原位合成的3，6-二羟基-2，5-苯醌-1，4-二甲酸（酯）与P区主族金属构筑的配位聚合物的合成、结构、机理研究
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摘要
水(溶剂)热下原位配体反应由于其高效、简单、环保、条件友好等特点,在过去的十几年内已被广泛地应用在配位聚合物的合成上。特别是原位配体的合成反应往往伴随着新的有机反应,这样探索和研究反应机理则成为了研究的重点。本论文主要介绍了三个含原位合成的3,6-二羟基-2,5-苯醌-1,4-二甲酸(酯)配体的主族金属配位聚合物,并对其结构和配体的形成机理进行了深入的探讨。全文共分两章：
第一章简要介绍了配位聚合物的水(溶剂)热合成反应,目前已报道的水(溶剂)热条件下常见的原位配体反应类型,苯醌类配位聚合物的研究进展以及本课题所取得的研究进展；
第二章,首先介绍了基于主族金属离子Bi(Ⅲ)和In(Ⅲ)的催化下,配体1,4-环己二酮-2,5-二甲酸二甲酯原位分别形成了配体3,6-二羟基-2,5-苯醌-1,4-二甲酸(H2dhbqdc)和3,6-二羟基-2,5-苯醌-1,4-二甲酸二甲酯(H2dhbqdce),并得到配合物[Bi(H0.5dhbqdc)2]·(DMF)n(1) Bi2(dhbqdce)(C2O4)2(DMF)4 (2)和[In(H0.5dhbqdc)2]·(DMF)n(3)。在配合物1-3中,金属中心均显示出了三角十二面体的构型。配合物1和3同构,以1为例,该结构中dhbqdc上的四个羟基氧以双-双齿螯合的配位模式与Bi(Ⅲ)相连接,而每个Bi(Ⅲ)与周围四个dhbqdc相连,由此构筑成了三维金刚石网状结构;2中的Bi(Ⅲ)中心的配位环境由两个来自dhbqdc上的羟基氧,四个来自两个C2O42-中的羧基氧以及两个来自DMF羰基氧构筑而成,dhbqdce和草酸都采取了双-双齿螯合配位模式,由此最终形成了二维(6,3)砖墙结构；其次我们对配合物的相关性质进行了表征,包括红外光谱,X-ray粉末衍射以及热重分析；最后,重点讨论了配体前体形成3,6-二羟基-2,5-苯醌-1,4-二甲酸(酯)的形成机理,涉及到的反应有烯醇互变、氧化—插入、H质子转移、氧化芳构化以及氧化—水解等。
Recently, in situ ligand synthesis under hydro(solvo)thermal conditions has been extensively applied in construction of coordination polymers due to its effectiveness, simplicity and environmental friendliness. In particular, in situ ligand synthesis is often accompanied by some new organic reactions. Thus, the analysis and exploration of reaction mechanism has also been the focus. This dissertation composed of two chapters mainly reports three P-block metal-organic compounds with in stiu synthesized 3,6-dihydroxy-2,5-benzoquinone-1,4-dicarboxylate (diester). Their structures and formation mechanism of the ligand from precursor were discussed in detail.
Chapter one is a brief introduction to the hydro(solvo)thermal method, in situ ligand synthesis and research progress of metal benzoquinone complexes.
In chapter two, three novel complexes, namely [Bi(dhbqdc)2]·(DMF)n(1), Bi2(dhbqdce)(C2O4)2(DMF)4 (2) and [Bi(dhbqdc)2]·(DMF)n(3) are reported firstly, in which the ligands dhbqdc and dhbqdce are in situ obtained from the precursor dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate. The 1 and 3 show isostructural 3D diamond network, in which eight-coordinated metal ion is chelated by eight hydroxyl groups from four dhbqdc in bis-bidentate fashion. In contrast, the eight-coordinated Bi atom in 2 show a triangular dodecahedron geometry, ligated by two hydroxy groups from one dhbqdce, four carboyxlate oxygen atoms from two oxalates and two carbonyl groups from two DMFs, and the final structure shows a 2D brickwall layer. In addition, the infrared spectrum, X-ray powder diffraction and thermogravimetric analysis are also introduced. Finally, the ligands formation mechanism is discussed, including enol interconversion, oxidation-insert, oxidative aromatization, proton transfer, ester cleavage and so on.
第一章简要介绍了配位聚合物的水(溶剂)热合成反应,目前已报道的水(溶剂)热条件下常见的原位配体反应类型,苯醌类配位聚合物的研究进展以及本课题所取得的研究进展；
第二章,首先介绍了基于主族金属离子Bi(Ⅲ)和In(Ⅲ)的催化下,配体1,4-环己二酮-2,5-二甲酸二甲酯原位分别形成了配体3,6-二羟基-2,5-苯醌-1,4-二甲酸(H2dhbqdc)和3,6-二羟基-2,5-苯醌-1,4-二甲酸二甲酯(H2dhbqdce),并得到配合物[Bi(H0.5dhbqdc)2]·(DMF)n(1) Bi2(dhbqdce)(C2O4)2(DMF)4 (2)和[In(H0.5dhbqdc)2]·(DMF)n(3)。在配合物1-3中,金属中心均显示出了三角十二面体的构型。配合物1和3同构,以1为例,该结构中dhbqdc上的四个羟基氧以双-双齿螯合的配位模式与Bi(Ⅲ)相连接,而每个Bi(Ⅲ)与周围四个dhbqdc相连,由此构筑成了三维金刚石网状结构;2中的Bi(Ⅲ)中心的配位环境由两个来自dhbqdc上的羟基氧,四个来自两个C2O42-中的羧基氧以及两个来自DMF羰基氧构筑而成,dhbqdce和草酸都采取了双-双齿螯合配位模式,由此最终形成了二维(6,3)砖墙结构；其次我们对配合物的相关性质进行了表征,包括红外光谱,X-ray粉末衍射以及热重分析；最后,重点讨论了配体前体形成3,6-二羟基-2,5-苯醌-1,4-二甲酸(酯)的形成机理,涉及到的反应有烯醇互变、氧化—插入、H质子转移、氧化芳构化以及氧化—水解等。
Recently, in situ ligand synthesis under hydro(solvo)thermal conditions has been extensively applied in construction of coordination polymers due to its effectiveness, simplicity and environmental friendliness. In particular, in situ ligand synthesis is often accompanied by some new organic reactions. Thus, the analysis and exploration of reaction mechanism has also been the focus. This dissertation composed of two chapters mainly reports three P-block metal-organic compounds with in stiu synthesized 3,6-dihydroxy-2,5-benzoquinone-1,4-dicarboxylate (diester). Their structures and formation mechanism of the ligand from precursor were discussed in detail.
Chapter one is a brief introduction to the hydro(solvo)thermal method, in situ ligand synthesis and research progress of metal benzoquinone complexes.
In chapter two, three novel complexes, namely [Bi(dhbqdc)2]·(DMF)n(1), Bi2(dhbqdce)(C2O4)2(DMF)4 (2) and [Bi(dhbqdc)2]·(DMF)n(3) are reported firstly, in which the ligands dhbqdc and dhbqdce are in situ obtained from the precursor dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate. The 1 and 3 show isostructural 3D diamond network, in which eight-coordinated metal ion is chelated by eight hydroxyl groups from four dhbqdc in bis-bidentate fashion. In contrast, the eight-coordinated Bi atom in 2 show a triangular dodecahedron geometry, ligated by two hydroxy groups from one dhbqdce, four carboyxlate oxygen atoms from two oxalates and two carbonyl groups from two DMFs, and the final structure shows a 2D brickwall layer. In addition, the infrared spectrum, X-ray powder diffraction and thermogravimetric analysis are also introduced. Finally, the ligands formation mechanism is discussed, including enol interconversion, oxidation-insert, oxidative aromatization, proton transfer, ester cleavage and so on.
引文
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