双二茂铁衍生物的合成、电化学和红外光谱电化学研究
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摘要
二茂铁类化合物是一类新型的有机金属化合物,由于其在电化学、光学、电磁等方面所具有的独特性能,因此在光电材料、分子器件、分子导线及生物传感器等方面具有重要的基础理论研究价值和广泛的应用前景。首先,对双二茂铁类化合物近年来在设计、合成及应用等方面的研究进行了归纳与总结；其次合成了两个系列桥联双二茂铁衍生物,利用FTIR、1HNMR, MS对其结构进行表征；最后采用循环伏安法(CV)、差分脉冲法(DPV)研究其电化学性质,结合现场红外光谱电化学(in situ FTIR)考察了这类桥联双二茂铁衍生物的电化学性质及现场红外光谱电化学信息,应用导数循环伏吸法(DCVAs)及电化学数字模拟、DFC(密度泛函数理论)计算方法,探讨桥联双二茂铁衍生物的结构与电子转移机理之间的关系,为设计和合成新型功能性分子材料提供理论和实验依据。
1、利用酯化反应和缩合反应等方法合成了两个系列双二茂铁类衍生物,系列为单碳桥联双二茂铁衍生物,另一系列为双二茂铁桥联苯衍生物。利用红外光谱(FTIR)、质谱(MS)以及核磁共振谱(NMR)对这些产物进行了结构表征,并对这些化合物的紫外-可见光谱((UV-Vis)和拉曼光谱进行研究。
2、单碳桥联双二茂铁衍生物(1-5)的晶体研究。获得了5种单碳桥联双二茂铁衍生物(1-5)单晶,经过单晶结构解析,研究发现单碳桥联双二茂铁衍生物(1-5),其Fc-C-Fc键角随苯环取代基推拉电子能力不同变化,两个Fc基团之间的距离越短和二面角越小则电子交流越强。另外,利用TD-DFT计算,研究了这五个化合物的轨道电子分布、电子能量及分子跃迁。研究结果表明,化合物1-5的HOMO和HOMO-1主要集中在两个Fc基团上。LUMO则主要集中在苯环。
3、运用循环伏安、差分脉冲等电化学手段研究了不同桥联双二茂铁衍生物的电化学行为和电子转移机理。通过研究发现,单碳桥联双二茂铁衍生物(1-8)表现出明显的两对可逆的氧化还原峰。双二茂铁甲酮(7)的氧化电位明显比其他化合物正移,主要是由于羰基的吸电子作用和共轭作用,导致氧化电位正移。这类化合物的电位移动取决于桥联基团的吸电子能力的大小。另外,比较化合物1-5,结果发现这些化合物的电位移动取决于单碳桥联苯环上的取代基吸电子能力大小,吸电子能力越强则电位正移越大。其中化合物3由于苯环对位引入吸电子三氟甲基而导致其氧化电位明显正移。相对另一体系双二茂铁甲酸苯酯类衍生物(9-12)的电化学性质研究,结果发现这些化合物在CV上只出现一对可逆的氧化还原峰。氧化电位移动取决于桥联基团的吸电子能力的大小。化合物9的氧化电位明显正移,这主要是因为甲酯基的吸电子效应,酯基的存在使二茂铁(Fc)上的电子云密度降低,更难氧化。2-甲基-双二茂铁甲酸苯酯(10)的氧化电位较其他化合物负移,表明苯环上甲基的存在既导致化合物不对称,又因为位阻的影响而导致负移的产生。
4、运用现场红外快速扫描光谱电化学技术研究了这些双二茂铁衍生物在二氯甲烷等溶剂中的电化学氧化还原过程。首先对单碳桥联双二茂铁衍生物(1-8)进行现场红外光谱电化学研究,尽管未观察到中间体的变化,但是结果表明它们的电子转移机制为明显的两步连续(快速)单电子过程。其次对双二茂铁桥联苯衍生物(9-12)进行现场红外光谱电化学研究。结果发现,除了化合物9与12明显观察到中间体在还原或是氧化过程中的生成和消去,其余化合物均未观察到中间体。对化合物9与12在红外谱图中的氧化产物、中间体峰进行了归属,采用导数循环伏吸法对其电子转移机理进行了详细研究。研究结果表明,化合物9和12的电子转移机制为两步一电子过程。基于以上的研究与分析,可以推断双二茂铁桥联苯衍生物(9-12)的电子转移机制为两步连续(快速)单电子过程。
5、电化学数字模拟(Numerical simulation of electrochemical processes)能提供非常重要的信息,如能够快速提供一些反应内在的重要参数如浓度、电位和电流密度等,因此特别适用于复杂的化学和电化学反应的机理研究。利用电化学模拟技术,对八种单桥桥联双二茂铁类化合物(1-8)电化学行为进行数字模拟。通过数据模拟,发现这类化合物电子转移机理为两步连续(快速)单电子的过程。其中对数字模拟影响最大的为反应动力常数和溶剂阻抗。
Ferrocenyl derivatives is a new type of organic metal compounds. Due to its unique nature in electronchemistry, optical and electromagnetic, it is of great value in studying the basic theory of optical materials, molecular devices, molecular wires and bio-sensor. Besides, it also has extensive application prospect in the aspects mentioned above. Firstly, the recent research in designing, synthesis and application of bisferrocenyl derivatives was summarized. Secondly, two series of bisferrocenyl derivatives were synthesized and characterized by FTIR,1H NMR, MS. Finally, electrochemical properties were studied by CV and DPV, electrochemical properties and in situ infrared spectroelectrochemistry information were investigated by combining the in situ FTIR and the relationship between the constructure of bridged bisferrocenyl derivatives and the electron transfer mechanism were explored by means of DCVAs, numerical simulation of electrochemical processes and DFC, which supplied theoretical and experimental basis for designing and synthesizing new types of functional molecular materials.
1. Two series of bridged bisferrocenyl derivatives were synthesized by means of esterification reaction and condensation reaction. One series was single carbon bridged bisferrocenyl derivatives and the other was bridged benzene bisferrocenyl derivatives. These compounds were characterized by means of FTIR, MS and NMR. The UV-Vis and Raman spectrum of these compounds were also studied.
2. The crystal research of single carbon bridged bisferrocenyl derivatives (1-5). Five types of single carbon bridged bisferrocenyl derivatives were obtained from the experiment. Through the single-crytal structure analysis, we found that the bond angle of Fc-C-Fc of single carbon bridged bisferrocenyl derivatives (1-5) varied with the contribution of the donor-acceptor groups of substitutes on benzene. The shorter the distance between the two Fc group was, the smaller the dihedral angles of Cp-ring plane of two-Fc were, the stronger the electron communication was. In addition, we studied the electronic distribution, orbital energy and molecular transition of these five compounds using TD-DFT. The result showed that HOMO and HOMO-1mainly concentrated in Fc groups, while LUMO mainly concentrated in benzene.
3. Electrochemical properties and electron transfer mechanism were invested by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). The result shows the single carbon bridged bisferrocenyl derivatives(1-8) clearly exhibit two pairs of reversible redox peaks. The oxidation potential value of compound7was more positive than others, which was mainly due to the electron withdrawing effect of the carbonyl group is stronger than its conjugation. Compounds1-5were contrasted and the result showed the potential shift of these compounds relied on the electron withdrawing effect of substitutes on benzene of single carbon bisferrocenyl derivatives. The stronger the electron withdrawing effect was, the more positive the shift was. There was considerably more positive of compound3, due to the p-trifluoromethyl of benzene. For the other series of bisferrocenyl carboxylate benzene, the potential shift of them depended on the electron withdrawing effect of the bridged groups. The ester group caused the electron cloud density to reduce and made the oxidation more difficult. The potential shift of1,4-bis(2-ferrocene carboxylate)-2'-methylbenzene was more negative than other compounds, which showed that the methyl group of benzene not only caused the asymmetric of these compounds, but also caused the negative shift due to the impact of steric hindrance.
4. The electrochemical redox process of the bisferrocenyl derivatives in CH2CI2was studied by means of in situ rapid scan FTIR spectroelectrochemistry. Firstly we studied the single carbon bisferrocenyl derivatives (1-8) by using in situ rapid scan FTIR spectroelectrochemistry. Although we didn't find the variation of intermediates, the result showed that their electron transfer mechanism were two consecutive one-electron steps. Secondly, we studied the bisferrocenyl bridged benzene derivatives (9-12) by using in situ rapid scan FTIR spectroelectrochemistry and the result showed that in this process, no intermediate was found in other compounds except that in compound9and12the appearance and disappearance of the intermediates during oxidation and reduction process could be easily observed. In combination with in situ rapid scan FTIR spectroelectrochemistry, the oxidation and reduction was conducted by means of DCVA and concerning electrochemical process was obtained. The result shows that compound9and12were two consecutive one-electron steps. On the basis of the research above, it could be concluded that the electron transfer mechanism of these compounds9-12were two consecutive one-electron steps.
5. Numerical simulation of electrochemical processes can provide very important information about some important references of electrochemical reaction. We simulated the electrochemical behavior of the eight kinds of single-carbon bridge bisferrocenyl derivatives. Through the simulation, we found that the electron transfer mechanism of these compounds exhibited a two-step process, during which the main impact included the kinetics constant and resistors.
1、利用酯化反应和缩合反应等方法合成了两个系列双二茂铁类衍生物,系列为单碳桥联双二茂铁衍生物,另一系列为双二茂铁桥联苯衍生物。利用红外光谱(FTIR)、质谱(MS)以及核磁共振谱(NMR)对这些产物进行了结构表征,并对这些化合物的紫外-可见光谱((UV-Vis)和拉曼光谱进行研究。
2、单碳桥联双二茂铁衍生物(1-5)的晶体研究。获得了5种单碳桥联双二茂铁衍生物(1-5)单晶,经过单晶结构解析,研究发现单碳桥联双二茂铁衍生物(1-5),其Fc-C-Fc键角随苯环取代基推拉电子能力不同变化,两个Fc基团之间的距离越短和二面角越小则电子交流越强。另外,利用TD-DFT计算,研究了这五个化合物的轨道电子分布、电子能量及分子跃迁。研究结果表明,化合物1-5的HOMO和HOMO-1主要集中在两个Fc基团上。LUMO则主要集中在苯环。
3、运用循环伏安、差分脉冲等电化学手段研究了不同桥联双二茂铁衍生物的电化学行为和电子转移机理。通过研究发现,单碳桥联双二茂铁衍生物(1-8)表现出明显的两对可逆的氧化还原峰。双二茂铁甲酮(7)的氧化电位明显比其他化合物正移,主要是由于羰基的吸电子作用和共轭作用,导致氧化电位正移。这类化合物的电位移动取决于桥联基团的吸电子能力的大小。另外,比较化合物1-5,结果发现这些化合物的电位移动取决于单碳桥联苯环上的取代基吸电子能力大小,吸电子能力越强则电位正移越大。其中化合物3由于苯环对位引入吸电子三氟甲基而导致其氧化电位明显正移。相对另一体系双二茂铁甲酸苯酯类衍生物(9-12)的电化学性质研究,结果发现这些化合物在CV上只出现一对可逆的氧化还原峰。氧化电位移动取决于桥联基团的吸电子能力的大小。化合物9的氧化电位明显正移,这主要是因为甲酯基的吸电子效应,酯基的存在使二茂铁(Fc)上的电子云密度降低,更难氧化。2-甲基-双二茂铁甲酸苯酯(10)的氧化电位较其他化合物负移,表明苯环上甲基的存在既导致化合物不对称,又因为位阻的影响而导致负移的产生。
4、运用现场红外快速扫描光谱电化学技术研究了这些双二茂铁衍生物在二氯甲烷等溶剂中的电化学氧化还原过程。首先对单碳桥联双二茂铁衍生物(1-8)进行现场红外光谱电化学研究,尽管未观察到中间体的变化,但是结果表明它们的电子转移机制为明显的两步连续(快速)单电子过程。其次对双二茂铁桥联苯衍生物(9-12)进行现场红外光谱电化学研究。结果发现,除了化合物9与12明显观察到中间体在还原或是氧化过程中的生成和消去,其余化合物均未观察到中间体。对化合物9与12在红外谱图中的氧化产物、中间体峰进行了归属,采用导数循环伏吸法对其电子转移机理进行了详细研究。研究结果表明,化合物9和12的电子转移机制为两步一电子过程。基于以上的研究与分析,可以推断双二茂铁桥联苯衍生物(9-12)的电子转移机制为两步连续(快速)单电子过程。
5、电化学数字模拟(Numerical simulation of electrochemical processes)能提供非常重要的信息,如能够快速提供一些反应内在的重要参数如浓度、电位和电流密度等,因此特别适用于复杂的化学和电化学反应的机理研究。利用电化学模拟技术,对八种单桥桥联双二茂铁类化合物(1-8)电化学行为进行数字模拟。通过数据模拟,发现这类化合物电子转移机理为两步连续(快速)单电子的过程。其中对数字模拟影响最大的为反应动力常数和溶剂阻抗。
Ferrocenyl derivatives is a new type of organic metal compounds. Due to its unique nature in electronchemistry, optical and electromagnetic, it is of great value in studying the basic theory of optical materials, molecular devices, molecular wires and bio-sensor. Besides, it also has extensive application prospect in the aspects mentioned above. Firstly, the recent research in designing, synthesis and application of bisferrocenyl derivatives was summarized. Secondly, two series of bisferrocenyl derivatives were synthesized and characterized by FTIR,1H NMR, MS. Finally, electrochemical properties were studied by CV and DPV, electrochemical properties and in situ infrared spectroelectrochemistry information were investigated by combining the in situ FTIR and the relationship between the constructure of bridged bisferrocenyl derivatives and the electron transfer mechanism were explored by means of DCVAs, numerical simulation of electrochemical processes and DFC, which supplied theoretical and experimental basis for designing and synthesizing new types of functional molecular materials.
1. Two series of bridged bisferrocenyl derivatives were synthesized by means of esterification reaction and condensation reaction. One series was single carbon bridged bisferrocenyl derivatives and the other was bridged benzene bisferrocenyl derivatives. These compounds were characterized by means of FTIR, MS and NMR. The UV-Vis and Raman spectrum of these compounds were also studied.
2. The crystal research of single carbon bridged bisferrocenyl derivatives (1-5). Five types of single carbon bridged bisferrocenyl derivatives were obtained from the experiment. Through the single-crytal structure analysis, we found that the bond angle of Fc-C-Fc of single carbon bridged bisferrocenyl derivatives (1-5) varied with the contribution of the donor-acceptor groups of substitutes on benzene. The shorter the distance between the two Fc group was, the smaller the dihedral angles of Cp-ring plane of two-Fc were, the stronger the electron communication was. In addition, we studied the electronic distribution, orbital energy and molecular transition of these five compounds using TD-DFT. The result showed that HOMO and HOMO-1mainly concentrated in Fc groups, while LUMO mainly concentrated in benzene.
3. Electrochemical properties and electron transfer mechanism were invested by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). The result shows the single carbon bridged bisferrocenyl derivatives(1-8) clearly exhibit two pairs of reversible redox peaks. The oxidation potential value of compound7was more positive than others, which was mainly due to the electron withdrawing effect of the carbonyl group is stronger than its conjugation. Compounds1-5were contrasted and the result showed the potential shift of these compounds relied on the electron withdrawing effect of substitutes on benzene of single carbon bisferrocenyl derivatives. The stronger the electron withdrawing effect was, the more positive the shift was. There was considerably more positive of compound3, due to the p-trifluoromethyl of benzene. For the other series of bisferrocenyl carboxylate benzene, the potential shift of them depended on the electron withdrawing effect of the bridged groups. The ester group caused the electron cloud density to reduce and made the oxidation more difficult. The potential shift of1,4-bis(2-ferrocene carboxylate)-2'-methylbenzene was more negative than other compounds, which showed that the methyl group of benzene not only caused the asymmetric of these compounds, but also caused the negative shift due to the impact of steric hindrance.
4. The electrochemical redox process of the bisferrocenyl derivatives in CH2CI2was studied by means of in situ rapid scan FTIR spectroelectrochemistry. Firstly we studied the single carbon bisferrocenyl derivatives (1-8) by using in situ rapid scan FTIR spectroelectrochemistry. Although we didn't find the variation of intermediates, the result showed that their electron transfer mechanism were two consecutive one-electron steps. Secondly, we studied the bisferrocenyl bridged benzene derivatives (9-12) by using in situ rapid scan FTIR spectroelectrochemistry and the result showed that in this process, no intermediate was found in other compounds except that in compound9and12the appearance and disappearance of the intermediates during oxidation and reduction process could be easily observed. In combination with in situ rapid scan FTIR spectroelectrochemistry, the oxidation and reduction was conducted by means of DCVA and concerning electrochemical process was obtained. The result shows that compound9and12were two consecutive one-electron steps. On the basis of the research above, it could be concluded that the electron transfer mechanism of these compounds9-12were two consecutive one-electron steps.
5. Numerical simulation of electrochemical processes can provide very important information about some important references of electrochemical reaction. We simulated the electrochemical behavior of the eight kinds of single-carbon bridge bisferrocenyl derivatives. Through the simulation, we found that the electron transfer mechanism of these compounds exhibited a two-step process, during which the main impact included the kinetics constant and resistors.
引文
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