新型苝二酰亚胺衍生物的合成及其在荧光探针与Knoevenagel反应中应用研究
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摘要
3,4：9,10-苝二酰亚胺类化合物(PBIs)基于其良好的光、化学稳定性和极高的荧光量子效率,近年来在功能性有机材料方面的应用研究日益增多。PBIs的港湾位连接上检测基团后可对金属、非金属阴阳离子及有机、无机小分子化合物进行检测。其次,酰胺位连接有机胺的PBIs衍生物易发生PET效应而导致其荧光猝灭,且可通过N的质子化阻断该分子内的PET效应并导致PBIs荧光增强,从而可利用该类化合物这一特性催化一些含活泼氢化合物的缩合反应并且跟踪研究反应机理。
本论文首先在PBIs的港湾位通过共轭或非共轭连接基引入了N,N-二-2-吡啶甲基胺(DPA)基团,从而合成了一系列对钯离子响应的荧光化合物(2-20、2-22及2-25)；在DMF及乙腈-水体系内的探针性能测试结果显示该类化合物对钯离子良好的选择性。化合物2-25的测试结果显示在1-5ppm区间内其荧光强度与钯离子浓度线性关系良好,拟合测试溶液荧光强度比(I/I0)与钯离子浓度关系曲线得到相关公式为y=-23.2437+35.3847x,相关度接近1。
其次,通过中间体1-氨基PBIs(2-15)在PBIs的港湾位引入烯丙基基团合成了基于钯催化去烯丙基化反应的钯离子荧光探针(3-12及3-15)。在THF-H20体系中对该类探针性能进行测试后取得了良好的效果。在一定的探针性能测试条件下,PBIs化合物3-15与钯离子作用结果表明其响应机理为化合物3-15与钯离子作用后脱去烯丙基,进而脱去一分子二氧化碳并生成荧光猝灭的化合物3-16。
在PBIs的港湾位引入硅氧烷基团合成了基于氟离子引发的硅氧键断裂的氟离子探针4-19,并在THF体系中对其进行了探针性能测试；探针分子4-19在有机溶剂中对氟离子表现出了良好的选择性且响应速度快、灵敏度高。在0-1×10-5M范围测试体系荧光强度与氟离子浓度线性关系良好；Origin拟合该浓度范围内溶液荧光强度减弱比例[(I586nm0-I586nm)/I586nm]与氟离子浓度关系曲线后得到了一次方程y=0.0088+0.84004x,相关度高达0.998。
通过偶联、缩合等反应合成了多种港湾位功能化的PBIs衍生物,特别是通过在PBIs港湾位引入哌嗪基团得到PBIs衍生物5-42,该化合物在铜离子作用下在港湾位发生成环反应,基于这一效应可将其用于铜离子的检测；在乙腈中该化合物对铜离子表现出了良好的选择性及较高的灵敏度。在乙腈溶液中将PBIs衍生物5-42与铜离子进行反应并对该反应产物结构进行分析表征后结合文献推测出其作用机理为铜催化PBIs的港湾位C-N键偶联成环反应。再者,1-N-甲基-哌嗪)-PBIs化合物5-43)与铜离子反应的结果进一步证实了如上反应机理。
最后,在PBIs的酰亚胺位连接有机胺后合成出PBIs衍生物6-28及6-29,继而利用二者的特性催化了氰基乙酸乙酯与芳香醛的缩合反应,并通过反应体系中氰基乙酸乙酯的浓度与反应液荧光强度关系对其反应跟踪,为进一步研究该反应的动力学奠定了基础。
3,4:9,10-perylene bisimide derivatives have been applied as functional organic dyes, such as fluorescent sensors and fluorescent solar collectors, as a result of their excellent chemical, photo stability and extraordinary photoluminescence efficiency. Meanwhile, the fluorescence of organic amine containing-PBIs is usually quenched according to the PET effect; and it can be enhanced by binding a proton to the N atom in the organic amine. Therefore, these compounds can be used as fluorescent labelling catalysts for some organic reactions.
PBI derivatives (Compound2-20,2-22and2-25) have been synthesized by inducing the di-(2-picolyl)amine (DPA) groups into the bay positions of PBIs. These compounds have a very good response to Pd2+compared to other cations in both DMF and CH3CN-H2O systems. And the tested results also showed that there was a good linearity between the fluorescence intensity of compound2-25and the concentrations of Pd2+in the range from0to5μM. The formula y=-23.2437+35.3847x has been obtained by fitting the curve of the relationship between I/Io and [Pd2+].
Then, sensor3-12and3-15for Pd2+detection based on the Pd-catalyzed deallylation reaction have been prepared. These compounds also showed higher sensitivity and selectivity for Pd2+detection over other cations in the THF-H2O system. By running a large scale reaction between the sensor3-15and PdCl2under the identical conditions with that has been used for chemical sensing studies, the fluorescence quenching compound3-16has been obtained.
By addition, a novel colorimetric and fluorescent senor (sensor4-19) has been synthesized and characterized. It showed higher sensitivity and selectivity toward F-over the other halide ions due to the special cleavage of Si-O bond induced by F-. And the linearity between the fluorescence intensity of sensor4-19and concentrations of F-in the range of0-10μM is extremely good. By fitting the curve of the relationship between [(I586nm0-l586nm)/I586nm] and [F-] the formula y=0.0088+0.84004x had been obtained with a correlation nearly1.
Trough the Suzuki coupling and condensation reactions some other PBI derivatives (especially compound5-42) have been synthesized. Compound5-42features a turn-on fluorescent response manner with high sensitivity for Cu2+in the CH3CN system. By running a large scale reaction between5-42and Cu2+in CH3CN a special cyclized product has been obtained. And we speculated that the sensing principle of compound5-42was the special C-N bond coupling reaction on the bay position of PBIs which is catalyzed by Cu2+. Result of the reaction between1-(N-methyl-piperazine)-PBI (compound5-43) and Cu2+further confirmed the principle.
Finally, PBI derivatives6-28and6-29which contain organic amines at the imide positions have been prepared and used as fluorescent labelling catalysts to investigate the Knoevenagel reactions between ethyl cyanoacetate and aromatic aldehydes. And these reactions can be tracked by the relationship between the concentration of ethyl cyanoacetate and the fluorescence intensity of reaction solution.
本论文首先在PBIs的港湾位通过共轭或非共轭连接基引入了N,N-二-2-吡啶甲基胺(DPA)基团,从而合成了一系列对钯离子响应的荧光化合物(2-20、2-22及2-25)；在DMF及乙腈-水体系内的探针性能测试结果显示该类化合物对钯离子良好的选择性。化合物2-25的测试结果显示在1-5ppm区间内其荧光强度与钯离子浓度线性关系良好,拟合测试溶液荧光强度比(I/I0)与钯离子浓度关系曲线得到相关公式为y=-23.2437+35.3847x,相关度接近1。
其次,通过中间体1-氨基PBIs(2-15)在PBIs的港湾位引入烯丙基基团合成了基于钯催化去烯丙基化反应的钯离子荧光探针(3-12及3-15)。在THF-H20体系中对该类探针性能进行测试后取得了良好的效果。在一定的探针性能测试条件下,PBIs化合物3-15与钯离子作用结果表明其响应机理为化合物3-15与钯离子作用后脱去烯丙基,进而脱去一分子二氧化碳并生成荧光猝灭的化合物3-16。
在PBIs的港湾位引入硅氧烷基团合成了基于氟离子引发的硅氧键断裂的氟离子探针4-19,并在THF体系中对其进行了探针性能测试；探针分子4-19在有机溶剂中对氟离子表现出了良好的选择性且响应速度快、灵敏度高。在0-1×10-5M范围测试体系荧光强度与氟离子浓度线性关系良好；Origin拟合该浓度范围内溶液荧光强度减弱比例[(I586nm0-I586nm)/I586nm]与氟离子浓度关系曲线后得到了一次方程y=0.0088+0.84004x,相关度高达0.998。
通过偶联、缩合等反应合成了多种港湾位功能化的PBIs衍生物,特别是通过在PBIs港湾位引入哌嗪基团得到PBIs衍生物5-42,该化合物在铜离子作用下在港湾位发生成环反应,基于这一效应可将其用于铜离子的检测；在乙腈中该化合物对铜离子表现出了良好的选择性及较高的灵敏度。在乙腈溶液中将PBIs衍生物5-42与铜离子进行反应并对该反应产物结构进行分析表征后结合文献推测出其作用机理为铜催化PBIs的港湾位C-N键偶联成环反应。再者,1-N-甲基-哌嗪)-PBIs化合物5-43)与铜离子反应的结果进一步证实了如上反应机理。
最后,在PBIs的酰亚胺位连接有机胺后合成出PBIs衍生物6-28及6-29,继而利用二者的特性催化了氰基乙酸乙酯与芳香醛的缩合反应,并通过反应体系中氰基乙酸乙酯的浓度与反应液荧光强度关系对其反应跟踪,为进一步研究该反应的动力学奠定了基础。
3,4:9,10-perylene bisimide derivatives have been applied as functional organic dyes, such as fluorescent sensors and fluorescent solar collectors, as a result of their excellent chemical, photo stability and extraordinary photoluminescence efficiency. Meanwhile, the fluorescence of organic amine containing-PBIs is usually quenched according to the PET effect; and it can be enhanced by binding a proton to the N atom in the organic amine. Therefore, these compounds can be used as fluorescent labelling catalysts for some organic reactions.
PBI derivatives (Compound2-20,2-22and2-25) have been synthesized by inducing the di-(2-picolyl)amine (DPA) groups into the bay positions of PBIs. These compounds have a very good response to Pd2+compared to other cations in both DMF and CH3CN-H2O systems. And the tested results also showed that there was a good linearity between the fluorescence intensity of compound2-25and the concentrations of Pd2+in the range from0to5μM. The formula y=-23.2437+35.3847x has been obtained by fitting the curve of the relationship between I/Io and [Pd2+].
Then, sensor3-12and3-15for Pd2+detection based on the Pd-catalyzed deallylation reaction have been prepared. These compounds also showed higher sensitivity and selectivity for Pd2+detection over other cations in the THF-H2O system. By running a large scale reaction between the sensor3-15and PdCl2under the identical conditions with that has been used for chemical sensing studies, the fluorescence quenching compound3-16has been obtained.
By addition, a novel colorimetric and fluorescent senor (sensor4-19) has been synthesized and characterized. It showed higher sensitivity and selectivity toward F-over the other halide ions due to the special cleavage of Si-O bond induced by F-. And the linearity between the fluorescence intensity of sensor4-19and concentrations of F-in the range of0-10μM is extremely good. By fitting the curve of the relationship between [(I586nm0-l586nm)/I586nm] and [F-] the formula y=0.0088+0.84004x had been obtained with a correlation nearly1.
Trough the Suzuki coupling and condensation reactions some other PBI derivatives (especially compound5-42) have been synthesized. Compound5-42features a turn-on fluorescent response manner with high sensitivity for Cu2+in the CH3CN system. By running a large scale reaction between5-42and Cu2+in CH3CN a special cyclized product has been obtained. And we speculated that the sensing principle of compound5-42was the special C-N bond coupling reaction on the bay position of PBIs which is catalyzed by Cu2+. Result of the reaction between1-(N-methyl-piperazine)-PBI (compound5-43) and Cu2+further confirmed the principle.
Finally, PBI derivatives6-28and6-29which contain organic amines at the imide positions have been prepared and used as fluorescent labelling catalysts to investigate the Knoevenagel reactions between ethyl cyanoacetate and aromatic aldehydes. And these reactions can be tracked by the relationship between the concentration of ethyl cyanoacetate and the fluorescence intensity of reaction solution.
引文
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