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

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• 作者：Yunjie Xiang^a ; ^{yjxiang@dhu.edu.cn" class="auth_mail" title="E-mail the corresponding author} ; Qiang Wang^a ; Gang Wang^a ; Xianying Li^b ; ^{seanlee@dhu.edu.cn" class="auth_mail" title="E-mail the corresponding author} ; Dengqing Zhang^a ; Wusong Jin^a ; ^c ; ^{wsjin@dhu.edu.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Hexaheteroarylbenzene derivatives ; Electron-deficient ; Cobalt-catalyzed cyclotrimerization ; Star-shaped
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：19 May 2016
• 年：2016
• 卷：72
• 期：20
• 页码：2574-2580
• 全文大小：1306 K

文摘

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.