3,6-二取代丙烯酰-9-乙基咔唑的合成及光谱研究

Synthesis of 3,6-disubstituted acryloyl-9-ethylcarbazole and its spectra

以咔唑为原料,经Friedel-Crafts酰基化、N-烷基化反应制得3,6-二乙酰-9-乙基咔唑(I),然后在碱性条件下分别与糠醛、5-甲基糠醛和苯甲醛反应,生成3,6-二(呋喃-2-)丙烯酰-9-乙基咔唑(II)、3,6-二(5-甲基呋喃-2-)丙烯酰-9-乙基咔唑(III)和3,6-二苯丙烯酰-9-乙基咔唑(IV),产率分别为74.1%、76.9%和71.4%。通过1H、13CNMR、质谱及红外光谱对其结构进行表征,并对其紫外-可见吸收光谱和荧光发射光谱进行研究。化合物I^IV的最强吸收峰分别为262、339、356、300 nm,最强发射峰分别为304、342、364、334 nm,最大吸收与发射波长均向长波长方向移动。表明此类材料具有较强的发射光谱,可作为潜在的荧光材料,有望应用于有机光致/电致发光材料。

3,6-diacetyl-9-ethylcarbazole（ I） was acquired with carbazole as raw material,and Friedel Crafts acylation and N-alkylation. 3,6-di（ furan-2-） acryloyl-9-ethylcarbazole（ II）,6-di（ 5-methyl furan-2-）acryloyl-9-ethylcarbazole（ III） and 3,6-dibenzene acryloyl-9-ethylcarbazole（ IV） were obtained under alkaline conditions 3,6-diacetyl-9-ethylcarbazole reacting with furfural,5-methyl furfural and benzaldehyde,respectively,and their yields were 74. 1%,76. 9% and 71. 4%. Their structure were characterized by1 HNMR,13 CNMR,Mass spectrometry and Infrared spectra. Meanwhile we studied their UV-Visible absorption and fluorescence spectra. The strongest absorption peaks of compounds II,III,and IV of are at 300,339,356 nm,and the strongest fluorescence peaks of theirs are 350,367,376 nm,to move the red shift direction of long wavelength from absorption spectra to fluorescence spectra. It is indicated that the materials have strong emission spectrum and can be used as a fluorescent material,which has potential applications in the field of organic light-emitting materials.