Synthesis And Properties Of Ferrocenyl Derivatives Containing Fluorophores

In recent years,fluorescent probe detection methods have been widely used in biology,clinical,environmental science,information science and other fields due to their advantages such as fast detection speed and simple operation.1,8-Naphthalimide,Fluorescein,and Rhodamine B derivatives are widely used for their excellent optical properties such as high fluorescence quantum yield,wide wavelength range,large molar absorption coefficient,and good light stability.Ferrocene and its derivatives due to stable redox activity and easy chemical modification,especially with good lipophilicity,can easily pass through the cell membrane,which is later in live cells Application laid the foundation.By introducing ferrocene with fluorescence quenching ability into fluorophore,three types of fluorescent probes of Naphthalimide-Ferrocene,Fluorescein-Ferrocene and Rhodamine B-Ferrocene were designed and synthesized in this paper.The structure was determined by infrared spectrum and nuclear magnetic resonance spectrum.Single crystals of four of these compounds were obtained by simultaneous cultivation,which further confirmed the structure of the obtained compounds.Four Naphthalimide-Ferrocene compounds were designed and synthesized by using4-Bromo-1,8-Naphthalic Anhydride,Ferrocene and Ferrocenecarboxylic Acid as raw materials.Compounds I,II,and III use thiourea group as the recognition group,and compound IV uses amide group as the recognition group.The ultraviolet,fluorescence and electrochemical methods are used to study the recognition of cations and anions.Through experiments,it is found that the target compound?can specifically identify Hg²⁺by colorimetry,and can be recognized Hg²⁺with naked eyes.The minimum detection limit is0.70?mol/L,and the linear detection interval for Hg²⁺is 0¹0?mol/L.Complexation is performed in a 1?1 manner.Compound?can detect Cu²⁺and Fe³⁺by electrochemical method.The target compound II can be recognizeded Hg²⁺and Ag⁺with naked eyes.The linear detection interval for Hg²⁺and Ag⁺is 0¹0?mol/L and the detection limit is 0.82?mol/L and 0.15?mol/L.The target compound II can detect Ag⁺by electrochemical method.Two Fluorescein-Ferrocene compounds V and VI were designed and synthesized by using Fluorescein,Ferrocene and FerroceneFormic acid as the raw materials.Compound V uses a thiourea group as a recognition group,and Compound VI uses a Schiff base as a recognition group.The ultraviolet,fluorescence and electrochemical methods were used to study the recognition of cations and anions.It is found that the target compound?can be recognized Hg²⁺and Cu²⁺through ultraviolet spectrum,and the ultraviolet absorption intensity has a good linear relationship with the guest concentration.When the concentration of Cu²⁺is 0⁷0?mol/L and the concentration of Hg²⁺is 0¹00?mol/L,the minimum detection limits of Cu²⁺,Hg²⁺are 0.55?mol/L and 0.72?mol/L,respectively.Cu²⁺can be identified by cyclic voltammetry,and a multi-channel response of the target compound?to Cu²⁺is achieved.From the job's curve,it was found that the compound ratio of the target compound?to Cu²⁺is 1?1,and the compound ratio of the target compound?to Hg²⁺is 2?3.It is found that the target compound?did not respond to any of the we tested is anions and is cations,and further studies are needed.Two Rhodamine B-Ferrocene compounds were designed and synthesized by using Rhodamine B,Ferrocene and Ferrocene Formate as raw materials.Compound?was identified by thiourea group,and compound?was identified by Schiff base.It is found through experiments that the target compound?can be recognized Cu²⁺and Hg²⁺with naked eyes in a solution of ethanol?deionized water=1?5?V?V?.The linear detection interval for Cu²⁺and Hg²⁺is 0¹0?mol/L and the detection limit is 0.62?mol/L and 0.17?mol/L.Hg²⁺can be selectively identified by ultraviolet and fluorescence spectra.The target compound?can be recognized Sn⁴⁺and Fe³⁺in a solution of ethanol?deionized water=1?5?V?V?.Sn⁴⁺and Fe³⁺can be selectively identified by ultraviolet spectrum and fluorescence spectrum.