分子筛封装金属Schiff-base配合物修饰电极的制备及其电化学和电催化氧还原反应的研究
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摘要
过渡金属Schiff-base配合物能模拟细胞色素生物单加氧酶中的活性部位,在温和条件下能够催化多种类型的化学反应,这已是不争的事实。但金属Schiff-base配合物在均相介质中很容易形成μ-oxo和μ-peroxo二聚或多聚物而导致金属配合物的催化活性随时间延长而明显下降。为此,人们用无机分子筛载体来模拟细胞色素P-450的蛋白质壳体,用分子筛的孔穴封装金属Schiff-base配合物,制备分子筛封装金属Schiff-base配合物的复合材料,以求从结构与功能上模拟天然酶的催化作用。结果显示,这类催化反应具有反应条件温和、选择性高、易与产物分离、可重复使用等特点,因而受到催化领域的广泛重视。
目前有关该类复合材料的研究报道已经很多,主要集中在制备、表征以及催化活性的评价上。但是,这些催化剂到底是如何催化氧化反应发生的?参与反应的氧化剂与催化剂是如何作用的?都是一些尚待解决的问题。而电化学技术是获得催化反应动力学数据很好的方法。另一方面,分子氧作为有机物氧化反应的氧化剂表现出比其它氧化剂更低的活性,使得氧气这种绿色环保、廉价氧化剂的使用受到了极大的限制。所以在理论上寻找能够活化氧气分子的催化剂也是化工过程需要解决的又一问题。而M(Salen)配合物又被认为是一种分子氧的携带者,具有好的与分子氧的亲和力。基于以上事实,我们对封装过渡金属Salen配合物的微孔分子筛复合材料进行了电化学及其电催化氧还原的研究。
本文所作的主要工作是,首先采用自由配体法制备了各种封装金属Salen配合物的沸石分子筛的复合材料,并用红外光谱、紫外光谱和XRD对它们进行了物理表征;其次,以此复合材料为修饰剂,制备了封装金属salen配合物的分子筛修饰电极,并采用循环伏安法对其自身的电化学性质进行了研究;然后运用循环伏安法、计时电流法或计时库仑法研究了分子氧在这些修饰电极上发生的电催化还原反应的动力学行为,并提出分子氧在此类修饰电极上的电催化还原反应机理。本论文的主要结论如下:
1.采用自由配体法制备了七种不同金属(Cr,Mn,Fe,Co,Ni,Cu,Zn)的Salen配合物封装于NaY分子筛中形成分子筛复合材料,并由此制备的分子筛修饰电极具有良好的电化学稳定性和重现性。
2.在中性缓冲溶液中,七种复合分子筛催化剂M(Salen)/Y均表现出对氧还原反应的电催化活性;其中Co(Salen)/Y的催化活性最高,其次,Fe(Salen)/Y,Mn(Salen)/Y,Cu(Salen)/Y也具有较好的催化作用。
3.在所研究的不同pH值(4.0-10.0)的电解质体系中,中性(pH=6.86)或接近中性(pH=7.4,8.0)的电解质溶液更有利于M(Salen)/Y修饰电极的电催化活性的提高。
4.根据Randles-Sev?ik方程计算所得的动力学参数和氧还原反应转移的表观电子数,提出氧气在M(Salen)/Z修饰电极上的电催化还原的反应机理为ECE机理。而且,氧气在M(Salen)/Y分子筛修饰电极上pH在6.86~8.0缓冲溶液中均被彻底还原为水(除Mn(Salen)修饰电极在9.18缓冲液中氧气被还原为过氧化氢外)。
5.CoL/Y (L: salen,salpn,salbn,salcn,salphen,tBu4salen)复合材料的修饰电极电催化氧还原的活性按下列顺序依次减弱:Co(salen)>Co(salpn)>Co(salcn)>Co(salbn)>Co(tBu4salen)>Co(salphen)t它与金属配合物在分子筛的骨架静电作用下结构变形的程度大小密切相关。
6.根据氧气在CoL/Y修饰电极上还原反应转移的电子数不同,其电催化反应机理也不同。其中,除氧气在Co(salphen)/Y上较难被还原外,在Co(salen),Co(salpn),Co(salcn),Co(salbn)的分子筛修饰电极上氧均被催化还原为水,而在Co(tBu4salen)修饰电极上氧被还原为过氧化氢。
7.M(Salen)/AlPO4-5 (M=Fe, Co, Mn)的磷铝分子筛修饰电极对氧气的电化学还原表现出良好的催化活性,在中性电解质溶液中其电催化活性大小按以下顺序递增: Mn(Salen)/AlPO4-5 , Fe(Salen)/AlPO4-5 ,Co(Salen)/AlPO4-5;即Co(Salen)/AlPO4-5的电催化活性最高。
8.根据循环伏安法和计时电流法计算得出氧气在M(Salen)/ AlPO4-5 (M=Fe, Co, Mn)修饰电极上的总的电极反应转移的表观电子数,推断氧还原反应机理为不可逆扩散控制的ECE机理,而且氧气被彻底还原为水;pH值的变化只改变氧还原反应的峰电位和峰电流,而不改变反应的动力学机理和氧还原反应的产物。此外,中性(pH 6.86)电解质缓冲溶液更有利于提高催化剂的电催化活性。
9.封装金属Salen配合物的沸石分子筛硅铝比越高,其修饰电极自身的电化学反应的可逆性就越好,由此导致该修饰电极对氧还原反应的电催化活性就越高。
10.在M(Salen)/Z(M=Co, Fe, Z=Y, X, LSX)修饰电极上电催化氧还原反应的E1CE2催化机理中,虽然E1不是控制步骤,但是E1反应是否参与反应和反应可逆性的好坏,直接影响着金属配合物催化剂的电催化活性。
总之,金属的性质是决定金属salen配合物/分子筛复合材料对氧还原反应的电催化活性的主要因素;其次,配体的结构导致配合物在分子筛孔腔中的构型变化也是影响催化活性的重要因素;此外,分子筛骨架的硅铝比同样也是影响封装在其中的金属配合物催化活性的又一因素。
It is a fact that metal complexes of Schiff-base can mimic the active site of cytocrome P-450 and catalyze a serious of chemical reaction under mild condition. But the catalytic activities of the Schiff-base metal complexes in homogeneous solution will decrease with time due to formation of dimericμ-oxo and/orμ-peroxo complexes. The encapsulation of metal Schiff-base complexes into micropores or cages of zeolites is a good method to isolate the complexes to prevent the dimerization and to obtain a serious of model catalysts mimicking the catalysis of nature enzymes about molecular structure and function. It has been showed from the research reports up to now that these encapsulated complexes are of many advantages of high selectivity, reaction under mild conditions, reusability and separation from products with ease.
Now there are lots of reports which focus on preparation, characterization and evaluation of the catalytic activities of these hybrid catalysts. But the details of mechanism for the catalytic oxidation reaction are not yet clear. Zeolite (Y, X, LSX, AlPO4-5)-encapsulated transition metal complexes of Schiff-base have been used as catalysts of oxidation reactions of hydrocarbons with oxidants including dioxygen. But the molecular oxygen as oxidant did not show good activity compared with other oxidants such as TBHP, PhIO and H2O2 in the above processes. It has restricted the use of oxygen as a green and environment-friendly, cheap oxidant.
In present work, zeolite-encapsulated M(Salen) [Salen: N, N’-bis(salicylidene)ethyleneediamine and its derivatives] complexes modified glassy carbon electrodes [M(Salen)/Z/GCEs (M=Cr, Mn, Fe, Co, Ni, Cu, Zn etc. and Z= Y, X, LSX, AlPO4-5)] were prepared and studied on their electrochemical behaviors in different pH buffer solution so as to evaluate the catalytical effect of the hybrid materials on the process of activating molecular oxygen. Then these zeolite-modified electrodes were used as electrocatalysts for oxygen reduction reaction (ORR) in aqueous solutions to check the electrocatalysis of the encapsulated complexes for ORR. The electrocatalytic reduction of dioxygen was investigated by cyclic voltammetry (CV) and chronocoulometry (CC) and chronoamperometry (CA) at glassy carbon electrodes (GCEs) modified with transition metal complexes of Salen encapsulated inside NaY, NaX, LSX and AlPO4-5 in a wide range of different pH aqueous solutions (4.0~10.0). The kinetic parameters were obtained for oxygen reduction on the modified electrodes and the elctrocatalytic mechanism of ORR was first proposed in aqueous solutions based on cyclic voltammetry and double-step technique of chronocoulometry and chronoamperometry.
The conclusions of this dissertation are listed as follows:
1. Zeolite Y encapsulated metal (Cr, Mn, Fe, Co, Ni, Cu, Zn) Salen complexes were prepared by flexible ligand method and characterized by XRD, FT-IR and UV-vis. And the zeolite modified glassy carbon electrodes were prepared with these hybrid catalysts as the major modifier by zeolite/polymer step-by-step coating method and showed well electrochemical stability and reproducibility.
2. The M(Salen)/Y/GCEs (M: Cr, Mn, Fe, Co, Ni, Cu, Zn) all behave moderate to good electrocatalytic activities. The Co(Salen)/Y/GCE is showed the best electrocatalytic activity for ORR among these different transition metal complexes, followed by Fe(Salen)/Y, Mn(Salen)/Y, Cu(Salen)/Y about their catalytic activity in neutral electrolyte.
3. The neutral electrolyte of pH 6.86 solution or near neutral solution such as pH 7.4 and/or 8.0 is more propitious to increase in electrocatalytic activity of M(Salen)/Y modified electrode.
4. The E1CE2 mechanism was first proposed for ORR on the M(Salen)/Y/GCEs according to kinetic parameters and the apparent numbers of electrons transferred obtained from Randles-Sevcik equation of the irreversible and diffusion-controlled reaction. And dioxygen is reduced to water on the M(Salen)/Y in neutral buffer solution.
5. The electrocatalytic activity of CoL/Y decreases in the order of Co(salen)>Co(salpn)>Co(salcn)>Co(salbn)>Co(tBu4salen)>Co(salphen), and it is related to that the configuration between square planar and tetrahedral of encapsulated complexes into the cage of zeolite.
6. Oxygen was reduced to water on the electrode modified with Co(salen)/Y, Co(salpn)/Y, Co(salcn)/Y and Co(salbn)/Y but to H2O2 on Co(tBu4salen)/Y modified electrode, while oxygen is hard to be reduced on Co(salphen)/Y electrode.
7. M(Salen)/AlPO4-5 (M=Fe, Co, Mn) also show good electrocatalysis for ORR and their activity increases in the order: Mn(Salen)/AlPO4-5, Fe(Salen)/AlPO4-5, Co(Salen)/AlPO4-5. So Co(Salen)/AlPO4-5 is best for ORR in neutral buffer solution.
8. E1CE2 mechanism is proposed for ORR on the M(Salen)/ AlPO4-5 (M=Fe, Co, Mn) modified electrodes based on the experiment data from CV and CA. The different pH value of electrolyte only change the peak potential and peak current but does change the kinetic mechanism. Also the pH 6.86 solution is the best system in this case.
9. The higher the ratio of SiO2:Al2O3, the better the reversibility of the couple MⅢ/MⅡof metal Salen complexes, and then the higher the electrocatalytic activity of metal Salen complexes.
10. The reversibility of E1 reaction in E1CE2 mechanism remain crucial for the electrocatalytic activity of M(Salen)/Z (M=Co, Fe, Z=Y, X, LSX) although the E1 reaction is not the speed-controlled step.
In conclusion, the nature of metal is the primary factor to determine the electrocatalytic activities of M(Salen) complexes encapsulated into zeolite for ORR. The ligand’s structure of complexes which result in the configuration change of metal complexes and ratio of SiO2:Al2O3 are also important impact factors on the electrocatalytic activity for ORR.
目前有关该类复合材料的研究报道已经很多,主要集中在制备、表征以及催化活性的评价上。但是,这些催化剂到底是如何催化氧化反应发生的?参与反应的氧化剂与催化剂是如何作用的?都是一些尚待解决的问题。而电化学技术是获得催化反应动力学数据很好的方法。另一方面,分子氧作为有机物氧化反应的氧化剂表现出比其它氧化剂更低的活性,使得氧气这种绿色环保、廉价氧化剂的使用受到了极大的限制。所以在理论上寻找能够活化氧气分子的催化剂也是化工过程需要解决的又一问题。而M(Salen)配合物又被认为是一种分子氧的携带者,具有好的与分子氧的亲和力。基于以上事实,我们对封装过渡金属Salen配合物的微孔分子筛复合材料进行了电化学及其电催化氧还原的研究。
本文所作的主要工作是,首先采用自由配体法制备了各种封装金属Salen配合物的沸石分子筛的复合材料,并用红外光谱、紫外光谱和XRD对它们进行了物理表征;其次,以此复合材料为修饰剂,制备了封装金属salen配合物的分子筛修饰电极,并采用循环伏安法对其自身的电化学性质进行了研究;然后运用循环伏安法、计时电流法或计时库仑法研究了分子氧在这些修饰电极上发生的电催化还原反应的动力学行为,并提出分子氧在此类修饰电极上的电催化还原反应机理。本论文的主要结论如下:
1.采用自由配体法制备了七种不同金属(Cr,Mn,Fe,Co,Ni,Cu,Zn)的Salen配合物封装于NaY分子筛中形成分子筛复合材料,并由此制备的分子筛修饰电极具有良好的电化学稳定性和重现性。
2.在中性缓冲溶液中,七种复合分子筛催化剂M(Salen)/Y均表现出对氧还原反应的电催化活性;其中Co(Salen)/Y的催化活性最高,其次,Fe(Salen)/Y,Mn(Salen)/Y,Cu(Salen)/Y也具有较好的催化作用。
3.在所研究的不同pH值(4.0-10.0)的电解质体系中,中性(pH=6.86)或接近中性(pH=7.4,8.0)的电解质溶液更有利于M(Salen)/Y修饰电极的电催化活性的提高。
4.根据Randles-Sev?ik方程计算所得的动力学参数和氧还原反应转移的表观电子数,提出氧气在M(Salen)/Z修饰电极上的电催化还原的反应机理为ECE机理。而且,氧气在M(Salen)/Y分子筛修饰电极上pH在6.86~8.0缓冲溶液中均被彻底还原为水(除Mn(Salen)修饰电极在9.18缓冲液中氧气被还原为过氧化氢外)。
5.CoL/Y (L: salen,salpn,salbn,salcn,salphen,tBu4salen)复合材料的修饰电极电催化氧还原的活性按下列顺序依次减弱:Co(salen)>Co(salpn)>Co(salcn)>Co(salbn)>Co(tBu4salen)>Co(salphen)t它与金属配合物在分子筛的骨架静电作用下结构变形的程度大小密切相关。
6.根据氧气在CoL/Y修饰电极上还原反应转移的电子数不同,其电催化反应机理也不同。其中,除氧气在Co(salphen)/Y上较难被还原外,在Co(salen),Co(salpn),Co(salcn),Co(salbn)的分子筛修饰电极上氧均被催化还原为水,而在Co(tBu4salen)修饰电极上氧被还原为过氧化氢。
7.M(Salen)/AlPO4-5 (M=Fe, Co, Mn)的磷铝分子筛修饰电极对氧气的电化学还原表现出良好的催化活性,在中性电解质溶液中其电催化活性大小按以下顺序递增: Mn(Salen)/AlPO4-5 , Fe(Salen)/AlPO4-5 ,Co(Salen)/AlPO4-5;即Co(Salen)/AlPO4-5的电催化活性最高。
8.根据循环伏安法和计时电流法计算得出氧气在M(Salen)/ AlPO4-5 (M=Fe, Co, Mn)修饰电极上的总的电极反应转移的表观电子数,推断氧还原反应机理为不可逆扩散控制的ECE机理,而且氧气被彻底还原为水;pH值的变化只改变氧还原反应的峰电位和峰电流,而不改变反应的动力学机理和氧还原反应的产物。此外,中性(pH 6.86)电解质缓冲溶液更有利于提高催化剂的电催化活性。
9.封装金属Salen配合物的沸石分子筛硅铝比越高,其修饰电极自身的电化学反应的可逆性就越好,由此导致该修饰电极对氧还原反应的电催化活性就越高。
10.在M(Salen)/Z(M=Co, Fe, Z=Y, X, LSX)修饰电极上电催化氧还原反应的E1CE2催化机理中,虽然E1不是控制步骤,但是E1反应是否参与反应和反应可逆性的好坏,直接影响着金属配合物催化剂的电催化活性。
总之,金属的性质是决定金属salen配合物/分子筛复合材料对氧还原反应的电催化活性的主要因素;其次,配体的结构导致配合物在分子筛孔腔中的构型变化也是影响催化活性的重要因素;此外,分子筛骨架的硅铝比同样也是影响封装在其中的金属配合物催化活性的又一因素。
It is a fact that metal complexes of Schiff-base can mimic the active site of cytocrome P-450 and catalyze a serious of chemical reaction under mild condition. But the catalytic activities of the Schiff-base metal complexes in homogeneous solution will decrease with time due to formation of dimericμ-oxo and/orμ-peroxo complexes. The encapsulation of metal Schiff-base complexes into micropores or cages of zeolites is a good method to isolate the complexes to prevent the dimerization and to obtain a serious of model catalysts mimicking the catalysis of nature enzymes about molecular structure and function. It has been showed from the research reports up to now that these encapsulated complexes are of many advantages of high selectivity, reaction under mild conditions, reusability and separation from products with ease.
Now there are lots of reports which focus on preparation, characterization and evaluation of the catalytic activities of these hybrid catalysts. But the details of mechanism for the catalytic oxidation reaction are not yet clear. Zeolite (Y, X, LSX, AlPO4-5)-encapsulated transition metal complexes of Schiff-base have been used as catalysts of oxidation reactions of hydrocarbons with oxidants including dioxygen. But the molecular oxygen as oxidant did not show good activity compared with other oxidants such as TBHP, PhIO and H2O2 in the above processes. It has restricted the use of oxygen as a green and environment-friendly, cheap oxidant.
In present work, zeolite-encapsulated M(Salen) [Salen: N, N’-bis(salicylidene)ethyleneediamine and its derivatives] complexes modified glassy carbon electrodes [M(Salen)/Z/GCEs (M=Cr, Mn, Fe, Co, Ni, Cu, Zn etc. and Z= Y, X, LSX, AlPO4-5)] were prepared and studied on their electrochemical behaviors in different pH buffer solution so as to evaluate the catalytical effect of the hybrid materials on the process of activating molecular oxygen. Then these zeolite-modified electrodes were used as electrocatalysts for oxygen reduction reaction (ORR) in aqueous solutions to check the electrocatalysis of the encapsulated complexes for ORR. The electrocatalytic reduction of dioxygen was investigated by cyclic voltammetry (CV) and chronocoulometry (CC) and chronoamperometry (CA) at glassy carbon electrodes (GCEs) modified with transition metal complexes of Salen encapsulated inside NaY, NaX, LSX and AlPO4-5 in a wide range of different pH aqueous solutions (4.0~10.0). The kinetic parameters were obtained for oxygen reduction on the modified electrodes and the elctrocatalytic mechanism of ORR was first proposed in aqueous solutions based on cyclic voltammetry and double-step technique of chronocoulometry and chronoamperometry.
The conclusions of this dissertation are listed as follows:
1. Zeolite Y encapsulated metal (Cr, Mn, Fe, Co, Ni, Cu, Zn) Salen complexes were prepared by flexible ligand method and characterized by XRD, FT-IR and UV-vis. And the zeolite modified glassy carbon electrodes were prepared with these hybrid catalysts as the major modifier by zeolite/polymer step-by-step coating method and showed well electrochemical stability and reproducibility.
2. The M(Salen)/Y/GCEs (M: Cr, Mn, Fe, Co, Ni, Cu, Zn) all behave moderate to good electrocatalytic activities. The Co(Salen)/Y/GCE is showed the best electrocatalytic activity for ORR among these different transition metal complexes, followed by Fe(Salen)/Y, Mn(Salen)/Y, Cu(Salen)/Y about their catalytic activity in neutral electrolyte.
3. The neutral electrolyte of pH 6.86 solution or near neutral solution such as pH 7.4 and/or 8.0 is more propitious to increase in electrocatalytic activity of M(Salen)/Y modified electrode.
4. The E1CE2 mechanism was first proposed for ORR on the M(Salen)/Y/GCEs according to kinetic parameters and the apparent numbers of electrons transferred obtained from Randles-Sevcik equation of the irreversible and diffusion-controlled reaction. And dioxygen is reduced to water on the M(Salen)/Y in neutral buffer solution.
5. The electrocatalytic activity of CoL/Y decreases in the order of Co(salen)>Co(salpn)>Co(salcn)>Co(salbn)>Co(tBu4salen)>Co(salphen), and it is related to that the configuration between square planar and tetrahedral of encapsulated complexes into the cage of zeolite.
6. Oxygen was reduced to water on the electrode modified with Co(salen)/Y, Co(salpn)/Y, Co(salcn)/Y and Co(salbn)/Y but to H2O2 on Co(tBu4salen)/Y modified electrode, while oxygen is hard to be reduced on Co(salphen)/Y electrode.
7. M(Salen)/AlPO4-5 (M=Fe, Co, Mn) also show good electrocatalysis for ORR and their activity increases in the order: Mn(Salen)/AlPO4-5, Fe(Salen)/AlPO4-5, Co(Salen)/AlPO4-5. So Co(Salen)/AlPO4-5 is best for ORR in neutral buffer solution.
8. E1CE2 mechanism is proposed for ORR on the M(Salen)/ AlPO4-5 (M=Fe, Co, Mn) modified electrodes based on the experiment data from CV and CA. The different pH value of electrolyte only change the peak potential and peak current but does change the kinetic mechanism. Also the pH 6.86 solution is the best system in this case.
9. The higher the ratio of SiO2:Al2O3, the better the reversibility of the couple MⅢ/MⅡof metal Salen complexes, and then the higher the electrocatalytic activity of metal Salen complexes.
10. The reversibility of E1 reaction in E1CE2 mechanism remain crucial for the electrocatalytic activity of M(Salen)/Z (M=Co, Fe, Z=Y, X, LSX) although the E1 reaction is not the speed-controlled step.
In conclusion, the nature of metal is the primary factor to determine the electrocatalytic activities of M(Salen) complexes encapsulated into zeolite for ORR. The ligand’s structure of complexes which result in the configuration change of metal complexes and ratio of SiO2:Al2O3 are also important impact factors on the electrocatalytic activity for ORR.
引文
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