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Citation: DING Guo-Hua, JING Shu-Ping, TIAN He. Synthesis and Fluorescent Properties of Coumarin Derivatives[J]. Chinese Journal of Applied Chemistry, ;2005, 22(5): 551-553. shu

Synthesis and Fluorescent Properties of Coumarin Derivatives

1.
a Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237;
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b Department of Material & Chemical Engineering, Guilin Institute of Technology, Guilin

Corresponding author: TIAN He,
Received Date: 20 July 2004
Available Online: 20 December 2004
Fund Project: 国家自然科学基金资助项目(20206007) (20206007)

3-Acetyl-4-hydroxyl coumarin was synthesized by acetylation and acyl chlorination of salicylic acid followed by the cyclocondensation of acetacetic ester.Its condensation with each of three aldehydes,N,N-dimethy-4-aminobenzaldehyde,N,N-di(4-methyphenyl)-4-aminobenzaldehyde and N,N-diphenyl-4-aminobenzaldehyde affords three 4-hydroxyl coumarin derivatives,i.e.,3[(para-dimethyamino)-cinnhyl]-4-hydroxyl coumarin[TM1],3{[para-di(4-methyphenyl) amino]-cinnhyl}-4-(hydroxyl) coumarin[TM2],and 3[(para-diphenylamino)-cinnhyl]-4-hydroxyl coumarin[TM3].The three derivatives have high extinction coefficients in UV-vis absorption,which were 5.25×10⁴ L/(mol·cm),3.39×10⁴ L/(mol·cm),and 3.24×10⁴ L/(mol·cm),respectively,and intensive luminescence in both the THF solution and solid state.Derivatives TM1 and TM2 emit intensive orange red luminescence with the same absorption peak at 500 nm and the identical small Stoke shift of 85 nm in the emission spectra in THF.The photoluminescence peaks of the three derivatives in solid state are at 705,643,and 660 nm,respectively.Derivative TM3 displays intensive red luminescence with the peak at 486 nm and a large Stoke shift of 152 nm in the emission spectrum in THF,which makes it a novel red luminescent material that may be used in OLEDs.
- salicylic acid,
- hydroxyl coumarin derivative,
- fluorescence
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