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Synthesis of nano-scale shape-persistent macrocycles via hydrogen bonding-promoted formation of amide and hydrazone bonds |
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| Authors: | Yuan-Yuan Chen Lu Wang Liang Zhang Jiang Zhu Hui Wang Dan-Wei Zhang Zhan-Ting Li |
| Institution: | 1. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China;2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China;3. School of Basic Medical Science, North Sichuan Medical College, Nanchong 637007, China |
| Abstract: | This paper describes the synthesis of two series of rigid macrocycles from hydrogen bonding-induced folded aryl amide and hydrazone oligomers that bear two amines or one amine and one aldehyde. The diamines reacted with diacyl chloride to produce amide macrocycles, whereas the latter underwent self-coupling reactions to afford imine macrocycles. DFT calculations revealed that the new macrocycles possess rigid planar conformations and their cavity diameters were estimated to be 1.86 nm–2.75 nm. |
| Keywords: | Macrocycles Aromatic amide Aromatic hydrazone Hydrogen bonding Preorganization |
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