[FeFe]-及[NiFe]-氢化酶活性中心仿生化学研究
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摘要
氢化酶是一类能够可逆催化氢气与质子间相互转化的生物酶，其中[FeFe]-及[NiFe]-氢化酶是两类最重要的天然氢化酶。近年来有关它们的仿生化学研究已经成为金属有机化学和生物无机化学领域研究的热点，这对解决当今人类面临日益严重的能源和环境问题具有重要的理论意义和潜在的应用前景。为了丰富和发展[FeFe]-和[NiFe]-氢化酶的化学模拟工作，本论文开展了新型[FeFe]-和[NiFe]-氢化酶活性中心模型物的合成、结构以及功能的研究，取得了如下创新性成果：
1，本论文共合成了28个新化合物，它们的结构均经过元素分析、IR、1HNMR谱表征，部分化合物还经~(31)PNMR、~(13)CNMR、~(77)SeNMR和~(125)TeNMR表征，并用X-射线衍射技术测定了其中21个模型物的单晶结构。此外，本论文还研究了部分氢化酶模型物的电化学性质。
2，在本论文第二章中，我们首先改进并且规范了文献有关合成原料(μ-Te_2)Fe_2(CO)_6的实验步骤，大大提高了模型物[(μ-TeCH_2)2CH_2]Fe_2(CO)_6(A)的产率，并且首次合成了模型物[(μ-TeCH_2)_2CH(OH)]Fe_2(CO)_6(B)；并且我们首次对此类含有[2Fe_2Te]的[FeFe]-氢化酶模型物进行了配体取代研究，合成了一系列模型物A的衍生模型物：(μ-PDTe)Fe_2(CO)_5(L_1)(1,L_1=PPh3;2,PPh2H;3,PMe3;4,IMes)，[(μ-PDTe)Fe_2(CO)_5]_2(L_2)(5,L_2=dppf;6,dppp;7,dppb)和(μ-PDTe)Fe_2(CO)4(L3)(8,L3=dppm;9,dppn)，通过X-射线衍射技术测定了除模型物3,8外的单晶结构，并利用循环伏安研究了模型物8的电化学性质。
3，在本论文的第三章中，通过直接分离、阳离子交换、冠醚包夹三种方法成功分离得到含有μ-CO的Fe/E簇盐中间体。首次通过直接分离得到含有μ-CO的Fe/Se簇盐[(μ-CO)(μ-DtpSe)Fe_2(CO)_6]·[Et3NH](3)(Dtp=2,6-di(p-tolyl)phenyl)，首次通过离子交换分离得到含有μ-CO的Fe/Te簇盐[(μ-CO]-(μ-DtpTe)Fe_2(CO)_6][Ph_4P]/[PPN](Ph_4P,4;PPN,6)，通过冠醚包夹得到含有μ-CO的Fe/Te簇盐[(μ-CO)-(μ-DtpTe)Fe_2(CO)_6](12-crown-4)Li(7)。
4，在本论文的第三章中，设计了一条新路线合成[FeFe]-氢化酶模型物，首次将含有μ-CO的Fe/E簇盐与氢化酶模型物结合起来。选用羟基官能化的2-羟基乙硫醇与Fe3(CO)_(12)/Et_3N反应首先得到含有μ-CO的络阴离子，然后与卤化磷(膦)进行亲电取代后发生分子内缩合，成功得到两个闭式的氢化酶模型物[(μ-SCH_2)(μ-POCl)CH_2]Fe_2(CO)_6(9)和[(μ-SCH_2)(μ-POPh)CH_2]Fe_2(CO)_6(10)。
5，在本论文的第四章中，设计合成了两个含有[N2E2]的三核[NiFe]-氢化酶模型物[(μ-E)_2-(2,2’-bpy)Fe_2(CO)_6Ni](E=S,1;Se,2)，两个含有[P_2E_2]的双核[NiFe]-氢化酶模型物{NiFe[E(CH_2)_3E](dppb)(CO)_3}(E=S,5;Se,7)，模型物5和7在HBF_4·Et_2O作用下质子化可得到其还原态产物{HNiFe[E(CH_2)_3E](dppb)(CO)_3}BF_4(E=S,6;Se,8)。其中，我们首次得到含有μ-Se的双核[NiFe]-氢化酶模型物7和8，此外通过电化学研究了模型物6和8的电催化性质，并做了比较。
Hydrogenases can catalyze the biological conversion between protons and dihydrogen.[FeFe] and [NiFe]-Hydrogenases are two classes of most important. Recently, the research on the structural and functional aspects has received great attention in both organometallic chemistry and bioinorganic chemistry, not only because of their theoretical interest but also the practical importance for solving the increasingly environmental pollution and energy crisis. In order to develop the biomimetic chemistry of [FeFe]-hydrogenases and [NiFe]-hydrogenases, we carried out studies on synthesis, structures, properties and functions of new models for [FeFe]-and [Ni-Fe]-hydrogenase active sites. The main results described in this thesis are as follows:
1, A total of28new compounds were successfully synthesized. The structures of these compounds were fully characterized by elemental analysis, IR,1H-NMR and some of them were further characterized by31P-NMR,13C-NMR,77Se-NMR and125Te-NMR spectroscopies, In addtion,20representatives were determined by X-ray diffraction analysis, and some representatives were investigated by electrochemistry.
2, In chapter two, Firstly, we improved the synthetic method for preparation of the starting materials (μ-Te2)Fe2(CO)6, and synthesized the model complex [(μ-TeCH2)2CH(OH)]Fe2(CO)6(B) and improved the yield of model complex [(μ-TeCH2)2CH2]Fe2(CO)6(A). Then through substitution reactions, a series of model complexes (μ-PDTe)Fe2(CO)5(Li)(1, L=PPh3;2, PPh2H;3, PMe3;4, IMes),[(μ-PDTe)Fe2(CO)5]2(L2)(5, L2=dppf;6, dppp;7, dppb) and (μ-PDTe)Fe2(CO)4(L3)(8, L3=dppm;9, dppn) were prepared. All the ten new complexes were determined by X-ray diffraction analysis except for complex3and8. In addition, a study on electrochemical and electrocatalytic properties of the model complex8was also carried out.
3, In chapter three, the μ-CO containing intermediate butterfly Fe/E clusters [(μ-CO)(μ-DtpSe)Fe2(CO)6]·[Et3NH](3),[(μ-CO]-(μ-DtpTe)Fe2(CO)6][Ph4P]/[PPN](Ph4P,4; PPN,6)[(μ-CO)-(μ-DtpTe)Fe2(CO)6](12-crown-4)Li (7)were successfully isolated by direct separation, exchange with cation and coordination with crown ether.
4, In chapter three, we designed a new route to synthesis the [FeFe]-hydrogenase models, which can combine the μ-CO Fe/S cluster and hydrogenase model together. The [FeFe]-hydrogenases models [(μ-SCH2)(μ-POCl)CH2]Fe2(CO)6(9) and [(μ-SCH2)(μ-POPh)CH2]Fe2(CO)6(10) were prepared by treatment of the μ-CO anion (generated in situ from Fe3(CO)12, Et3N and2-hydroxyethanethiol)with with electrophilic reagent halogenated phosphine.
5, In chapter four, two types of [NiFe]-hydrogenase model complexes [(μ-E)2-(2,2-bpy)Fe2(CO)6Ni (E=S,1; Se,2) and {NiFe[E(CH2)3E](dppb)(CO)3}(E=S,5; Se,7) containing the [N2E2] and [P2E2] units were prepare. The Hred model complexes{HNiFe[E(CH2)3E](dppb)(CO)3}BF4(E=S,6; Se,8) were prepared from complexes5and7reacting with HBF4·Et2O, respectively. It is worth to note that we synthesized the dual-core [NiFe]-hydrogenase models containing μ-Se for the first time. In addition, a comparative study on electrocatalytic properties of the model complexes6and8was carried out.
1，本论文共合成了28个新化合物，它们的结构均经过元素分析、IR、1HNMR谱表征，部分化合物还经~(31)PNMR、~(13)CNMR、~(77)SeNMR和~(125)TeNMR表征，并用X-射线衍射技术测定了其中21个模型物的单晶结构。此外，本论文还研究了部分氢化酶模型物的电化学性质。
2，在本论文第二章中，我们首先改进并且规范了文献有关合成原料(μ-Te_2)Fe_2(CO)_6的实验步骤，大大提高了模型物[(μ-TeCH_2)2CH_2]Fe_2(CO)_6(A)的产率，并且首次合成了模型物[(μ-TeCH_2)_2CH(OH)]Fe_2(CO)_6(B)；并且我们首次对此类含有[2Fe_2Te]的[FeFe]-氢化酶模型物进行了配体取代研究，合成了一系列模型物A的衍生模型物：(μ-PDTe)Fe_2(CO)_5(L_1)(1,L_1=PPh3;2,PPh2H;3,PMe3;4,IMes)，[(μ-PDTe)Fe_2(CO)_5]_2(L_2)(5,L_2=dppf;6,dppp;7,dppb)和(μ-PDTe)Fe_2(CO)4(L3)(8,L3=dppm;9,dppn)，通过X-射线衍射技术测定了除模型物3,8外的单晶结构，并利用循环伏安研究了模型物8的电化学性质。
3，在本论文的第三章中，通过直接分离、阳离子交换、冠醚包夹三种方法成功分离得到含有μ-CO的Fe/E簇盐中间体。首次通过直接分离得到含有μ-CO的Fe/Se簇盐[(μ-CO)(μ-DtpSe)Fe_2(CO)_6]·[Et3NH](3)(Dtp=2,6-di(p-tolyl)phenyl)，首次通过离子交换分离得到含有μ-CO的Fe/Te簇盐[(μ-CO]-(μ-DtpTe)Fe_2(CO)_6][Ph_4P]/[PPN](Ph_4P,4;PPN,6)，通过冠醚包夹得到含有μ-CO的Fe/Te簇盐[(μ-CO)-(μ-DtpTe)Fe_2(CO)_6](12-crown-4)Li(7)。
4，在本论文的第三章中，设计了一条新路线合成[FeFe]-氢化酶模型物，首次将含有μ-CO的Fe/E簇盐与氢化酶模型物结合起来。选用羟基官能化的2-羟基乙硫醇与Fe3(CO)_(12)/Et_3N反应首先得到含有μ-CO的络阴离子，然后与卤化磷(膦)进行亲电取代后发生分子内缩合，成功得到两个闭式的氢化酶模型物[(μ-SCH_2)(μ-POCl)CH_2]Fe_2(CO)_6(9)和[(μ-SCH_2)(μ-POPh)CH_2]Fe_2(CO)_6(10)。
5，在本论文的第四章中，设计合成了两个含有[N2E2]的三核[NiFe]-氢化酶模型物[(μ-E)_2-(2,2’-bpy)Fe_2(CO)_6Ni](E=S,1;Se,2)，两个含有[P_2E_2]的双核[NiFe]-氢化酶模型物{NiFe[E(CH_2)_3E](dppb)(CO)_3}(E=S,5;Se,7)，模型物5和7在HBF_4·Et_2O作用下质子化可得到其还原态产物{HNiFe[E(CH_2)_3E](dppb)(CO)_3}BF_4(E=S,6;Se,8)。其中，我们首次得到含有μ-Se的双核[NiFe]-氢化酶模型物7和8，此外通过电化学研究了模型物6和8的电催化性质，并做了比较。
Hydrogenases can catalyze the biological conversion between protons and dihydrogen.[FeFe] and [NiFe]-Hydrogenases are two classes of most important. Recently, the research on the structural and functional aspects has received great attention in both organometallic chemistry and bioinorganic chemistry, not only because of their theoretical interest but also the practical importance for solving the increasingly environmental pollution and energy crisis. In order to develop the biomimetic chemistry of [FeFe]-hydrogenases and [NiFe]-hydrogenases, we carried out studies on synthesis, structures, properties and functions of new models for [FeFe]-and [Ni-Fe]-hydrogenase active sites. The main results described in this thesis are as follows:
1, A total of28new compounds were successfully synthesized. The structures of these compounds were fully characterized by elemental analysis, IR,1H-NMR and some of them were further characterized by31P-NMR,13C-NMR,77Se-NMR and125Te-NMR spectroscopies, In addtion,20representatives were determined by X-ray diffraction analysis, and some representatives were investigated by electrochemistry.
2, In chapter two, Firstly, we improved the synthetic method for preparation of the starting materials (μ-Te2)Fe2(CO)6, and synthesized the model complex [(μ-TeCH2)2CH(OH)]Fe2(CO)6(B) and improved the yield of model complex [(μ-TeCH2)2CH2]Fe2(CO)6(A). Then through substitution reactions, a series of model complexes (μ-PDTe)Fe2(CO)5(Li)(1, L=PPh3;2, PPh2H;3, PMe3;4, IMes),[(μ-PDTe)Fe2(CO)5]2(L2)(5, L2=dppf;6, dppp;7, dppb) and (μ-PDTe)Fe2(CO)4(L3)(8, L3=dppm;9, dppn) were prepared. All the ten new complexes were determined by X-ray diffraction analysis except for complex3and8. In addition, a study on electrochemical and electrocatalytic properties of the model complex8was also carried out.
3, In chapter three, the μ-CO containing intermediate butterfly Fe/E clusters [(μ-CO)(μ-DtpSe)Fe2(CO)6]·[Et3NH](3),[(μ-CO]-(μ-DtpTe)Fe2(CO)6][Ph4P]/[PPN](Ph4P,4; PPN,6)[(μ-CO)-(μ-DtpTe)Fe2(CO)6](12-crown-4)Li (7)were successfully isolated by direct separation, exchange with cation and coordination with crown ether.
4, In chapter three, we designed a new route to synthesis the [FeFe]-hydrogenase models, which can combine the μ-CO Fe/S cluster and hydrogenase model together. The [FeFe]-hydrogenases models [(μ-SCH2)(μ-POCl)CH2]Fe2(CO)6(9) and [(μ-SCH2)(μ-POPh)CH2]Fe2(CO)6(10) were prepared by treatment of the μ-CO anion (generated in situ from Fe3(CO)12, Et3N and2-hydroxyethanethiol)with with electrophilic reagent halogenated phosphine.
5, In chapter four, two types of [NiFe]-hydrogenase model complexes [(μ-E)2-(2,2-bpy)Fe2(CO)6Ni (E=S,1; Se,2) and {NiFe[E(CH2)3E](dppb)(CO)3}(E=S,5; Se,7) containing the [N2E2] and [P2E2] units were prepare. The Hred model complexes{HNiFe[E(CH2)3E](dppb)(CO)3}BF4(E=S,6; Se,8) were prepared from complexes5and7reacting with HBF4·Et2O, respectively. It is worth to note that we synthesized the dual-core [NiFe]-hydrogenase models containing μ-Se for the first time. In addition, a comparative study on electrocatalytic properties of the model complexes6and8was carried out.
引文
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