Acta Phys. -Chim. Sin. ›› 2017, Vol. 33 ›› Issue (11): 2227-2236.doi: 10.3866/PKU.WHXB201705221

• ARTICLE • Previous Articles     Next Articles

Synthesis, Characterization and Memory Performance of Naphthalimides Containing Various Electron-Withdrawing Moieties

Yi WANG1,Nan-Fang JIA1,Sheng-Li QI1,2,*(),Guo-Feng TIAN1,2,De-Zhen WU1,2   

  1. 1 State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. China
    2 Changzhou Institute of Advanced Materials, Beijing University of Chemical Technology, Changzhou 213164, Jiangsu Province, P. R. China
  • Received:2017-04-24 Published:2017-08-25
  • Contact: Sheng-Li QI
  • Supported by:
    the National Natural Science Foundation of China(51673017);the National Natural Science Foundation of China(21404005);National Science Fund for Distinguished Young Scholars, China(BK20140006);Changzhou Sci & Tech Program, China(CZ20150001)


In order to clarify the influence of different electron-withdrawing groups on the electronic structures and memory properties of naphthalimides, three 1, 8-naphthalimides, namely 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(NO2)-ATPA), were designed and synthesized using triphenylamine (TPA) as the electron donor and 1, 8-naphthalene dianhydride containing different electron-withdrawing moieties (-H, -CN, -NO2) as the electron acceptor. The photophysical properties and electrochemical characteristics of the compounds were investigated by ultraviolet-visible spectroscopy (UV-Vis), fluorescence spectroscopy (FL) and cyclic voltammetry (CyV). The synthesized products were applied as the active layer in sandwich devices, whose memory characteristics were tested. NA-ATPA shows volatile static random access memory (SRAM) behavior, while NACN-ATPA and NANO2-ATPA show nonvolatile flash and write-once read-many times memory (WORM) behavior, respectively. Experimental results indicated that the synthesized compounds possessed small energy gaps and wide absorption ranges. The introduction of electron-withdrawing groups on the 4-position of the 1, 8-naphthalimides reduced the LUMO energy level and the energy gap, leading to improved stability of the charge-transfer state and volatile-to-nonvolatile memory transfer. To elucidate the switching mechanism, molecular simulation results, including molecular orbitals, energy levels, optimized geometries, and Mulliken charge populations, were discussed.

Key words: Naphthalimide, Electron-withdrawing group, Charge transfer, Molecular simulation, Storage property