以苯并咪唑类衍生物为识别基的共轭聚合物的设计、合成及化学传感特征
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摘要
共轭聚合物所具有的独特的物理光学特性以及相比较小分子所具有的荧光信号放大优势，已在生物及化学传感领域得到了广泛关注与研究。这其中，苯并咪唑类衍生物具有强的金属配位能力和多样的配位方式，却很少作为离子识别单元引入到含N杂环类共轭聚合物传感器中。在本文中，我们以苯并咪唑衍生物为识别位点，从结构与性能角度出发详细考察了其与聚合物不同链接方式时所产生的识别性能差异。研究主要分为以下四个方面：
1.首先设计合成了识别基ethyl2-(4,7-dibromo-2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)acetate (PBMA)，并将其4,7位与共轭聚合物相连得聚合物P1，并将其作为检测Ag~+的荧光传感器。研究结果显示其对Ag~+展现出极好的选择性。在其他离子存在的情况下，仍具有良好的识别能力。同时，该聚合物也表现出对Ag~+的高灵敏度。其最低检测限可达50nM。加入Ag~+后，聚合物不仅表现出荧光强度的降低，同时荧光颜色也由蓝色变为绿色。因此提供了一种新颖的能对Ag~+离子检测的共轭聚合物荧光传感材料。
2.从结构与性能的角度出发，改变前面合成的识别基与聚合物的链接方式，将其5,5'位与聚合物相连得聚合物P4，P5，考察其离子识别性能的变化。研究发现此时的聚合物表现出对Ni~(2+)的高选择性。而完全不识别Ag~+。实验进一步从分子结构和电化学特征方面考察了其可能引起这种变化的原因。随着Ni~(2+)浓度的增加，其启动氧化电位和氧化电位依次逐渐升高，这主要是由于识别基与聚合物链接位置的改变，聚合物链结构发生了改变，导致了其电子密度改变，也就改变了与金属离子的配位能力。同时也表明通过微调识别基与聚合物的链接方式或者滴加不同金属离子与聚合物配位可以达到调节聚合物能级的目的，从而有可能达到各种不同应用的目的。
3.在上面研究的基础上，进一步将识别基中的吡啶单元用噻吩单元替代，同样将其5,5'位与聚合物相连得P6，P7，考察了其离子识别性能的变化。研究显示此时聚合物表现出对Ag~+的高选择性。而完全不识别Ni~(2+)。实验进一步应用核磁滴定和电化学实验考察其原因。实验结果表明，S原子的引入对Ag~+的识别起到关键作用。互为同分异构的识别基仅仅由于酯基取代位置的不同，导致了其所构成的聚合物荧光光谱和电化学特征的较大差异，说明微调识别基不仅可以达到识别的目的，而且可以调节传感器的识别能力。这为我们进一步了解结构与性能的关系，设计更具特异识别性的传感器提供了有益的经验。
4.实验进一步将识别基放在聚合物的侧链(P8)，考察其离子识别性能。比较识别基在主链时聚合物(P2)的识别特征(识别Ag~+，Fe~(3+))，P8的对离子的识别性能发生了显著的变化。其表现出对Cu~(2+)和Ni~(2+)的高选择性和高灵敏度。在此基础上，进一步利用聚合物与金属离子形成的二级配合物作为“turn on”传感器检测氨基酸。加入半胱氨酸(Cys)，能使[聚合物-Cu~(2+)]配合物的荧光恢复。而加入组氨酸(His)和色氨酸(Tryp)能使[聚合物-Ni~(2+)]配合物荧光恢复。其对半胱氨酸(Cys)，组氨酸(His)和色氨酸(Tryp)的检测限分别达到了0.5,5和0.1ppm。这意味着共轭聚合物的检测性能可以通过与不同的金属作用来调节，同时也提供了一个新颖的检测氨基酸的方法。另一方面也表明识别基在聚合物中位置的不同(在主链还是在侧链)可以决定不同的识别性能。为我们认识结构与性能的关系以及系统设计更合理的化学传感器提供了一个非常有益的经验。
Conjugated polymers (CPs) has delocalized π-electronic conjugated ‘‘molecular wires’’ cangreatly amplify the fluorescence signal. As compared in small moleculaes, facile energymigration from polymer backbone upon light excitation and the amplification of fluorescentsignals resulted from the excitation energy transfer to the chromophore. CPs has receivedconsiderable attention as sensing materials used in bioanalysis and chemical sensors. In thesematerials, benzimidazole derivatives have excellent corrdination ability and diversecoordination modes with metal ions. However, few reports on benzimidazole derivativesutilized as congjugated polymer chemosensors. In this thesis, we designed, synthesized anddeveloped the new conjugated polymer sensing platform based on benzimidazole derivativesfor detection of matal ions and amino acids. The influence of connective monities on theonjugated polymer for the recognization performance was investigated in detail. Thisdissertation includes four parts:
First, The recognization group ethyl2-(4,7-dibromo-2-(pyridin-2-yl)-1H-benzo[d]imid-azol-1-yl)acetate (PBMA) was synthesized, and caped unit (4,7position) linked with conjugated polymer backone as a fluorescent chemosensor(P1) for the Ag~+ion sensing.The result indicated that P1showed excellent selectivity toward Ag~+by avoiding theinterference from other metal ions and the detection limt was down to50nm. The emission intensity of P1rapidly descreased and the fluorescent color also changed fromblue to green after addition of Ag~+. The sensing mechanism of the polymer was also investigated by applying a similar copolymer (P2, P3) and by measuring1H NMRspectra. This is the first copolymer (P1) containing PBMA units in the backbone structure as metal ion chemosensor, which will help to extend the number and the applications of fluorometric polymer sensors for metal ions detection.
Second, for the evaluation of relationship between structure and properties, we changed thelinker position (5,5’ position) between PBMA with polymer backone and synthesizedcopolymer P4and P5. The results showed that no significant spectral change was observed inthe fluorescence spectra except in the case of Ni~(2+). Specifically, Ag~+can not be recognized atall. We further inverstigated the reasons fot change in recognization behaviors with molecular structure and their electrochemied characteristics. With the increase of Ni~(2+)concentration, theonset oxidation potential and the oxidation potential of P4or P5were gradually improved.Plausibly, the linking moniety of PBMA with polymer chain has changed the electron densityof the polymer, so the complexing ability of conjugated polymer with metal ions was alsochanged. It is also indicated that the energy level of conjugated polymer could be adjusted bychanging the linking ways between recognization group and congjugated polymer backon oraddition of different metal ion complex with polymer.
Third, based on previous research results, pyridine unit in PBMA further replaced withthiophene unit, and the recognization performance of copolymer P6and P7were alsoinvestigated. The novel conjugated polymer P6and P7showed high selectivity for Ag~+detection. The results indicated that the introduction of S atoms in copolymer (P6, P7) play akey role for detection of Ag~+.This phenomen further give insight understanding relationshipbetween structure and their properties.
Fourth, on the bases of results from copolymer P2, the recognization group as side chain ofconjugated copolymer (P8), and binding and recognition behavior toward the metal ions andamino acids were investigated. The fluorescence of copolymer P8can be completelyquenched by Cu~(2+)and Ni~(2+)through a photoinduced electron transfer process, resulting information of metal complexes of polymer ([P8-Cu~(2+)] and [P8-Ni~(2+)]). These results indicatethat coplymer P8is expected to be a selective chemosensor for Cu~(2+)and Ni~(2+). Moreover, insitu formed [P8-Cu~(2+)] complex showed excellent fluorescence “turn on” properties with highselectivity towards Cys, while [P8-Ni~(2+)] complex with high selectivity towards His and Tryp.These complexes are expected to be promising chemosensors for amino acids due to highselectivity and high sensitivity (detection limit concentration is0.5ppm for Cys,5.0ppm forHis and0.1ppm for Tryp). It means that the detection selectivity of conjugated polymericchemosensor can be controlled by metal ions. Thus, this work provides a new type ofpromising polymeric fluorescent chemosensor for amino acids.
1.首先设计合成了识别基ethyl2-(4,7-dibromo-2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)acetate (PBMA)，并将其4,7位与共轭聚合物相连得聚合物P1，并将其作为检测Ag~+的荧光传感器。研究结果显示其对Ag~+展现出极好的选择性。在其他离子存在的情况下，仍具有良好的识别能力。同时，该聚合物也表现出对Ag~+的高灵敏度。其最低检测限可达50nM。加入Ag~+后，聚合物不仅表现出荧光强度的降低，同时荧光颜色也由蓝色变为绿色。因此提供了一种新颖的能对Ag~+离子检测的共轭聚合物荧光传感材料。
2.从结构与性能的角度出发，改变前面合成的识别基与聚合物的链接方式，将其5,5'位与聚合物相连得聚合物P4，P5，考察其离子识别性能的变化。研究发现此时的聚合物表现出对Ni~(2+)的高选择性。而完全不识别Ag~+。实验进一步从分子结构和电化学特征方面考察了其可能引起这种变化的原因。随着Ni~(2+)浓度的增加，其启动氧化电位和氧化电位依次逐渐升高，这主要是由于识别基与聚合物链接位置的改变，聚合物链结构发生了改变，导致了其电子密度改变，也就改变了与金属离子的配位能力。同时也表明通过微调识别基与聚合物的链接方式或者滴加不同金属离子与聚合物配位可以达到调节聚合物能级的目的，从而有可能达到各种不同应用的目的。
3.在上面研究的基础上，进一步将识别基中的吡啶单元用噻吩单元替代，同样将其5,5'位与聚合物相连得P6，P7，考察了其离子识别性能的变化。研究显示此时聚合物表现出对Ag~+的高选择性。而完全不识别Ni~(2+)。实验进一步应用核磁滴定和电化学实验考察其原因。实验结果表明，S原子的引入对Ag~+的识别起到关键作用。互为同分异构的识别基仅仅由于酯基取代位置的不同，导致了其所构成的聚合物荧光光谱和电化学特征的较大差异，说明微调识别基不仅可以达到识别的目的，而且可以调节传感器的识别能力。这为我们进一步了解结构与性能的关系，设计更具特异识别性的传感器提供了有益的经验。
4.实验进一步将识别基放在聚合物的侧链(P8)，考察其离子识别性能。比较识别基在主链时聚合物(P2)的识别特征(识别Ag~+，Fe~(3+))，P8的对离子的识别性能发生了显著的变化。其表现出对Cu~(2+)和Ni~(2+)的高选择性和高灵敏度。在此基础上，进一步利用聚合物与金属离子形成的二级配合物作为“turn on”传感器检测氨基酸。加入半胱氨酸(Cys)，能使[聚合物-Cu~(2+)]配合物的荧光恢复。而加入组氨酸(His)和色氨酸(Tryp)能使[聚合物-Ni~(2+)]配合物荧光恢复。其对半胱氨酸(Cys)，组氨酸(His)和色氨酸(Tryp)的检测限分别达到了0.5,5和0.1ppm。这意味着共轭聚合物的检测性能可以通过与不同的金属作用来调节，同时也提供了一个新颖的检测氨基酸的方法。另一方面也表明识别基在聚合物中位置的不同(在主链还是在侧链)可以决定不同的识别性能。为我们认识结构与性能的关系以及系统设计更合理的化学传感器提供了一个非常有益的经验。
Conjugated polymers (CPs) has delocalized π-electronic conjugated ‘‘molecular wires’’ cangreatly amplify the fluorescence signal. As compared in small moleculaes, facile energymigration from polymer backbone upon light excitation and the amplification of fluorescentsignals resulted from the excitation energy transfer to the chromophore. CPs has receivedconsiderable attention as sensing materials used in bioanalysis and chemical sensors. In thesematerials, benzimidazole derivatives have excellent corrdination ability and diversecoordination modes with metal ions. However, few reports on benzimidazole derivativesutilized as congjugated polymer chemosensors. In this thesis, we designed, synthesized anddeveloped the new conjugated polymer sensing platform based on benzimidazole derivativesfor detection of matal ions and amino acids. The influence of connective monities on theonjugated polymer for the recognization performance was investigated in detail. Thisdissertation includes four parts:
First, The recognization group ethyl2-(4,7-dibromo-2-(pyridin-2-yl)-1H-benzo[d]imid-azol-1-yl)acetate (PBMA) was synthesized, and caped unit (4,7position) linked with conjugated polymer backone as a fluorescent chemosensor(P1) for the Ag~+ion sensing.The result indicated that P1showed excellent selectivity toward Ag~+by avoiding theinterference from other metal ions and the detection limt was down to50nm. The emission intensity of P1rapidly descreased and the fluorescent color also changed fromblue to green after addition of Ag~+. The sensing mechanism of the polymer was also investigated by applying a similar copolymer (P2, P3) and by measuring1H NMRspectra. This is the first copolymer (P1) containing PBMA units in the backbone structure as metal ion chemosensor, which will help to extend the number and the applications of fluorometric polymer sensors for metal ions detection.
Second, for the evaluation of relationship between structure and properties, we changed thelinker position (5,5’ position) between PBMA with polymer backone and synthesizedcopolymer P4and P5. The results showed that no significant spectral change was observed inthe fluorescence spectra except in the case of Ni~(2+). Specifically, Ag~+can not be recognized atall. We further inverstigated the reasons fot change in recognization behaviors with molecular structure and their electrochemied characteristics. With the increase of Ni~(2+)concentration, theonset oxidation potential and the oxidation potential of P4or P5were gradually improved.Plausibly, the linking moniety of PBMA with polymer chain has changed the electron densityof the polymer, so the complexing ability of conjugated polymer with metal ions was alsochanged. It is also indicated that the energy level of conjugated polymer could be adjusted bychanging the linking ways between recognization group and congjugated polymer backon oraddition of different metal ion complex with polymer.
Third, based on previous research results, pyridine unit in PBMA further replaced withthiophene unit, and the recognization performance of copolymer P6and P7were alsoinvestigated. The novel conjugated polymer P6and P7showed high selectivity for Ag~+detection. The results indicated that the introduction of S atoms in copolymer (P6, P7) play akey role for detection of Ag~+.This phenomen further give insight understanding relationshipbetween structure and their properties.
Fourth, on the bases of results from copolymer P2, the recognization group as side chain ofconjugated copolymer (P8), and binding and recognition behavior toward the metal ions andamino acids were investigated. The fluorescence of copolymer P8can be completelyquenched by Cu~(2+)and Ni~(2+)through a photoinduced electron transfer process, resulting information of metal complexes of polymer ([P8-Cu~(2+)] and [P8-Ni~(2+)]). These results indicatethat coplymer P8is expected to be a selective chemosensor for Cu~(2+)and Ni~(2+). Moreover, insitu formed [P8-Cu~(2+)] complex showed excellent fluorescence “turn on” properties with highselectivity towards Cys, while [P8-Ni~(2+)] complex with high selectivity towards His and Tryp.These complexes are expected to be promising chemosensors for amino acids due to highselectivity and high sensitivity (detection limit concentration is0.5ppm for Cys,5.0ppm forHis and0.1ppm for Tryp). It means that the detection selectivity of conjugated polymericchemosensor can be controlled by metal ions. Thus, this work provides a new type ofpromising polymeric fluorescent chemosensor for amino acids.
引文
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