Synthesis, structure, and conformation of terphenylene-derived azacalix[4]aromatics

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• 作者：Wen-Jing Hu^a ; Ming-Liang Ma^a ; ^{mlma@brain.ecnu.edu.cn} ; Xiao-Li Zhao^b ; Fang Guo^c ; Xian-Qiang Mi^c ; Biao Jiang^c ; ^{jiangb@sari.ac.cn} ; Ke Wen^a ; ^c ; ^{wenk@sari.ac.cn} ; ^{kwen@brain.ecnu.edu.cn}
• 关键词：Azacalixarenes ; Terphenylene ; Structure ; Conformation
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：29 July, 2012
• 卷：68
• 期：30
• 页码：6071-6078
• 文件大小：804 K

摘要

Several novel azacalix[4]aromatics constituting terphenylene units have been synthesized via sequential nucleophilic aromatic substitution reactions of 5鈥?t-butyl-(1,1鈥?3鈥?1鈥?terphenyl)-3,3鈥?diamine 9 and 5鈥?t-butyl-(1,1鈥?3鈥?1鈥?terphenyl)- 4,4鈥?diamine 11 with 1,5-difluoro-2,4-dinitrobenzene and cyanuric chloride, respectively. The bridging -NH- functions of the tetra-nitro substituted azacalix[2]arene[2]terphenylenes 1 and 2 have been transformed to the corresponding -N(CH₃)- bridged azacalix[2]arene[2]terphenylenes 3 and 4 via N-alkylation. Single crystal X-ray analysis revealed that the terphenyl-3,3鈥?diamine derived azacalix[2]terphenylene[2]triazine 5 adopts a distorted chair conformation in the solid state, and the terphenyl-4,4鈥?diamine derived azacalix[2]terphenylene[2]triazine 6 was found to adopt a 1,3-alternate conformation.