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

摘要

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 C-3-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. (C) 2016 Elsevier Ltd. All rights reserved.