新型七甲川吲哚菁類熒光探針的設計合成及CN~-檢測性能研究
發(fā)布時間：2019-03-28 07:18
【摘要】：氰化物在工業(yè)生產(chǎn)中起著非常重要的作用,廣泛應用于金礦開采、電鍍、樹脂及纖維合成等領(lǐng)域。但是,氰根離子是劇毒物,可以通過肺,皮膚,受污染的食物和受污染的飲用水攝入人體內(nèi)。因此,在環(huán)境及生物體內(nèi)對氰化物進行有效迅速的檢測非常重要。本論文設計并合成了三種基于七甲川吲哚菁的近紅外氰根離子熒光探針,研究了探針的氰根離子檢測性能,具體內(nèi)容如下:(1)基于七甲川吲哚菁染料的熒光探針P1和P2的設計合成及氰根離子檢測性能研究。通過吲哚嗡鹽與2-氯-1-甲酰基-3-羥次甲基環(huán)己烯的縮合反應制備了探針P1和P2,通過1H NMR、13C NMR和MALDI-TOF質(zhì)譜表征了探針的分子結(jié)構(gòu)。通過紫外可見吸收光譜和熒光發(fā)射光譜研究了探針P1和P2的氰根離子檢測性能,結(jié)果表明:隨著氰根離子的加入,探針P1在776 nm和探針P2在795 nm處的吸收峰逐漸降低,并在短波區(qū)域出現(xiàn)新的吸收峰,溶液顏色由綠色轉(zhuǎn)變?yōu)榈S色;同時,探針P1在802 nm和探針P2在817 nm處的熒光發(fā)射峰強度逐漸降低,常見陰離子對探針的紫外吸收和熒光發(fā)射光譜幾乎沒有干擾;在一定濃度范圍內(nèi),探針P1和P2的熒光強度與氰根離子濃度存在良好的線性關(guān)系,其最低檢測限分別為0.017μM和0.20μM;通過1H NMR,MALDI-TOF質(zhì)譜和Job’s曲線證實了探針與氰根離子的親核加成反應機理;此外,探針P2實現(xiàn)了在生物體內(nèi)對氰根離子的有效檢測。(2)基于三苯胺-七甲川吲哚菁染料的熒光探針P3設計合成及氰根離子檢測性能研究。在探針P1的基礎(chǔ)上,通過改進的Sukuzi偶聯(lián)反應,在探針P1的中位引入電子給體三苯胺合成了探針P3,通過1H NMR、13C NMR和MALDI-TOF質(zhì)譜表征了探針P3的分子結(jié)構(gòu)。通過紫外可見吸收光譜和熒光發(fā)射光譜研究了探針P3的氰根離子檢測性能,結(jié)果表明:隨著氰根離子的加入,探針P3在750nm吸收峰逐漸降低,并在416 nm處出現(xiàn)新的吸收峰,溶液顏色由翠綠色轉(zhuǎn)變?yōu)榱咙S色;同時,探針P3在780 nm處的熒光發(fā)射峰強度逐漸降低,常見陰離子對探針的紫外吸收和熒光發(fā)射光譜幾乎沒有干擾;在乙腈溶液中,探針P3的熒光強度與氰根離子濃度(0-5μM)存在良好的線性關(guān)系,其最低檢測限為0.014μM;通過1H NMR,MALDI-TOF質(zhì)譜和Job’s曲線證實了探針P3的氰根離子檢測機理為親核加成反應;此外,基于P3的測試紙可以更方便檢測CN ,并且通過生物熒光成像實現(xiàn)了探針P3在細胞L929中對氰根離子的有效檢測。
[Abstract]:Cyanide plays a very important role in industrial production. It is widely used in gold mining, electroplating, resin and fiber synthesis. But cyanide ions are highly toxic and can be ingested into the human body through the lungs, skin, contaminated food and contaminated drinking water. Therefore, it is very important to detect cyanide effectively and rapidly in the environment and organism. In this paper, we designed and synthesized three kinds of near infrared cyanine ion fluorescence probes based on heptachuan indole cyanine, and studied the performance of cyanogen ion detection of the probes. The main contents are as follows: (1) the design and synthesis of fluorescent probes P1 and P2 based on heptachuan indocyanine dyes and the performance of cyanogen ion detection were studied. The probes P1 and P2were prepared by condensation of indole salt with 2-chloro-1-formyl-3-hydroxymethylcyclohexene. The molecular structures of the probes were characterized by 1H NMR,13C NMR and MALDI-TOF mass spectrometry. The detection performance of probe P1 and P2 was studied by UV visible absorption spectrum and fluorescence emission spectrum. The results showed that the absorption peak of probe P1 at 776 nm and probe P2 at 795 nm decreased gradually with the addition of cyano ion. A new absorption peak appeared in the shortwave region, and the color of the solution changed from green to yellowish. At the same time, the intensity of fluorescence emission peaks of probe P1 at 802 nm and probe P2 at 817 nm decreased gradually, and the ultraviolet absorption and fluorescence emission spectra of the probes were almost undisturbed by anions. Within a certain concentration range, there was a good linear relationship between the fluorescence intensity of the probes P1 and P2 and the concentration of cyanide ion, and the minimum detection limits were 0.017 渭 M and 0.20 渭 M, respectively. The nucleophilic addition mechanism of the probe with cyanogen ion was confirmed by 1H NMR,MALDI-TOF mass spectrometry and Job's curve. In addition, the probe P2 realized the effective detection of cyanogen ions in organisms. (2) Design and synthesis of fluorescence probe P3 based on triphenylamine-heptachlorocyanic indocyanine dye and study on the performance of cyanogen ion detection. On the basis of the probe P1, the probe P3 was synthesized by introducing electron donor triphenylamine into the middle position of the probe P1 by improved Sukuzi coupling reaction. The molecular structure of the probe P3 was characterized by 1H NMR,13C NMR and MALDI-TOF mass spectrometry. The detection performance of probe P3 was studied by UV visible absorption spectrum and fluorescence emission spectrum. The results showed that with the addition of cyano ion, the absorption peak of probe P3 decreased gradually in 750nm, and a new absorption peak appeared at 416nm. The color of the solution changed from emerald green to bright yellow. At the same time, the intensity of fluorescence emission peak of probe P3 at 780 nm decreased gradually, and the ultraviolet absorption and fluorescence emission spectra of probe P3 were almost undisturbed by anions. In acetonitrile solution, the fluorescence intensity of probe P3 has a good linear relationship with the concentration of cyanide ion (0-5 渭 M), and the detection limit is 0.014 渭 M. 1H NMR,MALDI-TOF mass spectrometry and Job's curve confirmed that the mechanism of cyanogen ion detection of probe P3 was nucleophilic addition reaction. In addition, the P3-based test paper is more convenient to detect CN, and the probe P3 can be used to detect cyanogen ions in L929 cells by bioluminescence imaging.
【學位授予單位】：湘潭大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O657.3
[Abstract]:Cyanide plays a very important role in industrial production. It is widely used in gold mining, electroplating, resin and fiber synthesis. But cyanide ions are highly toxic and can be ingested into the human body through the lungs, skin, contaminated food and contaminated drinking water. Therefore, it is very important to detect cyanide effectively and rapidly in the environment and organism. In this paper, we designed and synthesized three kinds of near infrared cyanine ion fluorescence probes based on heptachuan indole cyanine, and studied the performance of cyanogen ion detection of the probes. The main contents are as follows: (1) the design and synthesis of fluorescent probes P1 and P2 based on heptachuan indocyanine dyes and the performance of cyanogen ion detection were studied. The probes P1 and P2were prepared by condensation of indole salt with 2-chloro-1-formyl-3-hydroxymethylcyclohexene. The molecular structures of the probes were characterized by 1H NMR,13C NMR and MALDI-TOF mass spectrometry. The detection performance of probe P1 and P2 was studied by UV visible absorption spectrum and fluorescence emission spectrum. The results showed that the absorption peak of probe P1 at 776 nm and probe P2 at 795 nm decreased gradually with the addition of cyano ion. A new absorption peak appeared in the shortwave region, and the color of the solution changed from green to yellowish. At the same time, the intensity of fluorescence emission peaks of probe P1 at 802 nm and probe P2 at 817 nm decreased gradually, and the ultraviolet absorption and fluorescence emission spectra of the probes were almost undisturbed by anions. Within a certain concentration range, there was a good linear relationship between the fluorescence intensity of the probes P1 and P2 and the concentration of cyanide ion, and the minimum detection limits were 0.017 渭 M and 0.20 渭 M, respectively. The nucleophilic addition mechanism of the probe with cyanogen ion was confirmed by 1H NMR,MALDI-TOF mass spectrometry and Job's curve. In addition, the probe P2 realized the effective detection of cyanogen ions in organisms. (2) Design and synthesis of fluorescence probe P3 based on triphenylamine-heptachlorocyanic indocyanine dye and study on the performance of cyanogen ion detection. On the basis of the probe P1, the probe P3 was synthesized by introducing electron donor triphenylamine into the middle position of the probe P1 by improved Sukuzi coupling reaction. The molecular structure of the probe P3 was characterized by 1H NMR,13C NMR and MALDI-TOF mass spectrometry. The detection performance of probe P3 was studied by UV visible absorption spectrum and fluorescence emission spectrum. The results showed that with the addition of cyano ion, the absorption peak of probe P3 decreased gradually in 750nm, and a new absorption peak appeared at 416nm. The color of the solution changed from emerald green to bright yellow. At the same time, the intensity of fluorescence emission peak of probe P3 at 780 nm decreased gradually, and the ultraviolet absorption and fluorescence emission spectra of probe P3 were almost undisturbed by anions. In acetonitrile solution, the fluorescence intensity of probe P3 has a good linear relationship with the concentration of cyanide ion (0-5 渭 M), and the detection limit is 0.014 渭 M. 1H NMR,MALDI-TOF mass spectrometry and Job's curve confirmed that the mechanism of cyanogen ion detection of probe P3 was nucleophilic addition reaction. In addition, the P3-based test paper is more convenient to detect CN, and the probe P3 can be used to detect cyanogen ions in L929 cells by bioluminescence imaging.
【學位授予單位】：湘潭大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O657.3
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