有机锌试剂新型反应的研究有机染料分子的设计与合成
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摘要
本论文主要有两部分构成,前半部分主要工作是对有机锌试剂新反应的研究,考察有机锌试剂在这些反应中的适用性,以扩展有机锌试剂在有机合成中的应用范围。有机锌试剂是一类优良的有机金属试剂,由于反应活性较低,很多活性官能团都可以存在于这类金属试剂中。后半部分主要的工作是新型米氏酮类有机染料分子的设计与合成。
在第一章中对官能团化的有机锌试剂的发展做了简要的介绍,然后对主要的就官能团化的有机锌试剂的制备以及在有机合成中的应用选择了一些有应用价值和理论意义的制备方法和反应类型做了详细的综述。
在第二章中,我们开发了一种新的有机锌试剂对β-羰基酯化合物进行扩环或者碳链增长反应的方法.有机锌试剂(Et_2Zn)在CF_3COOH的存在下,然后跟CH_2I_2反应,制备出CF_3COOZnCH_2I,该试剂可与β-羰基酯化合物进行反应得到中等产率到高产率的γ-羰基酯化合物。通过这些研究,我们扩展了有机锌试剂的应用范围,提供了高产率的合成γ-羰基酯化合物的有效方法
在第三章中,我们研究了有机锌试剂在Baylis-Hillman类型反应中的应用。有机锌试剂CF_3COOZnEt可以与各种类型的α,β-炔酮及亚胺发生偶联反应,高产率的得到β-取代的Morita-Baylis-Hillman反应加合物,这类反应不需要任何的催化剂,产物具有立体单一型,完全是Z式结构。我们发展了一种新型的Morita-Baylis-Hillman类型反应,,利用这种反应高产率合成了立体单一的多官能团化的烯烃。
在第四章中首先概述了染料敏化太阳能电池(DSC)的最新研究进展,并对其的结构和工作基本原理进行介绍,目前,有机染料分子大部分都是D-π-A结构,我们按照这样的结构设计和合成出六种新型米氏酮-氰基类有机染料分子,该类染料是由米氏酮衍生而来的,合成步骤短,工艺简单。本染料分子具有两个含氮基团,即双供电基团的结构特点,易发生氧化和还原反应,有更强的给电子能力和更快从电解质中捕获电子的能力,因此我们提供了一类新型高效光敏化剂的有机染料分子的合成路线和合成方法。
This thesis is made up of two sections,The goal of the first section is to study the new reaction of organozinc reagents and applicability of it in the organic reaction.The second section reported the synthesis of organic dyes.The thesis includes four chapters.
Chapter one:in this section,a brief introduction of the development of polyfunctional organozinc regents was given,and then reviewed the preparation and reaction of organozinc regent.
Chapter two:We treat CF_3CO_2ZnCH_2I With cyclicβ-keto esters can afford the corresponding ring-expanded products in moderate to good yields.Althoughα-substituted acyclicβ-keto esters reacted with much less efficient,chain-extension reaction of simpleβ-keto esters also proceeded effectively to generateγ-keto esters in high yields.Through this research,we extended the appliacation of organozinc reagents in organic synthesis.
In chapter three,we investigated a new Baylis-Hillman-type reaction,organozinc speciesCF_3COOZnEt can react withα,β-acetylenic ketones and N-tosylated imines providing Baylis-Hillman adducts in good yield in the absence of any catalysts.A high Z-stereoselectivity was achieved.
In chapter four,we introduce the structure and the principle of dye-sensitized solar cells(DSC).The latest results about research on dye-sensitized solar cells are reviewed.So far,most of the organic dyes applied in DSSCs belong to typical D-π-A structures with both electron donor(D)and electron acceptor(A)linked by aπ-conjugation bridge.According to this structure,the novel conjugated organic dyes that have N,N-dimethylaniline(DMA)moieties as the electron donor and a cyanoacetic acid(CAA)moiety as the electron acceptor were synthesized for DSSCs. The organic dye molecules with two nitrogen groups,are prone to oxidation and reduction,they also have a stronger capacity for providing electronic and faster ability to capture electronic from the electrolyte.Therefore we offered a new type synthesis methods of high efficient photosensitive organic dye molecules.
在第一章中对官能团化的有机锌试剂的发展做了简要的介绍,然后对主要的就官能团化的有机锌试剂的制备以及在有机合成中的应用选择了一些有应用价值和理论意义的制备方法和反应类型做了详细的综述。
在第二章中,我们开发了一种新的有机锌试剂对β-羰基酯化合物进行扩环或者碳链增长反应的方法.有机锌试剂(Et_2Zn)在CF_3COOH的存在下,然后跟CH_2I_2反应,制备出CF_3COOZnCH_2I,该试剂可与β-羰基酯化合物进行反应得到中等产率到高产率的γ-羰基酯化合物。通过这些研究,我们扩展了有机锌试剂的应用范围,提供了高产率的合成γ-羰基酯化合物的有效方法
在第三章中,我们研究了有机锌试剂在Baylis-Hillman类型反应中的应用。有机锌试剂CF_3COOZnEt可以与各种类型的α,β-炔酮及亚胺发生偶联反应,高产率的得到β-取代的Morita-Baylis-Hillman反应加合物,这类反应不需要任何的催化剂,产物具有立体单一型,完全是Z式结构。我们发展了一种新型的Morita-Baylis-Hillman类型反应,,利用这种反应高产率合成了立体单一的多官能团化的烯烃。
在第四章中首先概述了染料敏化太阳能电池(DSC)的最新研究进展,并对其的结构和工作基本原理进行介绍,目前,有机染料分子大部分都是D-π-A结构,我们按照这样的结构设计和合成出六种新型米氏酮-氰基类有机染料分子,该类染料是由米氏酮衍生而来的,合成步骤短,工艺简单。本染料分子具有两个含氮基团,即双供电基团的结构特点,易发生氧化和还原反应,有更强的给电子能力和更快从电解质中捕获电子的能力,因此我们提供了一类新型高效光敏化剂的有机染料分子的合成路线和合成方法。
This thesis is made up of two sections,The goal of the first section is to study the new reaction of organozinc reagents and applicability of it in the organic reaction.The second section reported the synthesis of organic dyes.The thesis includes four chapters.
Chapter one:in this section,a brief introduction of the development of polyfunctional organozinc regents was given,and then reviewed the preparation and reaction of organozinc regent.
Chapter two:We treat CF_3CO_2ZnCH_2I With cyclicβ-keto esters can afford the corresponding ring-expanded products in moderate to good yields.Althoughα-substituted acyclicβ-keto esters reacted with much less efficient,chain-extension reaction of simpleβ-keto esters also proceeded effectively to generateγ-keto esters in high yields.Through this research,we extended the appliacation of organozinc reagents in organic synthesis.
In chapter three,we investigated a new Baylis-Hillman-type reaction,organozinc speciesCF_3COOZnEt can react withα,β-acetylenic ketones and N-tosylated imines providing Baylis-Hillman adducts in good yield in the absence of any catalysts.A high Z-stereoselectivity was achieved.
In chapter four,we introduce the structure and the principle of dye-sensitized solar cells(DSC).The latest results about research on dye-sensitized solar cells are reviewed.So far,most of the organic dyes applied in DSSCs belong to typical D-π-A structures with both electron donor(D)and electron acceptor(A)linked by aπ-conjugation bridge.According to this structure,the novel conjugated organic dyes that have N,N-dimethylaniline(DMA)moieties as the electron donor and a cyanoacetic acid(CAA)moiety as the electron acceptor were synthesized for DSSCs. The organic dye molecules with two nitrogen groups,are prone to oxidation and reduction,they also have a stronger capacity for providing electronic and faster ability to capture electronic from the electrolyte.Therefore we offered a new type synthesis methods of high efficient photosensitive organic dye molecules.
引文
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