Template-directed self-assembly of porphyrin nanorings through an imine condensation reaction†

IF 7.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2025-02-13 DOI:10.1039/D4SC08569H

Ziwei Xu, Xinwen Ying, Yi Li, Xiaoyan Dong, Jiyong Liu, Shuping Wang, Marc A. Little, Dahao Zhang, Yongshu Xie, Zibin Zhang, Ling Yu, Feihe Huang and Shijun Li

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Abstract

Template-directed self-assembly has proven to be an extremely effective method for the precise fabrication of biomacromolecules in natural systems, while artificial template-directed self-assembly systems for the preparation of highly intricate molecules remain a great challenge. In this article, we report the template-directed self-assembly of porphyrin nanorings with different cavity sizes from a tetraaldehyde-derived Zn(II) porphyrin and a diamine precursor through an imine condensation reaction. Up to 9 or 18 precursor molecules self-assemble together to produce a triporphyrin nanoring and a hexaporphyrin nanoring in one step, with the assistance of a tripyridine or hexapyridine template, respectively. The imine-linked porphyrin nanorings are further modified by reduction and acylation reactions to obtain more stable nanorings. The open cavities of porphyrin rings enable them to act as effective hosts to encapsulate fullerenes (C₆₀ and C₇₀). This work presents a highly efficient template-directed self-assembly strategy for the construction of complicated molecules by using dynamic covalent chemistry of imine bond formation.

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通过亚胺缩合反应的卟啉纳米粒模板定向自组装。

模板导向自组装已被证明是在自然系统中精确制备生物大分子的一种非常有效的方法，而人工模板导向自组装系统制备高度复杂的分子仍然是一个巨大的挑战。在这篇文章中，我们报道了由四醛衍生的Zn（ii）卟啉和二胺前体通过亚胺缩合反应，在模板导向下自组装出具有不同空腔大小的卟啉纳米结构。在三吡啶或六吡啶模板的帮助下，多达9或18个前体分子自组装在一起，一步分别产生三卟啉纳米环和六卟啉纳米环。通过还原和酰化反应对亚胺连接的卟啉纳米物进行进一步修饰，得到更稳定的纳米物。卟啉环的开放空腔使其成为包封富勒烯（C60和C70）的有效宿主。这项工作提出了一种高效的模板导向自组装策略，通过使用亚胺键形成的动态共价化学来构建复杂分子。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

期刊介绍： Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.