稠环芳烃分子与单壁碳纳米管之间的相互作用
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摘要
本文主要研究了不同的稠环芳烃分子对碳纳米管的非共价修饰,重点考察了稠环芳烃分子的结构对两者相互作用的影响,探讨了相互作用的机理,并借助稠环芳烃分子对不同碳纳米管的识别能力对手性碳纳米管的对映异构体拆分进行了尝试。主要内容如下:
1.本文首先研究了一系列含有稠杂环芳烃化合物与碳纳米管的非共价相互作用,发现杂原子对稠杂环芳香分子在碳管上的吸附存在一定的调控作用。吸附量数据表明无论氮原子以杂原子还是氨基的形式存在的时候对稠环分子和碳管之间的相互作用都是有利的,而氧原子和硫原子作为杂原子引入稠环结构中的时候对染料分子的吸附是不利的。这对与选择适用于碳纳米管非共价修饰的稠环分子提供了指导意义。
2.本文采用荧光滴定与时间分辨荧光技术对碳纳米管淬灭稠环分子荧光的机理进行了研究。时间分辨荧光光谱技术揭示染料分子吸附在碳纳米管后的荧光淬灭现象是一个静态淬灭的过程,即染料分子与碳纳米管形成了不发光的复合物。这一结果对设计含碳纳米管的有机光电器件有指导意义。
3.在以上研究的基础上,本文尝试了用手性稠环芳香分子对手性碳纳米管的对映异构体进行拆分。我们的实验结果表明,简单的手性稠环芳香分子联二萘酚的拆分效率很低。这可能与手性联二萘酚中萘环分支结构的共轭程度比较小以及萘环之间的有一定的旋转自由度有关。这一研究结果为今后的分子设计中提供了新的思路。
This work aimed at understanding the interactions between polycyclic aromatic molecules and single walled carbon nanotubes (SWNTs). Effects of polycyclic aromatic molecules' structure on the molecule/SWNT interaction were investigated and the mechnism that underlying were discussed. Additionally, attempts were made to separate the enatiomers of SWCNTs using chiral polycyclic aromatic molecules. The main findings of the work are:
1. The non-covalent functionalization of SWNTs using a series of polycyclic aromatic molecules containing hetero atoms were studied. The adsorption ratio data revealed that N atom, either in the form of hetero atom or amino group, improved the adsorption affinity between the molecules and the SWNTs. In contrast, the existences of O or S hetero atom in the framework were found to decrease the adsorption affinity. This finding provides useful information for the future selection of aromatic molecules for SWNT modification.
2. Fluorescence titration and time-resolved fluorescence measurements were performed to investigated the mechanism of SWNT induced fluorescence quenching of the aromatic molecules. Fluorescence lifetime decays exhibit no obvious change upon addition of different amount of SWNTs, which reveals that the static quenching mechanism is dominate in such molecule/SWNT systems. The understanding of the fluorescence quenching mechanism may help to design novel photoelectronic based on SWNT/molecule complex.
3. Attempt have been made to solve the challenge of separating SWNT enatiomers using chiral polycyclic aromatic molecules.. Our preliminary results showed chiral BINOL exhibited low efficient in separating SWNT enatiomers, which is attributed to the low conjugation of naphthalene rings and their easy rotation in solution. These factors should be considered in the future optimization of the separating molecules.
1.本文首先研究了一系列含有稠杂环芳烃化合物与碳纳米管的非共价相互作用,发现杂原子对稠杂环芳香分子在碳管上的吸附存在一定的调控作用。吸附量数据表明无论氮原子以杂原子还是氨基的形式存在的时候对稠环分子和碳管之间的相互作用都是有利的,而氧原子和硫原子作为杂原子引入稠环结构中的时候对染料分子的吸附是不利的。这对与选择适用于碳纳米管非共价修饰的稠环分子提供了指导意义。
2.本文采用荧光滴定与时间分辨荧光技术对碳纳米管淬灭稠环分子荧光的机理进行了研究。时间分辨荧光光谱技术揭示染料分子吸附在碳纳米管后的荧光淬灭现象是一个静态淬灭的过程,即染料分子与碳纳米管形成了不发光的复合物。这一结果对设计含碳纳米管的有机光电器件有指导意义。
3.在以上研究的基础上,本文尝试了用手性稠环芳香分子对手性碳纳米管的对映异构体进行拆分。我们的实验结果表明,简单的手性稠环芳香分子联二萘酚的拆分效率很低。这可能与手性联二萘酚中萘环分支结构的共轭程度比较小以及萘环之间的有一定的旋转自由度有关。这一研究结果为今后的分子设计中提供了新的思路。
This work aimed at understanding the interactions between polycyclic aromatic molecules and single walled carbon nanotubes (SWNTs). Effects of polycyclic aromatic molecules' structure on the molecule/SWNT interaction were investigated and the mechnism that underlying were discussed. Additionally, attempts were made to separate the enatiomers of SWCNTs using chiral polycyclic aromatic molecules. The main findings of the work are:
1. The non-covalent functionalization of SWNTs using a series of polycyclic aromatic molecules containing hetero atoms were studied. The adsorption ratio data revealed that N atom, either in the form of hetero atom or amino group, improved the adsorption affinity between the molecules and the SWNTs. In contrast, the existences of O or S hetero atom in the framework were found to decrease the adsorption affinity. This finding provides useful information for the future selection of aromatic molecules for SWNT modification.
2. Fluorescence titration and time-resolved fluorescence measurements were performed to investigated the mechanism of SWNT induced fluorescence quenching of the aromatic molecules. Fluorescence lifetime decays exhibit no obvious change upon addition of different amount of SWNTs, which reveals that the static quenching mechanism is dominate in such molecule/SWNT systems. The understanding of the fluorescence quenching mechanism may help to design novel photoelectronic based on SWNT/molecule complex.
3. Attempt have been made to solve the challenge of separating SWNT enatiomers using chiral polycyclic aromatic molecules.. Our preliminary results showed chiral BINOL exhibited low efficient in separating SWNT enatiomers, which is attributed to the low conjugation of naphthalene rings and their easy rotation in solution. These factors should be considered in the future optimization of the separating molecules.
引文
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