新型线性及环状多吡咯、多吡啶化合物的合成与离子识别研究
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摘要
锌离子和氰根等离子的检测在生物化学和环境科学等领域具有重要学术价值和应用背景。其中,荧光探针具有成本低、操作简便以及灵敏度高等优点,受到了广泛关注。其分子设计往往基于一些结构简单的五员或六员杂环发色团。毗咯为五员杂环,它可以与醛缩合生成线性二吡咯、三吡咯及多毗咯。这些线性吡咯低聚物广泛用作合成卟啉的中间体。但是在荧光探针方面却没有引起足够重视。考虑到其氮原子的配位性能及吡咯α-位的易修饰性,本文系统性地将其用于设计锌离子和氰根等离子的荧光探针。此外,多吡啶类化合物是良好的金属离子配体,本论文也将其用于荧光探针的设计。
本论文第一章详细介绍了荧光探针常见的识别机理、研究进展及本文研究思路。
第二章设计合成了四个meso位为五氟苯基取代的线性二吡咯(D1-D3)和三吡咯(D4),它们对锌离子表现出荧光增强型识别作用,并且荧光波长可在绿光到红光的范围内进行调控。荧光增强可归因于锌离子配位作用导致分子平面性和刚性的增强,分子内旋转所造成的能量损失得到抑制,即存在“螯合荧光增强效应(CHEF)".这些探针可用于含水体系中锌离子的高选择性检测,其灵敏度最高可达4.6×10-8M。此外,D4还可用于细胞内锌离子的荧光成像。
第三章,通过取代基的改变来进一步调控该类多吡咯探针对锌离子的识别性能。以对甲氧基苯甲酰氯为酰化试剂,酰化5-五氟苯基二吡咯甲烷时,伴随着常规的α-单酰化产物PS1和α-,α'-双酰化产物PS3的生成,意外得到了较高产率的新型α-,β'-双酰化产物PS2。PS1-PS3经过氧化得到次甲基二吡咯S1～S3,可用作荧光增强型锌离子探针。相对于D1～D3,不对称取代的S2具有更高的灵敏度和更长的荧光发射波长。
第四章,用DDQ氧化含有较多供电子取代基的二吡咯甲烷时,意外地得到了三个meso-位羟基取代的二吡咯甲烷DPMOH1-DPMOH3。由于其meso位碳原子为sp3杂化,整个分子不是共轭结构,溶液既没有颜色也没有荧光。向其溶液中加入锌离子后,DPMOH1-DPMOH3被空气氧化为其对应的次甲基二吡咯并与锌离子配位,导致共轭体系增大、刚性及平面性增强,最终溶液发出较强的橙色荧光。
第五章,研究了三个α-羰基取代次甲基二吡咯化合物DCN1-DCN3对氰离子的识别性能。在纯有机溶剂中,氟离子能使溶液由浅黄变为橙色,而氰离子的加入则使之变为粉红色。在含水溶剂体系中,氟离子不能引起明显的颜色变化,而氰离子的加入却使溶液颜色由浅黄变为红色。这是由于氟离子与主体的氢键作用在含水体系中被破坏。而氰离子对α-位羰基碳原子的亲核进攻在含水体系中仍能够正常进行。
第六章,将蒽与2,2'-二吡啶胺通过炔基或者直接相连,合成了ACN1-ACN3,它们具有较高荧光量子产率。其中,ACN1和ACN2的荧光在加入少量铜离子之后几乎完全淬灭,而随后加入氰离子又能够使荧光恢复,并且这一过程对氰离子表现出高选择性和高灵敏度,检测限可达2×10-7M。相比之下,ACN3的荧光较难被铜离子淬灭也因此不能用作氰根的荧光增强型探针。结果表明,蒽与二吡啶胺连接方式的微小差异对离子识别性能有非常显著的影响,这为今后设计相关的氰根荧光探针提供了新的思路。
第七章为实现分子的多个稳定状态,设计合成了对称性相对较低的新型meso-羰基卟啉化合物DPH22。在低极性溶剂中,它以酚式结构存在,四吡咯大环接近共面。而加入大极性溶剂之后,则立即转变成其醌式异构体,同时大环扭曲为非平面构象。此外,它还可以与酸碱作用,发生可逆的质子化及脱质子作用。基于这些过程,以酸、碱为输入信号,以其氯仿溶液在特定波长的吸光度为输出信号,成功构建了两个半减法器和一个数字比较器。
第八章对全文工作进行总结并对线性多毗咯化合物在荧光探针方面的应用前景进行了展望
The detection of ions such as Zn2+and CN is a subject of great importance in the areas of biochemistry and environmental science. Fluorescent probes have the advantages of low cost, ease of performance and high sensitivity, thus attracting increasing interests in recent years. The chromophores of fluorescent probes are usually constructed from simple five-or six-membered heterocyclic units. Pyrrole is a five-membered heterocycle, which can react with aldehydes to form dipyrromethanes, tripyrromethanes and other linear oligopyrroles, which have been used as intermediates in porphyrins synthesis. However, their applications as fluorescent probes have not caused much attention. In consideration of their potential emission capacity, coordination ability and ease of modification, this thesis is focused on the systematic investigations of the novel oligopyrroles that can be applied as practical Zn2+and CN-probes. Furthermore, considering the fact that polypyridyl ligands are also widely used in metal chelation, their applications as fluorescent probes were also investigated.
In Chapter1, common sensing principles of fluorescent probes are briefly introduced and the recent progresses in zinc and cyanide probes are also reviewed.
In Chapter2, meso-pentafluorophenyl substituted dipyrrins D1-D3and tripyrrin D4were readily synthesized and developed as fluorescence turn on Zn2+probes with emission colors varying from green to red. The fluorescence enhancement can be ascribed to the formation of corresponding zinc complexes, which show the "CHEF" type fluorescence. D1～D4can be applied to selectively detect Zn2+in aqueous systems, with the best detection limits of4.6×10-8M. In addition, D4was also successfully applied to image Zn2+in living KB cells.
In Chapter3, we tried to improve the sensing behavior of the dipyrrin probes by changing the substituents at the pyrrolic a-position. During the acylation of5-pentafluoro-phenyldipyrromethane by a Friedel-Crafts reaction using p-anisoyl chloride as the acylating agent, an a-, β'-diacylated product PS2was unexpectedly obtained in high yield accompanied with ordinary a-substituted mono-and diacylated products PS1and PS3. After oxidation of PS1-PS3to dipyrrins S1-S3with DDQ, they show fluorescence "turn on" upon addition of Zn2+in water-containing systems. Compared with D1-D3, the novel a-,β'-diacylated dipyrrin S2show a longer emission wavelength and higher sensitivity for Zn2+detection.
In Chapter4, three novel meso-hydroxyl substituted dipyrromethanes
DPMOH1-DPMOH3were unexpectedly obtained during the oxidation of dipyrromethanes bearing electron rich substituents at the meso position. Due to the interruption of the conjugated π system by an sp3carbon between the two pyrrolic units, they were found to be colourless and nonfluorescent. Interestingly, upon addition of Zn2+to their solutions, bright orange fluorescence was observed due to the oxidation of DPMOH1-DPMOH3to corresponding dipyrrins followed by the formation of zinc complexes.
In Chapter5, for the detection of CN-, three dipyrrins DCN1-DCN3were designed and synthesized. In pure organic solvents, the addition CN-induced a color change from light yellow to pink, while the color changed to orange upon addition of F-. In water-containing systems, DCN1-DCN3showed no response to F-, but the addition of CN-changed their solution color from light yellow to red. These observations can be rationalized by the fact that the hydrogen-bonding interactions between F-and the hosts was greatly suppressed in water-containing systems, but the nucleophilic addition of CN-was not obviously affected.
In Chapter6, three highly fluorescent compounds ACN1-ACN3were synthesized by linking strongly emissive anthracene unit to a Cu2+chelating2.2'-dipyridylamine moiety. The fluorescence of ACN1and ACN2can be easily quenched by the formation of non-fluorescent ACN1-Cu2+and ACN2-Cu2+ensembles, which can be applied as reversible and sensitive fluorescence turn on cyanide probes, with the best detection limit of2×10-1M. In contrast, a large molar excess of Cu2+is required to quench the fluorescence of ACN3. which is unsuitable for the detection of CN-. These results demonstrate that the linking modes between anthracene and2,2'-dipyridylamine have a great influence on their sensing properties, offering a designing strategy for relevant fluorescent CN-probes.
In Chapter7, with the purpose to realize multilple stable states, a relatively unsymmetrical novel dioxoporphyrin named DPH22was synthesized, which show a phenolic form (DPH22) in CHCl3with a nearly planar arrangement of the macrocyclic moiety, and transformed into the quinoidal form (DPH40) by adding a small amount of DMSO. accompanied with the distortion of the macrocyele to a nonplanar conformation. Besides, the interactions between DPH22and acid/base lead to reversible protonation and deprotonation processes. Based on these transformations, two half subtractors and a comparator were successfully constructed by using the addition of TFA and TBAF as the inputs, and the absorption values at412.510.562and603nm as the outputs.
Chapter8summarized the utilization of oligopyrroles as ion probes with an outlook on their further applications in related areas.
本论文第一章详细介绍了荧光探针常见的识别机理、研究进展及本文研究思路。
第二章设计合成了四个meso位为五氟苯基取代的线性二吡咯(D1-D3)和三吡咯(D4),它们对锌离子表现出荧光增强型识别作用,并且荧光波长可在绿光到红光的范围内进行调控。荧光增强可归因于锌离子配位作用导致分子平面性和刚性的增强,分子内旋转所造成的能量损失得到抑制,即存在“螯合荧光增强效应(CHEF)".这些探针可用于含水体系中锌离子的高选择性检测,其灵敏度最高可达4.6×10-8M。此外,D4还可用于细胞内锌离子的荧光成像。
第三章,通过取代基的改变来进一步调控该类多吡咯探针对锌离子的识别性能。以对甲氧基苯甲酰氯为酰化试剂,酰化5-五氟苯基二吡咯甲烷时,伴随着常规的α-单酰化产物PS1和α-,α'-双酰化产物PS3的生成,意外得到了较高产率的新型α-,β'-双酰化产物PS2。PS1-PS3经过氧化得到次甲基二吡咯S1～S3,可用作荧光增强型锌离子探针。相对于D1～D3,不对称取代的S2具有更高的灵敏度和更长的荧光发射波长。
第四章,用DDQ氧化含有较多供电子取代基的二吡咯甲烷时,意外地得到了三个meso-位羟基取代的二吡咯甲烷DPMOH1-DPMOH3。由于其meso位碳原子为sp3杂化,整个分子不是共轭结构,溶液既没有颜色也没有荧光。向其溶液中加入锌离子后,DPMOH1-DPMOH3被空气氧化为其对应的次甲基二吡咯并与锌离子配位,导致共轭体系增大、刚性及平面性增强,最终溶液发出较强的橙色荧光。
第五章,研究了三个α-羰基取代次甲基二吡咯化合物DCN1-DCN3对氰离子的识别性能。在纯有机溶剂中,氟离子能使溶液由浅黄变为橙色,而氰离子的加入则使之变为粉红色。在含水溶剂体系中,氟离子不能引起明显的颜色变化,而氰离子的加入却使溶液颜色由浅黄变为红色。这是由于氟离子与主体的氢键作用在含水体系中被破坏。而氰离子对α-位羰基碳原子的亲核进攻在含水体系中仍能够正常进行。
第六章,将蒽与2,2'-二吡啶胺通过炔基或者直接相连,合成了ACN1-ACN3,它们具有较高荧光量子产率。其中,ACN1和ACN2的荧光在加入少量铜离子之后几乎完全淬灭,而随后加入氰离子又能够使荧光恢复,并且这一过程对氰离子表现出高选择性和高灵敏度,检测限可达2×10-7M。相比之下,ACN3的荧光较难被铜离子淬灭也因此不能用作氰根的荧光增强型探针。结果表明,蒽与二吡啶胺连接方式的微小差异对离子识别性能有非常显著的影响,这为今后设计相关的氰根荧光探针提供了新的思路。
第七章为实现分子的多个稳定状态,设计合成了对称性相对较低的新型meso-羰基卟啉化合物DPH22。在低极性溶剂中,它以酚式结构存在,四吡咯大环接近共面。而加入大极性溶剂之后,则立即转变成其醌式异构体,同时大环扭曲为非平面构象。此外,它还可以与酸碱作用,发生可逆的质子化及脱质子作用。基于这些过程,以酸、碱为输入信号,以其氯仿溶液在特定波长的吸光度为输出信号,成功构建了两个半减法器和一个数字比较器。
第八章对全文工作进行总结并对线性多毗咯化合物在荧光探针方面的应用前景进行了展望
The detection of ions such as Zn2+and CN is a subject of great importance in the areas of biochemistry and environmental science. Fluorescent probes have the advantages of low cost, ease of performance and high sensitivity, thus attracting increasing interests in recent years. The chromophores of fluorescent probes are usually constructed from simple five-or six-membered heterocyclic units. Pyrrole is a five-membered heterocycle, which can react with aldehydes to form dipyrromethanes, tripyrromethanes and other linear oligopyrroles, which have been used as intermediates in porphyrins synthesis. However, their applications as fluorescent probes have not caused much attention. In consideration of their potential emission capacity, coordination ability and ease of modification, this thesis is focused on the systematic investigations of the novel oligopyrroles that can be applied as practical Zn2+and CN-probes. Furthermore, considering the fact that polypyridyl ligands are also widely used in metal chelation, their applications as fluorescent probes were also investigated.
In Chapter1, common sensing principles of fluorescent probes are briefly introduced and the recent progresses in zinc and cyanide probes are also reviewed.
In Chapter2, meso-pentafluorophenyl substituted dipyrrins D1-D3and tripyrrin D4were readily synthesized and developed as fluorescence turn on Zn2+probes with emission colors varying from green to red. The fluorescence enhancement can be ascribed to the formation of corresponding zinc complexes, which show the "CHEF" type fluorescence. D1～D4can be applied to selectively detect Zn2+in aqueous systems, with the best detection limits of4.6×10-8M. In addition, D4was also successfully applied to image Zn2+in living KB cells.
In Chapter3, we tried to improve the sensing behavior of the dipyrrin probes by changing the substituents at the pyrrolic a-position. During the acylation of5-pentafluoro-phenyldipyrromethane by a Friedel-Crafts reaction using p-anisoyl chloride as the acylating agent, an a-, β'-diacylated product PS2was unexpectedly obtained in high yield accompanied with ordinary a-substituted mono-and diacylated products PS1and PS3. After oxidation of PS1-PS3to dipyrrins S1-S3with DDQ, they show fluorescence "turn on" upon addition of Zn2+in water-containing systems. Compared with D1-D3, the novel a-,β'-diacylated dipyrrin S2show a longer emission wavelength and higher sensitivity for Zn2+detection.
In Chapter4, three novel meso-hydroxyl substituted dipyrromethanes
DPMOH1-DPMOH3were unexpectedly obtained during the oxidation of dipyrromethanes bearing electron rich substituents at the meso position. Due to the interruption of the conjugated π system by an sp3carbon between the two pyrrolic units, they were found to be colourless and nonfluorescent. Interestingly, upon addition of Zn2+to their solutions, bright orange fluorescence was observed due to the oxidation of DPMOH1-DPMOH3to corresponding dipyrrins followed by the formation of zinc complexes.
In Chapter5, for the detection of CN-, three dipyrrins DCN1-DCN3were designed and synthesized. In pure organic solvents, the addition CN-induced a color change from light yellow to pink, while the color changed to orange upon addition of F-. In water-containing systems, DCN1-DCN3showed no response to F-, but the addition of CN-changed their solution color from light yellow to red. These observations can be rationalized by the fact that the hydrogen-bonding interactions between F-and the hosts was greatly suppressed in water-containing systems, but the nucleophilic addition of CN-was not obviously affected.
In Chapter6, three highly fluorescent compounds ACN1-ACN3were synthesized by linking strongly emissive anthracene unit to a Cu2+chelating2.2'-dipyridylamine moiety. The fluorescence of ACN1and ACN2can be easily quenched by the formation of non-fluorescent ACN1-Cu2+and ACN2-Cu2+ensembles, which can be applied as reversible and sensitive fluorescence turn on cyanide probes, with the best detection limit of2×10-1M. In contrast, a large molar excess of Cu2+is required to quench the fluorescence of ACN3. which is unsuitable for the detection of CN-. These results demonstrate that the linking modes between anthracene and2,2'-dipyridylamine have a great influence on their sensing properties, offering a designing strategy for relevant fluorescent CN-probes.
In Chapter7, with the purpose to realize multilple stable states, a relatively unsymmetrical novel dioxoporphyrin named DPH22was synthesized, which show a phenolic form (DPH22) in CHCl3with a nearly planar arrangement of the macrocyclic moiety, and transformed into the quinoidal form (DPH40) by adding a small amount of DMSO. accompanied with the distortion of the macrocyele to a nonplanar conformation. Besides, the interactions between DPH22and acid/base lead to reversible protonation and deprotonation processes. Based on these transformations, two half subtractors and a comparator were successfully constructed by using the addition of TFA and TBAF as the inputs, and the absorption values at412.510.562and603nm as the outputs.
Chapter8summarized the utilization of oligopyrroles as ion probes with an outlook on their further applications in related areas.
引文
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