偶氮分子为连接臂的金属离子探针的设计、合成及光学性质研究
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摘要
本论文以偶氮苯为母体,在其两端连接不同的识别基团和荧光团,得到了一系列性质各异的金属离子探针,用荧光光谱和紫外光谱研究了这类探针对不同金属离子的识别能力。
在连接臂上分别引入O、N和S原子等作为识别基团,合成了侧链中不含荧光团的偶氮类化合物,测定了在紫外光照射下金属离子对光致异构化的影响。发现侧链基团的给电子能力越强,达到异构化平衡的时间越长,顺式异构体的比例也越大。同时发现一种对Cu~(2+)有紫外响应的偶氮化合物,通过研究其紫外和荧光光谱变化,证实该化合物与Cu~(2+)络合形成1:2的络合物。
当偶氮苯两侧为9-蒽甲硫基时,得到了一类Hg~(2+)荧光增强型探针,该类探针为典型的PET荧光探针。在该体系中,除了S原子参与的PET过程外,还首次发现了偶氮分子的共轭π电子体系参与的PET过程。基于此机理,我们设计合成了以二甲胺基为供电基的含蒽的荧光探针,研究证明,后者不仅对Hg~(2+)的识别具有专一性和高灵敏性,而且加入Hg~(2+)后紫外光谱发生明显红移,颜色由黄色变成红色。
以萘为荧光团时,分别用含S和N原子的侧链连接,得到了完全不同的识别效果。当侧链为亚丙二硫基连接时,得到的偶氮化合物对Cu~(2+)有专一性识别作用,且连接位置的改变对识别能力有很大的影响。我们用GAUSSIAN 03程序计算了该类化合物与Cu~(2+)的配位结构,发现偶氮分子中的N原子和侧链上的S原子都参与了配位,与Cu~(2+)形成1:1络合物,通过荧光滴定实验证实了该推论的正确性。以N原子代替S原子时,得到的偶氮类化合物对金属离子没有明显的选择性识别,同样以计算化学手段研究了这种识别能力的差异性,为今后设计合成荧光探针提供了理论基础。
A series of novel fluorescent probes for metal ions with different receptors were designed and synthesized based on the azobenzene.
The UV-visible and fluorescence properties of azobenzene derivatives with non-fluorescent groups in the receptors were investigated. O, N and S atoms were introduced into the receptors respectively as a ligand of metal ions. The cis/trans ratios of these compounds under irradiation of a high-pressure Hg-lamp equipped with a color filter (λ<360 nm), as well as and the effects of metal ions on photoisomerization were studied. The probe A6 was designed to exhibit selectivity to Cu~(2+).
Two novel fluorescent probes (C1 and C2) with a receptor containing anthracene group were designed and synthesized for recognition of heavy metal ions. It was found that C1 and C2 show a pronounced fluorescence enhancement response to Hg~(2+), respectively. Theπelectrons of the azobenzene probes exhibit photoinduced electron transfer (PET) effects to the fluorescent anthracene group as well as atom S, which was firstly reported in this paper. C4 was designed based on the above studies and it has higher selectivity to Hg~(2+) than C1 and C2.
The naphthyl group was also introduced to the azobenzene derivatives connected with 1,3-bis(methylthio)propane and N,N’-dimethylpropane-1,3-diamine, respectively. The fluorescent probe E2 show fluorescence enhancement response to Cu~(2+). The mechanism of this selectivity was proposed with the aid of computational chemistry (program of GAUSSIAN 03).
在连接臂上分别引入O、N和S原子等作为识别基团,合成了侧链中不含荧光团的偶氮类化合物,测定了在紫外光照射下金属离子对光致异构化的影响。发现侧链基团的给电子能力越强,达到异构化平衡的时间越长,顺式异构体的比例也越大。同时发现一种对Cu~(2+)有紫外响应的偶氮化合物,通过研究其紫外和荧光光谱变化,证实该化合物与Cu~(2+)络合形成1:2的络合物。
当偶氮苯两侧为9-蒽甲硫基时,得到了一类Hg~(2+)荧光增强型探针,该类探针为典型的PET荧光探针。在该体系中,除了S原子参与的PET过程外,还首次发现了偶氮分子的共轭π电子体系参与的PET过程。基于此机理,我们设计合成了以二甲胺基为供电基的含蒽的荧光探针,研究证明,后者不仅对Hg~(2+)的识别具有专一性和高灵敏性,而且加入Hg~(2+)后紫外光谱发生明显红移,颜色由黄色变成红色。
以萘为荧光团时,分别用含S和N原子的侧链连接,得到了完全不同的识别效果。当侧链为亚丙二硫基连接时,得到的偶氮化合物对Cu~(2+)有专一性识别作用,且连接位置的改变对识别能力有很大的影响。我们用GAUSSIAN 03程序计算了该类化合物与Cu~(2+)的配位结构,发现偶氮分子中的N原子和侧链上的S原子都参与了配位,与Cu~(2+)形成1:1络合物,通过荧光滴定实验证实了该推论的正确性。以N原子代替S原子时,得到的偶氮类化合物对金属离子没有明显的选择性识别,同样以计算化学手段研究了这种识别能力的差异性,为今后设计合成荧光探针提供了理论基础。
A series of novel fluorescent probes for metal ions with different receptors were designed and synthesized based on the azobenzene.
The UV-visible and fluorescence properties of azobenzene derivatives with non-fluorescent groups in the receptors were investigated. O, N and S atoms were introduced into the receptors respectively as a ligand of metal ions. The cis/trans ratios of these compounds under irradiation of a high-pressure Hg-lamp equipped with a color filter (λ<360 nm), as well as and the effects of metal ions on photoisomerization were studied. The probe A6 was designed to exhibit selectivity to Cu~(2+).
Two novel fluorescent probes (C1 and C2) with a receptor containing anthracene group were designed and synthesized for recognition of heavy metal ions. It was found that C1 and C2 show a pronounced fluorescence enhancement response to Hg~(2+), respectively. Theπelectrons of the azobenzene probes exhibit photoinduced electron transfer (PET) effects to the fluorescent anthracene group as well as atom S, which was firstly reported in this paper. C4 was designed based on the above studies and it has higher selectivity to Hg~(2+) than C1 and C2.
The naphthyl group was also introduced to the azobenzene derivatives connected with 1,3-bis(methylthio)propane and N,N’-dimethylpropane-1,3-diamine, respectively. The fluorescent probe E2 show fluorescence enhancement response to Cu~(2+). The mechanism of this selectivity was proposed with the aid of computational chemistry (program of GAUSSIAN 03).
引文
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