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通过氢键形成的双穴番(cavitand)封端卟啉胶囊

Doubly Cavitand-Capped Porphyrin Capsule by Hydrogen Bonds.

作者信息

Kishimoto Kazuki, Nakamura Munechika, Kobayashi Kenji

机构信息

Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.

出版信息

Chemistry. 2016 Feb 18;22(8):2629-33. doi: 10.1002/chem.201504893. Epub 2016 Jan 20.

DOI:10.1002/chem.201504893
PMID:26728330
Abstract

The components of a 1:2 mixture of meso-tetrakis(4-dodecyl-3,5-dihydroxyphenyl)porphyrin (1) and a bowl-shaped tetrakis(4-pyridylethynyl)cavitand (2) in CDCl3 or C6 D6 self-assemble quantitatively into the doubly cavitand-capped porphyrin capsule 2⋅1⋅2 through eight ArOH⋅⋅⋅Npy hydrogen bonds. Capsule 2⋅1⋅2 possesses two cavities divided by the porphyrin ring and encapsulates two molecules of 1-acetoxy-3,5-dimethoxybenzene (G) as a guest to form G/G@(2⋅1⋅2). Remarkable solvent effect was observed, in which the apparent association constant of 2⋅1⋅2 with G in C6 D6 was much greater than that in CDCl3.

摘要

中四(4 - 十二烷基 - 3,5 - 二羟基苯基)卟啉(1)与碗状四(4 - 吡啶乙炔基)穴状配体(2)按1:2比例混合于CDCl₃或C₆D₆中,通过八个ArOH∙∙∙Npy氢键定量自组装成双穴状配体封端的卟啉胶囊2∙∙1∙∙2。胶囊2∙∙1∙∙2具有两个由卟啉环分隔的空腔,并包封两个1 - 乙酰氧基 - 3,5 - 二甲氧基苯(G)分子作为客体,形成G/G@(2∙∙1∙∙2)。观察到显著的溶剂效应,其中2∙∙1∙∙2与G在C₆D₆中的表观缔合常数远大于在CDCl₃中的。

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