1,8-萘酰亚胺衍生物的合成、表征及电存储性能

引用本文: 王漪, 贾南方, 齐胜利, 田国峰, 武德珍. 1,8-萘酰亚胺衍生物的合成、表征及电存储性能[J]. 物理化学学报, 2017, 33(11): 2227-2236. doi: 10.3866/PKU.WHXB201705221 shu

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

1,8-萘酰亚胺衍生物的合成、表征及电存储性能

1.
北京化工大学, 化工资源有效利用国家重点实验室, 北京 100029;
2.
北京化工大学, 常州先进材料研究院, 江苏常州 213164
基金项目:
国家自然科学基金（51673017，21404005），江苏省杰出青年基金（BK20140006）和常州市科技计划项目（CZ20150001）资助项目

摘要: 本文以三苯胺结构作为电子给体，与三种接有不同吸电子基团的1，8-萘酐反应合成了具有电子给-受体结构的N-（4-三苯胺）-1，8-萘酰亚胺（NA-ATPA）、N-（4-三苯胺）-（4-氰基）-1，8-萘酰亚胺（NA（CN）-ATPA）和N-（4-三苯胺）-（4-硝基）-1，8-萘酰亚胺（NA（NO₂）-ATPA），并对它们的结构进行了表征。利用紫外可见光谱、荧光发射光谱和循环伏安法对产物的光物理性能和电化学性能进行了测试，并测试了其存储行为，结果显示NA-ATPA表现出易失的静态随机存储行为（SRAM），NACN-ATPA表现出非易失的闪存型存储（Flash），NA（NO₂）-ATPA表现出非易失只读型存储（WORM）。三种萘酰亚胺对存储行为中高导态的维持能力逐渐增强，其原因是引入的吸电子基团的吸电子性越强，其LUMO值和能隙值降低的越多，越利于电荷转移，形成更稳定的电荷转移络合物。另外，本文还对原料和产物的电子结构、分子轨道和能级进行了分子模拟计算，研究了三种化合物基态和激发态的差别，并对其电子转移过程进行了理论分析。

关键词:

English

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

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).

Abstract: 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:

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

1,8-萘酰亚胺衍生物的合成、表征及电存储性能

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

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

1,8-萘酰亚胺衍生物的合成、表征及电存储性能

English

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

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

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CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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