新型萘酰亚胺金属离子荧光探针的设计、合成及性能研究
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摘要
本论文由两部分内容组成:新型萘酰亚胺金属离子荧光探针的设计、合成及性能研究和丁二酰亚胺光解的研究。
研究了刚性的1,8-萘酰亚胺化合物在不同溶剂中及不同pH下的紫外和荧光光谱性质。发现这类荧光分子具有很强的溶剂敏感性,是潜在的极性微环境荧光探针的前体。在此基础上我们设计、合成了简单PET金属离子探针N-[4-二(2-羟乙基)氨基苯基]-4-(1-哌啶基)-1,8-萘酰亚胺。光谱滴定表明它是一个良好的铁(Ⅲ)离子选择性荧光分子探针。
以4-氨基-1,8-萘酰亚胺作为荧光探针的荧光信号发射基团,按照“杂原子-烷基-氨基荧光团”的模型,设计、合成了一系列新的不同识别基团的萘酰亚胺金属离子荧光探针。识别基团部分分别引入氧、氮、硫原子作为金属离子配位点,以研究不同配体对金属离子的选择性。同时,考虑到金属离子不同的配位数和空间因素,设计了“单臂”和“双臂”识别基团。通过金属离子滴定试验,发现双臂探针对金属离子比单臂探针有更明显的发射蓝移信号。
在识别单元中引入硫原子提高了对金属离子的选择性。含有硫原子识别单元的荧光探针对汞(Ⅱ)离子有选择性荧光淬灭作用,对铜(Ⅱ)或铁(Ⅲ)离子有选择性荧光增强作用。提出了不同的识别机理,对铜(Ⅱ)、铁(Ⅲ)离子的荧光增强作用主要是由于阻断了PET效应;对汞(Ⅱ)离子的荧光淬灭作用产生于金属离子―π电子的相互作用。基于金属离子―π电子相互作用机理的汞(Ⅱ)离子的选择性荧光探针是本文首次报道的。
设计、合成了四种新的双萘酰亚胺荧光分子探针,该类探针是具有较强ICT信号的荧光分子体系。
研究了丁二酰亚胺及N-烷基取代丁二酰亚胺在醇溶液中的光化学性质。通过密度泛函理论(DFT)计算的方法研究了光反应过程中分子间的相互作用,从而进一步阐述了光反应的机理。
This dissertation consists of two parts: Study on the naphthlimide fluorescent probes for metal ions and investigation on the photolysis mechanism of succinimides.
The UV-visible and fluorescent properties of rigid 1,8-naphthalimide derivatives in various solution or under various pH were investigated. It was found that these rigid molecules are precursors of fluorescent probes sensitive to solvent polarity. N-[4-di(2-hydroxyethyl)aminophenyl]-4-(1-piperidyl)-1,8-naphthalimide was designed based on the above studies. The titration experiments indicated that it is highly selective to Fe3+.
A series of novel fluorescent probes with different receptors were designed and synthesized based on the 4-amino-1,8-naphthalimide. O, N and S atoms were introduced into the receptors respectively as ligands of metal ions. At the same time, the receptors with one arm and double were introduced and it was found that the latter shows a larger blue-shift of the maximum emission than the former.
Two novel fluorescent probes (D4 and D5) with a receptor containing a pair of ethanthiolyl or N,N-diethyl-dithiocarbamyl groups were designed and synthesized for recognition of transition and heavy metal ions. It was found that D4 and D5 show a pronounced fluorescence enhancement response to Cu2+ and Fe3+, respectively. They both show a strong fluorescence quenching upon addition of Hg2+. Different mechanisms of recognition for transition and heavy metal ions were proposed. The response to Cu2+ or Fe3+ is a typical PET-suppressed process. The fluorescence quenching of Hg2+ may be related to the cation-πinteraction, which was firstly reported in this paper.
Four novel fluorescent probes with double naphthalimide fluorophores were designed and synthesized and found that they are characteristic ICT systems.
The photochemical behavior of succimide in alcohol was investigated and the photolysis mechanism was proposed with the aid of DFT (density functional theory) calculations.
研究了刚性的1,8-萘酰亚胺化合物在不同溶剂中及不同pH下的紫外和荧光光谱性质。发现这类荧光分子具有很强的溶剂敏感性,是潜在的极性微环境荧光探针的前体。在此基础上我们设计、合成了简单PET金属离子探针N-[4-二(2-羟乙基)氨基苯基]-4-(1-哌啶基)-1,8-萘酰亚胺。光谱滴定表明它是一个良好的铁(Ⅲ)离子选择性荧光分子探针。
以4-氨基-1,8-萘酰亚胺作为荧光探针的荧光信号发射基团,按照“杂原子-烷基-氨基荧光团”的模型,设计、合成了一系列新的不同识别基团的萘酰亚胺金属离子荧光探针。识别基团部分分别引入氧、氮、硫原子作为金属离子配位点,以研究不同配体对金属离子的选择性。同时,考虑到金属离子不同的配位数和空间因素,设计了“单臂”和“双臂”识别基团。通过金属离子滴定试验,发现双臂探针对金属离子比单臂探针有更明显的发射蓝移信号。
在识别单元中引入硫原子提高了对金属离子的选择性。含有硫原子识别单元的荧光探针对汞(Ⅱ)离子有选择性荧光淬灭作用,对铜(Ⅱ)或铁(Ⅲ)离子有选择性荧光增强作用。提出了不同的识别机理,对铜(Ⅱ)、铁(Ⅲ)离子的荧光增强作用主要是由于阻断了PET效应;对汞(Ⅱ)离子的荧光淬灭作用产生于金属离子―π电子的相互作用。基于金属离子―π电子相互作用机理的汞(Ⅱ)离子的选择性荧光探针是本文首次报道的。
设计、合成了四种新的双萘酰亚胺荧光分子探针,该类探针是具有较强ICT信号的荧光分子体系。
研究了丁二酰亚胺及N-烷基取代丁二酰亚胺在醇溶液中的光化学性质。通过密度泛函理论(DFT)计算的方法研究了光反应过程中分子间的相互作用,从而进一步阐述了光反应的机理。
This dissertation consists of two parts: Study on the naphthlimide fluorescent probes for metal ions and investigation on the photolysis mechanism of succinimides.
The UV-visible and fluorescent properties of rigid 1,8-naphthalimide derivatives in various solution or under various pH were investigated. It was found that these rigid molecules are precursors of fluorescent probes sensitive to solvent polarity. N-[4-di(2-hydroxyethyl)aminophenyl]-4-(1-piperidyl)-1,8-naphthalimide was designed based on the above studies. The titration experiments indicated that it is highly selective to Fe3+.
A series of novel fluorescent probes with different receptors were designed and synthesized based on the 4-amino-1,8-naphthalimide. O, N and S atoms were introduced into the receptors respectively as ligands of metal ions. At the same time, the receptors with one arm and double were introduced and it was found that the latter shows a larger blue-shift of the maximum emission than the former.
Two novel fluorescent probes (D4 and D5) with a receptor containing a pair of ethanthiolyl or N,N-diethyl-dithiocarbamyl groups were designed and synthesized for recognition of transition and heavy metal ions. It was found that D4 and D5 show a pronounced fluorescence enhancement response to Cu2+ and Fe3+, respectively. They both show a strong fluorescence quenching upon addition of Hg2+. Different mechanisms of recognition for transition and heavy metal ions were proposed. The response to Cu2+ or Fe3+ is a typical PET-suppressed process. The fluorescence quenching of Hg2+ may be related to the cation-πinteraction, which was firstly reported in this paper.
Four novel fluorescent probes with double naphthalimide fluorophores were designed and synthesized and found that they are characteristic ICT systems.
The photochemical behavior of succimide in alcohol was investigated and the photolysis mechanism was proposed with the aid of DFT (density functional theory) calculations.
引文
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