Template-driven construction of [8]-imidazolium macrocycles,Organic Chemistry Frontiers

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Template-driven construction of [8]-imidazolium macrocycles
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-1-4 , DOI: 10.1039/d0qo01617a
Kai Hua _{1,

2,

3,

4} , Ming-Ming Gan _{1,

2,

3,

4} , Xue-Ru Liu _{1,

2,

3,

4} , Le Zhang _{1,

2,

3,

4} , Yuan-Yuan An _{1,

2,

3,

4} , Ying-Feng Han _{1,

2,

3,

4}

Affiliation

Tetrakisimidazolium macrocycles have been widely used in supramolecular chemistry due to their inherently cationic nature and sizable cavity. However, [n]-imidazolium macrocycles (n > 4) are rather undeveloped. Reported here is a controllable synthetic strategy for [n]-imidazolium (n = 8) macrocycles, which involves the formation of metal–carbene templates, a double [2 + 2] photocycloaddition and the subsequent removal of metal ions. Two octakisimidazolium macrocycles H₈-2a(PF₆)₈ and H₈-2b(PF₆)₈ were prepared from linear tetrakisimidazolium salts H₄-1a(PF₆)₄ and H₄-1b(PF₆)₄. More significantly, the present work not only further verified the strategy of metal–carbene templated photochemical [2 + 2] cycloaddition for the construction of novel polyimidazolium macrocycles, but also offers a new synthetic approach for the preparation of functional acceptors for molecule recognition.

中文翻译：

模板驱动的[8]-咪唑大环化合物的构建

四烷基咪唑鎓大环化合物因其固有的阳离子性质和较大的空腔而已广泛用于超分子化学中。但是，[ n ]-咪唑鎓大环（n > 4）尚未开发。这里报道的是[ n ]-咪唑鎓（n = 8）大环化合物的可控合成策略，其中涉及金属-卡宾模板的形成，两次[2 + 2]光环加成以及随后去除金属离子的过程。两个octakisimidazolium大环化合物ħ ₈ -图2a（PF ₆）₈和H ₈ - 2B（PF ₆）₈从制备线性tetrakisimidazolium盐ħ ₄ - 1A（PF ₆）₄和H ₄ - 1B（PF ₆）₄。更重要的是，目前的工作不仅进一步验证了金属-卡宾模板光化学[2 + 2]环加成反应用于构建新型聚咪唑鎓大环化合物的策略，而且为制备用于分子识别的功能性受体提供了一种新的合成方法。

更新日期：2021-01-14

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