Synthesis and coordination of star-shaped electron-deficient hexaheteroarylbenzene derivatives containing three pyrimidylbenzene derivatives

Abstract

The synthesis of novel electron-deficient hexaheteroarylbenzene derivatives containing three pyrimidylbenzene derivatives 1 and 2 with carboxylic acidic arms is described. They are prepared through hydrolyzing pyrimidine-substituted carboxylated hexaheteroarylbenzene derivatives 8 and 9 by KOH, respectively. Compound 8 and 9 are synthesized via cobalt-catalyzed cyclotrimerization of methyl 4′-((2-dodecylpyrimidin-5-yl)ethynyl)-[1,1′-biphenyl]-4-carboxylate 7. The isomeric C3-symmetric compound 1 and unsymmetric 2 are successfully isolated by thin-layer chromatography in 1:2 ratios. The coordination of symmetric 1 titrated by Ag+, compared with unsymmetric 2, is investigated by UV–vis, fluorescence spectroscopy and TEM. The coordination of 1 and 2 with In3+ by solvothermal method is studied by SEM and TEM, respectively. These results indicate that the molecular configuration is an important factor, which influences the coordination behavior of these two hexaheteroarylbenzene derivatives.