Synthesis of novel Y-shaped asymmetrical conjugated 2,4,6-trisubstituted pyrimidines and investigation of their optical and electrochemical properties

Abstract

A set of novel Y-shaped asymmetrical pyrimidines has been prepared on the basis of 2-hydroxy-4,6-dimethylpyrimidine used as a starting compound. All of them are the chromophores of D-π-A-π-D' motif where A is a central pyrimidine core; D, D' are the thiophene-2-yl, thiophene-3-yl, 9-ethyl-9H-carbazol-3-yl or 9H-carbazole-9-yl-fragments and a π-bridge is a vinyl or styryl moiety. We have studied their optical, electrochemical and electrophysical characteristics, as well as their polymerizability with the help of electrochemical oxidation.

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

“…Numerous 4,6‐diarylvinylpyrimidines have been obtained by condensation of aldehydes with 4,6‐dimethylpyrimidines either in basic, or acidic media ,. Only a few examples of unsymmetrical 4,6‐dimethylpyrimidines prepared by successive condensation reactions have been described ,. Conjugated polymers that include 4,6‐diarylvinylpyrimidine fragments have also been reported…”

Synthesis of 2,4,6-Trisubstituted Pyrimidines through Copper-Catalyzed [4 + 2] Annulation of α,β-Unsaturated Ketoximes with Activated Nitriles

“…Functionalized pyrimidines, especially 2,4,6-trisubstituted pyrimidines, are important and privileged scaffolds widely distributed in natural products and medicinally valuable molecules, which exhibit a broad spectrum of biological activities such as antitumor, antibacterial, antifungal, and anti-inflammatory . Furthermore, they have widespread utilization as photophysical materials in light-emitting devices and molecular wires . Consequently, various synthetic methods for the assembly of 2,4,6-trisubstituted pyrimidines have been developed, such as the transition-metal or base-catalyzed reaction of amidines with carbonyls, multicomponent dehydrogenative coupling reaction of amidines with two different alcohols, [2 + 2 + 2] annulation of ketones or alkynes with two molecules of nitriles, and one-pot condensation of aldehydes, ketones with NH 4 OAc .…”