Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes

Beilstein Journal of Organic Chemistry

Shuo Jiang¹  Cui-Yun Nie¹  Chao-Guo Yan¹  Jing Sun¹  Li-Ming Xu¹  Ying Han¹ 

[1] College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. China;

关键词: bis-[1]rotaxane;    mechanically interlocked molecule;    pillar[5]arene;    [1]rotaxane;    self-assembly;   

DOI  :  10.3762/bjoc.14.142

来源: DOAJ

【 摘 要 】

The pillar[5]arene mono- and di(oxyalkoxy)benzoic acids were successfully prepared in high yields by sequential alkylation of ω-bromoalkoxy-substituted pillar[5]arenes with methyl or ethyl p-hydroxybenzoate followed by a hydrolytic reaction under basic conditions. Under catalysis of HOBt/EDCl, the amidation reaction of pillar[5]arene mono(oxybutoxy)benzoic acid with monoamido-functionalized pillar[5]arenes afforded diamido-bridged bis-pillar[5]arenes. 1H NMR and 2D NOESY spectra clearly indicated that [1]rotaxanes were formed by insertion of longer diaminoalkylene unit into the cavity of one pillar[5]arene with another pillar[5]arene acting as a stopper. The similar catalysed amidation reaction of pillar[5]arene di(oxybutoxy)benzoic acid with monoamido-functionalized pillar[5]arenes resulted in the diamido-bridged tris-pillar[5]arenes, which successfully form the unique bis-[1]rotaxanes bearing longer than diaminopropylene diamido bridges.

【 授权许可】

Unknown