荧光膦亚胺类衍生物的制备及性能分析
发布时间：2018-10-17 13:37
【摘要】：通过施陶丁格反应和Kirsanov反应成功合成了一系列含P=N键且具有荧光性质的膦亚胺类化合物,并对这些化合物的结构、光学性质和离子识别能力进行了分析,具体工作从以下几个方面开展:1通过无需催化的施陶丁格反应,合成出了含P=N键的膦亚胺类衍生物—2,6-二(4-三苯基膦亚胺基亚苄基)-环己酮(M1)。将M1与聚芴共混后加入水中制得纳米粒子PFO-M1。通过紫外-可见分光光度计和荧光分光光度计对PFOM1的光学性质和离子响应进行了研究。发现该纳米粒子对Cl O-的检测具有专一性(检出下限达~6.63×10-7 M)。在加入Cl O-后,体系的黄色荧光消失,并出现蓝色荧光,成功实现了对Cl O-的比率型检测。加入其它阴阳离子和活性氧化物均未引起PFO-M1纳米粒子显著的变化。使用紫外光谱和荧光光谱对可能的识别原理进行了研究。2通过施陶丁格反应,合成出了含P=N键结构的膦亚胺类聚合物—聚2,6-二(4 乙基二(二苯基膦亚胺基亚苄基)-环己酮(P2)。通过紫外-可见分光光度计和荧光分光光度计对其光学性质和离子响应行为进行了一系列的研究。发现向P2溶液中加入Cl O-后,P2溶液的黄色荧光发生显著淬灭(检测下限达~2.63×10-8 M),实现了对Cl O-的turn-off型检测。在加入其他阴阳离子和氧化物后,其荧光未发生明显变化。3通过室温的Kirsanov反应合成出含P=N结构的膦亚胺类衍生物—N-1-萘基三苯基膦亚胺(S1)。通过红外光谱,核磁氢谱和飞行时间质谱对S1的结构进行了表征。同时通过紫外-可见分光光度计和荧光分光光度计对离子的识别能力进行了研究。通过改变测试体系中水的比例,发现S1存在聚集态荧光增强性质。在S1的溶液中加入H+后,其荧光淬灭,实现了对H+的turn-off型探针识别(检测下限达~2.5×10-8 M)。在加入其他阴阳离子后,其荧光未发生明显变化。在加入OH-后,S1/H+混合物的荧光可恢复,表明S1有作为可逆p H指示剂的潜力。4通过Kirsanov反应,合成出了含P=N键结构的膦亚胺类衍生物:2-己基-5-三苯基亚正膦基-1H-苯并[de]异喹啉-1,3(2H)-二酮(S2)。通过紫外-可见分光光度计和荧光分光光度计对S2的光学性质进行了研究。苦味酸(PA)的加入使S2溶液的绿色荧光发生了显著地淬灭(检测下限达~6.98×10-8 M),加入其他的阴阳离子未发生显著变化,暗示其可以作为爆炸物PA的光学探针。
[Abstract]:A series of phosphine imines were synthesized successfully by Stauttinger reaction and Kirsanov reaction. The structure, optical properties and ion recognition ability of these compounds were analyzed. The specific work has been carried out in the following aspects: (1) the phosphine imines derivatives containing PN bond were synthesized by the uncatalyzed stadinger reaction-2H _ 6- bis (4-triphenylphosphine imitlidene benzylidene) -cyclohexanone (M1). Preparation of PFO-M1. nanoparticles by blending M1 with Polyfluorene in Water The optical properties and ion response of PFOM1 were studied by UV-Vis spectrophotometer and fluorescence spectrophotometer. It was found that the nanoparticles were specific for the detection of Cl O- (the detection limit was up to ~ 6.63 脳 10 ~ (-7) M). After the addition of Cl O -, the yellow fluorescence of the system disappeared and the blue fluorescence appeared. The ratio detection of Cl O-was successfully realized. Addition of other anions and active oxides did not cause significant changes in PFO-M1 nanoparticles. The possible recognition principle was studied by UV and fluorescence spectra. 2 Poly (2N) -bis (4-ethylphosphine benzyl) -cyclohexanone (P2) was synthesized by stoddinger reaction. The optical properties and ion response behavior were studied by UV-Vis spectrophotometer and fluorescence spectrophotometer. It was found that when Cl O- was added to P2 solution, the yellow fluorescence of P2 solution was significantly quenched (the detection limit was up to 2.63 脳 10 ~ (-8) M),) and the turn-off type detection of Cl O- was realized. After addition of other anions and oxides, the fluorescence of phosphine imines was not changed. 3 N-1-naphthyltriphenylphosphine (S1) was synthesized by Kirsanov reaction at room temperature. The structure of S1 was characterized by IR, NMR and time of flight mass spectrometry. At the same time, the ability of ion recognition was studied by ultraviolet-visible spectrophotometer and fluorescence spectrophotometer. By changing the proportion of water in the test system, it is found that there is a fluorescence enhancement property in S _ 1. After adding H into S1 solution, the fluorescence quenching of H was carried out, and the turn-off probe recognition of H was realized. The detection limit was up to 2.5 脳 10 ~ (-8) M). After the addition of other anions, the fluorescence did not change obviously. After the addition of OH-, the fluorescence of S _ 1 / H mixture recovered, indicating that S1 has the potential to act as a reversible pH indicator. 4 through Kirsanov reaction, The phosphine derivatives containing Pnbond structure: 2-hexyl-5-triphenyln-phosphonyl-1H-benzo [de] isoquinoline-1 (2H) -diketone (S2) were synthesized. The optical properties of S2 were studied by UV-vis spectrophotometer and fluorescence spectrophotometer. The addition of picric acid (PA) can significantly quench the green fluorescence of S2 solution (the detection limit is up to 6.98 脳 10 ~ (-8) M),). The addition of other anionic and anion ions does not change significantly, suggesting that it can be used as an optical probe for explosive PA.
【学位授予单位】：新疆大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O627.51
本文编号：2276827
[Abstract]:A series of phosphine imines were synthesized successfully by Stauttinger reaction and Kirsanov reaction. The structure, optical properties and ion recognition ability of these compounds were analyzed. The specific work has been carried out in the following aspects: (1) the phosphine imines derivatives containing PN bond were synthesized by the uncatalyzed stadinger reaction-2H _ 6- bis (4-triphenylphosphine imitlidene benzylidene) -cyclohexanone (M1). Preparation of PFO-M1. nanoparticles by blending M1 with Polyfluorene in Water The optical properties and ion response of PFOM1 were studied by UV-Vis spectrophotometer and fluorescence spectrophotometer. It was found that the nanoparticles were specific for the detection of Cl O- (the detection limit was up to ~ 6.63 脳 10 ~ (-7) M). After the addition of Cl O -, the yellow fluorescence of the system disappeared and the blue fluorescence appeared. The ratio detection of Cl O-was successfully realized. Addition of other anions and active oxides did not cause significant changes in PFO-M1 nanoparticles. The possible recognition principle was studied by UV and fluorescence spectra. 2 Poly (2N) -bis (4-ethylphosphine benzyl) -cyclohexanone (P2) was synthesized by stoddinger reaction. The optical properties and ion response behavior were studied by UV-Vis spectrophotometer and fluorescence spectrophotometer. It was found that when Cl O- was added to P2 solution, the yellow fluorescence of P2 solution was significantly quenched (the detection limit was up to 2.63 脳 10 ~ (-8) M),) and the turn-off type detection of Cl O- was realized. After addition of other anions and oxides, the fluorescence of phosphine imines was not changed. 3 N-1-naphthyltriphenylphosphine (S1) was synthesized by Kirsanov reaction at room temperature. The structure of S1 was characterized by IR, NMR and time of flight mass spectrometry. At the same time, the ability of ion recognition was studied by ultraviolet-visible spectrophotometer and fluorescence spectrophotometer. By changing the proportion of water in the test system, it is found that there is a fluorescence enhancement property in S _ 1. After adding H into S1 solution, the fluorescence quenching of H was carried out, and the turn-off probe recognition of H was realized. The detection limit was up to 2.5 脳 10 ~ (-8) M). After the addition of other anions, the fluorescence did not change obviously. After the addition of OH-, the fluorescence of S _ 1 / H mixture recovered, indicating that S1 has the potential to act as a reversible pH indicator. 4 through Kirsanov reaction, The phosphine derivatives containing Pnbond structure: 2-hexyl-5-triphenyln-phosphonyl-1H-benzo [de] isoquinoline-1 (2H) -diketone (S2) were synthesized. The optical properties of S2 were studied by UV-vis spectrophotometer and fluorescence spectrophotometer. The addition of picric acid (PA) can significantly quench the green fluorescence of S2 solution (the detection limit is up to 6.98 脳 10 ~ (-8) M),). The addition of other anionic and anion ions does not change significantly, suggesting that it can be used as an optical probe for explosive PA.
【学位授予单位】：新疆大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O627.51
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