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用于特定客体结合的吡啶连接柱[5]芳烃胶囊的单原子调谐

Single-Atom Tuning of Pyridine-Strapped Pillar[5]arene Capsules for Specific Guest Binding.

作者信息

Ruengsuk Araya, Vigromsitdet Sutthipoj, Saekee Amporn, Wichannananon Pornnaphat, Sangtawesin Tanagorn, Sukwattanasinitt Mongkol, Tantirungrotechai Jonggol, Harding David J, Bunchuay Thanthapatra

机构信息

Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, Thailand.

Agriculture Production Science Research and Development Division, Department of Agriculture, 50 Phahonyothin Rd, Lat Yao, Chatuchak, Bangkok 10900, Thailand.

出版信息

Org Lett. 2025 Mar 7;27(9):2093-2097. doi: 10.1021/acs.orglett.5c00110. Epub 2025 Feb 24.

DOI:10.1021/acs.orglett.5c00110
PMID:39992802
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11894638/
Abstract

Pyridine bis(carboxamide)-strapped pillar[5]arene capsules were synthesized with the serendipitous formation of macrotricyclic products. The structural integrity of the supramolecular capsules, determined by the specific orientation of a single nitrogen atom, controls the electronic properties of the confined binding cavity, facilitating length-selective recognition of aliphatic organic guests with nitrile, isocyanide, and amine functional groups with exceptional host-guest binding affinity and selectivity for 1,2-diaminoethane ( > 10 M) in a polar organic solvent.

摘要

吡啶双（甲酰胺）连接的柱[5]芳烃胶囊是在意外形成大环三环产物的情况下合成的。超分子胶囊的结构完整性由单个氮原子的特定取向决定，它控制着受限结合腔的电子性质，有助于对具有腈基、异氰基和胺官能团的脂肪族有机客体进行长度选择性识别，在极性有机溶剂中对1,2 - 二氨基乙烷具有出色的主客体结合亲和力和选择性（> 10 M）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/794b/11894638/5e2567e36546/ol5c00110_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/794b/11894638/3fa230941536/ol5c00110_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/794b/11894638/feef19226a2a/ol5c00110_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/794b/11894638/5e2567e36546/ol5c00110_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/794b/11894638/3fa230941536/ol5c00110_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/794b/11894638/feef19226a2a/ol5c00110_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/794b/11894638/5e2567e36546/ol5c00110_0003.jpg

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本文引用的文献

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Chem Sci. 2024 Nov 4;16(1):171-181. doi: 10.1039/d4sc04529g. eCollection 2024 Dec 18.
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Switchable Metal-Ion Selectivity in Sulfur-Functionalised Pillar[5]arenes and Their Host-Guest Complexes.硫官能化柱[5]芳烃及其主客体配合物中的可切换金属离子选择性
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Site-Selective Ligand Bridging among Multiple Internal Coordination Sites of a Metallomacrocycle and Its Conformational Regulation.
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Separation of pyrrolidine from tetrahydrofuran by using pillar[6]arene-based nonporous adaptive crystals.使用基于柱[6]芳烃的无孔自适应晶体从四氢呋喃中分离吡咯烷。
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Neutral isocyanide-templated assembly of pillar[5]arene [2] and [3]pseudorotaxanes.中性异腈模板化的柱[5]芳烃[2]和[3]准轮烷的组装
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Metallosupramolecules of pillar[5]-bis-trithiacrown including a mercury(ii) iodide ion-triplet complex.包含碘化汞(ii)离子三聚体复合物的[5]-双三噻轮冠醚金属超分子。
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