Acetate → HCID 15217412, compound

Participants

Reaction Conditions

Reaction Steps

3 g of p-nitrophenylhydrazine and 2 g of glutaric anhydride in 20 ml THF ("tetrahydrofuran") were stirred for 15 min at room temperature. Analysis by infrared spectroscopy showed high conversion to amide-acid. To the reaction mixture was added 2 g of acetic anhydride, 1 ml of triethylamine which as then heated to near reflux. 50 mg of colbalt(II) acetate was added which induced an exothermic reaction. Analysis (IR) after a few minutes showed high conversion to imide. The mixture was evaporated under nitrogen and then slurried with ethanol. The ethanol soluble fraction (main product) was removed and concentrated to 3.4 g of brown solid. This solid was washed twice with benzene to remove 0.2 g and then crystalized from methanol to yield yellow needles, mp=197-198° C. The structure was confirmed by elemental analysis, IR and NMR. DSC analysis showed no crystallization when the melt was cooled at 20° C./min. On reheating a Tg was detected at 65° C., a Tc was detected at 120° C. and a Tm was detected at 204° C. Thin films cast from THF were glassy (noncrystalline) with Tg of 65° C. and were shown, by IR, to contain hydrogen bonds involving the carbonyl and N-H groups. On heating to 120° C., crystallization occured and the H-bonding was lost. High viscosity above Tg was observed by the resistance to sliding of two glass plates sandwiching a thin film of the compound. The μβ, determined by EFISH in dioxane, was 26×10-48 esu. Thin films were prepared on a conducting glass by spin coating using Film Forming Procedure 1 and were poled using Poling Procedure 1. The resulting material retained a substantial portion of the induced molecular ordering for more than 6 months. The induced d33 determined from SHG Measurements was ≈4×10-12 m/V.

Provenance & Evidence