Study On Synthesis And Properties Of Novel Organic Two-photon Absorption Materials Containing Nitrogen Heterocycles

Two-photon absorption material has broad application prospects in the 3D data storage,optical limiting materials,photodynamic therapy and two-photon fluorescence microscopy and imaging,etc.,it had been a hot research filed in photoelectric functional materials nowadays.In this paper,five kinds of novel organic two-photon absorption materials containing nitrogen heterocycles(M1-M5)had been designed and synthesized.Then we studied the linear and nonlinear optical properties of four materials containing nitrogen heterocycles and explored the relationship between the structure and property.The main research content is as follows:9-[4-(4,5-Diphenyl-1H-imidazol-2-yl)phenyl]-9H-carbazole(M1)was synthesized by Ullmann reaction,Debus reaction using 9H-carbazole as materials.3,6-Bis(4,5-diphenyl-1H-imidazol-2-yl)-9-ethyl-9H-carbazole(M2)was synthesized by Vilsmeier reaction,Debus reaction using 9-Ethylcarbazole as materials.2,2'-[(2,5-Dimethoxy-l,4-phenylene)bis[(1E)-2,1-ethenediyl-4,1-phenylene]]bis(4,5-diphenyl-1H-imidazole)(M3)was synthesized by Blanc reaction,Arbuzov reaction,Horner-Wadsworth-Emmons reaction,Debus reaction using1,4-Dimethoxybenzene,HBr,(HCHO)_nas materials.9-Ethyl-3-[(1E)-2-[2,5-dicyano-[4-(1E)-2-[4-(9H-carbazol-9-yl)phenyl]ethenyl]p henyl]ethenyl]-9H-carbazole(M4)was synthesized by Aromatic ring halogenated reaction,Cyano reaction,Free radical reaction,Arbuzov reaction,Horner-Wadsworth-Emmons reaction,using p-xylene as material.1-(2-Hydroxyethyl)-4-[(1E)-2-[4-[(1E)-2-[2,5-dimethoxyl-4-[(1E)-2-(4-formylph enyl)ethenyl]phenyl]ethenyl]phenyl]ethenyl]pyridinium bromide(M5)was synthesized by Blanc reaction,Arbuzov reaction,Horner-Wadsworth-Emmons reaction,and Knoevenagel reaction,using 1,4-Dimethoxybenzene,HBr,(HCHO)_nas materials.Five novel organic two-photon absorption materials containing nitrogen hetero-cycles M1-M5 were characterized by NMR,IR,MS.This paper studied on the absorptivity of ultraviolet and visible light and single photon fluorescence of five novel organic two-photon absorption materials containing2-Substituted-4,5-diphenyl-1H-imidazoles(M0-M3)in different solvents.We get the optical performances of the maximum linear absorption wavelength,molar absorption coefficient,maximum single-photon excited fluorescence wavelength,stokes shift,fluorescence quantum yield.We explored effects of the solvent polarity and structure on the properties of linear optical material.Two-photon absorption and two-photon fluorescence of the four materials M0-M3 in THF and DMF were estimated by using the two-photon induced fluorescence technique with femtosecond laser pulses under the excitation of Ti:sapphire laser.We got the optical performances of the maximum excitation wavelength,the maximum two-photon excited fluorescence wavelength,two-photon absorption cross-section,and verified two-photon excitation mechanism.Combined with the DFT study,we explored the relationship of the four materials M0-M3 between the molecular structure and its optical properties.