西佛碱类衍生物的阴离子识别与多重刺激响应体系的构筑
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摘要
最近几年，小分子离子探针以及多重刺激响应性凝胶由于具有重要的应用价值而受到化学工作者越来越多的关注。其中，小分子探针和刺激响应性小分子凝胶都是建立在小分子体系对外界刺激的选择性响应的基础之上。适当的离子识别位点既可以应用于小分子探针的设计合成，也可以作为功能基团应用于刺激响应性小分子凝胶领域。到目前为止，阳离子探针已经发展的比较成熟，许多探针都具有简便高效的检测能力，甚至有些探针已经应用于活体检测。然而，阴离子探针的发展相对比较缓慢，目前还有许多问题需要解决，比如更低的检测限，更高的选择性，新颖有效的识别机理等等。同时，小分子凝胶作为一种新型的软材料，其应用也日益广泛。而其中对刺激响应性凝胶的研究还相对匮乏，这一点也在某种程度上制约了凝胶的应用。因此，如何开发出简单实用的新型刺激响应性小分子凝胶因子也成为了凝胶研究者努力的目标之一。
西佛碱类化合物合成简单，产率高，易提纯，同时具有优良的刺激响应性质，在医药、催化、检测、液晶、发光材料等领域都已经有了很好的应用。因此，该类分子是一类比较理想的设计阴离子探针和刺激响应性小分子凝胶的分子体系。本论文结合本组多年来在西佛碱类化合物方面的研究经验，设计合成了一系列西佛碱类阴离子探针，对这类化合物阴离子识别过程中影响选择性和灵敏性的因素进行研究，并开发新的识别机理；同时也对合成新型的西佛碱类多重刺激响应性凝胶因子进行了尝试。具体内容分为以下四个部分：
第一，以腙类水杨醛西佛碱分子体系为基础，通过改变不同的取代基团，较为系统地研究了推电子基团、吸电子基团、共轭效应对阴离子识别选择性和灵敏性的影响。结果表明，推电子基团的引入增强了阴离子识别的选择性，但降低了阴离子的结合能力，导致探针的灵敏度降低；而共轭基团和吸电子基团能够增强阴离子识别的灵敏度，但是却降低了阴离子识别的选择性。此外，核磁滴定实验表明该类分子对氟离子识别的机理是氟离子引起了该类化合物酚羟基的去质子化。
第二，以酚西佛碱类化合物为基础，合成了一种具有双通道分别识别不同阴离子的小分子探针。该探针在紫外可见吸收光谱上对氟离子具有很好的选择性，可以选择性裸眼识别氟离子；而在荧光光谱上则对氰离子具有特异响应性，而且荧光光谱在识别氰离子之后变化很大，荧光量子效率达到了0.9095，增强了大约606倍，这在文献报道中还是很罕见的。通过对识别机理的研究，我们揭示了产生上述双通道分别识别不同阴离子的原因，即氟离子的加入引起了酚羟基的去质子化，氰离子的加入促使酚西佛碱发生闭环反应而转变为苯并恶唑结构。这种氰离子促使的闭环反应还是第一次被报道，可以作为一种新的识别氰离子的机理和制备苯并恶唑类化合物的方法。
第三，以苯腙类西佛碱化合物为基础，利用该类分子的还原性，开发了一种新型的次氯酸根荧光探针。合成的探针由于分子内的PET效应而几乎没有荧光，但次氯酸根能有效的破坏这种PET作用，使荧光显著增强，识别后的荧光量子效率达到0.2259，增强了42.6倍。此外，常见的金属离子、阴离子、具有氧化性的离子、一些自由基都不会引起探针的荧光增强，表明该探针对次氯酸根具有非常好的选择性。同时，本章中用到的C=N-NH结构是一种新型的识别次氯酸根的分子结构，可以发展为新的次氯酸根识别位点。
第四，以水杨醛类西佛碱化合物为基础，结合之前对西佛碱类化合物识别性质的研究以及对西佛碱类化合物响应性质的认识，我们将具有多重响应性质的水杨醛类西佛碱引入到小分子凝胶因子的设计当中，成功合成了一种新型的ALS型凝胶因子。该分子在许多醇类溶剂中表现出了良好的成胶性质，可以通过加热-冷却或加热-超声的操作形成凝胶。形成的凝胶具有很好的纤维结构，并且具有荧光增强的性质。此外，该凝胶还具有热致变色、锌离子响应、氟离子响应性质。本章利用具有多重刺激响应性质的单一的官能团实现了凝胶的多重刺激响应性，这为多重刺激响应凝胶因子的设计合成提供了一种新的思路。
In recent years, it has cause a great attention to design and synthesize the smallmolecular ion probes and multiple stimuli responsive gels. Both ion probes and stimuliresponsive gel are based on selective response system，therefore, the design ofappropriate recognition sites, which can be integrated on the ion probes and stimuliresponsive gel become the research focus. Though the metal ion probes have beendeveloped quickly, the design of anion probes is relatively slow. Thus, the developing ofmultiple stimuli responsive gels with new molecular structures and properties is quitechallenging.
Schiff bases, as excellent stimuli responsive molecules, are good candidates fordesign and synthesize the new anion probes and multiple stimuli responsive gels.Therefore, we synthesized several anion probes and a new ALS type multiple stimuliresponsive gel based on schiff bases and conducted thoroughly examination on theselectivity, sensitivity, and mechanism of them. The main content contained fouraspects:
Firstly, based on the salicylic aldehyde hydrazone molecules, we studied the groupeffect on the anions sensing. By changing different substituents, including theelectron-donating groups, electron-withdrawing groups, the conjugate effect, we foundthe substituents had a great effect on the selectivity and sensitivity for anion recognition.For example, electron-donating groups could reduce the combination ability of probewith anion, but enhance the selectivity of anion recognition; in contrast, the conjugatedgroup and electron-withdrawing group could enhance the capacity for combining anions,but reduce the selectivity of probe. Furthermore, we found the mechanism of thesensing process was a deprotonation process.
Secondly, based on the phenol schiff bases, we had developed a dual channel probewhich could detect fluoride ions and cyanide ions in different channel respectively. Inthe UV-vis absorption spectra, the probe could response to fluoride ions with goodselectivity. It could be used as a naked eye probe to fluoride ions; while in the fluorescence spectra, the probe only responsed to cyanide ions with high selectivity.Furthermore, we proved that the colorimetric response to fluoride anions was based on adeprotonation process and the fluorescent response to cyanide anions (fluorescencequantum yield reached to0.9095,606-fold enhancement) was based on a cyclizationprocess. Moreover, it is the the first time to report cyclization of phenolic Schiff basesinduced by cyanide, and this mechanism could be used as a new way to synthesize2-substituted benzoxazoles.
Thirdly, the pyrene phenol–hydrazone has been selected as a hypochlorite probe. Thisprobe displayed a color bleaching and fluorescence turning on in the presence ofhypochlorite. The fluorescence quantum yield reached to0.2259(42.6-foldenhancement) after sensing hypochlorite. The probe also exhibited a high selectivity andsensitivity to hypochlorite. Furthermore, the structure of C=N NH plays a key role inthe sensing process. As the phenol–hydrazone structure is easily synthesized; thisstrategy has great potential application in designing simple and efficient probes forhypochlorite.
Fourthly, a new multi-response gelator based on salicylidene Schiff base has beensynthesized and demonstrated. The gelator can gelate many solvents by self-cooling orultrasonic processing. Scanning electron microscopy reveals that the xerogels of thestable gels have fibrillar microstructure. The gel exhibits an enhanced fluorescenceemission which is ascribed to the combination of inhibition of the intramolecularrotation and the formation of J-aggregates. Thermochromism is observed, which can beexplained by the equilibrium between the enol form and the keto form. Furthermore, thegel shows a selective fluorescent response to Zn2+in protic solvent ethanol and anexcellent colorimetric response to F in the aprotic solvent acetonitrile.
西佛碱类化合物合成简单，产率高，易提纯，同时具有优良的刺激响应性质，在医药、催化、检测、液晶、发光材料等领域都已经有了很好的应用。因此，该类分子是一类比较理想的设计阴离子探针和刺激响应性小分子凝胶的分子体系。本论文结合本组多年来在西佛碱类化合物方面的研究经验，设计合成了一系列西佛碱类阴离子探针，对这类化合物阴离子识别过程中影响选择性和灵敏性的因素进行研究，并开发新的识别机理；同时也对合成新型的西佛碱类多重刺激响应性凝胶因子进行了尝试。具体内容分为以下四个部分：
第一，以腙类水杨醛西佛碱分子体系为基础，通过改变不同的取代基团，较为系统地研究了推电子基团、吸电子基团、共轭效应对阴离子识别选择性和灵敏性的影响。结果表明，推电子基团的引入增强了阴离子识别的选择性，但降低了阴离子的结合能力，导致探针的灵敏度降低；而共轭基团和吸电子基团能够增强阴离子识别的灵敏度，但是却降低了阴离子识别的选择性。此外，核磁滴定实验表明该类分子对氟离子识别的机理是氟离子引起了该类化合物酚羟基的去质子化。
第二，以酚西佛碱类化合物为基础，合成了一种具有双通道分别识别不同阴离子的小分子探针。该探针在紫外可见吸收光谱上对氟离子具有很好的选择性，可以选择性裸眼识别氟离子；而在荧光光谱上则对氰离子具有特异响应性，而且荧光光谱在识别氰离子之后变化很大，荧光量子效率达到了0.9095，增强了大约606倍，这在文献报道中还是很罕见的。通过对识别机理的研究，我们揭示了产生上述双通道分别识别不同阴离子的原因，即氟离子的加入引起了酚羟基的去质子化，氰离子的加入促使酚西佛碱发生闭环反应而转变为苯并恶唑结构。这种氰离子促使的闭环反应还是第一次被报道，可以作为一种新的识别氰离子的机理和制备苯并恶唑类化合物的方法。
第三，以苯腙类西佛碱化合物为基础，利用该类分子的还原性，开发了一种新型的次氯酸根荧光探针。合成的探针由于分子内的PET效应而几乎没有荧光，但次氯酸根能有效的破坏这种PET作用，使荧光显著增强，识别后的荧光量子效率达到0.2259，增强了42.6倍。此外，常见的金属离子、阴离子、具有氧化性的离子、一些自由基都不会引起探针的荧光增强，表明该探针对次氯酸根具有非常好的选择性。同时，本章中用到的C=N-NH结构是一种新型的识别次氯酸根的分子结构，可以发展为新的次氯酸根识别位点。
第四，以水杨醛类西佛碱化合物为基础，结合之前对西佛碱类化合物识别性质的研究以及对西佛碱类化合物响应性质的认识，我们将具有多重响应性质的水杨醛类西佛碱引入到小分子凝胶因子的设计当中，成功合成了一种新型的ALS型凝胶因子。该分子在许多醇类溶剂中表现出了良好的成胶性质，可以通过加热-冷却或加热-超声的操作形成凝胶。形成的凝胶具有很好的纤维结构，并且具有荧光增强的性质。此外，该凝胶还具有热致变色、锌离子响应、氟离子响应性质。本章利用具有多重刺激响应性质的单一的官能团实现了凝胶的多重刺激响应性，这为多重刺激响应凝胶因子的设计合成提供了一种新的思路。
In recent years, it has cause a great attention to design and synthesize the smallmolecular ion probes and multiple stimuli responsive gels. Both ion probes and stimuliresponsive gel are based on selective response system，therefore, the design ofappropriate recognition sites, which can be integrated on the ion probes and stimuliresponsive gel become the research focus. Though the metal ion probes have beendeveloped quickly, the design of anion probes is relatively slow. Thus, the developing ofmultiple stimuli responsive gels with new molecular structures and properties is quitechallenging.
Schiff bases, as excellent stimuli responsive molecules, are good candidates fordesign and synthesize the new anion probes and multiple stimuli responsive gels.Therefore, we synthesized several anion probes and a new ALS type multiple stimuliresponsive gel based on schiff bases and conducted thoroughly examination on theselectivity, sensitivity, and mechanism of them. The main content contained fouraspects:
Firstly, based on the salicylic aldehyde hydrazone molecules, we studied the groupeffect on the anions sensing. By changing different substituents, including theelectron-donating groups, electron-withdrawing groups, the conjugate effect, we foundthe substituents had a great effect on the selectivity and sensitivity for anion recognition.For example, electron-donating groups could reduce the combination ability of probewith anion, but enhance the selectivity of anion recognition; in contrast, the conjugatedgroup and electron-withdrawing group could enhance the capacity for combining anions,but reduce the selectivity of probe. Furthermore, we found the mechanism of thesensing process was a deprotonation process.
Secondly, based on the phenol schiff bases, we had developed a dual channel probewhich could detect fluoride ions and cyanide ions in different channel respectively. Inthe UV-vis absorption spectra, the probe could response to fluoride ions with goodselectivity. It could be used as a naked eye probe to fluoride ions; while in the fluorescence spectra, the probe only responsed to cyanide ions with high selectivity.Furthermore, we proved that the colorimetric response to fluoride anions was based on adeprotonation process and the fluorescent response to cyanide anions (fluorescencequantum yield reached to0.9095,606-fold enhancement) was based on a cyclizationprocess. Moreover, it is the the first time to report cyclization of phenolic Schiff basesinduced by cyanide, and this mechanism could be used as a new way to synthesize2-substituted benzoxazoles.
Thirdly, the pyrene phenol–hydrazone has been selected as a hypochlorite probe. Thisprobe displayed a color bleaching and fluorescence turning on in the presence ofhypochlorite. The fluorescence quantum yield reached to0.2259(42.6-foldenhancement) after sensing hypochlorite. The probe also exhibited a high selectivity andsensitivity to hypochlorite. Furthermore, the structure of C=N NH plays a key role inthe sensing process. As the phenol–hydrazone structure is easily synthesized; thisstrategy has great potential application in designing simple and efficient probes forhypochlorite.
Fourthly, a new multi-response gelator based on salicylidene Schiff base has beensynthesized and demonstrated. The gelator can gelate many solvents by self-cooling orultrasonic processing. Scanning electron microscopy reveals that the xerogels of thestable gels have fibrillar microstructure. The gel exhibits an enhanced fluorescenceemission which is ascribed to the combination of inhibition of the intramolecularrotation and the formation of J-aggregates. Thermochromism is observed, which can beexplained by the equilibrium between the enol form and the keto form. Furthermore, thegel shows a selective fluorescent response to Zn2+in protic solvent ethanol and anexcellent colorimetric response to F in the aprotic solvent acetonitrile.
引文
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