氧桥杯芳烃衍生物的合成、结构及自组装研究
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摘要
超分子化学发展迅速,已经引起了化学、晶体学、材料学和生物学等各学科科学家的重视。该领域的研究热点是超分子主体分子的设计、合成及其与客体分子的自组装。杯芳烃作为第三代超分子主体化合物,自出现以来受到了科学工作者的广泛关注。随着主客体化学从单点识别发展到多重识别(或多点识别),而且正向不对称性识别方向发展,杯芳烃的合成正向着功能化方向发展。
本论文在已合成的杯芳烃基础之上,设计并合成了芳香环上带有功能取代基的杯芳烃衍生物。并对合成得到的羧酸衍生物与金属离子配位自组装进行了一些探索工作。
1.以2,3-二羟基苯甲酸为起始原料,合成了邻-氧桥2-羧基-苯[2]吡嗪[2]杯芳烃(化合物3.6),并用1H-NMR,13C-NMR、HRMass以及X-Ray单晶衍射对其结构进行了确认。研究发现化合物3.6在不同溶剂中,可以与溶剂分子产生氢键作用,形成不同的单晶结构。初步研究了化合物3.6与金属离子配位的能力,发现化合物3.6能与Ag+、Cu2+、Zn2+等金属离子形成配合物；与相同的金属盐在不同的溶剂体系中能形成不同空间结构的配合物；在与金属离子配位时,羧基参与配位作用,增加分子的配位能力。
2.以间-氧桥四氨基杯[4]芳烃为母体,合成了七个含有(磺)酰胺、酰(硫)脲基团的杯芳烃衍生物。它们的结构经1H-NMR、13C-NMR和HRMass得到确认,其中四个化合物的结构经X-Ray单晶衍射得到进一步确认。研究发现,含有(磺)酰胺、酰(硫)脲基团的杯芳烃衍生物可以通过分子间氢键作用进行自组装,形成二聚体或四聚体,对一些有机小分子客体有包合作用。
本文共合成得到了十个新化合物和四个有机金属配合物,得到了其中十一个化合物或配合物的单晶结构。
The quick growth of Supramolecular Chemistry has aroused great attention of scientists from the fields of Chemistry, Crystallography, Materials Science and Biology. Design and synthesis of the host molecules followed by self-assembly research of those host molecules is a hotspot of 'host-guest' chemistry. Calix[n]arene has been a research focus for decades as the appearance of third generation of supramolecular host compounds. As 'host-guest' chemistry is developed from single-point recognition to mult-point recognition, multiple recognition and asymmetric recognition, synthesis of new Calix[n]arenes derivatives is the development direction.
In this paper, we designed and synthesized several new Calix[n]arenes derivatives based on the reported Calix[n]arenes, and investigated the capablity of carboxylic acid functionalized oxacalixarene to coordinate with metal ions.
1. By employing 2,3-dihydroxybenzoic acid as precursor, we synthesized carboxylic acid functionalized ortho-linked oxacalix[2]benzene[2]pyrazine. The structure was confirmed by 1H-NMR,13C-NMR, HRMass and single crystal X-Ray analysis. We found that this oxacalixarene could form different types of single crystal structures in different solvent systems. Some studies on the possible formation of'supramolecular structures'for this carboxylic acid functionalized oxacalixarene have been carried out, and we found it could coordinate with Ag+, Cu2+, Zn2+ ions and form different types of complexes in different solvent systems with the same metal ion. Because of the carboxylic acid, this oxacalixarene have more coordination sites.
2. Based on tetraamido-oxacalix[4]arene, we synthesized seven tetraamido-oxacalix[4]arene derivatives. The resulting structures was confirmed by 1H-NMR,13C-NMR, HRMass and four of them was further confirmed by single crystal X-Ray analysis. We found that acidamide and ureide derivatives could form dipolymer or tetramer with intermolecular hydrogen bonds, to capture some guest molecules.
In this paper, we synthesized ten new Calix[n]arene derivatives and four metal-organic compounds. We got eleven single crystal structures.
本论文在已合成的杯芳烃基础之上,设计并合成了芳香环上带有功能取代基的杯芳烃衍生物。并对合成得到的羧酸衍生物与金属离子配位自组装进行了一些探索工作。
1.以2,3-二羟基苯甲酸为起始原料,合成了邻-氧桥2-羧基-苯[2]吡嗪[2]杯芳烃(化合物3.6),并用1H-NMR,13C-NMR、HRMass以及X-Ray单晶衍射对其结构进行了确认。研究发现化合物3.6在不同溶剂中,可以与溶剂分子产生氢键作用,形成不同的单晶结构。初步研究了化合物3.6与金属离子配位的能力,发现化合物3.6能与Ag+、Cu2+、Zn2+等金属离子形成配合物；与相同的金属盐在不同的溶剂体系中能形成不同空间结构的配合物；在与金属离子配位时,羧基参与配位作用,增加分子的配位能力。
2.以间-氧桥四氨基杯[4]芳烃为母体,合成了七个含有(磺)酰胺、酰(硫)脲基团的杯芳烃衍生物。它们的结构经1H-NMR、13C-NMR和HRMass得到确认,其中四个化合物的结构经X-Ray单晶衍射得到进一步确认。研究发现,含有(磺)酰胺、酰(硫)脲基团的杯芳烃衍生物可以通过分子间氢键作用进行自组装,形成二聚体或四聚体,对一些有机小分子客体有包合作用。
本文共合成得到了十个新化合物和四个有机金属配合物,得到了其中十一个化合物或配合物的单晶结构。
The quick growth of Supramolecular Chemistry has aroused great attention of scientists from the fields of Chemistry, Crystallography, Materials Science and Biology. Design and synthesis of the host molecules followed by self-assembly research of those host molecules is a hotspot of 'host-guest' chemistry. Calix[n]arene has been a research focus for decades as the appearance of third generation of supramolecular host compounds. As 'host-guest' chemistry is developed from single-point recognition to mult-point recognition, multiple recognition and asymmetric recognition, synthesis of new Calix[n]arenes derivatives is the development direction.
In this paper, we designed and synthesized several new Calix[n]arenes derivatives based on the reported Calix[n]arenes, and investigated the capablity of carboxylic acid functionalized oxacalixarene to coordinate with metal ions.
1. By employing 2,3-dihydroxybenzoic acid as precursor, we synthesized carboxylic acid functionalized ortho-linked oxacalix[2]benzene[2]pyrazine. The structure was confirmed by 1H-NMR,13C-NMR, HRMass and single crystal X-Ray analysis. We found that this oxacalixarene could form different types of single crystal structures in different solvent systems. Some studies on the possible formation of'supramolecular structures'for this carboxylic acid functionalized oxacalixarene have been carried out, and we found it could coordinate with Ag+, Cu2+, Zn2+ ions and form different types of complexes in different solvent systems with the same metal ion. Because of the carboxylic acid, this oxacalixarene have more coordination sites.
2. Based on tetraamido-oxacalix[4]arene, we synthesized seven tetraamido-oxacalix[4]arene derivatives. The resulting structures was confirmed by 1H-NMR,13C-NMR, HRMass and four of them was further confirmed by single crystal X-Ray analysis. We found that acidamide and ureide derivatives could form dipolymer or tetramer with intermolecular hydrogen bonds, to capture some guest molecules.
In this paper, we synthesized ten new Calix[n]arene derivatives and four metal-organic compounds. We got eleven single crystal structures.
引文
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