m-Terphenyl-3,3¡å-dioxo-derived oxacalixaromatics: synthesis, structure, and solvent encapsulation in the solid state

详细信息    查看全文

• 作者：Wen-Jing Hu^a ; Long-Qing Liu^b ; Ming-Liang Ma^b ; ^{mlma@brain.ecnu.edu.cn} ; Xiao-Li Zhao^c ; Yahu A. Liu^d ; Xian-Qiang Mi^a ; Biao Jiang^a ; ^{jiangb@sari.ac.cn} ; Ke Wen^a ; ^b ; ^{kwen@brain.ecnu.edu.cn} ; ^{wenk@sari.ac.cn}
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：13 May, 2013
• 年：2013
• 卷：69
• 期：19
• 页码：3934-3941
• 全文大小：1025 K

文摘

The synthesis of oxacalix[2]terphenylene[2]aromatics with enlarged macrocyclic holes by cyclooligomerization reaction of 5¡ä-tert-butyl-(1,1¡ä:3¡ä,1¡å-terphenyl)-3,3¡å-diol 1 with electron-deficient dihalogenated benzene and azaheterocycles is described. The structures of the macrocycles were characterized by NMR, HRMS spectroscopic and X-ray diffraction techniques. Single crystal X-ray analysis revealed that the terphenyl-3,3¡å-dioxo unit incorporated in the oxacalix[4]aromatics scaffold can adopt all three possible conformations (I, II, III). The cis-conformational terphenyl-3,3¡å-dioxo (I and II) derived oxacalix[4]aromatics were found to adopt both chair and boat conformations, resulted in creation of molecular cavities capable of hosting solvent molecules of chloroform. The trans-conformational terphenyl-3,3¡å-dioxo (III) derived oxacalix[4]aromatics, however, adopt a twisted chair conformation with a narrow void space incapable of hosting any guest molecules.