Helix-Rotaxane Hybrid Systems: Rotaxane-Stabilized, Saccharide-Induced Chiral Ethynylpyridine Helices by a Thermodynamic Process

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• 作者：Shu Hirokane ; Shunsuke Takashima ; Hajime Abe and Masahiko Inouye
• 刊名：European Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 18, 2017
• 年：2017
• 卷：2017
• 期：3
• 页码：726-733
• 全文大小：1379K
• ISSN：1099-0690

文摘

The helical structures of m-ethynylpyridine (2,6-pyridyleneethynylene) oligomers have been stabilized by mechanical crosslinking. A heptameric oligomer, in which the two terminal pyridine rings bear two carbaldehyde groups, has been designed. When this heptamer was treated with octyl β-d-glucopyranoside, a circular dichroism (CD) band was induced at around 330 nm, which corresponds to the formation of a chiral ethynylpyridine helix. The CD band was enhanced by the addition of a diamine and a diammonium dumbbell as a result of the formation of a [3]rotaxane structure linked to the terminal pyridines of the helical structure. A decameric oligomer containing four diformylarene units showed stronger CD enhancement in similar experiments owing to two crosslinking events.