从四氯化苝二亚胺环番到硅环高亲和受体

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-07-03 DOI:10.1016/j.tetlet.2025.155729

Bai-Yang Qian , Bi-Lian Chai , Jianbin Lin, Hui-Jun Zhang

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引用次数: 0

摘要

我们设计和合成了两种新型的四氯苝酰二亚胺（PDI）环番。以四氯-PDI环烷为前驱体，通过8倍钯催化偶联制备了硅环PDI环烷。主客体相互作用研究表明，所制得的硅烷- pdi环烷能有效结合π共轭分子，如富电子蒽（AN）和贫电子蒽醌（AQ）。值得注意的是，结构明确的AQ∧sila-PDI环烷复合物的结合常数高达Ka =（1.04±0.22）× 106 M−1，显示出其较强的亲和力。本研究强调了四氯pdi环烷作为构建各种杂环结构的模块化平台的潜在用途。

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From tetrachlorinated perylene diimide cyclophanes to sila-annulated high-affinity receptors

We present the design and synthesis of two novel tetrachlorinated perylene diimide (PDI) cyclophanes. Using the tetrachloro-PDI cyclophane as a precursor, a silicon-annulated PDI cyclophane was readily synthesized via an eight-fold palladium-catalyzed coupling strategy. Host-guest interaction studies demonstrate that the resulting sila-PDI cyclophane effectively binds π-conjugated molecules, such as electron-rich anthracene (AN) and electron-poor anthraquinone (AQ). Notably, the binding constant for the structurally well-defined AQ⊂sila-PDI cyclophane complex is as high as K_a = (1.04 ± 0.22) × 10⁶ M⁻¹, highlighting its strong affinity. This study underscores the potential utility of tetrachloro-PDI cyclophanes as modular platforms for constructing various heteroannulated architectures.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.