隐色染料的光谱特性及应用研究
摘要
隐色染料是一类广泛使用的功能材料,具有压热敏发色的性质,主要用于工程图纸、发票、传真打印等领域。荧烷染料是最重要的一类隐色染料,特点是发色灵敏、色调齐全、稳定性好,是隐色染料的主流品种。近年来,荧烷染料在生化分析、发光探针、基因测序和蛋白组学等领域的应用受到广泛关注,这方面的研究成为新的热点。
本论文分成四个部分,共七章。
论文的第一部分,也是第一章,简述了隐色染料的概念、分类、研究现状及发展趋势；主要介绍了荧烷染料的结构性质及国内外的发展概况,同时对本论文的研究意义、内容和创新点做了概括。
论文的第二部分(包括第二、三、四章),研究了隐色染料的显色反应、溶剂对其光谱性质的影响,探索隐色染料的应用性能及作为荧光探针在生物分析中的拓展应用。
在论文的第二章中,采用紫外-可见、荧光光谱法研究了隐色染料ODB-1、KODB-2、 B-15、 CK-5、 CK-16、CVL-S与酸或金属离子的显色反应,并采用红外、核磁和熔点仪对化合物显色反应前后的结构和性质进行了表征和测定。本章为隐色染料的应用提供理论依据。
在论文的第三章,由于隐色染料分子具有A-π-D结构,可以发生分子内电荷转移(ICT)过程,并对溶剂的极性较为敏感,分别用极性参数ET(30)和△f研究了溶剂对三种隐色染料ODB-1、CK-5、CK-37的光谱性质的影响。实验表明随着溶液极性增加,染料的最大发射波长红移,Stokes位移增加,且染料的荧光可以被强极性溶剂猝灭。因此,隐色染料可以作为敏感的荧光探针用于检测体系微环境的变化,应用在生物分析中,拓展了隐色染料在生物分析领域的应用。
在论文的第四章,采用紫外-可见、荧光光谱法对隐色染料ODB-1、CK-37在生物分析中的应用进行研究。以人血清白蛋白(HSA)作为靶分子,研究染料ODB-1与靶分子的相互作用机制。结果表明：染料ODB-1具有很强的猝灭HSA的固有荧光能力,且该过程属于静态猝灭；疏水作用在染料与HSA的作用中起了重要作用；染料ODB-1与HSA在不同温度下均形成1：1的配合物；染料可与HSA的IIA区的色氨酸残基形成堆积结构。
论文的第三部分(包括第五、六章)主要研究了隐色染料在书写印刷领域的应用性能。将染料用于配制可褪色教学白板笔墨水；以经选择的该类染料为着色剂,以水溶性高分子为载体,制备出可褪色水性油墨。
在论文的第五章,将隐色染料的显色体作为着色剂进行筛选,采用均匀正交实验法配制了红、蓝两色可擦白板笔墨水,并研制了擦剂。书写墨水着色剂分别如下：红色用CK-16；蓝色用CK-7或CVL-S。这部分工作开拓了隐色染料新的应用领域。
在论文的第六章,以隐色染料ODB-2、 CK-16、 CK-37、CVL-S的显色体为主要着色剂,将隐色染料用于合成可褪色水性油墨,并测试了油墨的印刷效果及褪色性能。结果表明,合成的油墨印刷效果良好,并具有常温常压下在十二烷基苯磺酸钠存在时迅速褪色的能力。这部分研究拓展了隐色染料的应用领域。
第四部分(第七章)总结全文,提出下一步工作设想。
The leuco dyes are widely used as functional materials for their chromogenic nature of pressure or thermal sensitive. It is mainly used in fields of engineering drawings, invoices, fax printing. Fluoran dyes are the most important kind of leuco dyes with the distinguishing feature of sensitive and complete chromatography, which become the mainstream varieties of leuco dyes. In recent years, the application researches of fluoran dyes in biochemical analysis, light-emitting probes, gene sequencing, proteomics and other areas are received extensive attentions.
This paper is a combination of three parts, including seven chapters in all.
Part I:Chapter1is the first part. In this chapter, the concept, classification, research and development trends of leuco dyes were introduced in brief, and the structure, characters, historical perspective of fluoran dyes were described in detail. The signification, contents and innovation of this thesis were disclosed.
Part II:The second part of this thesis includes chapter2, chapter3and chapter4. The synthesis, effects of solvent polarity on the spectrum, application performance and the application of leuco dyes in bioanalysis as a fluorescent probe were studied exhaustively.
In chapter2, The chromogenic reaction of leuco dyes:ODB-1、 ODB-2、 B-15、 CK-5、 CK-16and CVL-S were carefully investigated by UV-vis absorption and fluorescence spectra. The structures of leuco dyes in chromogenic reaction were characterized and determined using infrared, nuclear magnetic and melting point instrument.
In chapter3, with the character of intramolecular charge-transfer (ICT) arised from its A-π-D structure, the leuco dyes are very sensitive to solvent polarity. The polarity parameters, such as ET(30) and△f which can fairly express the local interaction between solute and solvent were used to discuss the effects of solvent on the spectral properties of leuco dyes for ODB-1、 CK-5and CK-37respectively. The experiment results showed that the excitation and emission wavelengths of compounds shift to long wavelength and Stokes shift increase with the increasing of solution polarity. And the fluorescence of leuco dyes can be quenched by strong polar solvent. The dyes can be used as sensitive fluorescent probes to detect the micro-environment changes in biological system. This research expanded the application of leuco dyes in the field of biological analysis.
In chapter4, Uv-vis, fluorescence spectroscopies were used to study the application of leuco dyes ODB-1and CK-37in biological analysis. The interaction mechanisms between dyes and human serum albumin (HSA) were studied using HSA as target molecule. The results demonstrated that leuco dyes have a strong ability to quench the inherent fluorescence of HSA in a static quenching mechanism. In addition, hydrophobic interaction plays an important role in the interaction between HSA and leuco dyes. The combination ratio of dyes and HSA is1:1at different temperatures. The results showes that accumulation structure is formed between the dyes and tryptophan residues in HSA at IIA section.
Part III:The third part of the thesis includes chapter5and chapter6. The characters of leuco dyes were studied in writing and printing applications. Leuco dyes which can be decoloured were selected and the decolourable teaching whiteboard inks were prepared. And leuco dyes were used as the coloring agents and water-soluble polymer as the carriers to prepare decolourable water-based ink.
In chapter5, two-color (red, blue) whiteboard writing inks were prepared using uniform and orthogonal experiment method by selected leuco dyes and its corresponding embrocation was developed. The coloring agents of writing inks were as following separately:CK-16for red ink; CVL-S or CK-7for blue ink. The work in this chapter exploited the application of leuco dyes in new fields.
In chapter6, ODB-2、CK-16、CK-37and CVL-S were used as coloring agents in printing ink. One kind of water-based ink which can be deinked was prepared and the printing effect of the ink and the deinked performance were determined. The results showes that the water-based ink made from leuco dyes have good printing effects and can be deinked quickly under normal temperature and pressure when sodium dodecyl benzene sulfonate (SDBS) existed. The research works in the thesis exploit the application field of leuco dyes.
Part IV:(Chapter7) All the experimental results in the thesis were summarized in this part. Further works were proposed as well.
本论文分成四个部分,共七章。
论文的第一部分,也是第一章,简述了隐色染料的概念、分类、研究现状及发展趋势；主要介绍了荧烷染料的结构性质及国内外的发展概况,同时对本论文的研究意义、内容和创新点做了概括。
论文的第二部分(包括第二、三、四章),研究了隐色染料的显色反应、溶剂对其光谱性质的影响,探索隐色染料的应用性能及作为荧光探针在生物分析中的拓展应用。
在论文的第二章中,采用紫外-可见、荧光光谱法研究了隐色染料ODB-1、KODB-2、 B-15、 CK-5、 CK-16、CVL-S与酸或金属离子的显色反应,并采用红外、核磁和熔点仪对化合物显色反应前后的结构和性质进行了表征和测定。本章为隐色染料的应用提供理论依据。
在论文的第三章,由于隐色染料分子具有A-π-D结构,可以发生分子内电荷转移(ICT)过程,并对溶剂的极性较为敏感,分别用极性参数ET(30)和△f研究了溶剂对三种隐色染料ODB-1、CK-5、CK-37的光谱性质的影响。实验表明随着溶液极性增加,染料的最大发射波长红移,Stokes位移增加,且染料的荧光可以被强极性溶剂猝灭。因此,隐色染料可以作为敏感的荧光探针用于检测体系微环境的变化,应用在生物分析中,拓展了隐色染料在生物分析领域的应用。
在论文的第四章,采用紫外-可见、荧光光谱法对隐色染料ODB-1、CK-37在生物分析中的应用进行研究。以人血清白蛋白(HSA)作为靶分子,研究染料ODB-1与靶分子的相互作用机制。结果表明：染料ODB-1具有很强的猝灭HSA的固有荧光能力,且该过程属于静态猝灭；疏水作用在染料与HSA的作用中起了重要作用；染料ODB-1与HSA在不同温度下均形成1：1的配合物；染料可与HSA的IIA区的色氨酸残基形成堆积结构。
论文的第三部分(包括第五、六章)主要研究了隐色染料在书写印刷领域的应用性能。将染料用于配制可褪色教学白板笔墨水；以经选择的该类染料为着色剂,以水溶性高分子为载体,制备出可褪色水性油墨。
在论文的第五章,将隐色染料的显色体作为着色剂进行筛选,采用均匀正交实验法配制了红、蓝两色可擦白板笔墨水,并研制了擦剂。书写墨水着色剂分别如下：红色用CK-16；蓝色用CK-7或CVL-S。这部分工作开拓了隐色染料新的应用领域。
在论文的第六章,以隐色染料ODB-2、 CK-16、 CK-37、CVL-S的显色体为主要着色剂,将隐色染料用于合成可褪色水性油墨,并测试了油墨的印刷效果及褪色性能。结果表明,合成的油墨印刷效果良好,并具有常温常压下在十二烷基苯磺酸钠存在时迅速褪色的能力。这部分研究拓展了隐色染料的应用领域。
第四部分(第七章)总结全文,提出下一步工作设想。
The leuco dyes are widely used as functional materials for their chromogenic nature of pressure or thermal sensitive. It is mainly used in fields of engineering drawings, invoices, fax printing. Fluoran dyes are the most important kind of leuco dyes with the distinguishing feature of sensitive and complete chromatography, which become the mainstream varieties of leuco dyes. In recent years, the application researches of fluoran dyes in biochemical analysis, light-emitting probes, gene sequencing, proteomics and other areas are received extensive attentions.
This paper is a combination of three parts, including seven chapters in all.
Part I:Chapter1is the first part. In this chapter, the concept, classification, research and development trends of leuco dyes were introduced in brief, and the structure, characters, historical perspective of fluoran dyes were described in detail. The signification, contents and innovation of this thesis were disclosed.
Part II:The second part of this thesis includes chapter2, chapter3and chapter4. The synthesis, effects of solvent polarity on the spectrum, application performance and the application of leuco dyes in bioanalysis as a fluorescent probe were studied exhaustively.
In chapter2, The chromogenic reaction of leuco dyes:ODB-1、 ODB-2、 B-15、 CK-5、 CK-16and CVL-S were carefully investigated by UV-vis absorption and fluorescence spectra. The structures of leuco dyes in chromogenic reaction were characterized and determined using infrared, nuclear magnetic and melting point instrument.
In chapter3, with the character of intramolecular charge-transfer (ICT) arised from its A-π-D structure, the leuco dyes are very sensitive to solvent polarity. The polarity parameters, such as ET(30) and△f which can fairly express the local interaction between solute and solvent were used to discuss the effects of solvent on the spectral properties of leuco dyes for ODB-1、 CK-5and CK-37respectively. The experiment results showed that the excitation and emission wavelengths of compounds shift to long wavelength and Stokes shift increase with the increasing of solution polarity. And the fluorescence of leuco dyes can be quenched by strong polar solvent. The dyes can be used as sensitive fluorescent probes to detect the micro-environment changes in biological system. This research expanded the application of leuco dyes in the field of biological analysis.
In chapter4, Uv-vis, fluorescence spectroscopies were used to study the application of leuco dyes ODB-1and CK-37in biological analysis. The interaction mechanisms between dyes and human serum albumin (HSA) were studied using HSA as target molecule. The results demonstrated that leuco dyes have a strong ability to quench the inherent fluorescence of HSA in a static quenching mechanism. In addition, hydrophobic interaction plays an important role in the interaction between HSA and leuco dyes. The combination ratio of dyes and HSA is1:1at different temperatures. The results showes that accumulation structure is formed between the dyes and tryptophan residues in HSA at IIA section.
Part III:The third part of the thesis includes chapter5and chapter6. The characters of leuco dyes were studied in writing and printing applications. Leuco dyes which can be decoloured were selected and the decolourable teaching whiteboard inks were prepared. And leuco dyes were used as the coloring agents and water-soluble polymer as the carriers to prepare decolourable water-based ink.
In chapter5, two-color (red, blue) whiteboard writing inks were prepared using uniform and orthogonal experiment method by selected leuco dyes and its corresponding embrocation was developed. The coloring agents of writing inks were as following separately:CK-16for red ink; CVL-S or CK-7for blue ink. The work in this chapter exploited the application of leuco dyes in new fields.
In chapter6, ODB-2、CK-16、CK-37and CVL-S were used as coloring agents in printing ink. One kind of water-based ink which can be deinked was prepared and the printing effect of the ink and the deinked performance were determined. The results showes that the water-based ink made from leuco dyes have good printing effects and can be deinked quickly under normal temperature and pressure when sodium dodecyl benzene sulfonate (SDBS) existed. The research works in the thesis exploit the application field of leuco dyes.
Part IV:(Chapter7) All the experimental results in the thesis were summarized in this part. Further works were proposed as well.
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