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[2]catenane assembly from calix[4]arene crown ethers
其他题名从杯芳烃冠醚自组装 [2]索烃
Li ZT(黎占亭); Zhang XL(张秀莲); Lian XD(练雄东); Yu YH(余亦华); Zhao CX(赵成学); Chen Z(陈璋); Lin ZP(林志萍); Chen H(陈欢); Xia G(夏戈)
2000
发表期刊J. Org. Chem.
ISSN0022-3263
卷号65期号:17页码:5136-5142
摘要A variety of novel calix[4]arene-incorporating crown ethers with or without intramolecular hydrogen bonding have been prepared by two efficient methods and utilized as donor rings to assemble calix-[4]arene [2]catenanes based on s-stacking interaction between hydroquinone and bipyridinium units. Treatment of calix[4]arene crown ethers 4, 10a, or l0b, whose cone conformation was fixed by intramolecular hydrogen bonding within the calix[4]arene moiety, with dicatlonic salt 15.2PF^6 and dibromide 16 afforded the corresponding [2]catenanes 17a’4PF^6, 17b4PF^6, and 17c4PF^6 in 20%, 53%, and 55% yields, respectively, whereas from the reactions of 15.2PF^6 and dibromide 16 in the presence of conformationally flexible 11 or 12 with a cone conformation kept by two propyl groups. [2]catenanes 18.4PF^6. And 19.4PF^6 were obtained in 12% and 6% yields. [2]Catenanes 21a 4Cl, 21b.4Cl, and 21c.4Cl, incorporating calix[4]arene in both the donor and acceptor rings, were also successfully assembled from lOa or lOb, 16, and dicationic salts 2Oa.2PF^6 or 2Ob.2PF^66. The dynamic 1~H NMR and absorption spectra of the [2]catenanes have been investigated, which revealed a strongest donor—acceptor interaction in 17a.4PF^6 and that the cone [2]catenanes 17a—c.4PF^6 can isomerize to the partial cone isomer at high temperature. The difference of the dynamic properties of these catenanes was discussed. The results demonstrate that catenation is one new general method to change the conformational distributions of calix[4]arenes.
学科领域物理有机化学
部门归属中国科学院上海有机化学研究所物理有机化学实验室
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收录类别SCI
语种英语
WOS记录号WOS:000088934300009
引用统计
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/20839
专题物理有机化学研究室
通讯作者Li ZT(黎占亭)
推荐引用方式
GB/T 7714
Li ZT,Zhang XL,Lian XD,et al. [2]catenane assembly from calix[4]arene crown ethers[J]. J. Org. Chem.,2000,65(17):5136-5142.
APA 黎占亭.,张秀莲.,练雄东.,余亦华.,赵成学.,...&夏戈.(2000).[2]catenane assembly from calix[4]arene crown ethers.J. Org. Chem.,65(17),5136-5142.
MLA 黎占亭,et al."[2]catenane assembly from calix[4]arene crown ethers".J. Org. Chem. 65.17(2000):5136-5142.
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