The Synthesis And Properties Of New Fluorescent Probes Based On BODIPY Derivative

In recent years, the fluorescence analysis method get smuch attention, because of its fairly simple technical implementation, high sensitivity, good selectivity, and great potential for bioimaging. It is applied more and more widely, involving biological medicine, food and environment and other fields. Boron-dipyrrolemethene?BODIPY? with high fluorescence quantum yield?even in aqueous media?, p H-independent emission, visible excitation/emission wavelength and excellent photostability is ideal fluorophores for fluorescent probe. So, in this thesis, we design and synthesize two BODIPY derivatives?B₁, B₂? to determine Ag⁺ and Hcy, repectively.Our studies are carried out as follows:In chapter 1, we presented the research background of this thesis and described the structure of fluorescent probe molecules and their recognition mechanism. This chapter focused on introducing the characteristics and advantages of BODIPY-based probe and the research status of BODIPY-based probe for mental ions and biological molecules.In chapter 2, we designed and synthesized two novel BODIPY derivatives?B₁, B₂? which were characterized by MS, NMR and elemental analysis.In chapter 3, we focused on introducing a turn-on BODIPY-based probe B₁ that is used to detect Ag⁺ in real samples. The probe B₁ was designed and synthesized via a simple approach. It displays highly sensitive fluorescent response toward Ag⁺ with a 40-fold fluorescence intensity enhancement when 60 mM of Ag⁺ is added. The probe can be applied to the quantification of Ag⁺ with a linear range covering from 0.1 to 60 mM and the detection limit is 0.03 mM. Most importantly, the fluorescence changes of the probe are remarkably specific for Ag⁺ in the presence of other metal ions, which meet the selective requirements for practical application. Moreover, the experiment results show that the response behavior of B₁ towards Ag⁺ is p H independent in the neutral range from 6.0 to 7.5. The response of B₁ toward Ag⁺ is fast?response time is less than 1 min? and the probe is chemically reversible. Furthermore, the binding mechanism of probe B₁ towards Ag⁺ is supported by Job's plot, MS and DFT theoretical calculations. Finally, the probe is applied for detection of Ag⁺ in real water samples and living cells with encouraging results.In chapter 4, we described a turn-on BODIPY-based probe B₂ that was used to detect Hcy in real samples. The probe B₂ displays highly selective detection of Hcy over other biological thiols such as Cys and GSH. The probe can be applied to the quantification of Hcy with a linear range covering from 0.2 to 30 mM and the detection limit is 0.05 mM. The experiment results show that the response behavior of B₂ towards Hcy is p H independent in the neutral range from 6.0 to 8.0 and the response of B₂ toward Hcy is fast?response time less than 5 min?. Moreover, the fluorescence sensing mechanism?PET? of the probe is fully demonstrated by MS, 1H NMR spectra and DFT calculations. Finally, the probe is applied for detection of Hcy in living cells with encouraging results.