Synthesis And Application Of Benzofuran Derivatives

Organic materials have the advantages of light weight,flexibility,and large area solution preparation,making organic electronic materials in lighting,display,photovoltaic,sensing and other fields have gradually been widely used and developed.Furan materials often has excellent luminous property,but poor aromaticity of furan system,lead to this kind of material stability is poorer,but compared to the outstanding electronic material-thiophene,furan system does not exist spin track coupling effect caused by fluorescence quenching,and by the appropriate molecular design is introduced into the conjugate aromatic system,can improve its stability and electronic transmission performance.In this work,a series of benzofurans were synthesized and long chain groups were introduced,and their luminescence and conductivity applications were investigated.1.Three cis-trans benzofuran long chain ester derivatives（BDF-1,BDF-2,BDF-3）were synthesized and their structures and properties were characterized by NMR.2.Bdf-3,a hexyl derivative of trans-benzofuran,was complexed with different metal ions to study its fluorescence response to metal ions.Bdf-3 showed a specific fluorescence response to zinc ions.The fluorescence excitation wavelength was 365 nm,and the fluorescence emission wavelength was 480nm（blue light）.This specific recognition only existed in methanol solution.Further,the detection limit was determined as 1.4072×10^-8through the fluorescence titration curve,and the binding constant was calculated as 1.52×10⁵after non-linear fitting of the curve.The binding ratio between the host molecule（BDF-3）and the guest molecule（zinc ion）was determined to be 1:1 through the working curve,which provided ideas for the application of furan molecules in metal ion detection.3.Three electron transfer complexes（TCNQ@BDF-1,TCNQ@BDF-2,TCNQ@BDF-3）were synthesized by solution method using benzodifuran electron-rich molecules as electron donors and TCNQ as electron acceptor.Voltammetry was used to measure the resistance of the powder after pressing.It was found that the small molecule which should not conduct electricity had conductive characteristics,and its composite behavior was confirmed by solid ultraviolet,nuclear magnetic,infrared and powder X-ray diffraction.4.The response of the device to different organic vapors was studied by linear voltammetry with TCNQ@BDF-3 as the organic semiconductor layer.It was found that the device had specific response to ammonia gas.Under the condition of moisture sensitization,the response level can reach 4.7 PPB;Through the real-time current method,it is found that the device has the characteristics of rapid response and rapid response to ammonia（response time:115 seconds,response time:28s）,which meets the requirements of medical detection of ammonia,indicating that this work has very broad application prospect and potential in the application of medical detection of ammonia.