半夹心结构有机金属自组装化合物的合成和性质研究
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摘要
有机金属自组装化合物的研究是当代化学的一个前沿,本论文选定含有半夹心结构Cp*Ir,Cp*Rh(Cp*=η5-C5Me5)的有机金属化合物为构筑单元,通过对金属单元和桥联配体进行合理的设计选择、裁剪、组装,合成了一系列有限结构的环状和笼状的有机金属自组装化合物,探讨了金属单元和桥联配体的选择与目标产物结构与性能的关系,发展并实践了若干有限多核具有特定结构有机金属超分子化合物的合成新方法,并对目标化合物的性能做出了一些有意义的探索。
(1)利用含硫族元素邻位碳硼烷配体作为封闭端和含氮双齿配体构筑了一系列含有半夹心结构有机金属双核碳硼烷化合物。通过改变双齿有机配体的结构,不仅可以调控金属-金属原子间的距离,而且可以合成具有新颖结构的超分子化合物。此外,本章亦研究了对位碳硼烷衍生物作为作为桥联基团的可行性。由此,一方面合成了一系列含有对位碳硼烷羧酸的稀土金属-有机框架化合物,它们由于镧系收缩而形成三种典型结构,并具有利用对位碳硼烷羧酸合成了若干中性的双核和多核自组装结构并考察其自组装模式。考察其气体吸附能力,发现其具有选择性吸附二氧化碳(相比氮和甲烷而言)的能力。另一方面,利用对位碳硼烷羧酸的硼-氢活化反应合成了若干中性的双核和多核自组装结构并考察其自组装模式。
(2)合成并表征了1,5-二羟基-9,10-蒽醌桥联的半夹心结构有机金属化合物。在合成了有机金属双核化合物的基础上,首先在银盐作用下夺去金属中心上的两个氯离子,利用得到的两个配位点与等摩尔量的含氮双齿配体如吡嗪、4,4'-联吡啶(bpy)、2,5'-二(4-吡啶)基-1,3,4-噁二唑(bpo)或1,2'-二(4-吡啶)基乙烯(bpe)反应时,可以得到不同的大环化合物,并且获得了部分化合物的晶体结构数据。当有机金属双核化合物与含氮三齿配体tpt反应时,可得到相应的六核三棱柱型化合物,此类化合物可具有较大的空腔体积。在此基础上,结合文献和自身工作,对6,11-二羟基-5,12-萘并萘醌、1,4-二羟基-9,10-蒽醌与1,5-二羟基-9,10-蒽醌所形成自组装结构的主客体化学表现进行了较为系统的讨论,讨论了不同宽度配体的边壁效应、对多核化合物固体结构和主客体效应的影响,并对彼此的联系与区别进行了比较。
(3)从[Cp*IrCl2]2和tpt配体出发,利用碳-氢活化驱动的自组装过程合成了一系列六核有机金属自组装笼体。这类笼状化合物可以和一系列富于π电子的分子(如Pt(acac)2、芘和蔻分子)发生主-客体作用,形成1：1的物种,并且被核磁、元素分析以及单晶数据证实。在未捕获客体的笼体中,tpt三唑环的距离较近,为3.3A。而在“捕获”形成的主-客体系统中,笼体被“撑开”,三唑环距离可达6.66A。
(4)研究了双功能配体2,4-二乙酰基-5-羟基-5-甲基-3-(3-吡啶基)环己酮与半夹心铱化合物的自组装,制备了四核的有机金属大环化合物。此类四核化合物在晶体中结晶成褶皱的结构从而提高了空间利用率,但也因此导致大环中间的孔道半径过小,至少在固相不足以容纳客体。
Supramolecular chemistry with organometallic half-sandwich complexes based on Ir, Rh, Ru fragments has received considerable attention over recent years. In this dissertation, some results in the rational design and synthesis of discrete organometallic half-sandwich complexes and their potential applications are presented. The advantage of the formation of these architectures via step-wise formations is, by employing functional ligands or metal centers in the assembly process, functionalities can readily be introduced onto the metallasupramolecular structures.
(1) Based on the rule of addition reaction at the metal center of [Cp*M[E2C2(B10H10)](M=Ir, Rh; E=S, Se), both of cluster-based carboranyl complexes and flexible bipyridyl ligands, have been proved to be versatile precursors to accomplish diverse architectures.
The probability of p-carborane derivatives as linker has also been explored. As a result, a series of microporous lanthanide coordination polymers containing p-dicarboxylate carborane ligand have been synthesized from the reactions of p-carboxylic acid with rare earth metals. Based on the well-known effect of lanthanide contraction, three distinct structure types were isolated. The structures of type Ⅰ polymers consist of four-connected2D lamellar networks, but type Ⅱ and type Ⅲ polymers are composed of six-connected3D structures. Gas sorption property of such complexes was studied, which showed selective CO2capture over CH4and N2. On the other hand, a newly tetranuclear half-sandwich iridium macrocycle was successfully obtained via cleaving B-H bonds of carborane-containing p-carboxylic acid under mild conditions.
(2) The binuclear complexes with two parallel coordination sites, such as1,5-dihydroxyanthracene-9,10-dione bridging iridium, rhodium complexes can be served as precursors, which can be interlinked by pyridyl-based ligands.
Many tetra-and hexanuclear organometallic self-assemblies bearing1,5-dihydroxyanthracene-9,10-dione ligands were synthesized. The tetranuclear species can be obtained if bridging ligands such pyrazine,4,4'-bipyridine are used.
The hexanuclear species can also be synthesized if tpt ligand is used. Crystal structure of some tetranuclear complexes has been obtained and host-guest behavior of them has been discussed. The similarity and difference between self-assemblies bearing1,5-dihydroxyanthracene-9,10-dione and1,4-dihydroxyanthracene-9,10-dione have been discussed and compared with results of self-assemblies of6,11-dihydroxy-5,12-naphthacenedione.
(3) Driven by C-H activation-directed self-assembly, a series of organometallic cages was obtained from the reaction of [Cp*IrCl2]2and tpt with terephthal-bis-aromatic imine ligands in the presence of AgOTf. In the resulting supramolecular assemblies, the two central triazine units are very close, and the centroid…centroid distance between the two triazine moieties is only3.3A. These discrete cages can form complexes with a wide variety of π-donor substrates, including Pt(acac)2, pyrene, and coronene. The transannular separation between the centers of the triazine rings in the host-guest complex is now enlarged to about6.66A. The preparation of host-guest systems in a one-pot procedure was accomplished. The1:1complexation between the guest and host was confirmed by1H NMR, elemental analyses and single-crystal X-ray diffraction analyses.
(4) Self-assembly of half-sandwich iridium fragment and ditopic ligand2,4-diacetyl-5-hydroxy-5-methyl-3-(3-pyridinyl)-cyclohexanone (HL) ligand has been researched. Several half-sandwich iridium-based metallamacrocycles have been synthesized. They are assembled by linking the deprotonated2,4-diacetyl-5-hydroxy-5-methyl-3-(3-pyridinyl)-cyclohexanone ligand in the presence of counteranions. Single-crystal X-ray analysis indicated that, in the solid state, the products crystallize as tetranuclear cations according to counteranions.
(1)利用含硫族元素邻位碳硼烷配体作为封闭端和含氮双齿配体构筑了一系列含有半夹心结构有机金属双核碳硼烷化合物。通过改变双齿有机配体的结构,不仅可以调控金属-金属原子间的距离,而且可以合成具有新颖结构的超分子化合物。此外,本章亦研究了对位碳硼烷衍生物作为作为桥联基团的可行性。由此,一方面合成了一系列含有对位碳硼烷羧酸的稀土金属-有机框架化合物,它们由于镧系收缩而形成三种典型结构,并具有利用对位碳硼烷羧酸合成了若干中性的双核和多核自组装结构并考察其自组装模式。考察其气体吸附能力,发现其具有选择性吸附二氧化碳(相比氮和甲烷而言)的能力。另一方面,利用对位碳硼烷羧酸的硼-氢活化反应合成了若干中性的双核和多核自组装结构并考察其自组装模式。
(2)合成并表征了1,5-二羟基-9,10-蒽醌桥联的半夹心结构有机金属化合物。在合成了有机金属双核化合物的基础上,首先在银盐作用下夺去金属中心上的两个氯离子,利用得到的两个配位点与等摩尔量的含氮双齿配体如吡嗪、4,4'-联吡啶(bpy)、2,5'-二(4-吡啶)基-1,3,4-噁二唑(bpo)或1,2'-二(4-吡啶)基乙烯(bpe)反应时,可以得到不同的大环化合物,并且获得了部分化合物的晶体结构数据。当有机金属双核化合物与含氮三齿配体tpt反应时,可得到相应的六核三棱柱型化合物,此类化合物可具有较大的空腔体积。在此基础上,结合文献和自身工作,对6,11-二羟基-5,12-萘并萘醌、1,4-二羟基-9,10-蒽醌与1,5-二羟基-9,10-蒽醌所形成自组装结构的主客体化学表现进行了较为系统的讨论,讨论了不同宽度配体的边壁效应、对多核化合物固体结构和主客体效应的影响,并对彼此的联系与区别进行了比较。
(3)从[Cp*IrCl2]2和tpt配体出发,利用碳-氢活化驱动的自组装过程合成了一系列六核有机金属自组装笼体。这类笼状化合物可以和一系列富于π电子的分子(如Pt(acac)2、芘和蔻分子)发生主-客体作用,形成1：1的物种,并且被核磁、元素分析以及单晶数据证实。在未捕获客体的笼体中,tpt三唑环的距离较近,为3.3A。而在“捕获”形成的主-客体系统中,笼体被“撑开”,三唑环距离可达6.66A。
(4)研究了双功能配体2,4-二乙酰基-5-羟基-5-甲基-3-(3-吡啶基)环己酮与半夹心铱化合物的自组装,制备了四核的有机金属大环化合物。此类四核化合物在晶体中结晶成褶皱的结构从而提高了空间利用率,但也因此导致大环中间的孔道半径过小,至少在固相不足以容纳客体。
Supramolecular chemistry with organometallic half-sandwich complexes based on Ir, Rh, Ru fragments has received considerable attention over recent years. In this dissertation, some results in the rational design and synthesis of discrete organometallic half-sandwich complexes and their potential applications are presented. The advantage of the formation of these architectures via step-wise formations is, by employing functional ligands or metal centers in the assembly process, functionalities can readily be introduced onto the metallasupramolecular structures.
(1) Based on the rule of addition reaction at the metal center of [Cp*M[E2C2(B10H10)](M=Ir, Rh; E=S, Se), both of cluster-based carboranyl complexes and flexible bipyridyl ligands, have been proved to be versatile precursors to accomplish diverse architectures.
The probability of p-carborane derivatives as linker has also been explored. As a result, a series of microporous lanthanide coordination polymers containing p-dicarboxylate carborane ligand have been synthesized from the reactions of p-carboxylic acid with rare earth metals. Based on the well-known effect of lanthanide contraction, three distinct structure types were isolated. The structures of type Ⅰ polymers consist of four-connected2D lamellar networks, but type Ⅱ and type Ⅲ polymers are composed of six-connected3D structures. Gas sorption property of such complexes was studied, which showed selective CO2capture over CH4and N2. On the other hand, a newly tetranuclear half-sandwich iridium macrocycle was successfully obtained via cleaving B-H bonds of carborane-containing p-carboxylic acid under mild conditions.
(2) The binuclear complexes with two parallel coordination sites, such as1,5-dihydroxyanthracene-9,10-dione bridging iridium, rhodium complexes can be served as precursors, which can be interlinked by pyridyl-based ligands.
Many tetra-and hexanuclear organometallic self-assemblies bearing1,5-dihydroxyanthracene-9,10-dione ligands were synthesized. The tetranuclear species can be obtained if bridging ligands such pyrazine,4,4'-bipyridine are used.
The hexanuclear species can also be synthesized if tpt ligand is used. Crystal structure of some tetranuclear complexes has been obtained and host-guest behavior of them has been discussed. The similarity and difference between self-assemblies bearing1,5-dihydroxyanthracene-9,10-dione and1,4-dihydroxyanthracene-9,10-dione have been discussed and compared with results of self-assemblies of6,11-dihydroxy-5,12-naphthacenedione.
(3) Driven by C-H activation-directed self-assembly, a series of organometallic cages was obtained from the reaction of [Cp*IrCl2]2and tpt with terephthal-bis-aromatic imine ligands in the presence of AgOTf. In the resulting supramolecular assemblies, the two central triazine units are very close, and the centroid…centroid distance between the two triazine moieties is only3.3A. These discrete cages can form complexes with a wide variety of π-donor substrates, including Pt(acac)2, pyrene, and coronene. The transannular separation between the centers of the triazine rings in the host-guest complex is now enlarged to about6.66A. The preparation of host-guest systems in a one-pot procedure was accomplished. The1:1complexation between the guest and host was confirmed by1H NMR, elemental analyses and single-crystal X-ray diffraction analyses.
(4) Self-assembly of half-sandwich iridium fragment and ditopic ligand2,4-diacetyl-5-hydroxy-5-methyl-3-(3-pyridinyl)-cyclohexanone (HL) ligand has been researched. Several half-sandwich iridium-based metallamacrocycles have been synthesized. They are assembled by linking the deprotonated2,4-diacetyl-5-hydroxy-5-methyl-3-(3-pyridinyl)-cyclohexanone ligand in the presence of counteranions. Single-crystal X-ray analysis indicated that, in the solid state, the products crystallize as tetranuclear cations according to counteranions.
引文
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