Citation: WANG Yi, JIA Nan-Fang, QI Sheng-Li, TIAN Guo-Feng, WU De-Zhen. Synthesis, Characterization and Memory Performance of Naphthalimides Containing Various Electron-Withdrawing Moieties[J]. Acta Physico-Chimica Sinica, ;2017, 33(11): 2227-2236. doi: 10.3866/PKU.WHXB201705221 shu

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

WANG Yi ^1, ,
JIA Nan-Fang ¹ ,
QI Sheng-Li ^1,2 ,
TIAN Guo-Feng ^1,2 ,
WU De-Zhen ^1,2

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 Date: 24 April 2017
Revised Date: 12 May 2017

Fund Project: The project was supported by the National Natural Science Foundation of China (51673017, 21404005), National Science Fund for Distinguished Young Scholars, China (BK20140006), and 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.
- Naphthalimide,
- Electron-withdrawing group,
- Charge transfer,
- Molecular simulation,
- Storage property
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