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学科主题: 物理有机化学
题名: Self-assemblingcalix[4]arene [2]catenanes. Preorganization,conformation,selectivity, and efficiency
其他题名: 杯芳烃[2]索烃的自组装
作者: Li ZT(黎占亭) ; Ji GZ(计国桢) ; Yuan SD(袁沈东) ; Ding H(丁辉) ; Du AL(杜爱林) ; Wei M(卫明) ; Zhao CX(赵承学) ; Huang C(黄晨)
通讯作者: 黎占亭
刊名: J. Org. Chem.
发表日期: 1999-01-01T00:00:00Z
卷: 64, 期:10, 页:3572-3584
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所物理有机化学研究室
英文摘要: Anovel class of preorganized U-shape calix[4]arene clefts. Dicationic salts 3a,c,e.2Cl, 3b.2PF^6. And 3f.2Br, consisting of one cone calix[4]arene and two bipyridine residues being linked by an aliphatic chain, have been designed and synthesized as precursors for self-assembly of calix[4]-arene [2]catenanes by utilizingπ-stacking interactions between the hydroquinone and bipyridinium units. Conformationally flexible 6.2PF^6 and cone 10.2Cl. Whoseconformation is fixed by two propyloxy groups on the lower rim, were also prepared in order to explore the effects of conformation and hydrogen bonding of the calix[4] arene moiety on self-assembly. For all reactions, bis-p-phenylene-34-crown ether-10(11) was employed as the donor component. Alternate cone [2]catenane 13.4Cl is obtained in 8% yield from reaction of ethylene-incorporating 3a.2Cl and 1,4-bis-(bromomethyl)benzene(12a). Three cone and one conformationally flexibel [2] catenanes were obtained in moderate to good yields from reactions of propylene-incorporating 3b.PF^6 and 3c.2Cl with 12a. 1,3-bis(bromomethyl) benzene(12b) or 4,4'-(bromomethyl)biphenyl(12c). Both cone and partial cone [2] catenanes were generated in moderate yields from butylene-incorporating 3c.2Cl with four tert-butyl groups on the calix[4]arene moiety and with 12a. In contrast, only cone [2]-catenane was obtained from similar tert-butyl-free cleft 3d.2Cl. Cone and conformationally flexible [2]catenanes were obtained in moderate yields, respectively, from the reactions of 3d.2Cl and 3e.2Cl with 12c. No catenanes wereisolated from reaction of phenylene-incorporating 3f.2Br or 6.2Cl. Whereas reaction of 10.2Cl afforded cone [2]catenane in low yield. It was demonstrated that hydrogen bonding, which may be destroyed after catenation, within the calix [4]arene moiety is crucial for efficient self-assembly of the [2]catenanes were investigated, which reveal that incorporation of calix[4]arene into the tetracationic cyclophane reduces π-stacking interactions between the donor and acceptor units and catenation has substantial influence on conformational distributions of the calix[4]arene moiety. The results demonstrate the versatility of calix[4]arene derivatives as building blocks in the construction of supramolecular structures.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/20835
Appears in Collections:物理有机化学研究室_期刊论文

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Recommended Citation:
Li ZT,Ji GZ,Yuan SD,et al. Self-assemblingcalix[4]arene [2]catenanes. Preorganization,conformation,selectivity, and efficiency[J]. J. Org. Chem.,1999,64(10):3572-3584.
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