Fast and Efficient Microwave‐Assisted Synthesis of Perylenebisimides

Abstract

Perylene‐3,4,9,10‐tetracarboxylic acid bisimides have been widely studied as industrial pigments. Lately, these dyes have drawn considerable attention because of applications as photocatalysts and organic semi‐conductors. Here, we report a novel method for fast and efficient synthesis of many different perylenebisimides, based on microwave‐assisted reactions.

Progress in the synthesis of perylene bisimide dyes

“…42 PBAs are also readily reacted with amines under microwave irradiation (see Scheme 7). 43 Product 18 can be converted into octabromo-PBA 19 upon treatment with dibromoisocyanuric acid (DBI) in oleum 44 or 1,3-dibromo-5,5-dimethylhydantoin (DBH) in concentrated sulfuric acid (Scheme 5). 45 An attractive alternative to these two-step bromination procedures was reported by Orentas and co-workers.…”

“…In 2015, Syrgiannis and Prato published an efficient microwave-assisted method for the synthesis of PBIs from the core-unsubstituted and halogenated PBAs (Scheme 7). 43 The procedures differed in some details, e.g. power, additive, reaction time, and workup, for various types of amines and PBAs.…”

Efficient Microwave‐Assisted Synthesis of Sonogashira‐Coupled Perylene Monoimide Derivatives: Impact of Electron‐Donating Groups on Optoelectronic Properties

“…Despite these benefits, microwave‐assisted synthesis remains underutilized for the chemical manipulation of rylene dyes. [10d], …”

Zwitterionic Conjugated Surfactant Functionalization of Graphene with pH‐Independent Dispersibility: An Efficient Electron Mediator for the Oxygen Evolution Reaction in Acidic Media

“…All solvents were of ACS grade unless otherwise noted. 2,9‐bis(3‐(dimethylamino)propyl)anthra[2,1,9‐ def :6,5,10‐ d′e′f ′]diisoquinoline‐1,3,8,10(2 H ,9 H )‐tetraone (1), 3,3′‐(1,3,8,10‐tetraoxoanthra[2,1,9‐ def :6,5,10‐ d ′ e ′ f ′]diisoquinoline‐2,9(1 H ,3 H ,8 H ,10 H )‐diyl)dipropanoic acid (2), 2,7‐bis(3‐(dimethylamino)propyl)benzo[ lmn ][3,8]phenanthroline‐1,3,6,8(2 H ,7 H )‐tetraone (3), and 3,3′‐(1,3,6,8‐tetraoxobenzo[ lmn ][3,8]phenanthroline‐2,7(1 H ,3 H ,6 H ,8 H )‐diyl)dipropanoic acid (4) were synthesized according to the previously reported methods 20,38–41…”

“…2,9-bis(3-(dimethylamino)propyl) anthra [2,1,9- [3,8]phenanthroline-2,7(1H,3H,6H,8H)diyl)dipropanoic acid (4) were synthesized according to the previously reported methods. [20,[38][39][40][41] Synthesis of PDI-NO: Compound 1 (1 g, 1.78 mmol) was suspended in 120 mL of ethanol. To the stirred suspension, hydrogen peroxide (30%, 5 mL) was added dropwise under the protection of an Ar atmosphere.…”