The Synthesis of Perylenebisimide Monocarboxylic Acids

One-Step Synthesis of Unsymmetrical N-Alkyl-N′-aryl Perylene Diimides

“…First, the yields for several previously reported PDIs are higher when accessed via the one-step protocol presented here. For example, utilizing 1 and 4-amino­benzoic acid, our method yielded 40% of the desired unsymmetrical product (Table , entry 7), while the previously reported synthesis gave only 25% after three steps . Similar overall yields were attained previously for the unsymmetrical PDIs prepared using aniline (28%), 4-iodo­aniline (33%), and 4-amino­styrene (14%) .…”

Excellent Control of Perylene Diimide End Group in Polyfluorene via Suzuki Catalyst Transfer Polymerization

“…As shown in Scheme , aryl bromides Ar1–Br and Ar2–Br as well as compound 2 containing asymmetrical PDI group were synthesized by imidization of the compound 1 with the corresponding aniline in 85%, 83%, and 88% yield according to the typical multistep process . Ar1–Br could also be obtained from the one‐step reaction of perylene‐3,4,9,10‐tetracarboxylic dianhydride with either simultaneous or sequential addition of alkyl and aryl amines, however, attempts to obtain the Ar2–Br and compound 2 were always unsuccessful probably due to the isolated problem resulting from the similar solubility or polarity.…”

Synthesis, Characterization, and Photophysical Study of Fluorescent N-substituted Benzo[ghi]perylene “Swallow Tail” Monoimides

“…Target compounds 3a – d were isolated via reductive amination of ketones a–d (step (ii)) with sodium cyanoborohydride according to the Borch amine synthesis . The condensation step (iii) was devised by our group according to similar syntheses of perylene-3,4:9,10-tetracarboxylic bisimide dyes. − ,, …”