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

Abstract

An efficient and facile protocol for the synthesis of unsymmetrical N-alkyl-N'-aryl perylene diimides is reported that circumvents the need for multiple reaction steps. A number of unsymmetrical perylene diimides containing a solubilizing swallowtail alkyl group and a variety of substituted aryl groups can be prepared in a single step from a simple mixture of amines.

Design, Synthesis, and Isomerization Studies of Light-Driven Molecular Motors for Single Molecular Imaging

“…Deprotection of the triisopropylsilyl group was achieved by treating 9 with TBAF, affording 10 which bears a terminal acetylene. Motor 10 was then coupled with a reported aryl iodide 2 ( 59 ) bearing a PBI unit by Sonagashira reaction, giving rise to a tetra-ester 11 , which was subsequently hydrolyzed in the presence of a base to generate the target molecule 1a .…”

Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors

“…Briefly, bis(6-dimethylaminohexyl) functionalized PDI (PDI-NMe 2 ) was synthesized in a one-step reaction starting from perylene tetracarboxylic acid dianhydride. 12 , 25 To form the alkyl tethered trimethylammonium functionalized PDI with hydroxide counterions, PDI-NMe 2 was first methylated using CH 3 I (forming PDI-I) and the I – anion subsequently exchanged for OH – (resulting in PDI-OH). Additional PDI variants lacking the dimethylamino group ( Fig.…”

Polyaromatic Profluorescent Nitroxide Probes with Enhanced Photostability

“…Similarly,p erylene nitroxide 25 was synthesised from as toichiometric mixture of 2,5-di-tert-butylaniline and nitroxide (22) in a2 2% yield following purification (Scheme 7). The corresponding methoxyamine derivatives 24 and 26 were prepared using Fentonc hemistry.T he obtained isolated yields for these reactions were low,h owever this can be rationalised by the poor solubility of nitroxides 23 and 25 in DMSO.…”