含硝基芳烃爆炸物及其残留物给公共安全和环境危害带来严重的社会问题，急需开发出能够快速的、选择性的检测硝基芳烃爆炸物的方法。由于具有灵敏度高，操作简便，实时监测和背景干扰小等优点，开发用于检测硝基芳烃的近红外荧光探针已成为研究热点。基于抑制分子内光诱导电子转移过程从而导致荧光增强的原理，结合密度泛函理论计算，本文精准设计合成了8-（4-氨基苯基）-1，2，6，7-四苯基氟硼二吡咯作为新型近红外BODIPY荧光探针分子用于苦味酸的荧光检测。

本论文主要的研究内容包含以下几个方面：

第一部分主要关注新型近红外BODIPY荧光探针的设计和合成。从亚氨基二乙酸原料出发，经过酯化反应、酰基化反应、与苯偶酰的缩合反应，脱羧反应、有机磷酸催化下与芳醛缩合反应得到一系列5-芳基取代-2，3，7，8-四苯基二吡咯甲烷、再经DDQ氧化脱氢生成二吡咯烯，原位与BF₃复合得到BODIPY荧光探针, 针对8-（4-氨基苯基）-1，2，6，7-四苯基氟硼二吡咯烷目标分子开展了一系列合成工作，用¹H NMR、¹³C NMR、¹⁹F NMR、HRMS和X-单晶衍射对相应化合物进行结构表征。

第二部分首先对多种含硝基化合物和BODIPY分子进行量子化学密度泛函理论计算，结构表明本文所设计合成的分子8-（4-氨基苯基）-1，2，6，7-四苯基氟硼二吡咯烷和苦味酸（PA）能级匹配。通过紫外可见吸收光谱和荧光发射光谱对合成的BODIPY衍生物进行光谱分析。为了评估8-（4-氨基苯基）-1，2，6，7-四苯基氟硼二吡咯烷作为荧光探针对PA的选择性检测，相应的荧光滴定实验给予测试分析。

It is become an increasing urgent need to devolpment a rapid and selective detection method for Explosives containing nitroaromatics and their residues, which have brought serious social problems to homeland security and environmental hazards. Owing to the advantages of high sensitivity, easy operation, realtime monitoring, and low background interference, developing near-infrared fluorescent probes for the detection of nitroaromatics have become research topics which are under strong spotlight. Based on the principle of inhibiting Intramolecular the photo-induced electron transfer process (PET) result in fluorescence enhancement, combined with density functional theory (DFT) calculation, 8-(4-aminophenyl)-1,2,6,7-tetraphenyl fluoride Boron dipyrromethene was precisely designed and synthesized as a novel near-infrared BODIPY fluorescent probe molecule for selectively detection of picric acid (PA).

In this dissertation, the main research contents are summarized as follows:

The first part (Chapter 2) of this dissertation focuses on the design and synthesis of a new type of near-infrared BODIPY fluorescent probe. Starting from iminodiacetic acid, via esterification reaction, acylation reaction, condensation reaction with benzil, decarboxylation reaction, organic phosphoric acid-catalyzed reaction with aromatic aldehyde to obtain a series of 5-aryl substitution-2,3,7,8-Tetraphenyldipyrromethanes, then DDQ oxidative dehydrogenation, and in situ complexation of BF₃·OEt₂ in the presence of a base to generate BODIPY fluorescent probe. A series of synthetic work has been carried out for the target molecule of 8-(4-aminophenyl)-1,2,6,7-tetraphenylfluoroboron dipyrromethene, the corresponding structures were characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR, HRMS and X-single crystal diffraction.

The second part (Chapters 3) of this dissertation focuses on DFT calculation of BODIPY molecules and nitro-containing compounds, which shows has a good math in energy level between 8-(4-aminophenyl)-1,2,6,7-tetraphenylfluoroboron dipyrromethene and picric acid. UV-Vis absorption and fluorescence emission data for the BODIPY derivatives were examined, and fluorescence titration experiments were test to assess the utility of 8-(4-aminophenyl)-1,2,6,7-tetraphenylfluoroboron dipyrromethene as fluorescent probe for selectively detection of picric acid.

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