含蒽荧光团金属离子探针的设计、合成及性能研究
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摘要
荧光分子开关作为超分子化学的重要组成部分,近年来得到了快速发展并成为化学家的研究热点。本论文结合蒽荧光受体的研究现状及其发展趋势,在该类物质的功能性分子设计、金属离子识别方面进行了进一步的研究。
设计并合成了一个二苯砜为连接臂含双蒽基团的钳状受体分子并通过荧光和紫外-可见光谱实验研究了其对阳离子识别的性质,发现该化合物对Hg~(2+)有一定的荧光增强作用,对Cu~(2+)有一定荧光淬灭作用。
设计、合成了六种新的含硫识别基团的蒽类荧光分子探针。通过金属离子滴定试验,发现该类探针对Cu~(2+)和Hg~(2+)离子具有明显的识别作用。特别是在此基础上设计的9,10-二(4-硝基苄硫甲基)蒽对Hg (Ⅱ)离子络合促进荧光增强429倍,该探针具有高度的专一性,是典型的PET体系。
设计并合成了两个以二硫代氨基甲酸基为识别基团的荧光分子。发现Hg~(2+)与二硫代氨基甲酸基配位抑制了PET效应,主体荧光得以恢复,发射强度增加。该类主体分子对Hg~(2+)有较高的选择性。
设计、合成了七种新的由不同识别基团相连接的含双蒽酰胺基荧光基团分子探针。通过金属离子滴定试验,发现含硫原子探针对Cu~(2+)和Hg~(2+)离子具有明显的荧光淬灭作用,并且这些离子分别和主体分子形成了1:1的络合物。
在以上研究的基础上,设计、合成了两个新的由不同识别基团相连接的双芘环荧光团的荧光探针。发现以3,6-二硫杂-1,8-辛二胺为连接基团和识别基团的含双芘环荧光团分子探针对Cd~(2+), Cu~(2+), Ag+和Hg~(2+)具有选择性识别作用。
As an important component of the supermolecular chemistry, the fluorescence molecular switch has developed rapidly and become interest of the chemists. In this dissertation the functional design and the molecular recognition of anthracene fluorescent receptors were studied deeply according to the trend in this field.
A fluorescent probe with two anthracene groups linked by diphenyl sulfone was designed. It was found that this probe exhibit fluorescence enhancement response to Hg~(2+) and fluorescence quenching to Cu~(2+).
In order to recognize the transition and the heavy metal ions, six of anthracene fluorescent probes with sulphur containing receptors were synthesized. The titration experiments indicated that the fluorescent probes are highly selective to Cu~(2+) and Hg~(2+). As a result, 9,10-bis(4-nitrobenzylthiomethyl)anthracene was designed and a 429-folds fluorescence enhancement response to Hg~(2+) was found. It was proposed that the enhancement mechanism is a typical PET-suppressed process.
Two fluorescent probes with each having two dithiocarbamates groups as receptors were designed. The titration experiment indicated that these probes are highly selective to Hg~(2+), which shows a pronounced fluorescence enhancement. It was also found that the response to Hg~(2+) is a typical PET-suppressed process.
Seven of bisanthracene fluoresent probes linked by different heterochain receptors were designed. The titration experiment indicates that only the sulfur containing fluorescent probes show evident fluorescence quenching upon additional Cu~(2+) and Hg~(2+). The stoichiometry of the probe-metal ion complex was estimated to be 1:1 by a nonlinear curve fitting of the fluorescence titration.
Two heterochain linked bispyrene fluorescent probes were synthesized. It is found that when 3,6-dithia-l,8-diaminooctane is used as spacer and acceptor, the probe can recognize Cd~(2+), Cu~(2+), Ag+ and Hg~(2+) respectively.
设计并合成了一个二苯砜为连接臂含双蒽基团的钳状受体分子并通过荧光和紫外-可见光谱实验研究了其对阳离子识别的性质,发现该化合物对Hg~(2+)有一定的荧光增强作用,对Cu~(2+)有一定荧光淬灭作用。
设计、合成了六种新的含硫识别基团的蒽类荧光分子探针。通过金属离子滴定试验,发现该类探针对Cu~(2+)和Hg~(2+)离子具有明显的识别作用。特别是在此基础上设计的9,10-二(4-硝基苄硫甲基)蒽对Hg (Ⅱ)离子络合促进荧光增强429倍,该探针具有高度的专一性,是典型的PET体系。
设计并合成了两个以二硫代氨基甲酸基为识别基团的荧光分子。发现Hg~(2+)与二硫代氨基甲酸基配位抑制了PET效应,主体荧光得以恢复,发射强度增加。该类主体分子对Hg~(2+)有较高的选择性。
设计、合成了七种新的由不同识别基团相连接的含双蒽酰胺基荧光基团分子探针。通过金属离子滴定试验,发现含硫原子探针对Cu~(2+)和Hg~(2+)离子具有明显的荧光淬灭作用,并且这些离子分别和主体分子形成了1:1的络合物。
在以上研究的基础上,设计、合成了两个新的由不同识别基团相连接的双芘环荧光团的荧光探针。发现以3,6-二硫杂-1,8-辛二胺为连接基团和识别基团的含双芘环荧光团分子探针对Cd~(2+), Cu~(2+), Ag+和Hg~(2+)具有选择性识别作用。
As an important component of the supermolecular chemistry, the fluorescence molecular switch has developed rapidly and become interest of the chemists. In this dissertation the functional design and the molecular recognition of anthracene fluorescent receptors were studied deeply according to the trend in this field.
A fluorescent probe with two anthracene groups linked by diphenyl sulfone was designed. It was found that this probe exhibit fluorescence enhancement response to Hg~(2+) and fluorescence quenching to Cu~(2+).
In order to recognize the transition and the heavy metal ions, six of anthracene fluorescent probes with sulphur containing receptors were synthesized. The titration experiments indicated that the fluorescent probes are highly selective to Cu~(2+) and Hg~(2+). As a result, 9,10-bis(4-nitrobenzylthiomethyl)anthracene was designed and a 429-folds fluorescence enhancement response to Hg~(2+) was found. It was proposed that the enhancement mechanism is a typical PET-suppressed process.
Two fluorescent probes with each having two dithiocarbamates groups as receptors were designed. The titration experiment indicated that these probes are highly selective to Hg~(2+), which shows a pronounced fluorescence enhancement. It was also found that the response to Hg~(2+) is a typical PET-suppressed process.
Seven of bisanthracene fluoresent probes linked by different heterochain receptors were designed. The titration experiment indicates that only the sulfur containing fluorescent probes show evident fluorescence quenching upon additional Cu~(2+) and Hg~(2+). The stoichiometry of the probe-metal ion complex was estimated to be 1:1 by a nonlinear curve fitting of the fluorescence titration.
Two heterochain linked bispyrene fluorescent probes were synthesized. It is found that when 3,6-dithia-l,8-diaminooctane is used as spacer and acceptor, the probe can recognize Cd~(2+), Cu~(2+), Ag+ and Hg~(2+) respectively.
引文
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