Desgin And Synthesis Of Water Soluble Pyrene Derivatives And Their Sensing Application To Picric Acid

Rapid detection of explosives has attracted increasing attention in recent years due to the concerns of public safety,forensic research and environmental contamination.2,4,6-trinitrophenol(TNP)is one of the common components of industrial explosives apart from 2,4,6-trinitromethyltoluene(TNT)and2,4-dinitrotoluene(DNT).TNP has stronger explosive power compared with these two analogues even at very low concentrations(picomolar),more and more attention had been paid to the rapid detection of TNP with high sensitivity and selectivity.Although several methods have been developed for the detection of TNP,some drawbacks associated with the existing methods have restricted their applications.For instance,requirement of sophisticated equipments,high cost of testing,and poor water-solubility of the probes are the most common problems.Hence,it is still highly desirable to develop new probes that can be easily prepared and used for the field testing of TNP with high sensitivity and selectivity.Small molecule fluorescent probes feature high sensitivity and selectivity,ease of operation and real-time detection.Pyrene derivatives have highly fluorescence quantum yield,stable photochemical properties.In this paper,desiged and synthesized two water-soluble pyrene derivatives and applied them in the detection of TNP by harnessing these advantages,including:1.In Chapter 2,two water-soluble pyrene derivatives are designed and synthesized,including,N,N,N-trimethyl-2-(pyren-1-yloxy)ethanaminium bromide and 4-(pyren-1-butyl)-1-sodium 1HNMR and 13 CNMR,High resolution mass spectrum,Infrared and UV-visible spectra were used to confirm their structure.2.In Chapter 3,we have developed a practical approach for the detection of TNP in 100% aqueous solution based on a cationic pyrene derivative.It features high selectivity,good sensitivity and rapid responses toward TNP.The LOD could reach23.2 nM.The sensing mechanism is attributed to the cooperative non-covalent interactions,including electrostatic,?-? stacking and charge transfer interactions between PyOEA and PA.In addition,test strips have been successfully fabricated by asimple immersion and drying method.The visual detection limit of paper strips can be as low as 1 ?M.3.In Chapter 4,we have developed a novel approach for the visual detection of TNP in aqueous media based on polyelectrolyte-induced pyrene nano-assemblies with excellent selectivity and sensitivity.The mechanism of this sensing system was attributed to the formation of PyBS/PDDA/TNP complex though cooperative non-covalent interactions including electrostatic,?-? stacking and charge transfer interactions.The linear detection range of TNP is 1.0 to 50 nM.The LOD is as low as1 nM.