“核—壳”结构分子线的合成及性质研究
摘要
本论文主要研究了“核-壳”结构分子线的合成与性质表征，以及新颖全脂肪链树状物的合成，同时也进行了二酰基哌嗪衍生物的合成及抗癌活性研究．论文共分为三章：
首先综述了分子线的研究进展，概述了分子线在纳米技术及分子电子学领域的重要作用，总结了近年来各类有机分子线的合成及性质测量技术进展．
第2章中详细介绍了“核-壳”结构分子线以及新颖全脂肪链树状物的合成．首先以Sonogashira偶联反应为关键步骤，将连有树状物“壳”的二碘代芳烃与4-乙炔基乙酰苯硫酚相接，合成了以零级、一级、二级树状物为“壳”的“核-壳”结构OPEs[oligo(1，4-phenylene ethynylene)s]分子线，以及三个小取代基的OPE分子线．用紫外和荧光谱证明了“核-壳”结构OPE的树状物效应，树状物能减小OPE间的π-π相互作用．用电化学的方法证明这些分子能组装在Au表面，可进行进一步的性质研究．用类似的策略，以Wittig反应为关键步骤合成了以零级、一级树状物为“壳”的“核一壳”结构OPVs[oligo(1，4-phenylene vinylene)s]分子线，端基为甲硫基．这两类分子线都含有两个巯基端基可连在两个金属电极上，树状物的“壳”不仅能减小分子线间的相互作用，而且通过控制级数来精确控制分子线组装时的间距，进而控制电导．随之，经过对多条合成路线的探索，找到了一条快速高效合成全脂肪链树状物的方法，以格氏试剂与酯加成反应为关键步骤，再经脱羟基、氢化等反应合成了一、二、三级的全脂肪链树状物．本章介绍的三级树状物合成路线比文献中类似的三级树状物合成步骤缩短了7步，适于大量制备样品．全脂肪链树状物的合成本身不仅是有机合成新路线的拓展，而且为今后合成“壳”更为绝缘的“核-壳”结构分子线打下了基础．
第3章详细介绍了一系列共十六个二酰基哌嗪衍生物的合成，以及它们对HL-60、Bel-7402和BGC-823的抗癌活性研究，分析归纳了取代基效应对其生物活性的影响．
This thesis is concerned with the studies on the synthesis of "core-shells" molecular wires and their electronic properties, and the synthesis of the aliphatic dendrimers. Additionally, sixteen novel N,N-diacylpiperazine derivatives were synthesized and evaluated as potential antitumor agents. It mainly consists of the following three parts:
First, we summarized the importance of the molecular wires in nanotechnology and molecular electronics, and the recent development of the synthesis and measurement of organic molecular wires.
In chapter 2, a series of oligo(phenylene ethynylene)s (OPEs) and two oligo(phenylene vinylene)s (OPVs) with different dendrimer side groups have been designed and synthesized. The key steps involved the Sonogashira and Wittig reaction respectively. The molecules contain thiol groups at both ends to enable interconnection between nanoscale gapped metallic electrodes. The different dendrimer groups act as "shells", allowing tailoring to the nanoscopic environment surrounding the OPE or OPV "core". Meanwhile, the dendrimer shells also act as spacers for the precise control of the packing density and intermolecular interaction between the OPE or OPV cores. In addition, novel aliphatic dendrimers were designed and synthesized by shorter synthesis route than that of literature. The key steps involved the addition of Grignard reagents to the suitable esters, dehydroxy group and reduction reaction. These dendrimers can be used to the synthesis of "core-shells" molecular wires with more insulating "shell".
In chapter 3, a series of N,N-diacylpiperazine derivatives were prepared and were evaluated for anticancer activity. Most of the compounds showed a moderate degree of anticancer activity for HL-60, BGC-823 and Bel-7402.
首先综述了分子线的研究进展，概述了分子线在纳米技术及分子电子学领域的重要作用，总结了近年来各类有机分子线的合成及性质测量技术进展．
第2章中详细介绍了“核-壳”结构分子线以及新颖全脂肪链树状物的合成．首先以Sonogashira偶联反应为关键步骤，将连有树状物“壳”的二碘代芳烃与4-乙炔基乙酰苯硫酚相接，合成了以零级、一级、二级树状物为“壳”的“核-壳”结构OPEs[oligo(1，4-phenylene ethynylene)s]分子线，以及三个小取代基的OPE分子线．用紫外和荧光谱证明了“核-壳”结构OPE的树状物效应，树状物能减小OPE间的π-π相互作用．用电化学的方法证明这些分子能组装在Au表面，可进行进一步的性质研究．用类似的策略，以Wittig反应为关键步骤合成了以零级、一级树状物为“壳”的“核一壳”结构OPVs[oligo(1，4-phenylene vinylene)s]分子线，端基为甲硫基．这两类分子线都含有两个巯基端基可连在两个金属电极上，树状物的“壳”不仅能减小分子线间的相互作用，而且通过控制级数来精确控制分子线组装时的间距，进而控制电导．随之，经过对多条合成路线的探索，找到了一条快速高效合成全脂肪链树状物的方法，以格氏试剂与酯加成反应为关键步骤，再经脱羟基、氢化等反应合成了一、二、三级的全脂肪链树状物．本章介绍的三级树状物合成路线比文献中类似的三级树状物合成步骤缩短了7步，适于大量制备样品．全脂肪链树状物的合成本身不仅是有机合成新路线的拓展，而且为今后合成“壳”更为绝缘的“核-壳”结构分子线打下了基础．
第3章详细介绍了一系列共十六个二酰基哌嗪衍生物的合成，以及它们对HL-60、Bel-7402和BGC-823的抗癌活性研究，分析归纳了取代基效应对其生物活性的影响．
This thesis is concerned with the studies on the synthesis of "core-shells" molecular wires and their electronic properties, and the synthesis of the aliphatic dendrimers. Additionally, sixteen novel N,N-diacylpiperazine derivatives were synthesized and evaluated as potential antitumor agents. It mainly consists of the following three parts:
First, we summarized the importance of the molecular wires in nanotechnology and molecular electronics, and the recent development of the synthesis and measurement of organic molecular wires.
In chapter 2, a series of oligo(phenylene ethynylene)s (OPEs) and two oligo(phenylene vinylene)s (OPVs) with different dendrimer side groups have been designed and synthesized. The key steps involved the Sonogashira and Wittig reaction respectively. The molecules contain thiol groups at both ends to enable interconnection between nanoscale gapped metallic electrodes. The different dendrimer groups act as "shells", allowing tailoring to the nanoscopic environment surrounding the OPE or OPV "core". Meanwhile, the dendrimer shells also act as spacers for the precise control of the packing density and intermolecular interaction between the OPE or OPV cores. In addition, novel aliphatic dendrimers were designed and synthesized by shorter synthesis route than that of literature. The key steps involved the addition of Grignard reagents to the suitable esters, dehydroxy group and reduction reaction. These dendrimers can be used to the synthesis of "core-shells" molecular wires with more insulating "shell".
In chapter 3, a series of N,N-diacylpiperazine derivatives were prepared and were evaluated for anticancer activity. Most of the compounds showed a moderate degree of anticancer activity for HL-60, BGC-823 and Bel-7402.
引文
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