A Self-Cyclocondensation Approach for the Synthesis of a Cycloparaphenylene-End-Capped Molecular Cylinder.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-08 DOI:10.1021/acs.orglett.5c02467

Zhuofan Xu,Xingchi Liu,Chang Ge,Xiaonan Ma,Zhe Sun

引用次数: 0

Abstract

The synthesis of molecular cylinders is challenging due to their intrinsic strain and the complexity of the structure. Here we report an efficient self-cyclocondensation approach for the construction of molecular cylinder MC3, taking advantage of a cycloparaphenylene precursor comprising both diamine and diketone moieties within the macrocyclic skeleton. The tilted cylindrical geometry of MC3 was revealed by X-ray single crystal analysis, and variable temperature NMR analysis suggested a dynamic time-averaged structure in the solution phase. MC3 exhibits distinct optical properties, including solvatofluorochromism and a moderate fluorescence quantum yield, associated with the CT characteristics of the excited state. The building block in this study may be further employed for the construction of polymeric structures and fully fused cylindrical structures.

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自环缩合法合成端部环对苯乙烯分子柱。

分子柱的合成由于其固有应变和结构的复杂性而具有挑战性。在这里，我们报道了一种高效的自环缩合方法，用于构建分子圆柱体MC3，利用环对苯炔前体在大环骨架内包含二胺和二酮部分。x射线单晶分析揭示了MC3的倾斜圆柱结构，变温核磁共振分析表明其在溶液中具有动态时均结构。MC3具有独特的光学性质，包括溶剂化荧光变色和适度的荧光量子产率，这与激发态的CT特性有关。本研究的构建块可以进一步用于构建聚合物结构和完全融合的圆柱形结构。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.