1. 离子液体存在下碳酸二甲酯的直接合成及其机理研究 2. 一甲川菁、苯乙烯染料的合成及结构与性质的理论研究
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摘要
本论文分为两部分,涉及到(ⅰ)离子液体存在下的碳酸二甲酯的直接合成及其机理研究;(ⅱ)一甲川菁染料、苯乙烯型染料的合成及其结构与性质的理论研究。
第一部分离子液体存在下碳酸二甲酯的直接合成及其机理研究
碳酸二甲酯是一种无毒、环保性能优异、用途广泛的化工原料,被誉为21世纪有机合成的“新基石”,市场前景看好,其合成工艺在国内外引起了广泛的关注。
本论文介绍了碳酸二甲酯的基本性质、应用现状以及新合成技术。制备了6种常见离子液体:BmimBr、BmimBF_4、BmimPF_6、PmimBr、PmimBF_4、PmimPF_6,并对其粘度进行了测定。以制备的离子液体为介质,利用甲醇、碳酸钾、二氧化碳等为原料在温和条件下直接合成了碳酸二甲酯,提出了一种温和条件下直接合成碳酸二甲酯的新方法。用气-质联用仪(GC-MS)探索了制备碳酸二甲酯的反应机理、优化了反应条件,使得碳酸二甲酯的产率达到30.8%。同时将该方法推广到其它六种对称碳酸酯的合成,其中有三种碳酸酯产率达到了60%以上。
第二部分一甲川菁、苯乙烯染料的合成及结构与性质的理论研究
近年来,吲哚一甲川菁染料和苯乙烯型染料在光盘存储、生物荧光检测等多种领域的应用引起了人们的广泛关注。运用密度泛函理论(DFT)和含时密度泛函理论(TD-DFT)能够很好地研究染料分子的结构、电子光谱性质、发色机理及非线性光学特性,现已成为当今化学家广泛使用的研究工具之一。
本论文简要介绍了吲哚一甲川菁染料和苯乙烯型染料的结构、应用以及本文理论研究所涉及到的DFT理论、TD-DFT理论和反应场理论,同时对近年来这两类染料分子结构与光谱性质的理论研究进展进行了介绍。利用吲哚啉和2-甲硫基喹啉季铵盐制备了四种吲哚一甲川菁染料、,并用~1H NMR,~(13)C NMR,IR,UV-Vis,MS对染料进行了结构表征。利用TD-DFT方法对吲哚一甲川菁染料的光谱性质进行了研究,并运用多元线性回归模型优化了其在不同溶剂中的吸收性质,其λ_(max)的相对偏差在-0.35%～-5.6%之间。分析了染料分子的前线轨道布居情况,其UV-Vis吸收光谱是源于π→π~*的电子跃迁。研究了一种染料的红外光谱,计算了其谐振频率,与实验值有着很好的一致性。
合成了一种2-苯乙烯基-β-萘噻唑染料,并利用X-射线单晶衍射技术,~1H NMR,IR,UV-Vis,MS进行了结构表征,同时采用DFT理论研究了2-苯乙烯基-β-萘噻唑染料的结构和波谱性质。研究发现,所采用的理论方法均能很好的重现染料分子的实验检测结果。
This paper contains two parts: (i) Research on the synthesis of dimethyl carbonate and its synthetic mechanism in the presence of ionic liquid; (ii) The synthesis and theoretical study on the structure and properties of four monomethine cyanine dyes and one styryl dye.
Part i: Research on the synthesis of dimethyl carbonate and its synthetic mechanism in the presence of ionic liquid.
Dimethyl carbonate is a non-toxic, environmental friendly, and broadly utilized chemical material with great market potential. It is honored as the cornerstone of organic synthesis in the 21st century.
In this paper, the basic property、application situation and new synthesis technology of dimethyl carbonate (DMC) are briefly introduced. A new direct synthesis technique of dimethyl carbonate from methanol、potassium carbonate and carbon dioxide etc. in the presence of ionic liquids under mild conditions is designed in this paper. Six kinds of ionic liquids (BmimBr、BmimBF_4、BmimPF_6、PmimBr、PmimBF_4、PmimPF_6) are prepared and their viscosity are also determined, respectively. The possible formation mechanism and the reaction conditions of DMC are studied under the assistance of GC-MS, and the yield of DMC is successfully improved. In addition, this new direct synthesis technique is also successfully extended to the synthesis of some other symmetric carbonates, and the yields of three carbonates rised up to more than 60%.
Part ii: The synthesis and the theoretical study on the structure and properties of four monomethine cyanine dyes and one styryl dye.
The application of monomethine cyanine dyes with indole nucleus and styryl dyes in the areas of CD-recording and biological fluorescence detection has been gaining more and more attention all over the world. The density functional theory/time-dependent density functional theory (DFT/TD-DFT) theories, which can accurately predict the molecular structure、electronic spectrum、chromatic mechanism and the non-linear optical property of dyes, has become the most widely used calculation program by the chemists. The molecular structure and the application situation of the two kinds of dyes in this work are briefly introduced. The concepts of DFT/TD-DFT theories and self-consistent reaction field are simply explained. The theoretical research progress of the molecular structure and spectrum properties of the two kinds of dyes are also presented in this paper.
A series of monomethine cyanine dyes with indole nucleus are prepared from indoline and 2-methylthio quinoline quaternary salts in the solvent of anhydride under nitrogen protection. The structures of dyes are confirmed by ~1H NMR, ~(13)C NMR, IR, UV-Vis, MS, and studied by DFT/TD-DFT method, respectively. The absorption of dyes in different solvents is optimized by a muti-linear regression model, and the relative deviation ofλ_(max) is in the range of -0.35%～-5.6%. The frontier orbital distribution analysis shows that the UV-Vis absorption spectrum derives from theπ→π~* transition. In addition, the IR spectrum of one dye was calculated and the results are in good agreement with the experimental value.
A kind of 2-styryl-β-naphthathiazole dye is prepared according to the reported literature and confirmed by X-ray diffraction technique, ~1H NMR, IR, UV-Vis and MS. The crystal structure and the spectrum property of it are studied by theoretical method (DFT/TD-DFT). The result shows that all of the theoretical ways chosen in this work can accurately reproduce the experimental data of this styryl dye.
第一部分离子液体存在下碳酸二甲酯的直接合成及其机理研究
碳酸二甲酯是一种无毒、环保性能优异、用途广泛的化工原料,被誉为21世纪有机合成的“新基石”,市场前景看好,其合成工艺在国内外引起了广泛的关注。
本论文介绍了碳酸二甲酯的基本性质、应用现状以及新合成技术。制备了6种常见离子液体:BmimBr、BmimBF_4、BmimPF_6、PmimBr、PmimBF_4、PmimPF_6,并对其粘度进行了测定。以制备的离子液体为介质,利用甲醇、碳酸钾、二氧化碳等为原料在温和条件下直接合成了碳酸二甲酯,提出了一种温和条件下直接合成碳酸二甲酯的新方法。用气-质联用仪(GC-MS)探索了制备碳酸二甲酯的反应机理、优化了反应条件,使得碳酸二甲酯的产率达到30.8%。同时将该方法推广到其它六种对称碳酸酯的合成,其中有三种碳酸酯产率达到了60%以上。
第二部分一甲川菁、苯乙烯染料的合成及结构与性质的理论研究
近年来,吲哚一甲川菁染料和苯乙烯型染料在光盘存储、生物荧光检测等多种领域的应用引起了人们的广泛关注。运用密度泛函理论(DFT)和含时密度泛函理论(TD-DFT)能够很好地研究染料分子的结构、电子光谱性质、发色机理及非线性光学特性,现已成为当今化学家广泛使用的研究工具之一。
本论文简要介绍了吲哚一甲川菁染料和苯乙烯型染料的结构、应用以及本文理论研究所涉及到的DFT理论、TD-DFT理论和反应场理论,同时对近年来这两类染料分子结构与光谱性质的理论研究进展进行了介绍。利用吲哚啉和2-甲硫基喹啉季铵盐制备了四种吲哚一甲川菁染料、,并用~1H NMR,~(13)C NMR,IR,UV-Vis,MS对染料进行了结构表征。利用TD-DFT方法对吲哚一甲川菁染料的光谱性质进行了研究,并运用多元线性回归模型优化了其在不同溶剂中的吸收性质,其λ_(max)的相对偏差在-0.35%～-5.6%之间。分析了染料分子的前线轨道布居情况,其UV-Vis吸收光谱是源于π→π~*的电子跃迁。研究了一种染料的红外光谱,计算了其谐振频率,与实验值有着很好的一致性。
合成了一种2-苯乙烯基-β-萘噻唑染料,并利用X-射线单晶衍射技术,~1H NMR,IR,UV-Vis,MS进行了结构表征,同时采用DFT理论研究了2-苯乙烯基-β-萘噻唑染料的结构和波谱性质。研究发现,所采用的理论方法均能很好的重现染料分子的实验检测结果。
This paper contains two parts: (i) Research on the synthesis of dimethyl carbonate and its synthetic mechanism in the presence of ionic liquid; (ii) The synthesis and theoretical study on the structure and properties of four monomethine cyanine dyes and one styryl dye.
Part i: Research on the synthesis of dimethyl carbonate and its synthetic mechanism in the presence of ionic liquid.
Dimethyl carbonate is a non-toxic, environmental friendly, and broadly utilized chemical material with great market potential. It is honored as the cornerstone of organic synthesis in the 21st century.
In this paper, the basic property、application situation and new synthesis technology of dimethyl carbonate (DMC) are briefly introduced. A new direct synthesis technique of dimethyl carbonate from methanol、potassium carbonate and carbon dioxide etc. in the presence of ionic liquids under mild conditions is designed in this paper. Six kinds of ionic liquids (BmimBr、BmimBF_4、BmimPF_6、PmimBr、PmimBF_4、PmimPF_6) are prepared and their viscosity are also determined, respectively. The possible formation mechanism and the reaction conditions of DMC are studied under the assistance of GC-MS, and the yield of DMC is successfully improved. In addition, this new direct synthesis technique is also successfully extended to the synthesis of some other symmetric carbonates, and the yields of three carbonates rised up to more than 60%.
Part ii: The synthesis and the theoretical study on the structure and properties of four monomethine cyanine dyes and one styryl dye.
The application of monomethine cyanine dyes with indole nucleus and styryl dyes in the areas of CD-recording and biological fluorescence detection has been gaining more and more attention all over the world. The density functional theory/time-dependent density functional theory (DFT/TD-DFT) theories, which can accurately predict the molecular structure、electronic spectrum、chromatic mechanism and the non-linear optical property of dyes, has become the most widely used calculation program by the chemists. The molecular structure and the application situation of the two kinds of dyes in this work are briefly introduced. The concepts of DFT/TD-DFT theories and self-consistent reaction field are simply explained. The theoretical research progress of the molecular structure and spectrum properties of the two kinds of dyes are also presented in this paper.
A series of monomethine cyanine dyes with indole nucleus are prepared from indoline and 2-methylthio quinoline quaternary salts in the solvent of anhydride under nitrogen protection. The structures of dyes are confirmed by ~1H NMR, ~(13)C NMR, IR, UV-Vis, MS, and studied by DFT/TD-DFT method, respectively. The absorption of dyes in different solvents is optimized by a muti-linear regression model, and the relative deviation ofλ_(max) is in the range of -0.35%～-5.6%. The frontier orbital distribution analysis shows that the UV-Vis absorption spectrum derives from theπ→π~* transition. In addition, the IR spectrum of one dye was calculated and the results are in good agreement with the experimental value.
A kind of 2-styryl-β-naphthathiazole dye is prepared according to the reported literature and confirmed by X-ray diffraction technique, ~1H NMR, IR, UV-Vis and MS. The crystal structure and the spectrum property of it are studied by theoretical method (DFT/TD-DFT). The result shows that all of the theoretical ways chosen in this work can accurately reproduce the experimental data of this styryl dye.
引文
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