Synthesis,structure, and conformation of terphenylene-derived azacalix[4]aromatics |
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| Authors: | Wen-Jing Hu Ming-Liang Ma Xiao-Li Zhao Fang Guo Xian-Qiang Mi Biao Jiang Ke Wen |
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| Institution: | 1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China;2. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China;3. Center for Nanomedicine, Shanghai Advanced Research Institute, Chinese Academy of Science, Shanghai 201210, China |
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| Abstract: | Several novel azacalix4]aromatics constituting terphenylene units have been synthesized via sequential nucleophilic aromatic substitution reactions of 5′-t-butyl-(1,1′:3′,1″-terphenyl)-3,3″-diamine 9 and 5′-t-butyl-(1,1′:3′,1″-terphenyl)– 4,4″-diamine 11 with 1,5-difluoro-2,4-dinitrobenzene and cyanuric chloride, respectively. The bridging –NH– functions of the tetra-nitro substituted azacalix2]arene2]terphenylenes 1 and 2 have been transformed to the corresponding –N(CH3)– bridged azacalix2]arene2]terphenylenes 3 and 4 via N-alkylation. Single crystal X-ray analysis revealed that the terphenyl-3,3″-diamine derived azacalix2]terphenylene2]triazine 5 adopts a distorted chair conformation in the solid state, and the terphenyl-4,4″-diamine derived azacalix2]terphenylene2]triazine 6 was found to adopt a 1,3-alternate conformation. |
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