4-羟基香豆素衍生物的荧光性能  

Synthesis and Fluorescent Properties of Coumarin Derivatives

作　　者：丁国华[1] 荆淑萍[1] 田禾[1] 

机构地区：[1]华东理工大学精细化工研究所

出　　处：《应用化学》2005年第5期551-553,共3页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金资助项目(20206007)

摘　　要：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\1\], 3{\[para-di（4-methyphenyl）amino\]-cinnhyl}-4-（hydroxyl） coumarin\2\], and （3\[（para-）diphenylamino）-cinnhyl\]-4-hydroxyl coumarin\3\]. 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.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\1\], 3{\[para-di(4-methyphenyl)amino\]-cinnhyl}-4-(hydroxyl) coumarin\2\], and (3\[(para-)diphenylamino)-cinnhyl\]-4-hydroxyl coumarin\3\]. The three derivatives have high extinction (coefficients) in UV-vis absorption, which were 5.25×10^(4) L/(mol·cm), 3.39×10^(4) L/(mol·cm), and 3.24×10^(4) 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.

关 键 词：水杨酸 羟基香豆素衍生物 荧光 

分 类 号：O626.3[理学—有机化学]