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溴化官能化柱[5]芳烃的构造异构体:合成、表征及晶体结构

Constitutional isomers of brominated-functionalized copillar[5]arenes: synthesis, characterization, and crystal structures.

作者信息

Al-Azemi Talal F, Vinodh Mickey, Alipour Fatemeh H, Mohamod Abdirahman A

机构信息

Chemistry Department, Kuwait University P. O. Box 5969, Safat 13060 Kuwait

出版信息

RSC Adv. 2019 May 3;9(24):13814-13819. doi: 10.1039/c9ra02313e. eCollection 2019 Apr 30.

DOI:10.1039/c9ra02313e
PMID:35519554
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9063920/
Abstract

We herein report the preparation of constitutional isomers of brominated-functionalized pillar[5]arenes co-condensation of 1,4-bis(2-bromoethoxy)benzene and 1,4-dimethoxybenzene. The structures of the obtained isomers were then established using single crystal X-ray diffraction. We also found that the isomeric yield distribution of the different constitutional isomers was independent of the monomer's mole feed ratio, as revealed by HPLC analysis of the crude mixture. Finally, further characterization of the separated constitutional isomers indicated that they possess different melting points, NMR spectra, crystal structures, binding constants and stacking patterns in the solid state.

摘要

我们在此报告了溴化功能化柱[5]芳烃的构造异构体的制备——1,4-双(2-溴乙氧基)苯与1,4-二甲氧基苯的共缩合反应。然后通过单晶X射线衍射确定了所得异构体的结构。我们还发现,通过对粗混合物的HPLC分析表明,不同构造异构体的异构产率分布与单体的摩尔进料比无关。最后,对分离出的构造异构体的进一步表征表明,它们具有不同的熔点、核磁共振谱、晶体结构、结合常数以及固态下的堆积模式。

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本文引用的文献

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An alternative route for the synthesis of hydroxylated pillar[5]arene-based amphiphiles.一种合成羟基化的柱[5]芳烃两亲物的替代路线。
Org Biomol Chem. 2018 Oct 17;16(40):7513-7517. doi: 10.1039/c8ob02074d.
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Constitutional Isomers of Pentahydroxy-Functionalized Pillar[5]arenes: Synthesis, Characterization, and Crystal Structures.五羟官能化[5]芳烃的同构物:合成、表征及晶体结构。
J Org Chem. 2017 Oct 20;82(20):10945-10952. doi: 10.1021/acs.joc.7b01837. Epub 2017 Oct 9.
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A1/A2-Diamino-Substituted Pillar[5]arene-Based Acid-Base-Responsive Host-Guest System.
基于A1/A2-二氨基取代柱[5]芳烃的酸碱响应型主客体体系
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Water-soluble pillar[7]arene: synthesis, pH-controlled complexation with paraquat, and application in constructing supramolecular vesicles.水溶性杯芳烃:合成、与百草枯的 pH 控制络合及在超分子囊泡构建中的应用。
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A sugar-functionalized amphiphilic pillar[5]arene: synthesis, self-assembly in water, and application in bacterial cell agglutination.糖功能化两亲性柱[5]芳烃:合成、在水中的自组装及在细菌细胞聚集中的应用。
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Monoester copillar[5]arenes: synthesis, unusual self-inclusion behavior, and molecular recognition.单酯杯芳烃:合成、不寻常的自包含行为和分子识别。
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J Org Chem. 2012 Dec 21;77(24):11146-52. doi: 10.1021/jo302283n. Epub 2012 Dec 10.