Selective and effective rotation mode of copillar[5]arene by mono-functionalizing bulky substituent. Issue 27 (6th July 2016)

• Record Type: Journal Article
• Authors: Liu, Lu-Zhi; Hua, Zhong-Ze; Duan, Wen-Gui; Huang, Hong-Fei; Huang, Yan; Lin, Gui-Shan; Cen, Bo
• Is Part Of: Tetrahedron letters. Volume 57:Issue 27/28(2016)
• Page Start: 2969
• Page End: 2971
• Publication Date: 2016-07-06
• Subjects: Copillar[5]arene -- Synthesis -- Conformational characteristic -- Rotation mode; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.085
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Mono-functionalized copillar[5]arenes were synthesized. Their rotation mode can be induced and controlled by mono-bulky substituent. Conformational freedom depends on the size and length of substituent. Their binding properties can be maintained as symmetrical pillar[5]arenes. Abstract: Two types of copillar[5]arenes bearing mono-functionalized bulky substituents such as phenyl and naphthyl groups were synthesized and their conformational characteristics were studied by 1 H NMR spectroscopy. Their rotation mode can be induced and controlled by the bulky substituents. The OCH3 groups on phenolic units, the same side as the bulky substituent, were rotating regularly in the mode of OR-opposite-the-annulus rotation while the mode of OR-through-the-annulus was seen for the other OCH3 groups on the other side. Furthermore, their excellent binding properties with 1, 4-dibromobutane(DBB) can be maintained as the fully symmetrical pillar[5]arenes.