked polymer networks comprised of PAA and PDA components is described here using SAR442357 as the specific example.…”

The Novel Phosphate and Bile Acid Sequestrant Polymer SAR442357 Delays Disease Progression in a Rat Model of Diabetic Nephropathy

“…Poly(allylamine hydrochloride) (PAA.HCl) and poly(diallylamine hydrochloride) (PDA.HCl) were synthesized by free radical polymerization of allylamine and diallylamine respectively, in the forms of their hydrochloride salts by following reported procedures (Harada and Hasegawa, 1984;Jang and Rasmussen, 1998). The crosslinked polymer networks comprised of PAA and PDA components is described here using SAR442357 as the specific example.…”

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

“…Variously 4,5-dicyanoimidazole-functionalized polymers were mainly investigated by Rasmussen et al [ 29 , 81 , 86 – 88 96 – 99 ]. However, these systems were not intended as nonlinear optical polymers.…”

Influence of the Reaction Conditions and Molecular Structure on the Kinetic of the Nucleophilic Aromatic Substitution of Fluoro Compounds with Poly(vinyl amine) in Water

“…Micelle techniques commonly used to carry out reactions between water‐soluble and water‐insoluble components cannot be cleanly applied to modify polyelectrolytes 12. Alternatively, water‐soluble polymers can be modified by the introduction of alkyl or aryl groups, thus mediating solubility in organic solvents 13. The use of cyclodextrins (CD) provides a further opportunity to solve these problems.…”

The Novel Phosphate and Bile Acid Sequestrant Polymer SAR442357 Delays Disease Progression in a Rat Model of Diabetic Nephropathy

“…Poly(allylamine hydrochloride) (PAA.HCl) and poly(diallylamine hydrochloride) (PDA.HCl) were synthesized by free radical polymerization of allylamine and diallylamine respectively, in the forms of their hydrochloride salts by following reported procedures (Harada and Hasegawa, 1984;Jang and Rasmussen, 1998). The crosslinked polymer networks comprised of PAA and PDA components is described here using SAR442357 as the specific example.…”

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

“…Variously 4,5-dicyanoimidazole-functionalized polymers were mainly investigated by Rasmussen et al [ 29 , 81 , 86 – 88 96 – 99 ]. However, these systems were not intended as nonlinear optical polymers.…”

Influence of the Reaction Conditions and Molecular Structure on the Kinetic of the Nucleophilic Aromatic Substitution of Fluoro Compounds with Poly(vinyl amine) in Water

“…Micelle techniques commonly used to carry out reactions between water‐soluble and water‐insoluble components cannot be cleanly applied to modify polyelectrolytes 12. Alternatively, water‐soluble polymers can be modified by the introduction of alkyl or aryl groups, thus mediating solubility in organic solvents 13. The use of cyclodextrins (CD) provides a further opportunity to solve these problems.…”

The Novel Phosphate and Bile Acid Sequestrant Polymer SAR442357 Delays Disease Progression in a Rat Model of Diabetic Nephropathy

“…Poly(allylamine hydrochloride) (PAA.HCl) and poly(diallylamine hydrochloride) (PDA.HCl) were synthesized by free radical polymerization of allylamine and diallylamine respectively, in the forms of their hydrochloride salts by following reported procedures (Harada and Hasegawa, 1984;Jang and Rasmussen, 1998). The crosslinked polymer networks comprised of PAA and PDA components is described here using SAR442357 as the specific example.…”

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

“…Variously 4,5-dicyanoimidazole-functionalized polymers were mainly investigated by Rasmussen et al [ 29 , 81 , 86 – 88 96 – 99 ]. However, these systems were not intended as nonlinear optical polymers.…”

Influence of the Reaction Conditions and Molecular Structure on the Kinetic of the Nucleophilic Aromatic Substitution of Fluoro Compounds with Poly(vinyl amine) in Water

“…Micelle techniques commonly used to carry out reactions between water‐soluble and water‐insoluble components cannot be cleanly applied to modify polyelectrolytes 12. Alternatively, water‐soluble polymers can be modified by the introduction of alkyl or aryl groups, thus mediating solubility in organic solvents 13. The use of cyclodextrins (CD) provides a further opportunity to solve these problems.…”