VII. Die Alkylierung des Anthranols

Meyer, Kurt H.; Schlösser, Hans

doi:10.1002/jlac.19204200203

Cited by 18 publications

(1 citation statement)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 H NMR and 13 C NMR chemical shifts are reported vs the respective solvent residue peak ( 1 H, 13 C: solvent ) CDCl3, δ 7.25 ppm, δ 76.9 ppm; solvent DMSO-d6, δ 2.62 ppm, δ 36.9 ppm). The compounds 4-ethynylbenzonitrile, 35 4-bromo-1-methoxynaphthalene, 36 and 9-bromo-1-methoxyanthracene 37 were prepared according to literature techniques. The compounds 4-bromobenzonitrile, 1-methoxynaphthalene, anthrone, 3,4′-oxydianiline, and 3,3′,4,4′biphenyltetracarboxylic dianhydride were purchased from Aldrich Chemical Co.…”

Section: Methodsmentioning

confidence: 99%

Accelerated Curing of Aryl−Ethynyl End-Capped Polyimide Oligomers and Model Compounds: A Kinetic Study Probing Substituent Effects

2002

View full text Add to dashboard Cite

phthalimide (1), N-phenyl-4-(4-methoxy-1-naphthylethynyl)phthalimide (2), and N-phenyl-4-(4-benzonitrileethynyl)phthalimide (3) were synthesized to probe the effect(s) of electronic subsituents on the thermal curing of aryl-ethynyl end-capped oligomers using end-cap model compounds. The curing kinetics were analyzed using SEC and NMR techniques and Arrhenius parameters were determined and compared to the anthracenyl, naphthyl, and phenyl analogues, 4, 5, and 6, respectively. A thermal curing rate acceleration was attributed to the electron-donating methoxy functionality. This acceleration is independent from the previously observed rate acceleration (phenyl < naphthyl < anthracenyl). Analyses of product distribution of 95% cured model compounds via SEC reveal slight differences between 1 and 4 but no discernible differences between 2 and 5. The incorporation of the electron-withdrawing group has no effect on the thermal cure rates, as the curing kinetics of 3 are nearly identical to those of 6. A new end-capping reagent, 4-(4methoxy-1-naphthylethynyl)phthalic anhydride ( 7) was synthesized and further used in the synthesis of 4-methoxynaphthylethynyl end-capped oligomer (4-MeO-NETI-5). By comparison to NETI-5, no significant changes are introduced by the methoxy-functionality except a reduction in thermal stability via SEC, DSC, and TGA. The curing kinetics of 4-MeO-NETI-5 were determined by monitoring the change in T g and analysis using the DiBenedetto equation. Unlike all analogous oligomers and model compounds including 2, a second-order rate law describes the curing kinetics of 4-MeO-NETI-5 better than a firstorder rate law. Arrhenius analysis of 4-MeO-NETI-5 using either a first-or second-order rate law results in indistinguishable Arrhenius parameters, and 4-MeO-NETI-5 cures with a lower Ea than NETI-5.

show abstract