水杨醛类西佛碱离子识别性质与分子逻辑功能的研究
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摘要
近年来,分子识别与分子逻辑功能的研究倍受人们关注,进一步地,利用简单分子开发复杂逻辑功能性质如分子键盘锁等也成为目前超分子领域研究的前沿和热点。然而,目前可以被用来研究阴离子识别,阳离子识别等分子识别并能进一步地发展为特殊分子逻辑功能的体系还比较少。本论文的主体思想是寻找合适受体分子体系,设计并合成结构较为理想的水杨醛类西佛碱受体分子,进一步地详细研究这些分子对阴离子、阳离子的识别能力以及分子逻辑功能。本论文开展了以下几个方面的工作:
1.设计并合成了含氯取代的联二萘桥联西佛碱分子,研究了这类分子对各种阴阳离子的识别能力,结果表明这类分子可以通过紫外吸收以及荧光光谱有效地识别氟离子以及二价锌离子,二价铜离子。进一步地,选择铜离子,锌离子以及EDTA分子作为输入信号,这类分子可完成比较特殊的逻辑功能。研究还发现,将此类分子通过超分子氢键自组装到有序介孔材料SBA-15上时,分子的离子识别性质得到了较好的保持,并存在具有自身特色的逻辑功能。
2.设计合成无氯取代的联二萘桥联西佛碱分子,研究了这类分子对阳离子识别能力,研究发现此类分子可以很好地识别二价锌离子。同时这类分子对紫外光照射比较敏感,当选用锌离子与紫外光照射作为两种输入信号时,我们可以得到逻辑上比较重要的半减法器功能。
3.设计合成简单的含氯取代的水杨醛西佛碱分子,研究了这类分子阴离子识别能力,结果表明此类分子可以在四氢呋喃溶剂中识别氟离子与氰根离子,而在乙醇溶剂中仅对氰根离子有识别作用。进一步地,在四氢呋喃溶剂体系中引入锌离子和EDTA分子两种输入,此类分子可以被开发为由氟离子,锌离子,EDTA分子共同作用的分子键盘锁。
Supramolecular chemistry is one new developing research area. Molecular recognition, once described as "lock and key" for the unique combination of molecules, which is one of the process related closely to supramolecular chemistry, has developed more and more function in synthesis chemistry, life sciences, material sciences and information sciences. Compared with electric and magnetic signal, optical signal has some advantages such as convenience, high sensitivity and selectivity. Moreover, the "naked eye" detection, watching the color change with no instruments, has become the focus in molecular recognition. Furthermore, molecular logic function has been another focus in many crossed studies, based on which, molecular brake and molecular keypad lock has become one foreland of this research area.
Firstly, we choose one binaphyl bridged salicylidene Schiff base with chlorine atoms in the phenyl of the salicylidene (BCHB), which was once applied as one ligand for molecular structure and asymmetric catalysis, as receptor to study its ability in cation and anion recognition. It can be concluded that, when the solution of BCHB was titrated with fluoride anion, the absorption would be affected dramaticly because of the deprotonation function. The color of the solution was then from colorless to yellow. In the same condition, other anions such as chloride, bromide, iodide, phosphate had no obvious change for this. Andthen, many kinds of metal cations were introduced to the fluoride acted solution. As can be seen from the result of absorbance and fluorescence that only the addition of Zn~(2+) and Cu~(2+) can cause a obvious change, indicating the presence of of unique coordination complex with deprotonated BCHB respectively. The naked eye observation also shows that only Zn~(2+) and Cu~(2+) can result in a yellow to light green color change, while the others remain the original state and the disturbance for color change can be neglected.
On the other hand, BCHB presents a tunable system integrated with one OR logic gate as well as one INHIBIT logic gate with Zn~(2+) and Cu~(2+) as chemical inputs by monitoring fluorescence and absorbance as output signals. Also, one IMPLICATION gate operating in fluorescence mode with Cu~(2+) and EDTA as chemical inputs, based on their different binding capability, is present in the system. This research has been rarely reported.
Furthermore, we choose the same structure as BCHB but with no chlorine atoms in the phenyl of the salicylidene (BHB) as another receptor for molecular recognition. Exhibiting absorption and fluorescence changes in the presence of Zn~(2+) in chloroform and ethanol mixed solution, BHB could be used as a fluorescent chemosensor for the detection of Zn~(2+). Furthermore, by monitoring the fluorescence and absorbance as output signals, BHB can function as a combinatorial logic circuit for a molecular half-subtractor with Zn~(2+) and UV irradiation as input variables. Most of the reported molecular half-subtractors mainly focused on acid, base, and other chemical input variables, with UV light irradiation as an independent input, to the best of our knowledge, has not been reported yet.
Lastly, we choose one simple salicylidene Schiff base SPEA as another receptor to study its ability for anions recognition. With THF as organic solvent, F- and CN- could be detected through both absorbance and fluorescence change. Noting that, F- can be detected in rather low concentration (10-8) for its high sensitivity with the receptor. When using ethanol as organic solvent, the spectrum of SPEA could only be affected by the additon of CN-. In conclusion, SPEA can be developed as a sensor for F- and CN- in different solution.
In additon, we also studied the stimulating spectral results of F- acted SPEA with Zn~(2+) and EDTA as inputs in THF solution. It could be found that with different input sequence, the result of fluorescence would be totally different. Then, SPEA can be also applied as a new receptor for developing one simple keypad lock for information secuirity in molecular level.
In summary, we choose three kinds of salicylidene Schiff base as receptors to study their molecular recognition and molecular logic function. It can be concluded that, BCHB exhibits“naked eye”colour change and significant fluorescence change in preference to other anions. And then, its deprotonated derivative behaves as a chromogenic detector for Cu~(2+) and a dual ratiometric fluorogenic and chromogenic chemosensor for Zn~(2+) over other metal ions. Moreover, we can describe two sets of integrated logic gates through the emission and absorbance mode respectively; BHB can be developed as a new selective fluorescence probe for Zn~(2+) among other metal cations. Furthermore, under the individual actions of Zn~(2+) ion and UV light as well as the combination of the two actions, we successfully obtained a monomolecular half-subtractor circuit, which responds to one optical and one chemical input producing two optical outputs; SPEA can be a effective sensor for F- and CN- in THF solution and can only detect CN- in ethanol solution. In addition, a keypad lock can be developed with Zn~(2+) and EDTA as two inputs with different results for different sequences. It can offer a new information secuirity platform in molecular level.
1.设计并合成了含氯取代的联二萘桥联西佛碱分子,研究了这类分子对各种阴阳离子的识别能力,结果表明这类分子可以通过紫外吸收以及荧光光谱有效地识别氟离子以及二价锌离子,二价铜离子。进一步地,选择铜离子,锌离子以及EDTA分子作为输入信号,这类分子可完成比较特殊的逻辑功能。研究还发现,将此类分子通过超分子氢键自组装到有序介孔材料SBA-15上时,分子的离子识别性质得到了较好的保持,并存在具有自身特色的逻辑功能。
2.设计合成无氯取代的联二萘桥联西佛碱分子,研究了这类分子对阳离子识别能力,研究发现此类分子可以很好地识别二价锌离子。同时这类分子对紫外光照射比较敏感,当选用锌离子与紫外光照射作为两种输入信号时,我们可以得到逻辑上比较重要的半减法器功能。
3.设计合成简单的含氯取代的水杨醛西佛碱分子,研究了这类分子阴离子识别能力,结果表明此类分子可以在四氢呋喃溶剂中识别氟离子与氰根离子,而在乙醇溶剂中仅对氰根离子有识别作用。进一步地,在四氢呋喃溶剂体系中引入锌离子和EDTA分子两种输入,此类分子可以被开发为由氟离子,锌离子,EDTA分子共同作用的分子键盘锁。
Supramolecular chemistry is one new developing research area. Molecular recognition, once described as "lock and key" for the unique combination of molecules, which is one of the process related closely to supramolecular chemistry, has developed more and more function in synthesis chemistry, life sciences, material sciences and information sciences. Compared with electric and magnetic signal, optical signal has some advantages such as convenience, high sensitivity and selectivity. Moreover, the "naked eye" detection, watching the color change with no instruments, has become the focus in molecular recognition. Furthermore, molecular logic function has been another focus in many crossed studies, based on which, molecular brake and molecular keypad lock has become one foreland of this research area.
Firstly, we choose one binaphyl bridged salicylidene Schiff base with chlorine atoms in the phenyl of the salicylidene (BCHB), which was once applied as one ligand for molecular structure and asymmetric catalysis, as receptor to study its ability in cation and anion recognition. It can be concluded that, when the solution of BCHB was titrated with fluoride anion, the absorption would be affected dramaticly because of the deprotonation function. The color of the solution was then from colorless to yellow. In the same condition, other anions such as chloride, bromide, iodide, phosphate had no obvious change for this. Andthen, many kinds of metal cations were introduced to the fluoride acted solution. As can be seen from the result of absorbance and fluorescence that only the addition of Zn~(2+) and Cu~(2+) can cause a obvious change, indicating the presence of of unique coordination complex with deprotonated BCHB respectively. The naked eye observation also shows that only Zn~(2+) and Cu~(2+) can result in a yellow to light green color change, while the others remain the original state and the disturbance for color change can be neglected.
On the other hand, BCHB presents a tunable system integrated with one OR logic gate as well as one INHIBIT logic gate with Zn~(2+) and Cu~(2+) as chemical inputs by monitoring fluorescence and absorbance as output signals. Also, one IMPLICATION gate operating in fluorescence mode with Cu~(2+) and EDTA as chemical inputs, based on their different binding capability, is present in the system. This research has been rarely reported.
Furthermore, we choose the same structure as BCHB but with no chlorine atoms in the phenyl of the salicylidene (BHB) as another receptor for molecular recognition. Exhibiting absorption and fluorescence changes in the presence of Zn~(2+) in chloroform and ethanol mixed solution, BHB could be used as a fluorescent chemosensor for the detection of Zn~(2+). Furthermore, by monitoring the fluorescence and absorbance as output signals, BHB can function as a combinatorial logic circuit for a molecular half-subtractor with Zn~(2+) and UV irradiation as input variables. Most of the reported molecular half-subtractors mainly focused on acid, base, and other chemical input variables, with UV light irradiation as an independent input, to the best of our knowledge, has not been reported yet.
Lastly, we choose one simple salicylidene Schiff base SPEA as another receptor to study its ability for anions recognition. With THF as organic solvent, F- and CN- could be detected through both absorbance and fluorescence change. Noting that, F- can be detected in rather low concentration (10-8) for its high sensitivity with the receptor. When using ethanol as organic solvent, the spectrum of SPEA could only be affected by the additon of CN-. In conclusion, SPEA can be developed as a sensor for F- and CN- in different solution.
In additon, we also studied the stimulating spectral results of F- acted SPEA with Zn~(2+) and EDTA as inputs in THF solution. It could be found that with different input sequence, the result of fluorescence would be totally different. Then, SPEA can be also applied as a new receptor for developing one simple keypad lock for information secuirity in molecular level.
In summary, we choose three kinds of salicylidene Schiff base as receptors to study their molecular recognition and molecular logic function. It can be concluded that, BCHB exhibits“naked eye”colour change and significant fluorescence change in preference to other anions. And then, its deprotonated derivative behaves as a chromogenic detector for Cu~(2+) and a dual ratiometric fluorogenic and chromogenic chemosensor for Zn~(2+) over other metal ions. Moreover, we can describe two sets of integrated logic gates through the emission and absorbance mode respectively; BHB can be developed as a new selective fluorescence probe for Zn~(2+) among other metal cations. Furthermore, under the individual actions of Zn~(2+) ion and UV light as well as the combination of the two actions, we successfully obtained a monomolecular half-subtractor circuit, which responds to one optical and one chemical input producing two optical outputs; SPEA can be a effective sensor for F- and CN- in THF solution and can only detect CN- in ethanol solution. In addition, a keypad lock can be developed with Zn~(2+) and EDTA as two inputs with different results for different sequences. It can offer a new information secuirity platform in molecular level.
引文
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