Synthesis of linear [7]- and [8]catenanes

IF 7.9 2区 综合性期刊 Q1 CHEMISTRY, MULTIDISCIPLINARY
Gray H. Harlan, Sheila L. Tran, Nathan D. Colley, Mark A. Nosiglia, Yipei Zhang, Jonathan C. Barnes
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引用次数: 0

Abstract

Catenanes are a family of mechanically interlocked molecules that consist of molecular rings that can be interlocked to give linear, radial, or cyclic structures. Although chemists have pursued extended linear poly[n]catenane architectures for many decades, there still exists a fundamental gap between the synthesis of well-defined, linear oligomers and that of disperse polymers that are often produced as a mixture of architectures. Here, we report two convergent one-pot syntheses that “zip-tie” together two pre-made [3]catenanes by first using orthogonal metal templation with phenanthroline (Cu(I)) and terpyridine (Fe(II)) ligands. These pre-catenate complexes were subjected to a ring-closing metathesis step to afford discrete, linear [7]- and [8]catenanes. The successful synthesis and isolation of the discrete [7]- and [8]catenanes were confirmed using multiple methods of characterization. Because these record-setting linear [n]catenanes possess open phenanthroline metal-binding sites at each end, further expansion to all-interlocked linear poly[n]catenanes is a realistic proposition.

Abstract Image

线性[7]-和[8]卡替烷的合成
双烯烷是一种机械互锁分子,由分子环组成,这些分子环可以互锁,形成线性、径向或环状结构。尽管几十年来化学家们一直在研究扩展的线性聚[n]卡替烷结构,但在合成定义明确的线性低聚物与合成分散聚合物之间仍然存在着根本性的差距,后者通常是以结构混合物的形式产生的。在此,我们报告了两种趋同的一锅合成方法,首先使用菲罗啉(Cu(I))和特吡啶(Fe(II))配体进行正交金属模板化,将两种预制 [3]catenanes "拉链式 "连接在一起。这些预缩氨酸配合物经过闭环偏析步骤,可得到离散的线性[7]-和[8]缩烯烃。通过多种表征方法,成功合成并分离出了离散的 [7]- 和 [8]腙。由于这些创纪录的线性[n]卡烯烷的两端都具有开放的菲罗啉金属结合位点,因此进一步扩展到全互锁的线性聚[n]卡烯烷是一个现实的命题。
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来源期刊
Cell Reports Physical Science
Cell Reports Physical Science Energy-Energy (all)
CiteScore
11.40
自引率
2.20%
发文量
388
审稿时长
62 days
期刊介绍: Cell Reports Physical Science, a premium open-access journal from Cell Press, features high-quality, cutting-edge research spanning the physical sciences. It serves as an open forum fostering collaboration among physical scientists while championing open science principles. Published works must signify significant advancements in fundamental insight or technological applications within fields such as chemistry, physics, materials science, energy science, engineering, and related interdisciplinary studies. In addition to longer articles, the journal considers impactful short-form reports and short reviews covering recent literature in emerging fields. Continually adapting to the evolving open science landscape, the journal reviews its policies to align with community consensus and best practices.
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