Synthesis And Photophysics Characteristics Of Naphthalimides Containing Varied Electron-withdrawing Moieties

In recent years,organic functional materials is widely used in photoelectric material because of its low cost,structure,diversity,and the molecular design can be strong,and can be cut at random.Among them,1,8-Naphthalimide?NA?and its derivatives have been widely used in optoelectronic filed nowadays owing to the excellent phot ? hemical stability,thermal stability and easy modification of the 4-position.In order to research the effect to optoelectronic with different electron-withdrawing substituent groups,In the present study,six 1,8-naphthalimides,i.e.,N-?4-triphenylamino?-1,8-naphthalimide?NA-ATPA?,N-?4-tripheny lamino?-?4-cyano?-1,8-naphthalimide?NA?CN?-ATPA?and N-?4-triphenylamine?-?4-nitro?-1,8-naphthalimide?NA?N02?-ATPA?,were designed and synthesized by using the triphenylamine?TPA?as the electron-donating unit and the 1,8-naphthalene dianhydrides containing three different electron-withdrawing moieties?-H,-CN,-NO₂?as the electron-accepting units.It is advantageous to the charge transfer which compounds have push-pull electronic structure.The structures of the six synthesized 1,8-naphthalimides were characterized by nuclear magnetic resonance?NMR?and Fourier transform infrared spectroscopy?FTIR?.The photophysical properties and electrochemical characteristics of the compounds were investigated by the ultraviolet-visible spectrometer?UV-vis?spectra,fluorescence spectra?FL?and cyclic voltammograms?CyV?.Testing the memory characteristics of the products with the semcondictiong parameter machine.Molecular simulation was carried out to elucidate the molecular orbitals,the energy levels,optimized geometry,and Mulliken charge distribution of the ground states and excited states of the compounds.Electronic transition occurring in the synthesized compounds was analyzed based on the molecular orbital analysis.Experimental results show that the synthesized compounds possess small energy gap and wide absorption range.The introduction of electron-withdrawing groups on the 4-poistion of the 1,8-naphthalimides reduced the LUMO energy level and the energy gap,facilitating the charge transition in the synthesized compounds.This work provides feasible guidance for the design of polymeric materials possessing excellent photoelectric properties.The total work as follow:1 six 1,8-naphthalimides,i.e.,N-?4-triphenylamino?-1,8-naphthalimide?NA-ATPA?,N-?4-triphenylamino?-?4-cyano?-1,8-naphthalimide?NA?CN?-ATPA?and N-?4-triphenylamine?-?4-nitro?-1,8-naphthalimide?NA?N02?-ATPA?,N-?4-amino-carbezole?-1,8-naphthalimide?NA-APCB?,N-?4-amino-carbezole?-?4-cyano?-1,8-naphthalimide?NA?CN?-APCB?and N-?4-amino-carbezole?-?4-nitro?-1,8-naphthalimide?NA?NO₂?-APCB?,were designed and synthesized by using the 4-amino-triphenylamine?TPA?and 4-amino-carbezole?APCB?as the electron-donating unit and the 1,8-naphthalene dianhydrides containing three different electron-withdrawing moieties?-H,-CN,-NO₂?as the electron-accepting units.The structures of the six synthesized 1,8-naphthalimides were characterized by nuclear magnetic resonance?NMR?and Fourier transform infrared spectroscopy?FTIR?.2 The photophysical properties and electrochemical characteristics of the compounds were investigated by the ultraviolet-visible spectrometer?UV-vis?spectra,fluorescence spectra?FL?and cyclic voltammograms?CyV?.Testing the memory characteristics of the products with the semcondictiong parameter machine.3 Molecular simulation was carried out to calculate the molecular orbitals,the energy levels,optimized geometry,and Mulliken charge distribution of the ground states and excited states of the compounds.