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Citation: CAO Jian-Xin, CHENG Yan-Xiang, XIE Zhi-Yuan, WANG Li-Xiang, JING Xia-Bin, WANG Fo-Song. Synthesis and Characterization of Novel Blue Light-Emitting 1,8-Naphthalimide Derivatives[J]. Chinese Journal of Applied Chemistry, ;2007, 24(8): 853-857. shu

Synthesis and Characterization of Novel Blue Light-Emitting 1,8-Naphthalimide Derivatives

1.
The State Key Laboratory of Polymer Physics and Chemistry Changchun Institute of Applied chemistry, Graduate School of Chinese Academy of Sciences, Chinese Academy of Sciences, Changchun 130022

Corresponding author: WANG Li-Xiang,
Received Date: 26 September 2006
Available Online: 30 November 2006
Fund Project: 科技部"九七三"项目(2002CB613X01)资助 (2002CB613X01)

A series of novel 1,8-naphthalimide fluorescent dyes have been designed and synthesized by introducing different aromatic units at 4-position through Suzuki and Stille coupling reactions,and their photophysical properties,e.g.UV-Vis absorption,photoluminescence and electrochemical behavior,were studied.All these compounds emit blue light,exhibiting photoluminescence (PL) with absorption and PL maxima in the range of 357~378 and 423~451 nm respectively in toluene.As increasing electron-donating capability of aromatic substituent,both absorption and photoluminescence are red shifted.The structures of the aromatic units significantly affect the PL properties of the compounds.The compound with methoxyphenyl substituent exhibits the highest PL quantum yield up to 0.98,while that bearing thienyl unit shows the lowest PL quantum yield of 0.17.Cyclic voltammogram measurements indicate that these compounds have high electron affinity attributed to the 1,8-naphthalimide unit.The aromatic units only affect the highest occupied molecular orbital (HOMO) energy levels,but not the lowest unoccupied molecular orbital (LUMO) energy levels,meaning that the LUMO energy levels are determined by 1,8-naphthalimide unit.
- organic light-emitting diode,
- naphthalimide,
- photoluminescence quantum yield,
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