芳脒类超分子和氮杂β-二亚胺化合物的合成及碳氮键裂分机理的研究
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摘要
在社会发展的过程中,随着人们对各种材料性能需求的不断提升及其有关化学新现象的呈现,推动着材料化学理论与应用的研究不断向着更高的层次深入。利用超分子化学体系的理论设计合成的功能性材料,因其性能独特且优良实用的特征满足了社会的需求,同时解决了人们在化学发展中的新问题,成为了21世纪科技发展的重点领域之一。作为该领域的重要分支,近些年来离子型超分子聚合结构材料和有机金属配合物的研究发展的很快。本文设计合成了一些芳脒基碳正离子和不同的负离子结合生成的离子型超分子聚合物,以及与其相关的有机化合物,在测定其结构的基础上,检测了部分化合物的荧光性能。
论文的研究工作建立在课题组以往的理论和实验的基础上,设计了芳基腈和不同的烷基胺基锂盐进行反应,得到了10个化合物,用X-ray单晶衍射分析测定了化合物2a,2b,2c,2d,3a,3b的结构,并用NMR、IR、ESI-MS进行了详细的表征。对化合物2e,2f,2g,2h进行了ESI-MS分析。论文主要可分为四部分。
第一部分：概括介绍了超分子化学和功能性材料的理论以及国内外研究发展状况,介绍了碳氮键的裂分反应和当前的研究进展。
第二部分：以2-甲基苯基腈、4-吡啶腈、2-硝基苯腈、苯甲腈为原料、与不同的烷基胺锂进行加成反应,在此基础上与金属氯化盐或一氯化二苯基膦进行置换反应,接着用双氧水氧化,合成了6个化合物2a,2b,2c,2d,2e,2f,2g,2h其中2a,2c为芳脒类离子型超分子,2b,2d为有机化合物。通过表征发现在形成化合物2a；2b,2c的过程中,有碳氮键裂分的现象。为探讨这一现象的原因,合成并分析了四种化合物2e,2f,2g,2h,对反应过程中所发生的碳氮键的裂分反应进行了着重的阐述和推测。对芳脒类离子型超分子2a,2c进行了荧光性质分析。
第三部分：以4-吡啶腈,4-硝基苯甲腈与不同的烷基胺锂反应后,再与一氯二苯基膦反应,暴露在空气中氧化得到了氮杂p-二亚胺离子型超分子聚合物3a,进一步证明了氮杂β-二亚胺是可以稳定存在的骨架；用双氧水氧化得到了N-P键未发生氧化裂分的氮杂p-二亚胺化合物,并对化合物3a,3b进行了结构测定和详细表征,探讨了其生成的机理。
第四部分：通过对前三部分的回顾总结,在分析有关碳氮键的裂分机理的基础上,设计了氧化剂影响氮磷键和碳氮键裂分反应的验证方法。展望了合成更好的芳脒基类离子型超分子荧光材料和氮杂β-二亚胺与金属离子配位所生成的化合物在催化领域的潜在价值。
化合物2a,2b,2c,2d,3a,3b的结构,经NMR、IR、ESI-MS和X-ray单晶衍射确证。化合物2e,2f,2g,2h经ESI-MS检测。其中,2a,2c,3a,3b这4种化合物为未见文献报道的新化合物。
In the process of human development, the theoretical research and application of material science towards a higher horizontal by the increasing needs to various of material properties and the appearance of new chemical phenomena. The functional materials based on the principle of supramolecular chemistry because of its unique characteristics of high performance meet the practical needs, which solves the new problems in chemical development and is one of the important of science and technology in 21st century. Ionic supramolecular polymeric structure material and organic metal complexes, as one of the branch, were developed quickly in recent years. In the thesis, we designed and synthesized several charge assisted hydrogen bond supramolecular polymeric compounds composed by benzamidine carbocation with various of anions. Structural characterization and fluorescence properties of them were determined.
Ten compounds by reactingα-hydrogen-free aryl nitriles with different alkyl amino lithium have been prepared. The molecular structures of compounds 2a,2c, 2d,2b,3a were determined by X-ray crystallography and confirmed by IR, NMR ESI-MS. Compounds 2e,2f,2g,2h were examined by ESI-MS. The main contents are divided into four sections.
Part I:The latest development of supramolecular chemistry and functional materials was introduced. What's more, the recent development of cleavage reaction about carbon nitrogen bonds was given.
Part II:The compounds of 2a,2b,2c,2d,2e,2f,2g,2h were synthesized by treatment of R2NLi(R=Me,Et) witha-hydrogen-free aryl nitriles, followed the metatheses of chlorodiphenylphosphine or metal chlorides and oxidizing by hydrogen peroxide,2a,2c belongs to benzamidine Ionic supramolecular polymerization,2b,2d were organic compounds. The cleavage phenomenon about C-N bond was found and the mechanism was proposed by the synthesis 2e,2f,2g and 2h. The fluorescence properties of 2a,2c were measured.
Part III:Two azaβ-diimine compounds have been prepared by 4-cyanopyridine and 4-nitrobenzonitrile reacting with R.2NLi(R=Me,Et) and chlorodiphenylphosphine. Azaβ-diimine charge assisted hydrogen bond supramolecular polymeric compound 3a was synthesized by exposing in air,while N-P bond cleavage reaction have been not observed in the 3b.The results demonstrated that azaβ-diimine was a stable skeleton and compounds structure were detailed characterized by X-ray crystallography, IR, NMR,ESI-MS.
Part IV:The contents of research were summarized. The experimental design about the influence of oxidant in C-N bond cleavage process was submitted. The application of these compounds in materials chemistry was viewed.
论文的研究工作建立在课题组以往的理论和实验的基础上,设计了芳基腈和不同的烷基胺基锂盐进行反应,得到了10个化合物,用X-ray单晶衍射分析测定了化合物2a,2b,2c,2d,3a,3b的结构,并用NMR、IR、ESI-MS进行了详细的表征。对化合物2e,2f,2g,2h进行了ESI-MS分析。论文主要可分为四部分。
第一部分：概括介绍了超分子化学和功能性材料的理论以及国内外研究发展状况,介绍了碳氮键的裂分反应和当前的研究进展。
第二部分：以2-甲基苯基腈、4-吡啶腈、2-硝基苯腈、苯甲腈为原料、与不同的烷基胺锂进行加成反应,在此基础上与金属氯化盐或一氯化二苯基膦进行置换反应,接着用双氧水氧化,合成了6个化合物2a,2b,2c,2d,2e,2f,2g,2h其中2a,2c为芳脒类离子型超分子,2b,2d为有机化合物。通过表征发现在形成化合物2a；2b,2c的过程中,有碳氮键裂分的现象。为探讨这一现象的原因,合成并分析了四种化合物2e,2f,2g,2h,对反应过程中所发生的碳氮键的裂分反应进行了着重的阐述和推测。对芳脒类离子型超分子2a,2c进行了荧光性质分析。
第三部分：以4-吡啶腈,4-硝基苯甲腈与不同的烷基胺锂反应后,再与一氯二苯基膦反应,暴露在空气中氧化得到了氮杂p-二亚胺离子型超分子聚合物3a,进一步证明了氮杂β-二亚胺是可以稳定存在的骨架；用双氧水氧化得到了N-P键未发生氧化裂分的氮杂p-二亚胺化合物,并对化合物3a,3b进行了结构测定和详细表征,探讨了其生成的机理。
第四部分：通过对前三部分的回顾总结,在分析有关碳氮键的裂分机理的基础上,设计了氧化剂影响氮磷键和碳氮键裂分反应的验证方法。展望了合成更好的芳脒基类离子型超分子荧光材料和氮杂β-二亚胺与金属离子配位所生成的化合物在催化领域的潜在价值。
化合物2a,2b,2c,2d,3a,3b的结构,经NMR、IR、ESI-MS和X-ray单晶衍射确证。化合物2e,2f,2g,2h经ESI-MS检测。其中,2a,2c,3a,3b这4种化合物为未见文献报道的新化合物。
In the process of human development, the theoretical research and application of material science towards a higher horizontal by the increasing needs to various of material properties and the appearance of new chemical phenomena. The functional materials based on the principle of supramolecular chemistry because of its unique characteristics of high performance meet the practical needs, which solves the new problems in chemical development and is one of the important of science and technology in 21st century. Ionic supramolecular polymeric structure material and organic metal complexes, as one of the branch, were developed quickly in recent years. In the thesis, we designed and synthesized several charge assisted hydrogen bond supramolecular polymeric compounds composed by benzamidine carbocation with various of anions. Structural characterization and fluorescence properties of them were determined.
Ten compounds by reactingα-hydrogen-free aryl nitriles with different alkyl amino lithium have been prepared. The molecular structures of compounds 2a,2c, 2d,2b,3a were determined by X-ray crystallography and confirmed by IR, NMR ESI-MS. Compounds 2e,2f,2g,2h were examined by ESI-MS. The main contents are divided into four sections.
Part I:The latest development of supramolecular chemistry and functional materials was introduced. What's more, the recent development of cleavage reaction about carbon nitrogen bonds was given.
Part II:The compounds of 2a,2b,2c,2d,2e,2f,2g,2h were synthesized by treatment of R2NLi(R=Me,Et) witha-hydrogen-free aryl nitriles, followed the metatheses of chlorodiphenylphosphine or metal chlorides and oxidizing by hydrogen peroxide,2a,2c belongs to benzamidine Ionic supramolecular polymerization,2b,2d were organic compounds. The cleavage phenomenon about C-N bond was found and the mechanism was proposed by the synthesis 2e,2f,2g and 2h. The fluorescence properties of 2a,2c were measured.
Part III:Two azaβ-diimine compounds have been prepared by 4-cyanopyridine and 4-nitrobenzonitrile reacting with R.2NLi(R=Me,Et) and chlorodiphenylphosphine. Azaβ-diimine charge assisted hydrogen bond supramolecular polymeric compound 3a was synthesized by exposing in air,while N-P bond cleavage reaction have been not observed in the 3b.The results demonstrated that azaβ-diimine was a stable skeleton and compounds structure were detailed characterized by X-ray crystallography, IR, NMR,ESI-MS.
Part IV:The contents of research were summarized. The experimental design about the influence of oxidant in C-N bond cleavage process was submitted. The application of these compounds in materials chemistry was viewed.
引文
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