Preparation,Properties And Biological Application Of Triphenyl Amine Derivatives Fluorescent Probe

Organic small molecular fluorescent probe is widely used in detecting metal ions of water,soil,air,organism,which is due to its smallmolecular weight,simple synthetic steps,easily obtianed and other advantages.Among them who are utilized in biological imaging of living cells and tissueshas provided a dependable technique in biomedicine and drug study.In this paper,we untilized triphenylamine as the fluorogen,through regulating and modifying its structure,and synthetized a series of novel triphenylamine-based derivatives by Vilsmeier-Haack reaction,Witting reaction and so on.Based on the structural features of these compounds,we have systematically studied their properties in the recognition aspects and explored their widely biological applicationscombined with the in-vitro experiment results.The main researchcontents are as follows:1.Triphenylamine was selected as an electron donor,connected with C=N and styrene to building molecular skeleton,hydroxyl groups which not only could add the probe's water-solubility but also build a half empty cavity of crown etherstructure with the C=N also introduced,to synthesize a triphenylamine-based Schiff base SASB,which might realize a recognition for main group element.The results showed that in ethanol SASB could recognized magnesium ion with no interference from calcium ion.Moreover,SASB presented a great photostability,low toxicity and good cellular permeability,which could realize to detect magnesium ion in lysosome.Furthermore,it was successfully used as a magnesium ion developer in plant tissues,which showed that it not only could be well tracking the transport of magnesium ion but also make a corresponding fluorescence response to different concentrations magnesium ion.2.Based on the previous chapter,we had changed terminal group to synthesis a new small organic compound.The experiment results showed that compound PBSB could realize a detection of copper ion by ratiometric fluorescence enhanced process in acetonitrile.We had taken a further mechanism exploration about the probe with copper ions by fluorescence and 1H-NMR titrations.The biological assays showed that it not only could locate in mitochondria but also present a rapid response to copper(II)through a ratiometric fluorescence "off-on" processin the mitochondria of living cell.3.Considering that Schiff base was easy to be decomposed,which restricted its application,at the same time,-C-N-single bond had greater flexibility than-C=N-double bond,which made the intramolecular rotation much more easier and then coordination with more ions;so we synthnized another organic small secondary amine molecular compound PBSA.The results showed PBSA had great properties:1)high selectivity for Ni2+ through fluorescence "turn-off ' response in acetonitrile;2)a lower detection limit;3)no interference;4)a recyclable detection.Its recognition mechanism had been established by fluorescence spectra,Job's curve,1H NMR study.Moreover,to further explore its utility in biological system,the results demonstrated that probe PBSA was a specific mitochondria-targeted fluorescent probewith excellent cell membrane permeability and the circulation experiment could also realize.